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Pivampicillin

Pivampicillin structure

CAS No:
33817-20-8
Formula:
C22H29N3O6S
Chemical Name:
Pivampicillin
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,(2,2-dimethyl-1-oxopropoxy)methyl ester,(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-,(2,2-dimethyl-1-oxopropoxy)methyl ester,[2S-[2α,5α,6β(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-,hydroxymethyl ester pivalate (ester),D-(-)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-,(2,2-dimethyl-1-oxopropoxy)methyl ester,(2S,5R,6R)-;MK 191;Pivampicillin;Pivaloylampicillin;Hydroxymethyl 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate (ester);Pivaloyloxymethyl D-α-aminobenzylpenicillinate;Ampicillin pivaloyloxymethyl ester;Pivaloyloxymethyl ampicillinate;26310-12-3;47707-04-0
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

White or almost white, crystalline powder.

Solid

Pivampicillin is a penicillanic acid ester that is the pivaloyloxymethyl ester of ampicillin. It is a prodrug of ampicillin. It has a role as a prodrug. It is a penicillanic acid ester and a pivaloyloxymethyl ester. It derives from an ampicillin.|Pivalate ester analog of ampicillin.|Pivampicillin is a semisynthetic, orally active pivalate ester of ampicillin with antibacterial activity. Upon absorption, pivampicillin is hydrolyzed into its active form ampicillin by esterases. Ampicillin binds to and inactivates penicillin-binding proteins (PBPs) 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, eventually causing cell lysis.|Pivalate ester analog of AMPICILLIN.

Pivampicillin Basic Attributes

Molecular Weight：

463.55

Exact Mass：

463.55

EC Number：

251-688-6

UNII：

0HLM346LL7

DSSTox ID：

DTXSID1045459

NCI Thesaurus Code：

C84068

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

153

XLogP3：

2.35260

Density：

1.33g/cm3

Boiling Point：

679ºC at 760mmHg

Flash Point：

364.5ºC

Refractive Index：

1.604

Water Solubility：

Practically insoluble in water, freely soluble in methanol, soluble in anhydrous ethanol. It dissolves in dilute acids.

Drug Information

Drug Indication：

or the treatment of respiratory tract infections (including acute bronchitis, acute exacerbations of chronic bronchitis and pneumonia); ear, nose and throat infections; gynecological infections; urinary tract infections (including acute uncomplicated gonococcal urethritis) when caused by non penicillinase-producing susceptible strains of the following organisms: gram-positive organisms, e.g., streptococci, pneumococci and staphylococci; gram-negative organisms, e.g., H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis.

Pharmacology：

Pivampicillin is the pivaloyloxymethyl ester of (the semi-synthetic penicillin) ampicillin. It is an inactive pro-drug, which is converted during its absorption from the gastrointestinal tract to the microbiologically active ampicillin, together with formaldehyde and pivalic acid, by non-specific esterases present in most body tissues. Amounts in excess of 99% of the pivampicillin absorbed are converted to ampicillin within 15 minutes of absorption.

MeSH：

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

Absorption：

Absorbed following oral administration.

Biological Half-Life：

Approximately 1 hour.

Mechanism of Action：

Ampicillin (the active metabolite of pivampicillin) has a bactericidal action resulting from inhibition of cell wall mucopeptide biosynthesis.

MeSH Entry Terms：

Ampicillin Pivaloyl Ester

Pivampicillin Use and Manufacturing

Antibacterial.

Computed Properties

Molecular Weight:463.5
XLogP3:2.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:9
Exact Mass:463.17770683
Monoisotopic Mass:463.17770683
Topological Polar Surface Area:153
Heavy Atom Count:32
Complexity:774
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes