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Pivampicillin

Catalog No. DB01604 Name DrugBank
CAS Number 33817-20-8 Website http://www.ualberta.ca/
M. F. C22H29N3O6S Telephone (780) 492-3111
M. W. 463.54716 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1381

SYNONYMS

IUPAC name
[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
IUPAC Traditional name
[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
Brand Name
Pondocillin
Synonyms
Pivaloylampicillin
Pivampicillinum [inn-latin]
Pivampicilline [inn-french]
Ampicillin pivaloyloxymethyl ester
Pivaloyloxymethyl ampicillinate
Pivampicilina [inn-spanish]

DATABASE IDS

CAS Number 33817-20-8
PubChem SID 46505340
PubChem CID 33478

PROPERTIES

DETAILS

Description (English)
Item Information
Drug Groups approved
Description Pivalate ester analog of ampicillin.
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.
Affected Organisms
Enteric bacteria and other eubacteria
Absorption Absorbed following oral administration.
Half Life Approximately 1 hour.
References
Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. [Pubmed]
Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. [Pubmed]
External Links
Wikipedia

REFERENCES

  • Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. Pubmed
  • Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. Pubmed