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{{drugbox |
{{Drugbox
| IUPAC_name = 2,2-dimethylpropanoyloxymethyl&nbsp;(2''S'',5''R'',6''R'')-<br>6-{[(2''R'')-2-amino-2-phenyl-acetyl]amino}-3,3-<br>dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]<br>heptane-2-carboxylate
| Verifiedfields = changed
| image = Pivampicillin.png
| Watchedfields = changed
| verifiedrevid = 464208299
| IUPAC_name = 2,2-Dimethylpropanoyloxymethyl&nbsp;(2''S'',5''R'',6''R'')-6-{[(2''R'')-2-amino-2-phenyl-acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
| image = Pivampicillin.svg
 
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|CONS|pivampicillin}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4  / S8 -->
| legal_CA = <!--                            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration = Oral
 
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = [[Kidney|Renal]] (76%)
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 33817-20-8
| CAS_number = 33817-20-8
| ATC_prefix = J01
| ATC_prefix = J01
| ATC_suffix = CA02
| ATC_suffix = CA02
| PubChem = 33478
| PubChem = 33478
| DrugBank =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C = 22 | H = 29 | N = 3 | O = 6 | S = 1
| DrugBank = DB01604
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 30899
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0HLM346LL7
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08396
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8255
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 323354
 
<!--Chemical data-->
| C=22 | H=29 | N=3 | O=6 | S=1  
| molecular_weight = 463.548 g/mol
| molecular_weight = 463.548 g/mol
| bioavailability =  
| 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
| protein_bound =  
| InChI = 1/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
| metabolism =  
| InChIKey = ZEMIJUDPLILVNQ-ZXFNITATBU
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion = [[Kidney|Renal]] (76%)
| StdInChI = 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
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US =  <!-- A / B            / C / D / X -->
| StdInChIKey = ZEMIJUDPLILVNQ-ZXFNITATSA-N
| pregnancy_category = 
| legal_AU =  <!-- Unscheduled / S2 / S3 / S4  / S8 -->
| legal_CA =  <!--                             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US =  <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status =  
| routes_of_administration = Oral
}}
}}
{{SI}}
{{EH}}


'''Pivampicillin''' is a [[pivaloyloxymethylester]] 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.  
'''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]].<ref>{{cite journal |author=Holme E |title=Carnitine deficiency induced by pivampicillin and pivmecillinam therapy |journal=Lancet |volume=2 |issue=8661 |pages=469–73 |date=August 1989 |pmid=2570185 |doi= 10.1016/S0140-6736(89)92086-2|url=http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(89)92086-2 |author-separator=, |author2=Greter J |author3=Jacobson CE |display-authors=3 |last4=Greter |first4=Joachim |last5=Lindstedt |first5=Sven |last6=Kristiansson |first6=Bengt |last7=Jodal |first7=Ulf}}</ref><ref name=Brass>{{cite journal |author=Brass EP |title=Pivalate-generating prodrugs and carnitine homeostasis in man |journal=Pharmacol Rev |volume=54 |issue=4 |pages=589–98 |date=December 2002 |pmid=12429869 |doi= 10.1124/pr.54.4.589|url=http://pharmrev.aspetjournals.org/cgi/pmidlookup?view=long&pmid=12429869}}</ref> This 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,<ref>{{cite journal |author=Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I |title=Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration—a risk irrespective of age |journal=Biochem. Mol. Med. |volume=55 |issue=1 |pages=77–9 |date=June 1995 |pmid=7551831 |doi= 10.1006/bmme.1995.1036|url=http://linkinghub.elsevier.com/retrieve/pii/S1077315085710368}}</ref> it is unlikely to be of clinical significance;<ref name=Brass/> long-term use, however, appears problematic and is not recommended.<ref name=Brass/><ref>{{cite journal |author=Holme E, Jodal U, Linstedt S, Nordin I |title=Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children |journal=Scand J Clin Lab Invest |volume=52 |issue=5 |pages=361–72 |date=September 1992 |pmid=1514015 |doi= 10.3109/00365519209088371|url=}}</ref><ref>{{cite journal |author=Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N |title=Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid |journal=Pediatrics |volume=120 |issue=3 |pages=e739–41 |date=September 2007 |pmid=17724113 |doi=10.1542/peds.2007-0339}}</ref>


==References==
{{Reflist}}


{{PenicillinAntiBiotics}}
{{PenicillinAntiBiotics}}
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[[Category:Prodrugs]]
[[Category:Prodrugs]]


{{SIB}}
{{antibiotic-stub}}
 
[[th:ไพแวมพิซิลลิน]]
{{WH}}
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Revision as of 18:02, 9 April 2015

Pivampicillin
File:Pivampicillin.svg
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration		Oral
ATC code
Pharmacokinetic data
ExcretionRenal (76%)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC22H29N3O6S
Molar mass463.548 g/mol
3D model (JSmol)
 ☒N☑Y (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.[1][2] This 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, appears problematic and is not recommended.[2][4][5]

References

  1. ↑ Holme E; Greter J; Jacobson CE; et al. (August 1989). "Carnitine deficiency induced by pivampicillin and pivmecillinam therapy". Lancet. 2 (8661): 469–73. doi:10.1016/S0140-6736(89)92086-2. PMID 2570185. Unknown parameter |author-separator= ignored (help)
  2. ↑ 2.0 2.1 2.2 Brass EP (December 2002). "Pivalate-generating prodrugs and carnitine homeostasis in man". Pharmacol Rev. 54 (4): 589–98. doi:10.1124/pr.54.4.589. PMID 12429869.
  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". Biochem. Mol. Med. 55 (1): 77–9. 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". Scand J Clin Lab Invest. 52 (5): 361–72. 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): e739–41. doi:10.1542/peds.2007-0339. PMID 17724113.

Template:Antibiotic-stub

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