CAS 983-85-7

Penamecillin

Description:

Penamecillin is a semi-synthetic antibiotic belonging to the penicillin class, primarily used for its antibacterial properties. It is characterized by its ability to inhibit bacterial cell wall synthesis, which is a crucial mechanism for combating bacterial infections. Penamecillin is effective against a range of Gram-positive bacteria and some Gram-negative organisms, making it valuable in treating various infections. The compound features a beta-lactam ring, a common structural motif in penicillins, which is essential for its antimicrobial activity. Its chemical structure includes a thiazolidine ring and a side chain that contributes to its spectrum of activity and pharmacokinetic properties. Penamecillin is typically administered via injection, as it is not well absorbed when taken orally. As with other antibiotics, it is important to use penamecillin judiciously to prevent the development of antibiotic resistance. Potential side effects may include allergic reactions, gastrointestinal disturbances, and interactions with other medications. Overall, penamecillin represents an important tool in the arsenal against bacterial infections.

Formula: C₁₉H₂₂N₂O₆S

InChI: InChI=1S/C19H22N2O6S/c1-11(22)26-10-27-18(25)15-19(2,3)28-17-14(16(24)21(15)17)20-13(23)9-12-7-5-4-6-8-12/h4-8,14-15,17H,9-10H2,1-3H3,(H,20,23)/t14-,15+,17-/m1/s1

InChI key: InChIKey=NLOOMWLTUVBWAW-HLLBOEOZSA-N

SMILES: C(OCOC(C)=O)(=O)[C@@H]1N2[C@@]([C@H](NC(CC3=CC=CC=C3)=O)C2=O)(SC1(C)C)[H]

Synonyms:

• (Acetyloxy)Methyl 3,3-Dimethyl-7-Oxo-6-[(Phenylacetyl)Amino]-4-Thia-1-Azabicyclo[3.2.0]Heptane-2-Carboxylate
• (acetyloxy)methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-(2S-(2alpha,5alpha,6beta))-, (acetyloxy)methyl ester
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-, hydroxymethyl ester acetate (ester)
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]- (2S,5R,6R)-, (acetyloxy)methyl ester
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- (2S,5R,6R)-, (acetyloxy)methyl ester
• 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-[(phenylacetyl)amino]- [2S-(2α,5α,6β)]-, (acetyloxy)methyl ester
• Acetoxymethyl benzylpenicillanate
• Acetoxymethyl benzylpenicillinate
• Benzylpenicillin acetoxymethyl ester
• Havapen
• Hydroxymethyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate, acetate (ester)
• Methanediol, acetate 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Penamecilina
• Penamecilina [INN-Spanish]
• Penamecillin [USAN:INN:BAN]
• Penamecillina
• Penamecillina [DCIT]
• Penamecilline
• Penamecilline [INN-French]
• Penamecillinum
• Penamecillinum [INN-Latin]
• Penicillin G hydromethyl ester acetate
• Penicillin G, hydroxymethyl ester, acetate
• Wy 20,788

Penamecillin

Controlled Product

CAS: 983-85-7

Applications Penamecillin is an ambulatory antibiotic used in the treatment of community-acquired pneumonia in adults. An antimicrobial agent also used in pharmacokinetics.
References Matuz, M., et al.: Basic Clin. Pharmacol. Toxicol., 117, 330 (2015), Chen, Z., et al.: Zhongguo Yiyuan Yaoxue Zazhi, 27, 220 (2007), Kovacs, I., et al.: Acta Pharmaceutica , 48, 54 (1978), Modr, Z., et al.: Farmakoterapeuticke Zpravy, 25, 199 (1979)

Formula: C₁₉H₂₂N₂O₆S

Color and Shape: Neat

Molecular weight: 406.453

Ref: TR-P220230

Penamecillin

CAS: 983-85-7

Penamecillin is a broad-spectrum antibiotic, classified as a penicillin derivative. It is a biosynthetic product originating from the modification of naturally occurring penicillin, designed to enhance activity and bioavailability. The mode of action of Penamecillin involves the inhibition of bacterial cell wall synthesis. It effectively targets the penicillin-binding proteins (PBPs) within bacteria, leading to the interruption of peptidoglycan cross-linking, which is essential for bacterial cell wall structural integrity. This ultimately results in the bactericidal effect against susceptible bacterial strains.

Formula: C₁₉H₂₂N₂O₆S

Purity: Min. 95%

Molecular weight: 406.5 g/mol

Ref: 3D-AAA98385

Penamecillin

CAS: 983-85-7

Penamecillin (Wy 20788) is an orally active antibacterial agent.

Formula: C₁₉H₂₂N₂O₆S

Color and Shape: Solid

Molecular weight: 406.45

Ref: TM-T62023