Guanidine

Identification

Summary

Guanidine is a strong organic base used to treat muscle weakness and fatigue associated with the myasthenic complications of Eaton-Lambert syndrome.

Generic Name
Guanidine
DrugBank Accession Number
DB00536
Background

A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 59.0705
Monoisotopic: 59.048347175
Chemical Formula
CH5N3
Synonyms
  • Aminomethanamidine
  • Gu
  • Guanidin
  • Guanidine
  • Imidourea
  • Iminourea

Pharmacology

Indication

For the reduction of the symptoms of muscle weakness and easy fatigability associated with the myasthenic syndrome of Eaton-Lambert. It is not indicated for treating myasthenia gravis.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofFatigue••••••••••••
Management ofMuscle weakness••••••••••••
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Guanidine apparently acts by enhancing the release of acetylcholine following a nerve impulse. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes.

Mechanism of action
TargetActionsOrganism
AAldehyde dehydrogenase, mitochondrial
inhibitor
Humans
URibonuclease pancreaticNot AvailableHumans
UDNANot AvailableHumans
UDisks large homolog 4Not AvailableHumans
ULysozymeNot AvailableEnterobacteria phage T4
UGuanidinoacetate N-methyltransferaseNot AvailableHumans
UArginaseNot AvailableBacillus caldovelox
Absorption

Rapidly absorbed and distributed

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not metabolized.

Route of elimination

Not Available

Half-life

7-8 hours

Clearance

Not Available

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

LD50 = 475 mg/kg (oral, rat). Can cause severe gastrointestinal symptoms (nausea, vomiting and diarrhea), bone marrow suppression, renal insufficiency and other hematologic abnormalities (anemia, leucopenia). Severe guanidine intoxication is characterized by nervous hyperirritability, fibrillary tremors and convulsive contractions of muscle, salivation, vomiting, diarrhea, hypoglycemia, and circulatory disturbances.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

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
AbemaciclibThe excretion of Abemaciclib can be decreased when combined with Guanidine.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Guanidine.
AcetylcholineThe risk or severity of adverse effects can be increased when Guanidine is combined with Acetylcholine.
AcyclovirThe excretion of Acyclovir can be decreased when combined with Guanidine.
AllopurinolThe excretion of Allopurinol can be decreased when combined with Guanidine.
Food Interactions
No interactions found.

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Guanidine hydrochloride3YQC9ZY4YB50-01-1PJJJBBJSCAKJQF-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Guanidine hydrochlorideTablet125 mg/1OralMerck Sharp & Dohme Corp.1939-10-02Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Guanidines
Direct Parent
Guanidines
Alternative Parents
Carboximidamides / Organopnictogen compounds / Imines / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Carboximidamide / Guanidine / Hydrocarbon derivative / Imine / Organopnictogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
one-carbon compound, guanidines, carboxamidine (CHEBI:42820) / a small molecule (CPD-13517)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
JU58VJ6Y3B
CAS number
113-00-8
InChI Key
ZRALSGWEFCBTJO-UHFFFAOYSA-N
InChI
InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)
IUPAC Name
guanidine
SMILES
NC(N)=N

References

Synthesis Reference

Helmut Hoffmann, Carlhans Suling, "Process for the production of guanidine salts of aliphatic mercaptosulphonic acids." U.S. Patent US3956368, issued November, 1954.

US3956368
General References
Not Available
Human Metabolome Database
HMDB0001842
PubChem Compound
3520
PubChem Substance
46507543
ChemSpider
3400
BindingDB
50420178
RxNav
50675
ChEBI
42820
ChEMBL
CHEMBL821
ZINC
ZINC000008101126
PharmGKB
PA164781028
PDBe Ligand
GAI
Drugs.com
Drugs.com Drug Page
Wikipedia
Guanidine
PDB Entries
1jxm / 1kp2 / 1kp3 / 1o01 / 1o02 / 1o04 / 1pxv / 1rbw / 1t8a / 1umj
show 91 more
MSDS
Download (72.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Schering corp
Packagers
  • Schering Corp.
Dosage Forms
FormRouteStrength
TabletOral125 mg/1
Prices
Unit descriptionCostUnit
Guanidine hcl 125 mg tablet0.25USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)50 °CPhysProp
water solubility1840 mg/L (at 20 °C)GREENWALD,I (1926)
logP-0.6Not Available
pKa12.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility11.5 mg/mLALOGPS
logP-1.9ALOGPS
logP-1.2Chemaxon
logS-0.71ALOGPS
pKa (Strongest Basic)12.55Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area75.89 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity25.86 m3·mol-1Chemaxon
Polarizability5.57 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9378
Blood Brain Barrier+0.8502
Caco-2 permeable-0.7527
P-glycoprotein substrateNon-substrate0.8033
P-glycoprotein inhibitor INon-inhibitor0.977
P-glycoprotein inhibitor IINon-inhibitor0.932
Renal organic cation transporterNon-inhibitor0.7825
CYP450 2C9 substrateNon-substrate0.8402
CYP450 2D6 substrateNon-substrate0.6619
CYP450 3A4 substrateNon-substrate0.8447
CYP450 1A2 substrateNon-inhibitor0.9843
CYP450 2C9 inhibitorNon-inhibitor0.9588
CYP450 2D6 inhibitorNon-inhibitor0.9695
CYP450 2C19 inhibitorNon-inhibitor0.9772
CYP450 3A4 inhibitorNon-inhibitor0.9763
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9789
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.7148
BiodegradationNot ready biodegradable0.7652
Rat acute toxicity1.9367 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9733
hERG inhibition (predictor II)Non-inhibitor0.9798
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.28 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-00dj-0920000000-b2c19a9125b059b573fd
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-9000000000-6e00e9be1957670e422b
GC-MS Spectrum - GC-MSGC-MSsplash10-00dj-0920000000-b2c19a9125b059b573fd
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-03di-9000000000-4df2949d18a754b6aa19
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-18b92fabd8878a75412f
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-6675e99565dbe0735311
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-e5474b0a61d04092d9e1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000000000-82e5c63dbf3b095dcf4c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-9000000000-ecb994e3f1ef4ed2643a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-a61d096f1b417ab690b0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-52df4b8cfdb6e2805831
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-efa82b6336aa4b4e9385
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-94.3984245
predicted
DarkChem Lite v0.1.0
[M-H]-94.4213245
predicted
DarkChem Lite v0.1.0
[M-H]-94.3340245
predicted
DarkChem Lite v0.1.0
[M-H]-114.839325
predicted
DeepCCS 1.0 (2019)
[M+H]+95.2227245
predicted
DarkChem Lite v0.1.0
[M+H]+95.5827245
predicted
DarkChem Lite v0.1.0
[M+H]+95.6810245
predicted
DarkChem Lite v0.1.0
[M+H]+116.715576
predicted
DeepCCS 1.0 (2019)
[M+Na]+94.7697245
predicted
DarkChem Lite v0.1.0
[M+Na]+94.8878245
predicted
DarkChem Lite v0.1.0
[M+Na]+94.8329245
predicted
DarkChem Lite v0.1.0
[M+Na]+124.07245
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Literature at this time did not specifically point to the mitochondrial aldehyde dehydrogenase, but rather, is more directed to aldehyde dehydrogenase in general.
General Function
Electron carrier activity
Specific Function
Not Available
Gene Name
ALDH2
Uniprot ID
P05091
Uniprot Name
Aldehyde dehydrogenase, mitochondrial
Molecular Weight
56380.93 Da
References
  1. Kikonyogo A, Pietruszko R: Cimetidine and other H2-receptor antagonists as inhibitors of human E3 aldehyde dehydrogenase. Mol Pharmacol. 1997 Aug;52(2):267-71. doi: 10.1124/mol.52.2.267. [Article]
  2. Kopczynski Z, Dryl T, Chmiel J: Studies on the effects of low-molecular uraemic toxins on the activity of 3-phospho-D-glycerol aldehyde dehydrogenase (E.C.1.2.1.12) in human erythrocytes. Acta Physiol Pol. 1984 Sep-Dec;35(5-6):539-45. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ribonuclease a activity
Specific Function
Endonuclease that catalyzes the cleavage of RNA on the 3' side of pyrimidine nucleotides. Acts on single-stranded and double-stranded RNA.
Gene Name
RNASE1
Uniprot ID
P07998
Uniprot Name
Ribonuclease pancreatic
Molecular Weight
17644.125 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. Dodge RW, Laity JH, Rothwarf DM, Shimotakahara S, Scheraga HA: Folding pathway of guanidine-denatured disulfide-intact wild-type and mutant bovine pancreatic ribonuclease A. J Protein Chem. 1994 May;13(4):409-21. [Article]
  4. Nasiri H, Forouzandeh M, Rasaee MJ, Rahbarizadeh F: Modified salting-out method: high-yield, high-quality genomic DNA extraction from whole blood using laundry detergent. J Clin Lab Anal. 2005;19(6):229-32. [Article]
  5. Loh SN, Rohl CA, Kiefhaber T, Baldwin RL: A general two-process model describes the hydrogen exchange behavior of RNase A in unfolding conditions. Proc Natl Acad Sci U S A. 1996 Mar 5;93(5):1982-7. [Article]
  6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Nucleotide
Organism
Humans
Pharmacological action
Unknown
Curator comments
Literature suggests guanidine complexes bind to DNA.
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
References
  1. Matic J, Supljika F, Tandaric T, Duksi M, Piotrowski P, Vianello R, Brozovic A, Piantanida I, Schmuck C, Stojkovic MR: DNA/RNA recognition controlled by the glycine linker and the guanidine moiety of phenanthridine peptides. Int J Biol Macromol. 2019 Aug 1;134:422-434. doi: 10.1016/j.ijbiomac.2019.05.063. Epub 2019 May 10. [Article]
  2. Legin AA, Jakupec MA, Bokach NA, Tyan MR, Kukushkin VY, Keppler BK: Guanidine platinum(II) complexes: synthesis, in vitro antitumor activity, and DNA interactions. J Inorg Biochem. 2014 Apr;133:33-9. doi: 10.1016/j.jinorgbio.2013.12.007. Epub 2013 Dec 22. [Article]
  3. Shibata T, Murakami E, Nakatani K: 1,3-Di(quinolin-2-yl)guanidine binds to GGCCCC hexanucleotide repeat DNA in C9ORF72. Bioorg Med Chem Lett. 2018 Aug 1;28(14):2364-2368. doi: 10.1016/j.bmcl.2018.06.032. Epub 2018 Jun 18. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Scaffold protein binding
Specific Function
Interacts with the cytoplasmic tail of NMDA receptor subunits and shaker-type potassium channels. Required for synaptic plasticity associated with NMDA receptor signaling. Overexpression or depleti...
Gene Name
DLG4
Uniprot ID
P78352
Uniprot Name
Disks large homolog 4
Molecular Weight
80494.615 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. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Enterobacteria phage T4
Pharmacological action
Unknown
General Function
Lysozyme activity
Specific Function
Endolysin with lysozyme activity that degrades host peptidoglycans and participates with the holin and spanin proteins in the sequential events which lead to the programmed host cell lysis releasin...
Gene Name
E
Uniprot ID
P00720
Uniprot Name
Endolysin
Molecular Weight
18691.385 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. Junn HJ, Youn J, Suh KH, Lee SS: Cloning and expression of Klebsiella phage K11 lysozyme gene. Protein Expr Purif. 2005 Jul;42(1):78-84. Epub 2005 Apr 19. [Article]
  4. Garcia-Orozco KD, Lopez-Zavala AA, Puentes-Camacho D, Calderon-de-la-Barca AM, Sotelo-Mundo RR: Recombinant bacterial expression of the lysozyme from the tobacco-hornworm Manduca sexta with activity at low temperatures. Biotechnol Lett. 2005 Aug;27(15):1075-80. [Article]
  5. Shiraki K, Kudou M, Sakamoto R, Yanagihara I, Takagi M: Amino Acid esters prevent thermal inactivation and aggregation of lysozyme. Biotechnol Prog. 2005 Mar-Apr;21(2):640-3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Methyltransferase activity
Specific Function
Not Available
Gene Name
GAMT
Uniprot ID
Q14353
Uniprot Name
Guanidinoacetate N-methyltransferase
Molecular Weight
26317.925 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. Komoto J, Yamada T, Takata Y, Konishi K, Ogawa H, Gomi T, Fujioka M, Takusagawa F: Catalytic mechanism of guanidinoacetate methyltransferase: crystal structures of guanidinoacetate methyltransferase ternary complexes. Biochemistry. 2004 Nov 16;43(45):14385-94. [Article]
  4. Karelin AA, Mardashev SR: [The stimulating effect of cyclic AMP, glucagon and insulin on guanidine acetate-N-methyltransferase activity in rat liver and pancreas]. Biokhimiia. 1976 Feb;41(2):316-23. [Article]
  5. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Bacillus caldovelox
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Controls arginine catabolism.
Gene Name
rocF
Uniprot ID
P53608
Uniprot Name
Arginase
Molecular Weight
32432.98 Da

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [Article]
  2. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [Article]
  3. Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [Article]
  4. Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [Article]
  5. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Zhang L, Dresser MJ, Chun JK, Babbitt PC, Giacomini KM: Cloning and functional characterization of a rat renal organic cation transporter isoform (rOCT1A). J Biol Chem. 1997 Jun 27;272(26):16548-54. [Article]
  2. Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [Article]
  3. Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Wu X, Huang W, Ganapathy ME, Wang H, Kekuda R, Conway SJ, Leibach FH, Ganapathy V: Structure, function, and regional distribution of the organic cation transporter OCT3 in the kidney. Am J Physiol Renal Physiol. 2000 Sep;279(3):F449-58. [Article]
  2. Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [Article]
  2. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
  3. Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [Article]
  4. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [Article]
  2. Winter TN, Elmquist WF, Fairbanks CA: OCT2 and MATE1 provide bidirectional agmatine transport. Mol Pharm. 2011 Feb 7;8(1):133-42. doi: 10.1021/mp100180a. Epub 2010 Dec 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Drug transmembrane transporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name
SLC47A2
Uniprot ID
Q86VL8
Uniprot Name
Multidrug and toxin extrusion protein 2
Molecular Weight
65083.915 Da
References
  1. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K: Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71. doi: 10.1016/j.bcp.2007.04.010. Epub 2007 Apr 13. [Article]
  2. Loncar J, Popovic M, Krznar P, Zaja R, Smital T: The first characterization of multidrug and toxin extrusion (MATE/SLC47) proteins in zebrafish (Danio rerio). Sci Rep. 2016 Jun 30;6:28937. doi: 10.1038/srep28937. [Article]
  3. Yonezawa A, Inui K: Importance of the multidrug and toxin extrusion MATE/SLC47A family to pharmacokinetics, pharmacodynamics/toxicodynamics and pharmacogenomics. Br J Pharmacol. 2011 Dec;164(7):1817-25. doi: 10.1111/j.1476-5381.2011.01394.x. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:33