364622-82-2 Usage
Description
Doripenem hydrate is a carbapenem derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of infections such as HOSPITAL-ACQUIRED PNEUMONIA, and complicated intra-abdominal or urinary-tract infections, including PYELONEPHRITIS.Doripenem hydrate was first approved by Pharmaceuticals and Medical Devices Agency of Japan (PMDA) on July 25, 2005, then approved by the U.S. Food and Drug Administration (FDA) on Oct 12, 2007, and approved by European Medicines Agency (EMA) on July 25, 2008. It was developed by Shionogi and Janssen, then marketed as Finibax? in Japan and as Doribax? in the US by Shionogi and as Doribax? by Janssen in BE.
Chemical Properties
Doripenem Hydrate occurs as a white to pale yellow-brown-white crystalline powder. It is sparingly soluble in water, slightly soluble in methanol, and practically insoluble in ethanol (99.5). It is gradually colored to pale yellow-brown-white by light.
Uses
Different sources of media describe the Uses of 364622-82-2 differently. You can refer to the following data:
1. Doripenem monohydrate is a broad spectrum antibiotic belonging to the class of antibiotics called carbapenems.
2. Doripenem (doripenem monohydrate) is an ultra-broad spectrum injectable antibiotic. It is a beta-lactam and belongs to the subgroup of carbapenems. It is particularly active against Pseudomonas aeruginosa
Application
Doripenem monohydrate can be used as the precursor for the preparation of doripenem which may be used as an analytical reference standard for the determination of doripenem in:Bovine muscle by liquid chromatography combined with tandem mass spectrometry (LC-MS/MS).Bulk drug and formulations by high performance thin layer chromatography (HPTLC).Medicinal products by capillary electrophoresis coupled to ultraviolet (UV) detector as well as micellar electrokinetic chromatography (MEKC) with UV detection.
Biochem/physiol Actions
Doripenem is an ultra-broad spectrum carbopenem antibiotic. Doripenem is active against both gram-positive and gram-negative bacteria.
Mode of action
Doripenem hydrate is a β-lactam antibiotic of the carbapenem class. It is effective against extended spectrum beta-lactamase (ESBL) producing Enterobacteriaceae, a microbe resistant to many first line beta-lactam antibiotics and certain cephalosporins. Doripenem hydrate is sparingly soluble in aqueous solution.β-lactams interfere with PBP (penicillin binding protein) activity involved in the final phase of peptidoglycan synthesis. PBP's are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to β-lactams is commonly due to cells containing plasmid encoded β-lactamases; however, carbapenems, including doripenem, are highly resistant to β-lactamases.
references
[1]. yutaka nishino, makoto kobayashi, taneyoshi shinno, et al. practical large-scale synthesis of doripenem: a novel 1a-methylcarbapenem antibiotic. organic process research & development, 2003, 7:846-850.[2]. masakatsu tsuji, yoshikazu ishii, akira ohno, et al. in vitro and in vivo antibacterial activities of s-4661, a new carbapenem. antimicrobial agents and chemotherapy, 1998, 42(1): 94-99.[3]. yunhua chen, elizabeth garber, qiuqu zhao, et al. in vitro activity of doripenem (s-4661) against multidrug-resistant gram-negative bacilli isolated from patients with cystic fibrosis. antimicrobial agents and chemotherapy, 2005, 49(6):2510-2511.
Check Digit Verification of cas no
The CAS Registry Mumber 364622-82-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,6,4,6,2 and 2 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 364622-82:
(8*3)+(7*6)+(6*4)+(5*6)+(4*2)+(3*2)+(2*8)+(1*2)=152
152 % 10 = 2
So 364622-82-2 is a valid CAS Registry Number.
InChI:InChI=1/C15H24N4O6S2.H2O/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25;/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25);1H2/t6-,7-,8+,9+,10-,11-;/m1./s1
364622-82-2Relevant articles and documents
Crystalline form doripenem monohydrate and preparation method thereof
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Paragraph 0047; 0048; 0049; 0050, (2016/10/09)
The present invention relates to a method for preparing doripenem monohydrate, and more particularly, to a method for preparing doripenem monohydrate produced through the steps of: conducting a deprotecting reaction by reacting doripenem-PNB with a zinc powder in a mixture solution including an organic solvent and an aqueous phosphate solution (step 1); removing phosphate from the product of step 1 (step 2); and crystallizing the product of step 2 using a solvent for crystallization to crystallize the doripenem monohydrate (step 3). According to the method for preparing the doripenem monohydrate, the method can be conducted at room temperature and at a moderate atmospheric pressure without using an expensive metal catalyst and special equipment. Thus, the method is economical and safe, and the doripenem monohydrate can be obtained at a high yield. Accordingly, the preparation method of the present invention can be usefully applied in an industrial field related to doripenem monohydrate.
