Nafcillin

Synonym(s): WY-3277

Class: Beta-lactam (penicillin, naphthalen)

Details of activity:	Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis. Active against Gram-positive bacteria, especially staphylococci including penicillinase producing strains
Description:	Semisynthetic penicillin, derived from 6-aminopenicillanic acid (6-APA). Parenteral application
Year first mentioned:	1961
Development status:	Approved, off-patent, not available in many countries

Chemical structure(s):
Canonical SMILES:	CCOC1=C(C2=C(C=CC=C2)C=C1)C(=O)N[C@@H]3C(=O)N4[C@@H](C(=O)O)C(C)(C)S[C@H]34
Isomeric SMILES:	CCOC1=C(C2=CC=CC=C2C=C1)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChI:	InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1
InChI Key:	GPXLMGHLHQJAGZ-JTDSTZFVSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/8982

External links:
Guide to Pharmacology:	nafcillin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5980628/
Citations:	https://pubmed.ncbi.nlm.nih.gov/32376001/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4958157/