Pivampicillin
Also called Pivaloylampicillin, Ampicillin Pivaloyl Ester
Overview
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. __TOC__ WP
Risks and side effects
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.[1–5] WP
Chemistry
- Formula
- C22H29N3O6S PC
- CAS number
- 33817-20-8 PC
- Molar mass (g/mol)
- 463.5 PC
- IUPAC name (computed by PubChem)
- 2,
2- PCdimethylpropanoyloxymethyl (2S, 5R, 6R) - 6- [[(2R) - 2- amino- 2- phenylacetyl] amino] - 3, 3- dimethyl- 7- oxo- 4- thia- 1- azabicyclo[3.2.0] heptane- 2- carboxylate - SMILES
- CC1([C@@H]
(N2[C@H] PC(S1) [C@@H] (C2=O) NC(=O) [C@@H] (C3=CC=CC=C3) N) C(=O) OCOC(=O) C(C) (C) C) C - InChIKey
- ZEMIJUDPLILVNQ-
ZXFNITATSA- PCN - PubChem CID
- 33478
Harm reduction information
No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.
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Sources
- Journal / agency Holme E, Greter J, Jacobson CE, Lindstedt S, Nordin I, Kristiansson B, Jodal U. Carnitine deficiency induced by pivampicillin and pivmecillinam therapy. Lancet. August 1989. doi:10.1016/S0140-6736(89)92086-2 · PMID 2570185
- Journal / agency Brass EP. Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacological Reviews. December 2002. doi:10.1124/pr.54.4.589 · PMID 12429869
- Journal / agency Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I. Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration--a risk irrespective of age. Biochemical and Molecular Medicine. June 1995. doi:10.1006/bmme.1995.1036 · PMID 7551831
- Journal / agency Holme E, Jodal U, Linstedt S, Nordin I. Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children. Scandinavian Journal of Clinical and Laboratory Investigation. September 1992. doi:10.3109/00365519209088371 · PMID 1514015
- Journal / agency Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N. Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid. Pediatrics. September 2007. doi:10.1542/peds.2007-0339 · PMID 17724113
Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.