Compound ID | 1948

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Sultamicillin

Class: Beta-lactam (Aminopenicillin)

Spectrum of activity: Gram-positive & Gram-negative
Details of activity: Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-positive bacteria and some Enterobacteriaceae, not vulnerable to penicillinases produced by staphylococci and E. coli
Description: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA). Chemically linked double ester of ampicillin plus the beta-lactamase inhibitor sulbactam. Oral application
Year first mentioned: 1982
Highest developmental phase: Approved by FDA in 1986
Development status: Approved
Chemical structure(s):
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Molecular weight: 594.66
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)OCOC(=O)[C@H]4C(S(=O)(=O)[C@H]5N4C(=O)C5)(C)C)C
InChI Key: OPYGFNJSCUDTBT-PMLPCWDUSA-N
Can. SMILES: CC1(C)[C@H](C(=O)OCOC(=O)[C@H]2C(C)(C)S(=O)(=O)[C@@H]3CC(=O)N32)N4C(=O)[C@H]([C@H]4S1)NC(=O)[C@@H](C5=CC=CC=C5)N
InChI: InChI=1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/444022
Guide to Pharmacology: sultamicillin
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/2660868/
  • https://pubmed.ncbi.nlm.nih.gov/2660871/
  • https://pubmed.ncbi.nlm.nih.gov/2661196/

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