海他西林

海他西林英語:Hetacillin)是一種β-內酰胺類抗生素,屬於氨基青黴素家族。它是一種前藥,本身無抗菌活性,[1]但在人體內迅速分解出丙酮,形成氨苄青黴素[2]對多種細菌均有活性。

海他西林
臨床資料
商品名英語Drug nomenclatureHetacin、Versapen
AHFS/Drugs.com藥物獸用信息
給藥途徑乳腺注射
ATC碼
法律規範狀態
法律規範
識別資訊
  • (2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS號3511-16-8  checkY
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard英語CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.020.466 編輯維基數據鏈接
化學資訊
化學式C19H23N3O4S
摩爾質量389.47 g·mol−1
3D模型(JSmol英語JSmol
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)c4ccccc4)C(=O)O)C
  • InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1 ☒N
  • Key:DXVUYOAEDJXBPY-NFFDBFGFSA-N ☒N

給藥

海他西林可以口服。它的鉀鹽海他西林鉀通過靜脈[3]肌肉注射給藥。[4]它以商品名Hetacin出售,用於獸醫乳腺注射。[5]

當發現海他西林與氨苄西林相比沒有優勢時,海他西林被撤出市場。[6]

化學

海他西林由氨苄青黴素和丙酮製備而成。在水溶液中它不穩定,在37°C和pH7下半衰期為15至30分鐘,並迅速再次釋放丙酮。[7]

與氨苄西林相反,海他西林僅被細菌酶β-內酰胺酶輕微分解,至少在體外是這樣。

參考資料

  1. ^ Hetacillin. Drugbank. [2023-03-01]. (原始內容存檔於2016-08-08). 
  2. ^ Sutherland R, Robinson OP. Laboratory and pharmacological studies in man with hetacillin and ampicillin. British Medical Journal. June 1967, 2 (5555): 804–8. PMC 1843140 . PMID 5182358. doi:10.1136/bmj.2.5555.804. 
  3. ^ Tsuji Y, Tomita M. [Clinical effect of intravenous injection of potassium hetacillin (Versapen 'Bristol') on pre- and post-operative infections] (in Japanese). The Japanese Journal of Antibiotics. August 1970, 23 (4): 400–2. PMID 5312791. 
  4. ^ Hara M, Takemoto S, Kawazu T. [Therapeutic experience with intramuscular injection of hetacillin (Versapen 'Bristol') in infection in children] (in Japanese). The Japanese Journal of Antibiotics. December 1970, 23 (5): 482–6. PMID 5314634. 
  5. ^ Hetacin-K Intramammary Infusion for 藥物獸用信息
  6. ^ Smith JT, Hamilton-Miller J. Hetacillin: A Chemical and Biological Comparison with Ampicillin. Chemotherapy. 1970, 15 (6): 366–78. PMID 5514976. doi:10.1159/000220703. 
  7. ^ Faine S, Harper M. Independent antibiotic actions of hetacillin and ampicillin revealed by fast methods. Antimicrobial Agents and Chemotherapy. January 1973, 3 (1): 15–8. PMC 444353 . PMID 4597707. doi:10.1128/aac.3.1.15.