匹美西林

匹美西林
臨床資料
商品名（英語：Drug nomenclature）	Selexid、Penomax、Coactabs
AHFS/Drugs.com	Micromedex詳細消費者藥物信息
懷孕分級	; 懷孕期間安全;
給藥途徑	口服
ATC碼	J01CA08 (WHO) ;
法律規範狀態
法律規範	處方藥（℞-only）;
藥物動力學數據
生物利用度	低
血漿蛋白結合率	5至10%（作為美西林）
藥物代謝	匹美西林水解成美西林
生物半衰期	1至3小時
排泄途徑	腎和膽，通常作為美西林
識別資訊
	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號	32886-97-8
PubChem CID	36272;
ChemSpider	33356 ;
UNII	1WAM1OQ30B;
KEGG	D02889 ;
ChEMBL	ChEMBL1650818 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID7048538 ;
ECHA InfoCard	100.046.600
化學資訊
化學式	C21H33N3O5S
摩爾質量	439.57 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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（一種廣譜青黴素類抗生素）的口服活性前藥。匹美西林是美西林的叔戊醯氧甲酯。

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匹美西林僅對革蘭氏陰性菌有活性，主要用於治療下尿路感染。在北歐國家，自1970年代以來，它已被廣泛用於該適應症。它已被提議作為急性膀胱炎經驗性治療的首選一線藥物。^[1]^[2]它也被用於治療副傷寒和志賀桿菌病。^[3]

匹美西林的副作用與其他青黴素相似。使用美西林最常見的副作用是皮疹和胃腸道不適，包括噁心和嘔吐。^[1]^[4]

人們早就知道，在被身體分解時會釋放叔戊酸的前體藥物（如匹美西林、匹氨西林和頭孢妥侖匹酯）會消耗肉鹼。^[5]^[6]這不是由於藥物本身，而是由於叔戊酸鹽，叔戊酸鹽主要通過與肉鹼形成結合物而從體內清除。雖然短期使用這些藥物會導致血液中肉毒鹼水平顯著下降，^[7]但不太可能具有臨床意義；^[6]但是，長期使用會出現問題，因此不推薦使用。^[6]^[8]^[9]

[1]
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.
[4]
Selexid Tablets. electronic Medicines Compendium. June 5, 2008.^{[失效連結]} 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.
[6]
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. （原始內容存檔於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.

Thumb — Skeletal formula of mecillinam, the active moiety of pivmecillinam

[Nicolle-1] [1]
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] [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] [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] [4]
Selexid Tablets. electronic Medicines Compendium. June 5, 2008.^{[失效連結]} Retrieved on August 31, 2008.

[5] [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]
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. （原始內容存檔於2019-12-14）.

[7] [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] [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] [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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匹美西林

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