Compound ID | 1932

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Hetacillin

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, but vulnerable to penicillinases produced by staphylococci and E. coli
Description: Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA). Parenteral and oral (prodrug) application. Replaced by ampicillin
Year first mentioned: 1965
Highest developmental phase: Approved by FDA in 1971
Development status: Discontinued
Chemical structure(s):
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Molecular weight: 389.47
Iso. SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)C4=CC=CC=C4)C(=O)O)C
InChI Key: DXVUYOAEDJXBPY-NFFDBFGFSA-N
Can. SMILES: CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)N3C(=O)[C@@H](C4=CC=CC=C4)NC3(C)C
InChI: InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/443387
Guide to Pharmacology: hetacillin
Citation: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1843140/

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