Pivampicillin

Pivampicillin
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Oral
ATC code	J01CA02 (WHO) ;
Pharmacokinetic data
Excretion	Renal (76%)
Identifiers
	IUPAC name 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	33817-20-8 ;
PubChem CID	33478;
DrugBank	DB01604 ;
ChemSpider	30899 ;
UNII	0HLM346LL7;
KEGG	D08396 ;
ChEBI	CHEBI:8255 ;
ChEMBL	ChEMBL323354 ;
CompTox Dashboard (EPA)	DTXSID1045459 ;
ECHA InfoCard	100.046.975
Chemical and physical data
Formula	C22H29N3O6S
Molar mass	463.55 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:ZEMIJUDPLILVNQ-ZXFNITATSA-N ;
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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.^[1]^[2] 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,^[3] it is unlikely to be of clinical significance;^[2] long-term use, however, is not recommended.^[2]^[4]^[5]

Availability

Worldwide, pivampicillin is only available in Denmark, where it is sold as Pondocillin by PharmaCoDane, or Miraxid by LEO Pharma.^[6]

References

^ Holme E, Greter J, Jacobson CE, Lindstedt S, Nordin I, Kristiansson B, Jodal U (August 1989). "Carnitine deficiency induced by pivampicillin and pivmecillinam therapy". Lancet. 2 (8661): 469–473. doi:10.1016/S0140-6736(89)92086-2. PMID 2570185. S2CID 31555161.
^ ^a ^b ^c Brass EP (December 2002). "Pivalate-generating prodrugs and carnitine homeostasis in man". Pharmacological Reviews. 54 (4): 589–598. doi:10.1124/pr.54.4.589. PMID 12429869. S2CID 14507215.
^ Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I (June 1995). "Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration--a risk irrespective of age". Biochemical and Molecular Medicine. 55 (1): 77–79. doi:10.1006/bmme.1995.1036. PMID 7551831.
^ Holme E, Jodal U, Linstedt S, Nordin I (September 1992). "Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children". Scandinavian Journal of Clinical and Laboratory Investigation. 52 (5): 361–372. doi:10.3109/00365519209088371. PMID 1514015.
^ Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N (September 2007). "Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid". Pediatrics. 120 (3): e739 – e741. doi:10.1542/peds.2007-0339. PMID 17724113. S2CID 40136171.
^ "Pondocillin®". Retrieved 2016-09-18.

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[1] Holme E, Greter J, Jacobson CE, Lindstedt S, Nordin I, Kristiansson B, Jodal U (August 1989). "Carnitine deficiency induced by pivampicillin and pivmecillinam therapy". Lancet. 2 (8661): 469–473. doi:10.1016/S0140-6736(89)92086-2. PMID 2570185. S2CID 31555161.

[Brass-2] Brass EP (December 2002). "Pivalate-generating prodrugs and carnitine homeostasis in man". Pharmacological Reviews. 54 (4): 589–598. doi:10.1124/pr.54.4.589. PMID 12429869. S2CID 14507215.

[3] Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I (June 1995). "Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration--a risk irrespective of age". Biochemical and Molecular Medicine. 55 (1): 77–79. doi:10.1006/bmme.1995.1036. PMID 7551831.

[4] Holme E, Jodal U, Linstedt S, Nordin I (September 1992). "Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children". Scandinavian Journal of Clinical and Laboratory Investigation. 52 (5): 361–372. doi:10.3109/00365519209088371. PMID 1514015.

[5] Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N (September 2007). "Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid". Pediatrics. 120 (3): e739 – e741. doi:10.1542/peds.2007-0339. PMID 17724113. S2CID 40136171.

[6] "Pondocillin®". Retrieved 2016-09-18.

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