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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:45
Primary Accession Number DB01015
Secondary Accession Number
  • APRD00076
Name Sulfamethoxazole
Drug Type
  • Approved
  • Small Molecule
Description A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)
Synonyms Not Available
Brand Names
  1. Apo-Sulfamethoxazole
  2. Azo Gantanol
  3. Azo-Gantanol
  4. Bactrimel
  5. Gamazole
  6. Gantanol
  7. Gantanol-DS
  8. Metoxal
  9. Radonil
  10. SIM
  11. Septran
  12. Simsinomin
  13. Sinomin
  14. Sulfamethalazole
  15. Sulfamethoxazol
  16. Sulfamethoxizole
  17. Sulfamethylisoxazole
  18. Sulfisomezole
  19. Sulpha-Methoxizole
  20. Sulphamethalazole
  21. Sulphamethoxazol
  22. Sulphamethoxazole
  23. Sulphamethoxazole BP 98
  24. Sulphamethylisoxazole
  25. Sulphisomezole
  26. Trib
  27. Urobak
Brand Mixtures
  1. Apo Sulfatrim DS Tab (Sulfamethoxazole + Trimethoprim)
  2. Apo Sulfatrim Pediatric (Sulfamethoxazole + Trimethoprim)
  3. Apo Sulfatrim Tab (Sulfamethoxazole + Trimethoprim)
  4. Bactrim DS Roche Tab (Sulfamethoxazole + Trimethoprim)
  5. Bactrim Roche Inj (Sulfamethoxazole + Trimethoprim)
  6. Bactrim Roche Suspension Paediatric (Sulfamethoxazole + Trimethoprim)
  7. Bactrim Roche Tab (Sulfamethoxazole + Trimethoprim)
  8. Novo-Trimel DS Tab (Sulfamethoxazole + Trimethoprim)
  9. Novo-Trimel Oral Sus (Sulfamethoxazole + Trimethoprim)
  10. Novo-Trimel Tab (Sulfamethoxazole + Trimethoprim)
  11. Protrin DF Tab (Sulfamethoxazole + Trimethoprim)
  12. Protrin Tab (Sulfamethoxazole + Trimethoprim)
  13. Riva-Sep DS (Sulfamethoxazole + Trimethoprim)
  14. Roubac Tab 160/800 (Sulfamethoxazole + Trimethoprim)
  15. Roubac Tab 80/400 (Sulfamethoxazole + Trimethoprim)
  16. Septra (Sulfamethoxazole + Trimethoprim)
  17. Septra DS Tablets (Sulfamethoxazole + Trimethoprim)
  18. Septra Injection (Sulfamethoxazole + Trimethoprim)
  19. Septra Pediatric Suspension (Sulfamethoxazole + Trimethoprim)
  20. Sulfamethoxazole and Trimethoprim Tablets (Sulfamethoxazole + Trimethoprim)
Chemical IUPAC Name 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
Chemical Formula C10H11N3O3S
Chemical Structure Structure
CAS Registry Number 723-46-6
InChI Identifier InChI=1/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)/f/h13H
InChI Key JLKIGFTWXXRPMT-NDKGDYFDCV
KEGG Drug D00447 Link Image
KEGG Compound C07315 Link Image
PubChem Compound 5329 Link Image
PubChem Substance 156228 Link Image
ChEBI ID 9332 Link Image
PharmGKB ID PA451544 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00421480 Link Image
RxList Link http://www.rxlist.com/cgi/generic3/gantanol.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Sulfamethoxazole Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Kano et al., U.S. Pat. 2,888,455 (1959)
Average Molecular Weight 253.2780
Monoisotopic Molecular Weight 253.0521
State Solid
Melting Point 167 oC
Experimental Water Solubility 610 mg/L Source: PhysProp
Predicted Water Solubility 4.59e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.7 Source: PhysProp
Predicted LogP 0.79 Calculated using ALOGPS
Experimental LogS -2.62 [ADME Research, USCD]
Predicted LogS -2.74 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1W7K Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
Canonical SMILES CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
Drug Category
  • Anti-Infective Agents
  • Anti-Infectives
  • Sulfonamides
ATC Codes
AHFS Codes
  • 08:12.20
Indication For the treatment of bronchitis, prostatitis and urinary tract infections.
Pharmacology Sulfamethoxazole is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA). Sulfamethoxazole is normally given in combination with Trimethoprim (a dihydrofolate reductase inhibitor). Studies have shown that bacterial resistance develops more slowly with the combination of the two drugs than with either Trimethoprim or Sulfamethoxazole alone.
Mechanism of Action Sulfonamides inhibit bacterial dihydrofolate synthetase, causing interference in the conversion of p-aminobenzoic acid (PABA) into folic acid. As folic acid is a coenzyme responsible for the transport of one-carbon fragments from one molecule to another, it is an essential component of bacterial development. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, the immediate next step, and therefore act synergistically with the sulfonamides.
Absorption Rapidly absorbed following oral administration.
Toxicity Not Available
Protein Binding 70%
Biotransformation Hepatic. The metabolism of sulfamethoxazole occurs predominately by N4-acetylation, although the glucuronide conjugate has been identified.
Half Life 10 hours
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions
  • Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
  • Take on empty stomach: 1 hour before or 2 hours after meals.
  • Take with a full glass of water.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Gram negative and gram positive bacteria
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C9 (CYP2C9)
Targets
  1. FolC bifunctional protein [Includes: Folylpolyglutamate synthase
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C9 (CYP2C9)
Enzyme 1 Gene Name CYP2C9
Enzyme 1 SwissProt ID P11712 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P11712|CP2C9_HUMAN Cytochrome P450 2C9 (EC 1.14.13.80) 
MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDISKSLTNLSKV
YGPVFTLYFGLKPIVVLHGYEAVKEALIDLGEEFSGRGIFPLAERANRGFGIVFSNGKKW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFHKRFDYKDQQFLNLMEKLNENIKILSSPWIQICNNFSPIIDYFPGTHNKLLKNVAFM
KSYILEKVKEHQESMDMNNPQDFIDCFLMKMEKEKHNQPSEFTIESLENTAVDLFGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVIGRNRSPCMQDRSHMPYTDAVVHEVQRYID
LLPTSLPHAVTCDIKFRNYLIPKGTTILISLTSVLHDNKEFPNPEMFDPHHFLDEGGNFK
KSKYFMPFSAGKRICVGEALAGMELFLFLTSILQNFNLKSLVDPKNLDTTPVVNGFASVP
PFYQLCFIPV
Drug Target 1 [top]
Target 1 ID 137
Target 1 Name FolC bifunctional protein [Includes: Folylpolyglutamate synthase
Target 1 Synonyms
  1. EC 6.3.2.17
  2. FPGS
  3. Folylpoly-gamma-glutamate synthetase
  4. Tetrahydrofolate synthase
Target 1 Gene Name folC
Target 1 Protein Sequence >FolC bifunctional protein [Includes: Folylpolyglutamate synthase 
MIIKRTPQAASPLASWLSYLENLHSKTIDLGLERVSLVAARLGVLKPAPFVFTVAGTNGK
GTTCRTLESILMAAGYKVGVYSSPHLVRYTERVRVQGQELPESAHTASFAEIESARGDIS
LTYFEYGTLSALWLFKQAQLDVVILEVGLGGRLDATNIVDADVAVVTSIALDHTDWLGPD
RESIGREKAGIFRSEKPAIVGEPEMPSTIADVAQEKGALLQRRGVEWNYSVTDHDWAFSD
AHGTLENLPLPLVPQPNAATALAALRASGLEVSENAIRDGIASAILPGRFQIVSESPRVI
FDVAHNPHAAEYLTGRMKALPKNGRVLAVIGMLHDKDIAGTLAWLKSVVDDWYCAPLEGP
RGATAEQLLEHLGNGKSFDSVAQAWDAAMADAKAEDTVLVCGSFHTVAHVMEVIDARRSG
GK
Target 1 Number of Residues 429
Target 1 Molecular Weight 45406
Target 1 Theoretical pI 5.59
Target 1 GO Classification
Function
binding
nucleotide binding
purine nucleotide binding
adenyl nucleotide binding
ATP binding
catalytic activity
ligase activity
ligase activity, forming carbon-nitrogen bonds
acid-amino acid ligase activity
tetrahydrofolylpolyglutamate synthase activity
Process
biosynthesis
physiological process
metabolism
cellular metabolism
aromatic compound metabolism
folic acid and derivative metabolism
folic acid and derivative biosynthesis
Component
Not Available
Target 1 General Function Coenzyme transport and metabolism
Target 1 Specific Function Conversion of folates to polyglutamate derivatives
Target 1 Pathways
Name SMPDB Link KEGG Link
Folate biosynthesis map00790 Link Image
Target 1 Reactions
  • ATP + 7,8-dihydropteroate + L-glutamate = ADP + phosphate + 7,8-dihydropteroylglutamate
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 146020 Link Image
Target 1 UniProtKB/Swiss-Prot ID P08192 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name FOLC_ECOLI Link Image
Target 1 PDB ID 1W7K Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >1269 bp 
ATGATTATCAAACGCACTCCTCAAGCCGCGTCGCCTCTGGCTTCGTGGCTTTCTTATCTG
GAAAACCTGCACAGTAAAACTATCGATCTCGGCCTTGAGCGCGTGAGCCTGGTCGCGGCG
CGTCTTGGCGTCCTGAAACCAGCGCCATTTGTGTTTACCGTTGCGGGTACGAATGGCAAA
GGCACCACCTGCCGTACGCTGGAGTCGATTCTGATGGCGGCAGGGTACAAAGTGGGCGTC
TACAGTTCGCCTCATCTGGTGCGTTATACCGAGCGCGTACGTGTGCAGGGCCAGGAATTG
CCGGAATCGGCCCACACCGCCTCTTTTGCGGAGATTGAATCGGCACGCGGTGATATTTCC
CTGACCTATTTCGAGTACGGTACGCTGTCGGCGTTGTGGCTGTTCAAGCAGGCACAACTT
GACGTGGTGATTCTGGAAGTAGGGCTGGGCGGTCGTCTGGACGCAACCAATATTGTCGAC
GCCGATGTCGCGGTAGTAACCAGTATTGCGCTGGATCATACCGACTGGCTGGGTCCAGAT
CGCGAAAGTATTGGTCGCGAGAAAGCAGGCATCTTCCGCAGCGAAAAACCGGCAATTGTC
GGTGAGCCGGAAATGCCTTCTACCATTGCTGATGTGGCGCAGGAAAAAGGTGCACTGTTA
CAACGTCGGGGCGTTGAGTGGAACTATTCCGTCACCGATCATGACTGGGCGTTTAGCGAT
GCTCACGGCACGCTGGAAAATCTGCCGTTGCCGCTTGTCCCGCAACCGAATGCCGCAACA
GCGCTGGCGGCACTGCGTGCCAGCGGGCTGGAAGTCAGTGAAAATGCCATTCGCGACGGG
ATTGCCAGCGCAATTTTGCCGGGACGTTTCCAGATTGTGAGCGAGTCGCCACGCGTTATT
TTTGATGTCGCGCATAATCCACATGCGGCGGAATATCTCACCGGGCGTATGAAAGCGCTA
CCGAAAAACGGGCGCATGCTGGCGGTTATCGGTATGCTACATGATAAAGATATTGCCGGA
ACTCTGGCCTGGTTGAAAAGCGTGGTTGATGACTGGTATTGTGCGCCACTGGAAGGGCCG
CGCGGTGCCACGGCAGAACAACTGCTTGAGCATTTGGGTAACGGCAAATCATTTGATAGC
GTTGCGCAGGCATGGGATGCCGCAATGGCGGACGCTAAAGCGGAAGACACCGTGCTGGTG
TGTGGTTCTTTCCACACGGTCGCACATGTCATGGAAGTGATTGACGCGAGGAGAAGCGGT
GGCAAGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Kimlova LJ, Pyne C, Keshavjee K, Huy J, Beebakhee G, Bognar AL: Mutagenesis of the folC gene encoding folylpolyglutamate synthetase-dihydrofolate synthetase in Escherichia coli. Arch Biochem Biophys. 1991 Jan;284(1):9-16. [PubMed Link Image]
  2. Nonet ML, Marvel CC, Tolan DR: The hisT-purF region of the Escherichia coli K-12 chromosome. Identification of additional genes of the hisT and purF operons. J Biol Chem. 1987 Sep 5;262(25):12209-17. [PubMed Link Image]
  3. Bognar AL, Osborne C, Shane B: Primary structure of the Escherichia coli folC gene and its folylpolyglutamate synthetase-dihydrofolate synthetase product and regulation of expression by an upstream gene. J Biol Chem. 1987 Sep 5;262(25):12337-43. [PubMed Link Image]
  4. Yamamoto Y, Aiba H, Baba T, Hayashi K, Inada T, Isono K, Itoh T, Kimura S, Kitagawa M, Makino K, Miki T, Mitsuhashi N, Mizobuchi K, Mori H, Nakade S, Nakamura Y, Nashimoto H, Oshima T, Oyama S, Saito N, Sampei G, Satoh Y, Sivasundaram S, Tagami H, Horiuchi T, et al.: Construction of a contiguous 874-kb sequence of the Escherichia coli -K12 genome corresponding to 50.0-68.8 min on the linkage map and analysis of its sequence features. DNA Res. 1997 Apr 28;4(2):91-113. [PubMed Link Image]
  5. Blattner FR, Plunkett G 3rd, Bloch CA, Perna NT, Burland V, Riley M, Collado-Vides J, Glasner JD, Rode CK, Mayhew GF, Gregor J, Davis NW, Kirkpatrick HA, Goeden MA, Rose DJ, Mau B, Shao Y: The complete genome sequence of Escherichia coli K-12. Science. 1997 Sep 5;277(5331):1453-74. [PubMed Link Image]
Target 1 Drug References
  1. 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. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.