匹氨西林

匹氨西林
臨床資料
其他名稱	匹凡西林; 吡呋青黴素; 匹氨青黴素; 吡呋氨卡西林
AHFS/Drugs.com	Micromedex詳細消費者藥物信息
給藥途徑	口服
ATC碼	J01CA02 (WHO) ;
藥物動力學數據
排泄途徑	腎 (76%)
識別資訊
	IUPAC命名法 2,2-Dimethylpropanoyloxymethyl (2S,5R,6R)-6[(2R)-2-amino-2-phenyl-acetyl]amino3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; ;
CAS編號	33817-20-8
PubChem CID	33478;
DrugBank	DB01604 ;
ChemSpider	30899 ;
UNII	0HLM346LL7;
KEGG	D08396 ;
ChEBI	CHEBI:8255 ;
ChEMBL	ChEMBL323354 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID1045459 ;
ECHA InfoCard	100.046.975
化學資訊
化學式	C22H29N3O6S
摩爾質量	463.55 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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;
	InChI 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 ; Key:ZEMIJUDPLILVNQ-ZXFNITATSA-N ;

匹氨西林（英語：Pivampicillin）是安比西林的叔戊酰氧甲酯。它是一種前體藥物，由於與安比西林相比具有更高的親脂性，因此被認為可以提高安比西林的口服生物利用度。

不利影響

人體分解時會釋放叔戊酸的前體藥物（如匹氨西林、匹美西林和頭孢妥侖匹酯）早就被認為會消耗肉鹼。^[1]^[2]這種作用不是由於藥物本身，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鹼水平顯着下降，^[3]但不太可能具有臨床意義；^[2]但是，不建議長期使用。^[2]^[4]^[5]

合法性

在全球範圍內，匹氨西林僅在丹麥售賣，PharmaCoDane以Pondocillin®出售，利奧製藥以Miraxid®出售。^[6]

參考資料

^ 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.
^ ^2.0 ^2.1 ^2.2 Brass EP. Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacol Rev. December 2002, 54 (4): 589–98 [2023-02-28]. PMID 12429869. doi:10.1124/pr.54.4.589. （原始內容存檔於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.
^ Pondocillin®. [2016-09-18]. （原始內容存檔於2023-02-28）.

[1] 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-2] 2.0 ^2.1 ^2.2 Brass EP. Pivalate-generating prodrugs and carnitine homeostasis in man. Pharmacol Rev. December 2002, 54 (4): 589–98 [2023-02-28]. PMID 12429869. doi:10.1124/pr.54.4.589. （原始內容存檔於2019-12-14）.

[3] 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.

[4] 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.

[5] 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.

[6] Pondocillin®. [2016-09-18]. （原始內容存檔於2023-02-28）.

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臨床資料

其他名稱	匹凡西林吡呋青黴素匹氨青黴素吡呋氨卡西林
AHFS/Drugs.com	Micromedex詳細消費者藥物信息
給藥途徑	口服
ATC碼	J01CA02 (WHO)
藥物動力學數據
排泄途徑	腎 (76%)
識別資訊
IUPAC命名法 2,2-Dimethylpropanoyloxymethyl (2S,5R,6R)-6[(2R)-2-amino-2-phenyl-acetyl]amino3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
CAS編號	33817-20-8 ^Y
PubChem CID	33478
DrugBank	DB01604^Y
ChemSpider	30899^Y
UNII	0HLM346LL7
KEGG	D08396^Y
ChEBI	CHEBI:8255^Y
ChEMBL	ChEMBL323354^N
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID1045459
ECHA InfoCard	100.046.975
化學資訊
化學式	C₂₂H₂₉N₃O₆S
摩爾質量	463.55 g·mol⁻¹
3D模型（JSmol（英語：JSmol））	交互式圖像
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
InChI 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 Key:ZEMIJUDPLILVNQ-ZXFNITATSA-N^Y