Irinotecan

Identification

Summary

Irinotecan is a topoisomerase inhibitor used to treat metastatic carcinoma of the colon or rectum and pancreatic adenocarcinoma.

Brand Names
Camptosar, Onivyde
Generic Name
Irinotecan
DrugBank Accession Number
DB00762
Background

Irinotecan is a topoisomerase inhibitor used for chemotherapy. It is a water-soluble analogue of camptothecin, which is extracted from the Chinese tree Camptotheca acuminate.5 The bis-piperidine side chain in the structure of irinotecan bestows enhanced water solubility.6 As an anticancer drug, irinotecan was first commercially available in Japan in 1994 to treat various cancers such as lung, cervical and ovarian cancer.5 Approved by the FDA in 1996,3 irinotecan is used to treat colorectal cancer and pancreatic adenocarcinoma.7,8,10 Irinotecan liposome was approved by the FDA in February 2024.8

The active metabolite SN-38 is also a potent inhibitor of DNA topoisomerase I. Both irinotecan and SN-38 mediate antitumor activity by forming a complex with topoisomerase I and blocking its enzymatic activity, thereby interfering with DNA synthesis. This leads to the arrest of the cell cycle in the S-G2 phase and cancer cell death.5

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 586.678
Monoisotopic: 586.279134968
Chemical Formula
C33H38N4O6
Synonyms
  • (+)-Irinotecan
  • (S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 4-(2-(5-(3-(2,4-dihydroxy-5-isopropylphenyl)-5-hydroxy-4H-1,2,4-triazol-4-yl)-1H-indol-1-yl)ethyl)piperidine-1-carboxylate
  • Irinotecan
  • Irinotecan lactone
  • Irinotecan liposome injection
  • Irinotecanum
External IDs
  • CPT 11
  • CPT-11
  • CPT11
  • NSC-728073

Pharmacology

Indication

Irinotecan is indicated for the treatment of: - Metastatic carcinoma of the colon or rectum as first-line treatment in combination with fluorouracil and leucovorin.7,10 - Metastatic carcinoma of the colon or rectum whose disease has recurred or progressed following initial fluorouracil-based therapy, as monotherapy 10 or in combination with fluorouracil and leucovorin.7

Irinotecan liposome injection is used in adults for the treatment of: - Metastatic pancreatic adenocarcinoma in combination with oxaliplatin, fluorouracil, and leucovorin as first-line treatment.8 - Metastatic pancreatic adenocarcinoma in combination with fluorouracil and leucovorin after disease progression following gemcitabine-based therapy.8

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatEsophageal cancer••• •••••
Used in combination to treatGastric cancer••• •••••
Used in combination to treatGlioblastoma••• •••••
Treatment ofMetastatic cervical cancer••• •••••
Treatment ofMetastatic colorectal cancer (crc)•••••••••••••••••••••• ••••••• •••• •••••••••••• ••••••••••••• ••••••• ••••••••••• ••••• •••••••• •••••••••••••••••• ••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Irinotecan is an antineoplastic agent. The administration of irinotecan has resulted in antitumor activity in mice bearing cancers of rodent origin and in human carcinoma xenografts of various histological types.7

Mechanism of action

DNA topoisomerase I is a nuclear enzyme that ensures proper DNA topology during replication and transcription.6 It relieves torsional strain in the DNA double helix during replication and transcription by creating reversible single-strand breaks.4,7

Upon administration, irinotecan is converted into its active metabolite, SN-38, by carboxylesterase in the liver and gastrointestinal tract.3 Irinotecan and SN-38 both inhibit DNA topoisomerase I, acting on the S and G2 phases of the cell cycle.4,7 Irinotecan and SN-38 bind to the topoisomerase I-DNA complex and prevent the religation of single-strand breaks.7 The ternary complex formed by topoisomerase I, DNA, and either irinotecan or SN-38 interferes with the moving replication fork, inducing replication arrest and lethal double-stranded breaks in DNA. Because double-stranded breaks cannot be efficiently repaired by mammalian cells, apoptosis of cancer cells occurs.7

TargetActionsOrganism
ADNA topoisomerase I, mitochondrial
inhibitor
Humans
ADNA topoisomerase 1
inhibitor
Humans
Absorption

Over the recommended dose range of 50 to 350 mg/m2, the AUC of irinotecan increases linearly with dose; the AUC of SN-38 increases less than proportionally with dose. Maximum concentrations of the active metabolite SN-38 are generally seen within 1 hour following the end of a 90-minute infusion of irinotecan.7 The plasma levels of SN-38 are much lower than that of irinotecan.2,7

Following intravenous infusion in patients with solid tumours, the mean (± standard deviation) Cmax was 1,660 ± 797 ng/mL at a dose of 125 mg/m2 and 3,392 ± 874 ng/mL at a dose of 340 mg/m2. The AUC0–24 was 10,200 ± 3,270 ng x h/mL at a dose of 125 mg/m2 and 20,604 ± 6,027 ng x h/mL at a dose of 340 mg/m2.7

Volume of distribution

Following intravenous infusion in patients with solid tumours, the mean (± standard deviation) volume of distribution of terminal elimination phase was 110 ± 48.5 L/m2 at a dose of 125 mg/m2 and 234 ± 69.6 L/m2 at a dose of 340 mg/m2.7

Protein binding

Irinotecan is about 30% to 68% bound to plasma proteins. SN-38 is approximately 95% bound to plasma proteins. Irinotecan and SN-38 are mainly bound to albumin.7

Metabolism

Upon administration, irinotecan is converted primarily in the liver into its active metabolite, SN-38, by carboxylesterase.3 SN-38 is formed by cleavage of the carbamate bond between the camptothecin moiety and the dipiperidino side chain.7 While in vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies, SN-38 is approximately 1000 times as potent as irinotecan as an inhibitor of topoisomerase I.2,7 SN-38 can further be glucuronidated by UGT1A1 to form SN-38G.1,3,7

Irinotecan can also undergo CYP3A4-mediated oxidation to form NPC and APC. While some sources state that NPC and APC are weak inhibitors of topoisomerase I,1,2 they are unlikely to contribute to the pharmacological activity of irinotecan.

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Route of elimination

The disposition of irinotecan has not been fully elucidated in humans. The urinary excretion of irinotecan, SN-38, and SN-38 glucuronide are 11% to 20%, <1%, and 3%, respectively. The cumulative biliary and urinary excretion of irinotecan and its metabolites (SN-38 and SN-38 glucuronide) over a period of 48 hours in two patients ranged from approximately 25% (100 mg/m2) to 50% (300 mg/m2).7

Half-life

After intravenous infusion of irinotecan in humans, the mean terminal elimination half-life of irinotecan is about 6 to 12 hours. The mean terminal elimination half-life of the active metabolite SN-38 is about 10 to 20 hours.7

Clearance

The mean (± standard deviation) total systemic clearance of irinotecan in patients with solid tumours was 13.3 ± 6.01 L/h/m2 at a dose of 125 mg/m2 and 13.9 ± 4.0 L/h/m2 at a dose of 340 mg/m2.7

Adverse Effects
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Toxicity

The oral LD50 is 1045 mg/kg in mice and 867 mg/kg in rats.9

In clinical trials involving patients with various cancers, single doses of up to 750 mg/m2 of irinotecan were associated with similar adverse events reported with the recommended dosage and regimen. There have been reports of overdosage at doses up to approximately twice the recommended therapeutic dose, which may be fatal. The most significant adverse reactions reported were severe neutropenia and severe diarrhea. Because there is no known antidote for overdosage of irinotecan, maximum supportive care should be instituted to prevent dehydration due to diarrhea and to treat any infectious complications.7

Pathways
PathwayCategory
Irinotecan Metabolism PathwayDrug metabolism
Irinotecan Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Solute carrier organic anion transporter family member 1B1SLCO1B1*15(C;C) / (C;T)C Allele / G AlleleDirectly Studied EffectPatients with this genotype have reduced transport of the active metabolite of irinotecan resulting in increased plasma concentrations.Details
UDP-glucuronosyltransferase 1-1UGT1A1*28 or UGT1A 7/7Not Availableextra TA in promoterADR Directly StudiedThe presence of this genotype in UGT1A1 may indicate an increased risk of bone marrow toxicity when treated with irinotecan.Details
UDP-glucuronosyltransferase 1-7UGT1A7*2/*2(G;G) / (G;T) / (A;C) / (A;A) / (A;G)G allele / A allele  … show all ADR Directly StudiedThe presence of this genotype in UGT1A1 may indicate an increased risk of bone marrow toxicity when treated with irinotecan.Details
UDP-glucuronosyltransferase 1-1UGT1A1*93(A;A) / (A;G)A AlleleADR Directly StudiedThe presence of this genotype in UGT1A1 may indicate an increased risk of bone marrow toxicity when treated with irinotecan.Details
UDP-glucuronosyltransferase 1-1UGT1A1*28Not Availableextra TA in promoter, homozygousADR Directly StudiedPatients who carry this genotype in UGT1A1 are at increased risk for neutropenia following initiation of irinotecan treatment.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Irinotecan can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Irinotecan can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Irinotecan.
AbemaciclibAbemaciclib may decrease the excretion rate of Irinotecan which could result in a higher serum level.
AcalabrutinibThe metabolism of Irinotecan can be decreased when combined with Acalabrutinib.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Irinotecan hydrochloride06X131E4OE100286-90-6GURKHSYORGJETM-WAQYZQTGSA-N
Irinotecan hydrochloride hydrate042LAQ1IIS136572-09-3KLEAIHJJLUAXIQ-JDRGBKBRSA-N
Irinotecan sucrosofateOL741S3N8B1361317-83-0BCPSLKYBXGKPIW-RTXWKGGWSA-N
Product Images
International/Other Brands
Biotecan / Campto (YakultHonsha Co. Ltd.)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CamptosarInjection, solution20 mg/1mLIntravenousPharmacia and Upjohn Company LLC1996-06-142018-05-31US flag
CamptosarInjection, solution20 mg/1mLIntravenousPharmacia & Upjohn Company LLC1996-06-14Not applicableUS flag
CamptosarSolution20 mg / mLIntravenousPfizer Canada Ulc1997-08-272022-06-02Canada flag
IrinotecanSolution20 mg / mLIntravenousPfizer Canada Ulc2014-03-072022-06-03Canada flag
Irinotecan for InjectionSolution20 mg / mLIntravenousTEVA Canada Limited2008-10-31Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Irinotecan hydrochloideInjection20 mg/1mLIntravenousGland Pharma Limited2019-11-18Not applicableUS flag
Irinotecan hydrochloideInjection20 mg/1mLIntravenousBluePoint Laboratories2020-12-14Not applicableUS flag
Irinotecan hydrochloideInjection20 mg/1mLIntravenousXiromed Llc2019-11-18Not applicableUS flag
Irinotecan HydrochlorideInjection, solution20 mg/1mLIntravenousApotex Corp.2017-11-30Not applicableUS flag
Irinotecan HydrochlorideInjection20 mg/1mLIntravenousThyMoorgan GmbH Pharmazir & Co. K.G2010-12-202011-01-02US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
IRINOTEKAN HYDROCHLORIDE DBL HOSPIRA 100 MG/5 ML IV INFUZYON COZ.ICEREN FLAKON, 1 ADETIrinotecan (100 mg/5ml)InjectionIntravenousORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ.2020-03-17Not applicableTurkey flag
IRINOTEKAN HYDROCHLORIDE DBL HOSPIRA 40 MG/2 ML IV INFUZYON COZ.ICEREN FLAKON, 1 ADETIrinotecan (40 mg/2ml)InjectionIntravenousORNA İLAÇ TEKSTİL KİMYEVİ MAD. SAN. VE DIŞ TİC. LTD. ŞTİ.2020-03-17Not applicableTurkey flag

Categories

ATC Codes
L01CE02 — Irinotecan
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring).
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Camptothecins
Sub Class
Not Available
Direct Parent
Camptothecins
Alternative Parents
Quinolines and derivatives / Pyranopyridines / Piperidinecarboxylic acids / Aminopiperidines / Pyridinones / Benzenoids / Tertiary alcohols / Carbamate esters / Heteroaromatic compounds / Trialkylamines
show 11 more
Substituents
4-aminopiperidine / Alcohol / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Camptothecin / Carbamic acid ester / Carbonic acid derivative
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyranoindolizinoquinoline (CHEBI:80630) / Quinoline alkaloids (C16641)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7673326042
CAS number
97682-44-5
InChI Key
UWKQSNNFCGGAFS-XIFFEERXSA-N
InChI
InChI=1S/C33H38N4O6/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3/t33-/m0/s1
IUPAC Name
(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl [1,4'-bipiperidine]-1'-carboxylate
SMILES
CCC1=C2CN3C(=CC4=C(COC(=O)[C@]4(O)CC)C3=O)C2=NC2=CC=C(OC(=O)N3CCC(CC3)N3CCCCC3)C=C12

References

Synthesis Reference
US4604463
General References
  1. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [Article]
  2. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [Article]
  3. Rothenberg ML: Irinotecan (CPT-11): recent developments and future directions--colorectal cancer and beyond. Oncologist. 2001;6(1):66-80. doi: 10.1634/theoncologist.6-1-66. [Article]
  4. Reyhanoglu G, Smith T: Irinotecan. . [Article]
  5. Fujita K, Kubota Y, Ishida H, Sasaki Y: Irinotecan, a key chemotherapeutic drug for metastatic colorectal cancer. World J Gastroenterol. 2015 Nov 21;21(43):12234-48. doi: 10.3748/wjg.v21.i43.12234. [Article]
  6. Kciuk M, Marciniak B, Kontek R: Irinotecan-Still an Important Player in Cancer Chemotherapy: A Comprehensive Overview. Int J Mol Sci. 2020 Jul 12;21(14):4919. doi: 10.3390/ijms21144919. [Article]
  7. FDA Approved Drug Products: CAMPTOSAR (irinotecan hydrochloride) injection, for intravenous use (January 2022) [Link]
  8. FDA Approved Drug Products: ONIVYDE (irinotecan liposome injection), for intravenous use (February 2024) [Link]
  9. Cayman Chemical: Irinotecan (hydrochloride hydrate) MSDS [Link]
  10. Health Canada Approved Drug Products: Irinotecan Hydrochloride Intravenous Injection [Link]
Human Metabolome Database
HMDB0014900
KEGG Drug
D08086
KEGG Compound
C16641
PubChem Compound
60838
PubChem Substance
46505871
ChemSpider
54825
BindingDB
50128267
RxNav
51499
ChEBI
80630
ChEMBL
CHEMBL481
ZINC
ZINC000001612996
Therapeutic Targets Database
DAP001339
PharmGKB
PA450085
PDBe Ligand
CP0
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Irinotecan
PDB Entries
1u65

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentColorectal Cancer2
4CompletedTreatmentColorectal Neoplasms1
4CompletedTreatmentMetastatic Colorectal Cancer (CRC)1
4CompletedTreatmentSolid Tumors1
4CompletedTreatmentUpper Gastrointestinal Tumours1

Pharmacoeconomics

Manufacturers
  • Pfizer inc
  • Accord healthcare inc
  • Actavis totowa llc
  • Akorn inc
  • App pharmaceuticals
  • Bedford laboratories
  • Dr reddys laboratories ltd
  • Ebewe pharma ges mbh nfg kg
  • Fresenius kabi oncology plc
  • Hospira inc
  • Pharmaforce inc
  • Pliva lachema as
  • Sandoz inc
  • Sun pharma global inc
  • Teva parenteral medicines inc
  • Watson laboratories inc
Packagers
  • Actavis Group
  • APP Pharmaceuticals
  • Barr Pharmaceuticals
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Cipla Ltd.
  • Ebewe Pharma
  • Fresenius Kabi AB
  • Greenstone LLC
  • Hospira Inc.
  • Jiangsu Hengrui Medicine Co. Ltd.
  • Pfizer Inc.
  • Pharmacia Inc.
  • Pliva Inc.
  • Sagent Pharmaceuticals
  • Sandoz
  • SC Sindan Pharma SRL
  • Sicor Pharmaceuticals
  • Sun Pharmaceutical Industries Ltd.
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
Injection; injection, solution, concentrateIntravenous
SolutionIntravenous20.00 mg
InjectionParenteral
InjectionIntravenous20 mg/ml
SolutionParenteral100.000 mg
SolutionParenteral40 mg
SolutionIntravenous20 mg
Injection, solution, concentrateIntravenous40 mg/2ml
SolutionIntravenous40.000 mg
Injection, solution, concentrateIntravenous20 mg/1ml
SolutionIntravenous100.000 mg
SolutionIntravenous100.0 mg
SolutionIntravenous20 mg/1ml
Injection, solution, concentrateIntravenous20 mg/mL
Injection, solutionIntravenous20.0 mg/ml
SolutionParenteral100 mg
SolutionIntravenous20 mg/ml
SolutionIntravenous100 mg/5ml
SolutionIntravenous150 mg/7.5ml
SolutionIntravenous40 mg/2ml
Solution, concentrateIntravenous100 mg
SolutionIntravenous20 mg / mL
Injection, solution, concentrateIntravenous; Parenteral20 MG/ML
Injection, solution, concentrateIntravenous
InjectionIntravenous
InjectionIntravenous100 mg/5mL
InjectionIntravenous20 mg/1mL
InjectionIntravenous40 mg/2mL
InjectionIntravenous500 mg/25mL
Injection, solutionIntravenous100 mg/5mL
Injection, solutionIntravenous20 mg/1mL
Injection, solutionIntravenous40 mg/2mL
SolutionIntravenous100 mg / 5 mL
SolutionIntravenous300 mg / 15 mL
SolutionIntravenous40 mg / 2 mL
SolutionIntravenous500 mg / 25 mL
Injection, solutionIntravenous1.5 MG/ML
Injection, solutionIntravenous20 MG/ML
SolutionIntravenous100 mg
SolutionIntravenous
SolutionIntravenous300 mg/15ml
SolutionIntravenous40 mg
Injection, solutionIntravenous300 mg/15ml
Injection, solutionIntravenous500 mg/25ml
Injection, solution, concentrateIntravenous100 mg/5ml
Injection, solution, concentrateIntravenous300 mg/15ml
Injection, solution, concentrateIntravenous500 mg/25ml
InjectionIntravenous4.3 mg/1mL
Injection, powder, for solutionIntravenous4.3 mg/1mL
SuspensionIntravenous43 mg
InjectionIntravenous4.3 MG/ML
SolutionIntravenous4.33 mg/mL
Injection, solutionIntravenous
Solution20 mg/1ml
Prices
Unit descriptionCostUnit
Irinotecan hcl 40 mg/2 ml inj138.07USD ml
Camptosar 20 mg/ml vial36.0USD ml
Irinotecan hcl 40 mg/2 ml vial22.2USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2202531No2005-05-032015-10-11Canada flag
CA2294031No2005-01-182018-07-27Canada flag
US6403569Yes2002-06-112020-10-28US flag
US6794370Yes2004-09-212020-11-01US flag
US8703181No2014-04-222025-05-02US flag
US8329213No2012-12-112025-05-02US flag
US8992970No2015-03-312025-05-02US flag
US8147867No2012-04-032028-08-29US flag
US9364473No2016-06-142033-06-12US flag
US9492442No2016-11-152033-06-12US flag
US9339497No2016-05-172033-06-12US flag
US9452162No2016-09-272033-06-12US flag
US9717724No2017-08-012033-06-12US flag
US9730891No2017-08-152025-05-02US flag
US9724303No2017-08-082025-05-02US flag
US9782349No2017-10-102025-05-02US flag
US10456360No2019-10-292036-10-15US flag
US10722508No2020-07-282025-05-02US flag
US10980795No2021-04-202033-06-12US flag
US10993914No2021-05-042036-10-15US flag
US11369597No2013-06-122033-06-12US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.107 mg/mLALOGPS
logP3.94ALOGPS
logP2.78Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.71Chemaxon
pKa (Strongest Basic)9.47Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area112.51 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity161.33 m3·mol-1Chemaxon
Polarizability65.27 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.969
Blood Brain Barrier+0.6284
Caco-2 permeable-0.6065
P-glycoprotein substrateSubstrate0.7861
P-glycoprotein inhibitor IInhibitor0.7092
P-glycoprotein inhibitor IINon-inhibitor0.5337
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8174
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.8564
CYP450 2C9 inhibitorNon-inhibitor0.7377
CYP450 2D6 inhibitorNon-inhibitor0.7779
CYP450 2C19 inhibitorNon-inhibitor0.6625
CYP450 3A4 inhibitorInhibitor0.8295
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5081
Ames testNon AMES toxic0.6977
CarcinogenicityNon-carcinogens0.8045
BiodegradationNot ready biodegradable0.9956
Rat acute toxicity2.7960 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9457
hERG inhibition (predictor II)Inhibitor0.5413
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0006-0091000000-b15811b1af58e71b3ec6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-0091000000-b15811b1af58e71b3ec6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0101190000-eed1a0e57a719811aa8e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0200090000-0f5dd3137025d3d4caef
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0300090000-aafa382124194f43cacd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-0000090000-daecfee7fe60f2556c7c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ku-0200090000-ed01f4bfb269ff1208b7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-2900140000-fb4dcf5970724d9c68fd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dr-2742490000-21a7209349ae32b57fac
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-263.1305005
predicted
DarkChem Lite v0.1.0
[M-H]-263.7708005
predicted
DarkChem Lite v0.1.0
[M-H]-234.96065
predicted
DeepCCS 1.0 (2019)
[M+H]+263.0239005
predicted
DarkChem Lite v0.1.0
[M+H]+265.0358005
predicted
DarkChem Lite v0.1.0
[M+H]+236.85606
predicted
DeepCCS 1.0 (2019)
[M+Na]+262.8313005
predicted
DarkChem Lite v0.1.0
[M+Na]+264.0576005
predicted
DarkChem Lite v0.1.0
[M+Na]+242.63426
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dna topoisomerase type ii (atp-hydrolyzing) activity
Specific Function
Releases the supercoiling and torsional tension of DNA introduced during duplication of mitochondrial DNA by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a single-str...
Gene Name
TOP1MT
Uniprot ID
Q969P6
Uniprot Name
DNA topoisomerase I, mitochondrial
Molecular Weight
69871.39 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Yoshikawa M, Ikegami Y, Hayasaka S, Ishii K, Ito A, Sano K, Suzuki T, Togawa T, Yoshida H, Soda H, Oka M, Kohno S, Sawada S, Ishikawa T, Tanabe S: Novel camptothecin analogues that circumvent ABCG2-associated drug resistance in human tumor cells. Int J Cancer. 2004 Jul 20;110(6):921-7. [Article]
  4. Yoshikawa M, Ikegami Y, Sano K, Yoshida H, Mitomo H, Sawada S, Ishikawa T: Transport of SN-38 by the wild type of human ABC transporter ABCG2 and its inhibition by quercetin, a natural flavonoid. J Exp Ther Oncol. 2004 Apr;4(1):25-35. [Article]
  5. Yang X, Hu Z, Chan SY, Chan E, Goh BC, Duan W, Zhou S: Novel agents that potentially inhibit irinotecan-induced diarrhea. Curr Med Chem. 2005;12(11):1343-58. [Article]
  6. Nakagawa H, Saito H, Ikegami Y, Aida-Hyugaji S, Sawada S, Ishikawa T: Molecular modeling of new camptothecin analogues to circumvent ABCG2-mediated drug resistance in cancer. Cancer Lett. 2006 Mar 8;234(1):81-9. Epub 2005 Nov 23. [Article]
  7. Ishikawa T, Ikegami Y, Sano K, Nakagawa H, Sawada S: Transport mechanism-based drug molecular design: novel camptothecin analogues to circumvent ABCG2-associated drug resistance of human tumor cells. Curr Pharm Des. 2006;12(3):313-25. [Article]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  9. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [Article]
  10. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Poly(a) rna binding
Specific Function
Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a singl...
Gene Name
TOP1
Uniprot ID
P11387
Uniprot Name
DNA topoisomerase 1
Molecular Weight
90725.19 Da
References
  1. Yoshikawa M, Ikegami Y, Hayasaka S, Ishii K, Ito A, Sano K, Suzuki T, Togawa T, Yoshida H, Soda H, Oka M, Kohno S, Sawada S, Ishikawa T, Tanabe S: Novel camptothecin analogues that circumvent ABCG2-associated drug resistance in human tumor cells. Int J Cancer. 2004 Jul 20;110(6):921-7. [Article]
  2. Yoshikawa M, Ikegami Y, Sano K, Yoshida H, Mitomo H, Sawada S, Ishikawa T: Transport of SN-38 by the wild type of human ABC transporter ABCG2 and its inhibition by quercetin, a natural flavonoid. J Exp Ther Oncol. 2004 Apr;4(1):25-35. [Article]
  3. Yang X, Hu Z, Chan SY, Chan E, Goh BC, Duan W, Zhou S: Novel agents that potentially inhibit irinotecan-induced diarrhea. Curr Med Chem. 2005;12(11):1343-58. [Article]
  4. Nakagawa H, Saito H, Ikegami Y, Aida-Hyugaji S, Sawada S, Ishikawa T: Molecular modeling of new camptothecin analogues to circumvent ABCG2-mediated drug resistance in cancer. Cancer Lett. 2006 Mar 8;234(1):81-9. Epub 2005 Nov 23. [Article]
  5. Ishikawa T, Ikegami Y, Sano K, Nakagawa H, Sawada S: Transport mechanism-based drug molecular design: novel camptothecin analogues to circumvent ABCG2-associated drug resistance of human tumor cells. Curr Pharm Des. 2006;12(3):313-25. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [Article]
  8. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [Article]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ramesh M, Ahlawat P, Srinivas NR: Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed Chromatogr. 2010 Jan;24(1):104-23. doi: 10.1002/bmc.1345. [Article]
  2. Kuhn JG: Pharmacology of irinotecan. Oncology (Williston Park). 1998 Aug;12(8 Suppl 6):39-42. [Article]
  3. Santos A, Zanetta S, Cresteil T, Deroussent A, Pein F, Raymond E, Vernillet L, Risse ML, Boige V, Gouyette A, Vassal G: Metabolism of irinotecan (CPT-11) by CYP3A4 and CYP3A5 in humans. Clin Cancer Res. 2000 May;6(5):2012-20. [Article]
  4. Zhou S, Yung Chan S, Cher Goh B, Chan E, Duan W, Huang M, McLeod HL: Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin Pharmacokinet. 2005;44(3):279-304. doi: 10.2165/00003088-200544030-00005. [Article]
  5. Smith NF, Figg WD, Sparreboom A: Pharmacogenetics of irinotecan metabolism and transport: an update. Toxicol In Vitro. 2006 Mar;20(2):163-75. doi: 10.1016/j.tiv.2005.06.045. Epub 2005 Nov 3. [Article]
  6. Flockhart Table of Drug Interactions [Link]
  7. FDA Approved Drug Products: CAMPTOSAR (irinotecan hydrochloride) injection, for intravenous use (January 2022) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Santos A, Zanetta S, Cresteil T, Deroussent A, Pein F, Raymond E, Vernillet L, Risse ML, Boige V, Gouyette A, Vassal G: Metabolism of irinotecan (CPT-11) by CYP3A4 and CYP3A5 in humans. Clin Cancer Res. 2000 May;6(5):2012-20. [Article]
  2. Smith NF, Figg WD, Sparreboom A: Pharmacogenetics of irinotecan metabolism and transport: an update. Toxicol In Vitro. 2006 Mar;20(2):163-75. doi: 10.1016/j.tiv.2005.06.045. Epub 2005 Nov 3. [Article]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Kuhn JG: Pharmacology of irinotecan. Oncology (Williston Park). 1998 Aug;12(8 Suppl 6):39-42. [Article]
  2. Smith NF, Figg WD, Sparreboom A: Pharmacogenetics of irinotecan metabolism and transport: an update. Toxicol In Vitro. 2006 Mar;20(2):163-75. doi: 10.1016/j.tiv.2005.06.045. Epub 2005 Nov 3. [Article]
  3. Innocenti F, Undevia SD, Iyer L, Chen PX, Das S, Kocherginsky M, Karrison T, Janisch L, Ramirez J, Rudin CM, Vokes EE, Ratain MJ: Genetic variants in the UDP-glucuronosyltransferase 1A1 gene predict the risk of severe neutropenia of irinotecan. J Clin Oncol. 2004 Apr 15;22(8):1382-8. Epub 2004 Mar 8. [Article]
  4. O'Dwyer PJ, Catalano RB: Uridine diphosphate glucuronosyltransferase (UGT) 1A1 and irinotecan: practical pharmacogenomics arrives in cancer therapy. J Clin Oncol. 2006 Oct 1;24(28):4534-8. [Article]
  5. FDA Approved Drug Products: CAMPTOSAR (irinotecan hydrochloride) injection, for intravenous use (January 2022) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Chabot GG: Clinical pharmacokinetics of irinotecan. Clin Pharmacokinet. 1997 Oct;33(4):245-59. [Article]
  2. Smith NF, Figg WD, Sparreboom A: Pharmacogenetics of irinotecan metabolism and transport: an update. Toxicol In Vitro. 2006 Mar;20(2):163-75. doi: 10.1016/j.tiv.2005.06.045. Epub 2005 Nov 3. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Methylumbelliferyl-acetate deacetylase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and ...

Components:
References
  1. Rothenberg ML: Irinotecan (CPT-11): recent developments and future directions--colorectal cancer and beyond. Oncologist. 2001;6(1):66-80. doi: 10.1634/theoncologist.6-1-66. [Article]
  2. Sanghani SP, Quinney SK, Fredenburg TB, Davis WI, Murry DJ, Bosron WF: Hydrolysis of irinotecan and its oxidative metabolites, 7-ethyl-10-[4-N-(5-aminopentanoic acid)-1-piperidino] carbonyloxycamptothecin and 7-ethyl-10-[4-(1-piperidino)-1-amino]-carbonyloxycamptothecin, by human carboxylesterases CES1A1, CES2, and a newly expressed carboxylesterase isoenzyme, CES3. Drug Metab Dispos. 2004 May;32(5):505-11. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: CAMPTOSAR (irinotecan hydrochloride) injection, for intravenous use (January 2022) [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Shnitsar V, Eckardt R, Gupta S, Grottker J, Muller GA, Koepsell H, Burckhardt G, Hagos Y: Expression of human organic cation transporter 3 in kidney carcinoma cell lines increases chemosensitivity to melphalan, irinotecan, and vincristine. Cancer Res. 2009 Feb 15;69(4):1494-501. doi: 10.1158/0008-5472.CAN-08-2483. Epub 2009 Feb 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Nozawa T, Minami H, Sugiura S, Tsuji A, Tamai I: Role of organic anion transporter OATP1B1 (OATP-C) in hepatic uptake of irinotecan and its active metabolite, 7-ethyl-10-hydroxycamptothecin: in vitro evidence and effect of single nucleotide polymorphisms. Drug Metab Dispos. 2005 Mar;33(3):434-9. Epub 2004 Dec 17. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Chen ZS, Furukawa T, Sumizawa T, Ono K, Ueda K, Seto K, Akiyama SI: ATP-Dependent efflux of CPT-11 and SN-38 by the multidrug resistance protein (MRP) and its inhibition by PAK-104P. Mol Pharmacol. 1999 May;55(5):921-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Wang X, Furukawa T, Nitanda T, Okamoto M, Sugimoto Y, Akiyama S, Baba M: Breast cancer resistance protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol Pharmacol. 2003 Jan;63(1):65-72. [Article]
  2. Maliepaard M, van Gastelen MA, Tohgo A, Hausheer FH, van Waardenburg RC, de Jong LA, Pluim D, Beijnen JH, Schellens JH: Circumvention of breast cancer resistance protein (BCRP)-mediated resistance to camptothecins in vitro using non-substrate drugs or the BCRP inhibitor GF120918. Clin Cancer Res. 2001 Apr;7(4):935-41. [Article]
  3. Smith NF, Figg WD, Sparreboom A: Pharmacogenetics of irinotecan metabolism and transport: an update. Toxicol In Vitro. 2006 Mar;20(2):163-75. doi: 10.1016/j.tiv.2005.06.045. Epub 2005 Nov 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Kroetz DL: Role for drug transporters beyond tumor resistance: hepatic functional imaging and genotyping of multidrug resistance transporters for the prediction of irinotecan toxicity. J Clin Oncol. 2006 Sep 10;24(26):4225-7. Epub 2006 Aug 8. [Article]
  2. Han JY, Lim HS, Park YH, Lee SY, Lee JS: Integrated pharmacogenetic prediction of irinotecan pharmacokinetics and toxicity in patients with advanced non-small cell lung cancer. Lung Cancer. 2009 Jan;63(1):115-20. doi: 10.1016/j.lungcan.2007.12.003. Epub 2008 Jan 24. [Article]
  3. Smith NF, Figg WD, Sparreboom A: Pharmacogenetics of irinotecan metabolism and transport: an update. Toxicol In Vitro. 2006 Mar;20(2):163-75. doi: 10.1016/j.tiv.2005.06.045. Epub 2005 Nov 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Kroetz DL: Role for drug transporters beyond tumor resistance: hepatic functional imaging and genotyping of multidrug resistance transporters for the prediction of irinotecan toxicity. J Clin Oncol. 2006 Sep 10;24(26):4225-7. Epub 2006 Aug 8. [Article]
  2. Han JY, Lim HS, Park YH, Lee SY, Lee JS: Integrated pharmacogenetic prediction of irinotecan pharmacokinetics and toxicity in patients with advanced non-small cell lung cancer. Lung Cancer. 2009 Jan;63(1):115-20. doi: 10.1016/j.lungcan.2007.12.003. Epub 2008 Jan 24. [Article]
  3. Smith NF, Figg WD, Sparreboom A: Pharmacogenetics of irinotecan metabolism and transport: an update. Toxicol In Vitro. 2006 Mar;20(2):163-75. doi: 10.1016/j.tiv.2005.06.045. Epub 2005 Nov 3. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 29, 2024 06:25