Compound ID | 2085

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Sulfamethoxazole+trimethoprim

Synonym(s): Cotrimoxazole

Class: Drug combination

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Interferes sequentially with the folate biosynthesis. Sulfamethoxazole inhibits dihydropteroate synthase (DHPS); trimethoprim inhibits dihydrofolate reductase (DHFR). Combination is typically bactericidal and delays emergence of resistance compared to use of either component alone.
Combined with other compounds: Yes
Description: Synthetic sufanilamide derivative; intermediate-acting (8-12 hours). Used as therapeutic and prophylactic drug for urinary tract, respiratory, gastrointestinal and sexually transmitted infections and for infections caused by protozoae.
Year first mentioned: 1959
Development status: Approved, off-patent
Chemical structure(s):
Trimethoprim
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Molecular weight: 290.32
Iso. SMILES: COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
InChI Key: IEDVJHCEMCRBQM-UHFFFAOYSA-N
Can. SMILES: COC1=CC(=CC(=C1OC)OC)CC2=C(N)N=C(N)N=C2
InChI: InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
Sulfamethoxazole
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Molecular weight: 253.28
Iso. SMILES: CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI Key: JLKIGFTWXXRPMT-UHFFFAOYSA-N
Can. SMILES: CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI: InChI=1S/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)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5329
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5578
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/34553814/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9304920/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9310516/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1630548/

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