 Home > Encyclopedia > Bacampicillin

Bacampicillin

Bacampicillin structure

CAS No:
50972-17-3
Formula:
C21H27N3O7S
Chemical Name:
Bacampicillin
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,1-[(ethoxycarbonyl)oxy]ethyl ester,(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-,1-[(ethoxycarbonyl)oxy]ethyl ester,[2S-[2α,5α,6β(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-,1-[(ethoxycarbonyl)oxy]ethyl ester,(2S,5R,6R)-;Bacampicillin;Carampicillin;91115-55-8
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Bacampicillin is a penicillin antibiotic, is a prodrug of ampicillin with improved oral bioavailability.

Solid

Bacampicillin is a penicillanic acid ester that is the 1-ethoxycarbonyloxyethyl ester of ampicillin. It is a semi-synthetic, microbiologically inactive prodrug of ampicillin. It has a role as a prodrug. It derives from an ampicillin.|Bacampicillin is a prodrug of ampicillin and is microbiologically inactive. It is absorbed following oral administration. During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc.|Bacampicillin is a prodrug of ampicillin, a broad-spectrum, semisynthetic, beta-lactam aminopenicillin antibiotic with bactericidal activity. Bacampicillin is hydrolyzed in vivo by esterases to its active metabolite ampicillin. Ampicillin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall and causes cell lysis.

Bacampicillin Basic Attributes

Molecular Weight：

465.52

Exact Mass：

465.52

DSSTox ID：

DTXSID2048030

NCI Thesaurus Code：

C65245

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

163

XLogP3：

2.32490

Appearance：

white to yellowish crystalline powder

Density：

1.37 g/cm3

Melting Point：

171-176

Boiling Point：

678.4ºC at 760 mmHg

Flash Point：

364.1ºC

Refractive Index：

1.607

Water Solubility：

1.23e-01 g/L

Drug Information

Drug Indication：

For infections at the following sites: upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis, when due to sensitive strains of the following organisms: Gram-positive: streptococci (including S. faecalis and S. pneumoniae) and nonpenicillinase-producing staphylococci; Gram-negative: H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis, Salmonellae and Shigellae.

Pharmacology：

Bacampicillin is a prodrug of ampicillin and is microbiologically inactive.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Absorbed following oral administration.

Mechanism of Action：

During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides.

MeSH Entry Terms：

bacampicillin

Computed Properties

Molecular Weight:465.5
XLogP3:2.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:10
Exact Mass:465.15697138
Monoisotopic Mass:465.15697138
Topological Polar Surface Area:163
Heavy Atom Count:32
Complexity:756
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes