methicillin

Also known as Celpillina, Staphcillin, Methicillinum, Methycillin, (2,6-Dimethoxyphenyl)penicillin, 6-(2,6-Dimethoxybenzamido)penicillanic acid, 6beta-(2,6-Dimethoxybenzamido)penicillanic acid

Methicillin (USAN), also known as meticillin (INN), is a narrow-spectrum β-lactam antibiotic of the penicillin class.

Chemical data

Formula: C17H20N2O6S
Molecular weight: 380.4 g/mol
IUPAC name: (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)O)C
InChIKey: RJQXTJLFIWVMTO-TYNCELHUSA-N
XLogP: 1.2
Polar surface area: 130 Å²
H-bond donors: 2
H-bond acceptors: 7
Formal charge: 0

via PubChem

Research

55,949 papers

Methicillin-resistant Staphylococcus aureus.Nature reviews. Disease primers · 2018
Methicillin-resistant staphylococci.Clinical microbiology reviews · 1988
Methicillin nephritis.Medicine · 1977
Methicillin-resistant staphylococci.Clinics in laboratory medicine · 1989
Methicillin resistance in Staphylococcus aureus: mechanisms and modulation.Science progress · 2002

via PubMed

Wikidata facts

Mass: 380.104

Show 6 more facts

chemical formula: C
defined daily dose: 4
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
canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)O)C
World Health Organisation international non-proprietary name: meticillin
Commons category: Methicillin

Sources (4)

via Wikidata · CC0

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