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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
Structure for Sulfadoxine (DB01299)
- 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
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 ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for prophylaxis of Malaria caused by plasmodium falciparum Combination Product in combination with: Pyrimethamine (DB00205) •••••••••••• ••••••••••• ••••••••••• •••• •• •••••••••• •• •••••••••••• ••••••••••• ••••••• •• ••••••••• Used in combination to treat Plasmodium infections Combination Product in combination with: Pyrimethamine (DB00205) •••••••••••• •••••• Used in combination to treat Acute, uncomplicated malaria caused by plasmodium falciparum Combination Product in combination with: Pyrimethamine (DB00205) •••••••••••• ••••••••••• •••••••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism ADihydropteroate synthetase Not Available Plasmodium falciparum AAmine oxidase [flavin-containing] B inhibitorHumans ADihydropteroate synthase binderEscherichia coli (strain K12) UBifunctional dihydrofolate reductase-thymidylate synthase inhibitorPlasmodium 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Sulfadoxine. Acetohexamide The therapeutic efficacy of Acetohexamide can be increased when used in combination with Sulfadoxine. Acetophenazine The risk or severity of QTc prolongation can be increased when Sulfadoxine is combined with Acetophenazine. Albiglutide The therapeutic efficacy of Albiglutide can be increased when used in combination with Sulfadoxine. Alimemazine The 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 regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Fansidar Sulfadoxine (500 mg/1) + Pyrimethamine (25 mg/1) Tablet Oral Genentech, Inc. 1981-10-28 2012-04-18 US 
Fansidar Tablets Sulfadoxine (500 mg) + Pyrimethamine (25 mg) Tablet Oral Hoffmann La Roche 1989-12-31 2000-07-27 Canada 
SULFADOXINA 500 MG + PIRIMETAMINA 25 MG TABLETAS Sulfadoxine (500 mg) + Pyrimethamine (25 mg) Tablet Oral COLOMPACK S.A. 2006-11-10 Not applicable Colombia 
พลาสโมดิน Sulfadoxine (500 MG) + Pyrimethamine (25 MG) Tablet Oral บริษัท วี.เอส.ฟาร์ม่า (1971) จำกัด จำกัด 2005-08-06 2019-10-21 Thailand 
ฟอเรส เม็ด Sulfadoxine (500 MG) + Pyrimethamine (25 MG) Tablet Oral บริษัท ไบร์วู๊ดฟาร์มาซูติคอล จำกัด 1986-12-11 2019-10-21 Thailand
Categories
- ATC Codes
- P01BF09 — Artesunate, sulfadoxine and pyrimethamine
- P01BF — Artemisinin and derivatives, combinations
- P01B — ANTIMALARIALS
- P01 — ANTIPROTOZOALS
- P — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antimalarials
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiprotozoals
- Benzene Derivatives
- Benzenesulfonamides
- Genito Urinary System and Sex Hormones
- Gynecological Antiinfectives and Antiseptics
- Long-Acting Antibacterial Sulfonamides
- Sulfanilamides
- Sulfonamides
- Sulfones
- Sulfur Compounds
- 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
- FDA Approved Drug Products: FANSIDAR (sulfadoxine and pyrimethamine) tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0015413
- KEGG Drug
- D00580
- KEGG Compound
- C07630
- PubChem Compound
- 17134
- PubChem Substance
- 46507915
- ChemSpider
- 16218
- BindingDB
- 50238671
- 10173
- ChEBI
- 9329
- ChEMBL
- CHEMBL1539
- ZINC
- ZINC000000002094
- Therapeutic Targets Database
- DAP000638
- PharmGKB
- PA451540
- Wikipedia
- Sulfadoxine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Malaria 1 somestatus stop reason just information to hide Not Available Completed Not Available Malaria caused by Plasmodium falciparum 1 somestatus stop reason just information to hide Not Available Completed Educational/Counseling/Training Human Immunodeficiency Virus (HIV) Infections / Malaria caused by Plasmodium falciparum 1 somestatus stop reason just information to hide Not Available Completed Health Services Research Malaria 1 somestatus stop reason just information to hide Not Available Completed Other Controlled Human Malaria Infection (CHMI) / Gametocytes / Malaria caused by Plasmodium falciparum / Transmission 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- F Hoffmann La Roche Ltd.
- F Hoffmann-La Roche Ltd.
- Dosage Forms
Form Route Strength Tablet Oral Suspension Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 190-194 °C PhysProp logP 0.70 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.296 mg/mL ALOGPS logP 0.72 ALOGPS logP 0.58 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 6.12 Chemaxon pKa (Strongest Basic) 3.44 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 116.43 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 77.81 m3·mol-1 Chemaxon Polarizability 30.01 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9602 Blood Brain Barrier - 0.5345 Caco-2 permeable - 0.59 P-glycoprotein substrate Non-substrate 0.8126 P-glycoprotein inhibitor I Non-inhibitor 0.832 P-glycoprotein inhibitor II Non-inhibitor 0.8892 Renal organic cation transporter Non-inhibitor 0.9164 CYP450 2C9 substrate Non-substrate 0.693 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6464 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8703 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6052 Ames test Non AMES toxic 0.6456 Carcinogenicity Non-carcinogens 0.8265 Biodegradation Not ready biodegradable 0.996 Rat acute toxicity 1.8756 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9907 hERG inhibition (predictor II) Non-inhibitor 0.7221
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 179.2580003 predictedDarkChem Lite v0.1.0 [M-H]- 182.2663003 predictedDarkChem Lite v0.1.0 [M-H]- 164.9059 predictedDeepCCS 1.0 (2019) [M+H]+ 179.9041003 predictedDarkChem Lite v0.1.0 [M+H]+ 182.6784003 predictedDarkChem Lite v0.1.0 [M+H]+ 167.26392 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.3216003 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.5369003 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.35707 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Plasmodium falciparum
- Pharmacological action
- Yes
- General Function
- Not Available
- Specific Function
- dihydropteroate synthase activity
- Gene Name
- Not Available
- Uniprot ID
- Q27738
- Uniprot Name
- Dihydropteroate synthetase
- Molecular Weight
- 43370.845 Da
References
- 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]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the oxidative deamination of primary and some secondary amines such as neurotransmitters, and exogenous amines including the tertiary amine, neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), with concomitant reduction of oxygen to hydrogen peroxide and participates in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924). Preferentially degrades benzylamine and phenylethylamine (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924)
- Specific Function
- aliphatic amine oxidase activity
- Gene Name
- MAOB
- Uniprot ID
- P27338
- Uniprot Name
- Amine oxidase [flavin-containing] B
- Molecular Weight
- 58762.475 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate (H2Pte), the immediate precursor of folate derivatives.
- Specific Function
- dihydropteroate synthase activity
- Gene Name
- folP
- Uniprot ID
- P0AC13
- Uniprot Name
- Dihydropteroate synthase
- Molecular Weight
- 30614.855 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Plasmodium falciparum (isolate K1 / Thailand)
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General 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 for the conversion of dUMP to dTMP.
- Specific Function
- dihydrofolate reductase activity
- Gene Name
- Not Available
- Uniprot ID
- P13922
- Uniprot Name
- Bifunctional dihydrofolate reductase-thymidylate synthase
- Molecular Weight
- 71816.775 Da
References
- 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]
- 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]
- 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 August 26, 2024 19:24