匹美西林

匹美西林
临床资料
商品名（英语：Drug nomenclature）	Selexid、Penomax、Coactabs
AHFS/Drugs.com	Micromedex详细消费者药物信息
怀孕分级	; 怀孕期间安全;
给药途径	口服
ATC码	J01CA08 (WHO) ;
法律规范状态
法律规范	处方药（℞-only）;
药物动力学数据
生物利用度	低
血浆蛋白结合率	5至10%（作为美西林）
药物代谢	匹美西林水解成美西林
生物半衰期	1至3小时
排泄途径	肾和胆，通常作为美西林
识别信息
	IUPAC命名法 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; ;
CAS号	32886-97-8
PubChem CID	36272;
ChemSpider	33356 ;
UNII	1WAM1OQ30B;
KEGG	D02889 ;
ChEMBL	ChEMBL1650818 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID7048538 ;
ECHA InfoCard	100.046.600
化学信息
化学式	C21H33N3O5S
摩尔质量	439.57 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C;

匹美西林（INN：Pivmecillinam；USAN：amdinocillin pivoxil）是美西林（一种广谱青霉素类抗生素）的口服活性前药。匹美西林是美西林的叔戊酰氧甲酯。

匹美西林仅对革兰氏阴性菌有活性，主要用于治疗下尿路感染。在北欧国家，自1970年代以来，它已被广泛用于该适应症。它已被提议作为急性膀胱炎经验性治疗的首选一线药物。^[1]^[2]它也被用于治疗副伤寒和志贺杆菌病。^[3]

活性

有害影响

匹美西林的副作用与其他青霉素相似。使用美西林最常见的副作用是皮疹和胃肠道不适，包括恶心和呕吐。^[1]^[4]

人们早就知道，在被身体分解时会释放叔戊酸的前体药物（如匹美西林、匹氨西林和头孢妥仑匹酯）会消耗肉碱。^[5]^[6]这不是由于药物本身，而是由于叔戊酸盐，叔戊酸盐主要通过与肉碱形成结合物而从体内清除。虽然短期使用这些药物会导致血液中肉毒碱水平显着下降，^[7]但不太可能具有临床意义；^[6]但是，长期使用会出现问题，因此不推荐使用。^[6]^[8]^[9]

参考资料

^ ^1.0 ^1.1 ^1.2 Nicolle LE. Pivmecillinam in the treatment of urinary tract infections. J Antimicrob Chemother. August 2000, 46 (Suppl A): 35–39. PMID 10969050. doi:10.1093/jac/46.suppl_1.35 .
^ Graninger W. Pivmecillinam—therapy of choice for urinary tract infection. Int J Antimicrob Agents. 22. October 2003,. Suppl 2: 73–8. PMID 14527775. doi:10.1016/S0924-8579(03)00235-8.
^ Tanphaichitra D, Srimuang S, Chiaprasittigul P, Menday P, Christensen OE. The combination of pivmecillinam and pivampicillin in the treatment of enteric fever. Infection. 1984, 12 (6): 381–3. PMID 6569851. doi:10.1007/BF01645219.
^ Selexid Tablets. electronic Medicines Compendium. June 5, 2008. ^{[失效链接]} Retrieved on August 31, 2008.
^ Holme E, Greter J, Jacobson CE, et al. Carnitine deficiency induced by pivampicillin and pivmecillinam therapy. Lancet. August 1989, 2 (8661): 469–73. PMID 2570185. doi:10.1016/S0140-6736(89)92086-2.
^ ^6.0 ^6.1 ^6.2 Brass EP. Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacol Rev. December 2002, 54 (4): 589–98 [2023-03-02]. PMID 12429869. doi:10.1124/pr.54.4.589. （原始内容存档于2019-12-14）.
^ 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. Biochem. Mol. Med. June 1995, 55 (1): 77–9. PMID 7551831. doi:10.1006/bmme.1995.1036.
^ Holme E, Jodal U, Linstedt S, Nordin I. Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children. Scand J Clin Lab Invest. September 1992, 52 (5): 361–72. PMID 1514015. doi:10.3109/00365519209088371.
^ 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, 120 (3): e739–41. PMID 17724113. doi:10.1542/peds.2007-0339.

Skeletal formula of mecillinam, the active moiety of pivmecillinam

[Nicolle-1] 1.0 ^1.1 ^1.2 Nicolle LE. Pivmecillinam in the treatment of urinary tract infections. J Antimicrob Chemother. August 2000, 46 (Suppl A): 35–39. PMID 10969050. doi:10.1093/jac/46.suppl_1.35 .

[2] Graninger W. Pivmecillinam—therapy of choice for urinary tract infection. Int J Antimicrob Agents. 22. October 2003,. Suppl 2: 73–8. PMID 14527775. doi:10.1016/S0924-8579(03)00235-8.

[3] Tanphaichitra D, Srimuang S, Chiaprasittigul P, Menday P, Christensen OE. The combination of pivmecillinam and pivampicillin in the treatment of enteric fever. Infection. 1984, 12 (6): 381–3. PMID 6569851. doi:10.1007/BF01645219.

[eMC-4] Selexid Tablets. electronic Medicines Compendium. June 5, 2008. ^{[失效链接]} Retrieved on August 31, 2008.

[5] Holme E, Greter J, Jacobson CE, et al. Carnitine deficiency induced by pivampicillin and pivmecillinam therapy. Lancet. August 1989, 2 (8661): 469–73. PMID 2570185. doi:10.1016/S0140-6736(89)92086-2.

[Brass-6] 6.0 ^6.1 ^6.2 Brass EP. Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacol Rev. December 2002, 54 (4): 589–98 [2023-03-02]. PMID 12429869. doi:10.1124/pr.54.4.589. （原始内容存档于2019-12-14）.

[7] 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. Biochem. Mol. Med. June 1995, 55 (1): 77–9. PMID 7551831. doi:10.1006/bmme.1995.1036.

[8] Holme E, Jodal U, Linstedt S, Nordin I. Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children. Scand J Clin Lab Invest. September 1992, 52 (5): 361–72. PMID 1514015. doi:10.3109/00365519209088371.

[9] 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, 120 (3): e739–41. PMID 17724113. doi:10.1542/peds.2007-0339.

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