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
Development status:	Approved, off-patent, mainly available for veterinary medicine

Chemical structure(s):
Canonical 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
Isomeric 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:	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
InChI Key:	DXVUYOAEDJXBPY-NFFDBFGFSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/443387

External links:
Guide to Pharmacology:	hetacillin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1843140/