Methicillin Sodium
Title: Methicillin Sodium
CAS Registry Number: 132-92-3
CAS 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 monosodium salt
Additional Names: 6-(2,6-dimethoxybenzamido)penicillanic acid sodium salt; sodium 2,6-dimethoxyphenylpenicillin; 2,6-dimethoxyphenylpenicillin sodium salt; sodium 6-(2,6-dimethoxybenzamido)penicillinate; 2,6-dimethoxybenzoylpenin sodium salt; dimethoxyphenecillin sodium; sodium methicillin
Manufacturers' Codes: BRL-1241; X-1497
Trademarks: Azapen (Pfizer); Belfacillin; Celpillina; Celbenin (SKB); Cinopenil (Hoechst); Flabelline; Penistaph; Staphcillin (BMS)
Molecular Formula: C17H19N2NaO6S
Molecular Weight: 402.40
Percent Composition: C 50.74%, H 4.76%, N 6.96%, Na 5.71%, O 23.86%, S 7.97%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepn starting with 6-aminopenicillanic acid: Doyle et al., J. Chem. Soc. 1962, 1457; Doyle et al., US 2951839 (1960); Glombitza, Ann. 673, 166 (1964). Physical-chemical properties: Cotta-Ramusino, Intonti, Farmaco Ed. Prat. 16, 227 (1961).
 
Derivative Type: Monohydrate
Properties: Crystals from acetone, mp 196-197° (dec). [a]D20 +230° (c = 5); +225° (c = 1). uv max: 281 nm (E1%1cm 55); min 264 nm. Solubilities (mg/ml) at 20°: water >300; ethanol 40; ether <0.03; acetone 0.35; chloroform 0.06; isooctane <0.03.
Melting point: mp 196-197° (dec)
Optical Rotation: [a]D20 +230° (c = 5); +225° (c = 1)
Absorption maximum: uv max: 281 nm (E1%1cm 55); min 264 nm
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antimicrobial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.

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