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Prodrug
Pivampicillin
Другие языки:

Pivampicillin

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Pivampicillin
Pivampicillin.svg
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Routes of
administration		 Oral
ATC code
Pharmacokinetic data
Excretion Renal (76%)
Identifiers
  • 2,2-Dimethylpropanoyloxymethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenyl-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.046.975
Chemical and physical data
Formula C22H29N3O6S
Molar mass 463.55 g·mol−1
3D model (JSmol)
  • O=C(OCOC(=O)C(C)(C)C)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]3SC2(C)C
  • InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1 checkY
  • Key:ZEMIJUDPLILVNQ-ZXFNITATSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Pivampicillin is a pivaloyloxymethyl ester of ampicillin. It is a prodrug, which is thought to enhance the oral bioavailability of ampicillin because of its greater lipophilicity compared to that of ampicillin.

Adverse effects

Prodrugs that release pivalic acid when broken down by the body—such as pivampicillin, pivmecillinam, and cefditoren pivoxil—have long been known to deplete levels of carnitine. This effect is not due to the drug itself but to pivalate, which is mostly removed from the body by forming a conjugate with carnitine. Although short-term use of these drugs can cause a marked decrease in blood levels of carnitine, it is unlikely to be of clinical significance; long-term use, however, is not recommended.

Availability

Worldwide, pivampicillin is only available in Denmark, where it is sold as Pondocillin® by PharmaCoDane, or Miraxid® by LEO Pharma.


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