Methicillin

Synonym(s): Meticillin

Class: Beta-lactam (penicillin)

Spectrum of activity:	Gram-positive
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:	1960
Development status:	Approved, discontinued

Chemical structure(s):
Canonical SMILES:	CC1(C)[C@H](C(=O)O)N2C(=O)[C@H]([C@H]2S1)NC(=O)C3=C(C=CC=C3OC)OC
Isomeric SMILES:	CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)O)C
InChI:	InChI=1S/C17H20N2O6S/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23)/t11-,12+,15-/m1/s1
InChI Key:	RJQXTJLFIWVMTO-TYNCELHUSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/6087

External links:
Guide to Pharmacology:	methicillin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1482072/
Citations:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC124322/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6939889/