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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/12/01 17:15:57」(JST)

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Pivmecillinam (INN) or amdinocillin pivoxil (USAN, trade names Selexid, Penomax and Coactabs) is an orally active prodrug of mecillinam, an extended-spectrum penicillin antibiotic. Pivmecillinam is the pivaloyloxymethyl ester of mecillinam. Neither drug is available in the United States.^[2]

Pivmecillinam is only considered to be active against Gram-negative bacteria, and is used primarily in the treatment of lower urinary tract infections. In the Nordic countries, it has been widely used in that indication since the 1970s. It has been proposed as the first-line drug of choice for empirical treatment of acute cystitis.^[1]^[3] It has also been used to treat paratyphoid fever.^[4]

Activity[edit]

Adverse effects[edit]

See also: Beta-lactam antibiotic: Adverse effects

The adverse effect profile of pivmecillinam is similar to that of other penicillins. The most common side effects of mecillinam use are rash and gastrointestinal upset, including nausea and vomiting.^[1]^[5]

Prodrugs that release pivalic acid when broken down by the body — such as pivmecillinam, pivampicillin and cefditoren pivoxil — have long been known to deplete levels of carnitine.^[6]^[7] 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,^[8] it is unlikely to be of clinical significance;^[7] long-term use, however, appears problematic and is not recommended.^[7]^[9]^[10]

References[edit]

^ ^a ^b ^c Nicolle LE (August 2000). "Pivmecillinam in the treatment of urinary tract infections". J Antimicrob Chemother 46 (Suppl A): 35–39. doi:10.1093/jac/46.suppl_1.35. PMID 10969050.
^ Pham P, Bartlett JG (August 28, 2008). "Amdinocillin (Mecillinam)". Point-of-Care Information Technology ABX Guide. Johns Hopkins University. Retrieved on August 31, 2008. Freely available with registration.
^ Graninger W (October 2003). "Pivmecillinam—therapy of choice for urinary tract infection". Int J Antimicrob Agents. 22. Suppl 2: 73–8. doi:10.1016/S0924-8579(03)00235-8. PMID 14527775.
^ Tanphaichitra D, Srimuang S, Chiaprasittigul P, Menday P, Christensen OE (1984). "The combination of pivmecillinam and pivampicillin in the treatment of enteric fever". Infection 12 (6): 381–3. doi:10.1007/BF01645219. PMID 6569851.
^ "Selexid Tablets". electronic Medicines Compendium. June 5, 2008. Retrieved on August 31, 2008.
^ 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.

Skeletal formula of mecillinam, the active moiety of pivmecillinam

UpToDate Contents

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1. 女性における急性単純性膀胱炎および腎盂腎炎 acute uncomplicated cystitis and pyelonephritis in women
2. 小児における赤痢菌感染症の治療および予防 treatment and prevention of shigella infections in children
3. 開発途上国の小児における持続性下痢 persistent diarrhea in children in developing countries

English Journal

Different patterns in use of antibiotics for lower urinary tract infection in institutionalized and home-dwelling elderly: a register-based study.

Haasum Y, Fastbom J, Johnell K.SourceAging Research Center, Department of Neurobiology, Care Sciences and Society (NVS), Karolinska Institutet and Stockholm University, Gävlegatan 16, 113 30, Stockholm, Sweden, Ylva.Haasum@ki.se.
European journal of clinical pharmacology.Eur J Clin Pharmacol.2013 Mar;69(3):665-71. doi: 10.1007/s00228-012-1374-7. Epub 2012 Aug 25.
PURPOSE: We compared the quality and pattern of use of antibiotics to treat urinary tract infection (UTI) between institutionalized and home-dwelling elderly.METHODS: We analyzed the quality of use of UTI antibiotics in Swedish people aged ≥65 years at 30 September 2008 (1,260,843 home-dwelling a
PMID 22922683

Alternatives to carbapenems in ESBL-producing Escherichia coli infections.

Fournier D, Chirouze C, Leroy J, Cholley P, Talon D, Plésiat P, Bertrand X.SourceService de bactériologie, centre hospitalier universitaire de Besançon, 25030 Besançon, France.
Medecine et maladies infectieuses.Med Mal Infect.2013 Feb 19. pii: S0399-077X(13)00010-3. doi: 10.1016/j.medmal.2013.01.006. [Epub ahead of print]
OBJECTIVES: The authors had for objective to assess the activity of a wide panel of antibiotics on extended-spectrum-β-lactamase producing Escherichia coli isolates (ESBL-Ec), because of the sharp increase of their frequency, leading to an increased use of carbapenems.MATERIAL AND METHODS: We selec
PMID 23433608

Neonatal outcomes after gestational exposure to nitrofurantoin.

Nordeng H, Lupattelli A, Romøren M, Koren G.SourceSchool of Pharmacy, University of Oslo, Oslo, Norway. h.m.e.nordeng@farmasi.uio.no
Obstetrics and gynecology.Obstet Gynecol.2013 Feb;121(2 Pt 1):306-13. doi: http://10.1097/AOG.0b013e31827c5f88.
OBJECTIVE: To estimate whether first-trimester exposure to nitrofurantoin is associated with increased malformation rates and, secondarily, to estimate whether exposure to nitrofurantoin is associated with increased rates of negative pregnancy outcomes and perinatal complications.METHODS: We conduct
PMID 23344280

Japanese Journal

Carnitine deficiency induced by pivampicillin and pivmecillinam therapy

HOLME E
Lancet 2, 469-473, 1989
NAID 80004735255

KW-1100の臨床第I相試験

熊澤浄一,宇治康明,井上顕信,小林智
CHEMOTHERAPY 33(Supplement3), 86-97, 1985
… 同時に実施したpivmecillinam (PMPC) 200mg単回経口投与群 (13名) の成績と比較すると, 最高血清中濃度および尿中回収率のいずれもBMPC投与群の方がPMPC投与群よりも有意に大で, BMPCの腸管吸収がすぐれていることが示唆された。 …
NAID 130004195024

Bacmecillinam (KW-1100) の<I>in vivo</I>抗菌活性:マウス腹腔内感染および上行性尿路感染モデルに於ける感染治療効果

望月治美,山下錦也,佐藤清,岡地諒
CHEMOTHERAPY 33(Supplement3), 20-26, 1985
… Bacmecillinam (KW-1100, BMPC) とpivmecillinam (PMPC) を実験的マウス腹腔内感染モデルにおいて感染治療効果を比較検討した。 …
NAID 130004195009

Related Pictures

★リンクテーブル★

リンク元	「ピブメシリナム」「amdinocillin pivoxil」「PMPC」
拡張検索	「pivmecillinam hydrochloride」

「ピブメシリナム」

Pivmecillinam
Systematic (IUPAC) name
	2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[(azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy cat.	B (US); Appears safe in pregnancy
Legal status	℞ Prescription only
Routes	Oral
Pharmacokinetic data
Bioavailability	Low
Protein binding	5 to 10% (as mecillinam)
Metabolism	Pivmecillinam is hydrolyzed to mecillinam
Half-life	1 to 3 hours
Excretion	Renal and biliary, mostly as mecillinam
Identifiers
CAS number	32886-97-8
ATC code	J01CA08
PubChem	CID 36272
ChemSpider	33356
UNII	1WAM1OQ30B
KEGG	D02889
Chemical data
Formula	C21H33N3O5S
Mol. mass	439.569 g/mol
	SMILES CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C;
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