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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/06/30 11:35:04」(JST)
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Pivampicillin
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Systematic (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
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Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Routes of
administration |
Oral |
Pharmacokinetic data |
Excretion |
Renal (76%) |
Identifiers |
CAS Number |
33817-20-8 Y |
ATC code |
J01CA02 (WHO) |
PubChem |
CID 33478 |
DrugBank |
DB01604 Y |
ChemSpider |
30899 Y |
UNII |
0HLM346LL7 Y |
KEGG |
D08396 Y |
ChEBI |
CHEBI:8255 Y |
ChEMBL |
CHEMBL323354 N |
Chemical data |
Formula |
C22H29N3O6S |
Molar mass |
463.548 g/mol |
SMILES
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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
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InChI
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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 Y
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Key:ZEMIJUDPLILVNQ-ZXFNITATSA-N Y
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NY (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
- ^ 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.
- ^ a b c 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.
- ^ 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.
- ^ 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.
- ^ 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.
Antibacterials: cell envelope antibiotics (J01C-J01D)
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Intracellular |
- Inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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Glycopeptide |
- Inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(Inhibit PBP
cross-links) |
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Other |
- polymyxins/detergent
- depolarizing
- Hydrolyze NAM-NAG
- Gramicidin
- Isoniazid
- Teixobactin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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English Journal
- Pontine abscess with initial treatment failure following infectious endocarditis with Streptococcus salivarius.
- Knudtzen FC1, Lynge M2, Gaini S1.
- BMJ case reports.BMJ Case Rep.2015 Jul 2;2015. pii: bcr2014205949. doi: 10.1136/bcr-2014-205949.
- We present a case report of a 65-year-old man admitted to the department of infectious diseases on suspicion of meningitis with headache, fever and double vision. A cerebral MRI revealed a 17×30 mm pontine abscess with surrounding oedema. The patient had, 2 months prior to admission, been treat
- PMID 26139646
- Management of respiratory tract infections in primary care in Poland--results of the happy audit 2 project.
- Strumiło J, Chlabicz S, Ovhed I, Zieliński A, Pytel-Krolczuk B, Krzysztof B, Godycki-Cwirko M, Gowin E, Gugnowski Z, Panasiuk L, Makowiec-Dyrda M, Mierzecki A, Sieberto J, Sławin A, Tomiak E.
- Przegla̧d epidemiologiczny.Przegl Epidemiol.2014;68(1):33-8, 121-5.
- OBJECTIVE: The Polish results of the international Happy Audit 2 project are reported which objective was to present therapeutic decisions made by general practitioners (especially antibiotics prescribed) and diagnostic methods applied to patients with respiratory tract infections (RTI).MATERIAL AND
- PMID 25004629
- Pharmacokinetics in pulmonary epithelial lining fluid and plasma of ampicillin and pivampicillin administered to horses.
- Winther L1, Baptiste KE, Friis C.
- Research in veterinary science.Res Vet Sci.2012 Feb;92(1):111-5. doi: 10.1016/j.rvsc.2010.11.001. Epub 2010 Dec 7.
- Ampicillin concentrations in pulmonary epithelial lining fluid (PELF) and plasma was studied after single intravenous ampicillin administration (15mg/kg) or single intragastric administration of its prodrug, pivampicillin (19.9mg/kg) to horses and discussed in relation to minimum inhibitory concentr
- PMID 21144541
Japanese Journal
- Bacampicillin Uptake Is Shared with Thiamine in Caco-2 Cells(Biopharmacy)
- Differential excretion of xenobiotic acyl-esters of carnitine due to administration of pivampicillin and valproate
- Carnitine deficiency induced by pivampicillin and pivmecillinam therapy
Related Links
- Pivampicillin is a medicine available in a number of countries worldwide. A list of US medications equivalent to Pivampicillin is available on the Drugs.com website. ... Drugs.com provides accurate and independent information on more ...
- Pivampicillin | C22H29N3O6S | CID 33478 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. ... National ...
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