NAV

Sulfadoxine

Identification

Summary

Sulfadoxine is a long acting sulfonamide used for the treatment or prevention of malaria.

Generic Name
Sulfadoxine
DrugBank Accession Number
DB01299
Background

A long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections.

Type
Small Molecule
Groups
Approved, Investigational
Structure
3D
Similar Structures
Weight
Average: 310.329
Monoisotopic: 310.073575646
Chemical Formula
C12H14N4O4S
Synonyms
  • 4-Sulfanilamido-5,6-dimethoxypyrimidine
  • Sulfadoxina
  • Sulfadoxine
  • Sulfadoxinum
  • Sulforthomidine
  • Sulphadoxine
  • Sulphormethoxine
External IDs
  • J21.373J
  • RO 4-4393
  • RO-4-4393
  • RO-44393
  • WR-4073
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Sulfadoxine is used in combination with pyrimethamine for the treatment or prevention of malaria. It can also be used to treat various infections in livestock as well. Sulfadoxine and pyrimethamine is indicated for the treatment of Plasmodium falciparum malaria in those patients in whom chloroquine resistance is suspected.

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
Used in combination for prophylaxis ofMalaria caused by plasmodium falciparumCombination Product in combination with: Pyrimethamine (DB00205)••••••••••••••••••••••• ••••••••••• •••• •• •••••••••• •• •••••••••••• ••••••••••• ••••••• •• •••••••••
Used in combination to treatPlasmodium infectionsCombination Product in combination with: Pyrimethamine (DB00205)••••••••••••••••••
Used in combination to treatAcute, uncomplicated malaria caused by plasmodium falciparumCombination Product in combination with: Pyrimethamine (DB00205)••••••••••••••••••••••• ••••••••••
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

Sulfadoxine helps inhibit the enzyme dihydropteroate synthetase which is an enzyme necessary in the conversion of PABA to folic acid. As folic acid is vital to the synthesis, repair, and methylation of DNA which is vital to cell growth in Plasmodium falciparum. With this vital nutrient lacking, the parasite has difficulty in reproducing.

Mechanism of action

Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.

TargetActionsOrganism
ADihydropteroate synthetaseNot AvailablePlasmodium falciparum
UBifunctional dihydrofolate reductase-thymidylate synthase
inhibitor
Plasmodium falciparum (isolate K1 / Thailand)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

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

Not Available

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
Integrate drug-drug
interactions in your software
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Sulfadoxine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfadoxine.
AcetophenazineThe risk or severity of QTc prolongation can be increased when Sulfadoxine is combined with Acetophenazine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfadoxine.
AlimemazineThe risk or severity of QTc prolongation can be increased when Sulfadoxine is combined with Alimemazine.
Food Interactions
  • Take after a meal. Taking sulfadoxine with food, may reduce gastrointestinal irritation.
  • Take with a full glass of water.

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
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FansidarSulfadoxine (500 mg/1) + Pyrimethamine (25 mg/1)TabletOralGenentech, Inc.1981-10-282012-04-18US flag
Fansidar TabletsSulfadoxine (500 mg) + Pyrimethamine (25 mg)TabletOralHoffmann La Roche1989-12-312000-07-27Canada flag
SULFADOXINA 500 MG + PIRIMETAMINA 25 MG TABLETASSulfadoxine (500 mg) + Pyrimethamine (25 mg)TabletOralCOLOMPACK S.A.2006-11-10Not applicableColombia flag
พลาสโมดินSulfadoxine (500 MG) + Pyrimethamine (25 MG)TabletOralบริษัท วี.เอส.ฟาร์ม่า (1971) จำกัด จำกัด2005-08-062019-10-21Thailand flag
ฟอเรส เม็ดSulfadoxine (500 MG) + Pyrimethamine (25 MG)TabletOralบริษัท ไบร์วู๊ดฟาร์มาซูติคอล จำกัด1986-12-112019-10-21Thailand flag

Categories

ATC Codes
P01BF09 — Artesunate, sulfadoxine and pyrimethamineG01AE10 — Combinations of sulfonamides
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Aminobenzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Aniline and substituted anilines / Alkyl aryl ethers / Pyrimidines and pyrimidine derivatives / Organosulfonamides / Imidolactams / Heteroaromatic compounds / Aminosulfonyl compounds / Azacyclic compounds / Primary amines
show 3 more
Substituents
Alkyl aryl ether / Amine / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonyl group / Ether / Heteroaromatic compound
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfonamide, pyrimidines (CHEBI:9329)
Affected organisms
Not Available

Chemical Identifiers

UNII
88463U4SM5
CAS number
2447-57-6
InChI Key
PJSFRIWCGOHTNF-UHFFFAOYSA-N
InChI
InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
IUPAC Name
4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
SMILES
COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC

References

General References
  1. FDA Approved Drug Products: FANSIDAR (sulfadoxine and pyrimethamine) tablets [Link]
Human Metabolome Database
HMDB0015413
KEGG Drug
D00580
KEGG Compound
C07630
PubChem Compound
17134
PubChem Substance
46507915
ChemSpider
16218
BindingDB
50238671
RxNav
10173
ChEBI
9329
ChEMBL
CHEMBL1539
ZINC
ZINC000000002094
Therapeutic Targets Database
DAP000638
PharmGKB
PA451540
Wikipedia
Sulfadoxine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionMalaria3
4CompletedPreventionAnemia in Children / Malaria caused by Plasmodium falciparum1
4CompletedPreventionAnemia / Malaria2
4CompletedPreventionMalaria3
4CompletedPreventionMalaria caused by Plasmodium falciparum1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • F Hoffmann La Roche Ltd.
  • F Hoffmann-La Roche Ltd.
Dosage Forms
FormRouteStrength
TabletOral
SuspensionOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)190-194 °CPhysProp
logP0.70SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.296 mg/mLALOGPS
logP0.72ALOGPS
logP0.58Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)6.12Chemaxon
pKa (Strongest Basic)3.44Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area116.43 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity77.81 m3·mol-1Chemaxon
Polarizability30.01 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9602
Blood Brain Barrier-0.5345
Caco-2 permeable-0.59
P-glycoprotein substrateNon-substrate0.8126
P-glycoprotein inhibitor INon-inhibitor0.832
P-glycoprotein inhibitor IINon-inhibitor0.8892
Renal organic cation transporterNon-inhibitor0.9164
CYP450 2C9 substrateNon-substrate0.693
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6464
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8703
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6052
Ames testNon AMES toxic0.6456
CarcinogenicityNon-carcinogens0.8265
BiodegradationNot ready biodegradable0.996
Rat acute toxicity1.8756 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9907
hERG inhibition (predictor II)Non-inhibitor0.7221
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0pb9-4960000000-7bae9693017c80170870
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a4i-3910000000-fbde0b31ef009afef44d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-2901000000-8862dd6e93b57f07349b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-3910000000-fbde0b31ef009afef44d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0109000000-94bbee118c5df770fa31
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0209000000-b8e7fcb03acddae66a08
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0902000000-5d845ef89f0f1851873b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1932000000-d4275fcab5f096e19b82
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-2900000000-eb9e632134e5b76e4376
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-6930000000-3800295ee8f423e89ae4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.2580003
predicted
DarkChem Lite v0.1.0
[M-H]-182.2663003
predicted
DarkChem Lite v0.1.0
[M-H]-164.9059
predicted
DeepCCS 1.0 (2019)
[M+H]+179.9041003
predicted
DarkChem Lite v0.1.0
[M+H]+182.6784003
predicted
DarkChem Lite v0.1.0
[M+H]+167.26392
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.3216003
predicted
DarkChem Lite v0.1.0
[M+Na]+182.5369003
predicted
DarkChem Lite v0.1.0
[M+Na]+173.35707
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
Details1. Dihydropteroate synthetase
Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
Yes
General Function
Dihydropteroate synthase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q27738
Uniprot Name
Dihydropteroate synthetase
Molecular Weight
43370.845 Da
References
  1. Raman J, Little F, Roper C, Kleinschmidt I, Cassam Y, Maharaj R, Barnes KI: Five years of large-scale dhfr and dhps mutation surveillance following the phased implementation of artesunate plus sulfadoxine-pyrimethamine in Maputo Province, Southern Mozambique. Am J Trop Med Hyg. 2010 May;82(5):788-94. doi: 10.4269/ajtmh.2010.09-0401. [Article]
  2. Zhang GQ, Guan YY, Zheng B, Wu S, Tang LH: Molecular assessment of Plasmodium falciparum resistance to antimalarial drugs in China. Trop Med Int Health. 2009 Oct;14(10):1266-71. doi: 10.1111/j.1365-3156.2009.02342.x. [Article]
  3. Lumb V, Das MK, Mittra P, Ahmed A, Kumar M, Kaur P, Dash AP, Singh SS, Sharma YD: Emergence of an unusual sulfadoxine-pyrimethamine resistance pattern and a novel K540N mutation in dihydropteroate synthetase in Plasmodium falciparum isolates obtained from Car Nicobar Island, India, after the 2004 Tsunami. J Infect Dis. 2009 Apr 1;199(7):1064-73. doi: 10.1086/597206. [Article]
Details2. Bifunctional dihydrofolate reductase-thymidylate synthase
Kind
Protein
Organism
Plasmodium falciparum (isolate K1 / Thailand)
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Thymidylate synthase activity
Specific Function
Bifunctional enzyme. Involved in de novo dTMP biosynthesis. Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, DNA precursor synthesis, and f...
Gene Name
Not Available
Uniprot ID
P13922
Uniprot Name
Bifunctional dihydrofolate reductase-thymidylate synthase
Molecular Weight
71816.775 Da
References
  1. Eriksen J, Mwankusye S, Mduma S, Kitua A, Swedberg G, Tomson G, Gustafsson LL, Warsame M: Patterns of resistance and DHFR/DHPS genotypes of Plasmodium falciparum in rural Tanzania prior to the adoption of sulfadoxine-pyrimethamine as first-line treatment. Trans R Soc Trop Med Hyg. 2004 Jun;98(6):347-53. [Article]
  2. Happi CT, Gbotosho GO, Folarin OA, Akinboye DO, Yusuf BO, Ebong OO, Sowunmi A, Kyle DE, Milhous W, Wirth DF, Oduola AM: Polymorphisms in Plasmodium falciparum dhfr and dhps genes and age related in vivo sulfadoxine-pyrimethamine resistance in malaria-infected patients from Nigeria. Acta Trop. 2005 Sep;95(3):183-93. [Article]
  3. Fernandes NE, Cravo P, do Rosario VE: [Sulfadoxine-pyrimethamine resistance in Maputo, Mozambique: presence of mutations in the dhfr and dhps genes of Plasmodium falciparum]. Rev Soc Bras Med Trop. 2007 Jul-Aug;40(4):447-50. [Article]

Drug created at June 30, 2007 14:21 / Updated at October 02, 2021 21:28