CAS 61-32-5

Methicillin

Description:

Methicillin is a semi-synthetic antibiotic belonging to the penicillin class, primarily used to treat infections caused by certain Gram-positive bacteria, particularly Staphylococcus aureus. It is characterized by its beta-lactam structure, which is essential for its antibacterial activity. Methicillin is resistant to degradation by penicillinase, an enzyme produced by some bacteria that can inactivate other penicillins. This resistance makes it effective against penicillin-resistant strains of Staphylococcus. However, its use has declined due to the emergence of methicillin-resistant Staphylococcus aureus (MRSA), which poses significant treatment challenges. Methicillin is typically administered via injection, as it is not well absorbed when taken orally. Its pharmacokinetics involve rapid distribution in body tissues, with a relatively short half-life, necessitating multiple doses for effective treatment. Adverse effects can include allergic reactions, gastrointestinal disturbances, and potential nephrotoxicity. Overall, while methicillin played a crucial role in treating bacterial infections, its clinical relevance has diminished in the face of antibiotic resistance.

Formula: C₁₇H₂₀N₂O₆S

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: InChIKey=RJQXTJLFIWVMTO-TYNCELHUSA-N

SMILES: C(O)(=O)[C@@H]1N2[C@@]([C@H](NC(=O)C3=C(OC)C=CC=C3OC)C2=O)(SC1(C)C)[H]

Synonyms:

• (2,6-Dimethoxyphenyl)penicillin
• (2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]-
• 6-(2,6-Dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• 6-(2,6-Dimethoxybenzamido)penicillanic acid
• Metacillin
• Methicillin
• Methycillin
• Meticilina
• Meticilline
• Penicillin, (2,6-dimethoxyphenyl)-
• Staphcillin

Meticillin

CAS: 61-32-5

Methicillin: Narrow-spectrum beta-lactam, penicillin-type antibiotic for certain gram-positive bacterial infections.

Formula: C₁₇H₂₀N₂O₆S

Color and Shape: Solid

Molecular weight: 380.42

Ref: TM-T33359