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ドリペネム

ドリペネム 化学構造式
148016-81-3
CAS番号.
148016-81-3
化学名:
ドリペネム
别名:
ドリペネム
英語化学名:
Doripenem
英語别名:
S 4661;DORIPENEM;Donipenem;DoripeneM Monohydrate;InterMediates of DoripeneM;(4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-Methyl-7-oxo-3-((3S,5S)-5-((sulfaMoylaMino)Methyl)pyrrolidin-3-ylthio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;(+)-(4r,5s,6s)-6-[(1r)-1-hydro-xyethyl]-4-methyl-7-oxo-3-[[(3s,5s)-5-[(sulfamoylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;(4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid;Doripenem/(+)-(4R,5S,6S)-6-[(1R)-1-Hydro-xyethyl]-4-methyl-7-oxo-3-[[(3S,5S)-5-[(sulfamoylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;(+)-(4R,5S,6S)-6-[(1R)-1-Hydro-xyethyl]-4-methyl-7-oxo-3-[[(3S,5S)-5-[(sulfamoylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate
CBNumber:
CB1547391
化学式:
C15H24N4O6S2
分子量:
420.509
MOL File:
148016-81-3.mol

ドリペネム 物理性質

融点 :
>186°C dec.
貯蔵温度 :
-20°C Freezer
CAS データベース:
148016-81-3

安全性情報

ドリペネム 価格 もっと(5)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01TRCD534800 ドリペネム
Doripenem
148016-81-3 5mg ¥11300 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01TRCD534800 ドリペネム
Doripenem
148016-81-3 10mg ¥12500 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01TRCD534800 ドリペネム
Doripenem
148016-81-3 25mg ¥27500 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01TRCD534800 ドリペネム
Doripenem
148016-81-3 50mg ¥53800 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01TRCD534800 ドリペネム
Doripenem
148016-81-3 100mg ¥82500 2018-12-26 購入

ドリペネム 化学特性,用途語,生産方法

説明

Doripenem is a parenteral carbapenem antibiotic launched in Japan for the treatment of bacterial respiratory and urinary tract infections. It is a 1β-methyl carbapenem derivative, and it is the fourth analog to be marketed in this series following the launch of meropenem, biapenem, and ertapenem in previous years. The introduction of a 1β-methyl group to the carbapenem skeleton enhances metabolic stability to renal dehydropeptidase-1 (DHP-1) and leads to improved antibacterial potency. The mechanism of action is likely to involve covalent modification of peptidoglycan biosynthetic enzymes responsible for catalyzing the final transpeptidation step of cell wall biosynthesis. The chemical synthesis of doripenem involves the coupling of a commercially available 4-nitrobenzyl protected 1β-methylcarbapenem enolphosphate intermediate with a protected version of 2-(sulfamidomethyl)- 4-mercaptopyrrolidine as the key step. The requisite pyrrolidine intermediate is prepared in six steps starting from trans-4-hydroxy-L-proline. In vitro, doripenem exhibits activity similar to that of imipenem against Grampositive pathogens, and to that of meropenem against Gram-negative pathogens. The key differentiator for doripenem is its superior activity against Pseudomonas aeruginosa (MIC90=3.13 μg/mL) as compared with meropenem and imipenem. Additionally, it possesses higher stability than imipenem or meropenem against mammalian dehydropeptidase I, and it is stable to most serine-based beta-lactamases. The route of administration of doripenem is either intravenous or intramuscular. It has low plasma protein binding (8.1%), and the primary route of elimination is renal.

化学的特性

White to Off-White Powder

Originator

Shinogi (Japan)

使用

Antibacterial agent

使用

antibiotic

brand name

Finibax

抗菌性

Activity against aerobic and anaerobic Gram-negative pathogens is similar to that of other carbapenems. MIC values against Gram-positive cocci are generally higher than for imipenem and those for Gram-negative bacilli are lower.

薬物動態学

Cmax 500 mg intravenous infusion (1 h): c. 23 mg/L after 1 h
500 mg intravenous infusion (4 h): c. 8 mg/L
Plasma half-life: 1 h
Volume of distribution: 16.8 L (steady state)
Plasma protein binding: 8.1%
Absorption and distribution
Doripenem is not absorbed after oral administration. It penetrates well into most tissues and fluid, achieving concentrations matching or exceeding those required to inhibit most susceptible bacteria at the site of infection for the approved indications.
Metabolism and excretion
Metabolism of doripenem to the microbiologically inactive ring-opened metabolite occurs primarily by renal dehydropeptidase. Based on area under the concentration–time curve (AUC) values in plasma following a single 500 mg dose in healthy volunteers, 18% appears as metabolite and the rest as unchanged drug.
Excretion is primarily by the renal route. Within 24 h after dosing, 78.7% and 18.5% of the dose was recovered in urine as unchanged drug and the ring-opened metabolite, respectively. After administration of radiolabeled doripenem, 0.7% of the total radioactivity was recovered in feces after 1 week.

臨床応用

Complicated intra-abdominal infections
Complicated urinary tract infections, including pyelonephritis
Nosocomial pneumonia, including ventilator-associated pneumonia (Europe)

副作用

Seizure and central nervous system (CNS) side effects are observed rarely (<1%), though headache is reported by 2.3% of patients. Other common drug-related adverse reactions are diarrhea (2.0%), nausea (1.9%), anemia (1.4%) and phlebitis (1.4%). Hypersensitivity reactions related to intravenous administration of the study drug and Clostridium difficile colitis occurred at a rate of less than 1%. However, patients with a history of hypersensitivity reactions to other β-lactam agents should be treated cautiously.

ドリペネム 上流と下流の製品情報

原材料

準備製品


ドリペネム 生産企業

Global( 137)Suppliers
名前 電話番号 ファックス番号 電子メール 国籍 製品カタログ 優位度
Henan DaKen Chemical CO.,LTD.
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Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20786 55
PI & PI BIOTECH INC.
020-81716320
020-81716319 Sales@pipitech.com CHINA 2548 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 663 60
Biochempartner
0086-13720134139
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Chemwill Asia Co.,Ltd.
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QUALITY CONTROL CHEMICALS INC.
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career henan chemical co
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Beijing Lunarsun Pharmaceutical Co.,LTD. 86-10-64911848-8020.8010
86-10-64946614 sales@lunarsun.com.cn China 96 60
Shanghai Boyle Chemical Co., Ltd.
86-21-57758967 sales@boylechem.com China 2928 55

148016-81-3(ドリペネム)キーワード:


  • 148016-81-3
  • (+)-(4r,5s,6s)-6-[(1r)-1-hydro-xyethyl]-4-methyl-7-oxo-3-[[(3s,5s)-5-[(sulfamoylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • DORIPENEM
  • Doripenem/(+)-(4R,5S,6S)-6-[(1R)-1-Hydro-xyethyl]-4-methyl-7-oxo-3-[[(3S,5S)-5-[(sulfamoylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • (4R,5S,6S)-3-[[(3S,5S)-5-[[(Aminosulfonyl)amino]methyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid
  • S 4661
  • (4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-Methyl-7-oxo-3-((3S,5S)-5-((sulfaMoylaMino)Methyl)pyrrolidin-3-ylthio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • InterMediates of DoripeneM
  • DoripeneM Monohydrate
  • (+)-(4R,5S,6S)-6-[(1R)-1-Hydro-xyethyl]-4-methyl-7-oxo-3-[[(3S,5S)-5-[(sulfamoylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate
  • Donipenem
  • ドリペネム
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