Metisilin

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

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

In the Vinony graph

Vinony's link graph records 258 inbound references to Metisilin, and connects out to β-lactam antibiotic, methicillin-resistant Staphylococcus aureus and beta-lactamase.

It sits within the topics Benzamides, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.

Vinony links it to 29 Wikipedia language editions.

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

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1982
Admin. routes: parenteral
Indications: osteomyelitis, bacterial disease

via ChEMBL · EBI

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

Has part: carbon
Mass: 380.104
Has use: medication

Show 8 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
medical condition treated: bacterial pneumonia
subject has role: bactericide
Commons category: Methicillin