364622-82-2

Basic information

• Product Name: Doripenem hydrate
• Synonyms: (+)-(4r,5s,6s)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3s,5s)-5-[(sulfamoylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid hydrate;doripenem hydrate;DoripeneM Crude;1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[(3S,5S)-5-[[(aminosulfonyl)amino]methyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-, hydrate;(4R,5S,6S)-6-[(1R)-1-Hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;Doripenem monohydrate, >=99%;(4R,5S,6S)-6-((R)-1-Hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((sulfamoylamino)methyl)pyrroli
• CAS NO: 364622-82-2
• Molecular Formula: C₁₅H₂₄N₄O₆S₂*H₂O
• Molecular Weight: 438.51954
• EINECS: 1312995-182-4
• Product Categories: Doribax, Doripenem monohydrate, S-4661, Finibax;Inhibitors
• Mol File: 364622-82-2.mol

Chemical Properties

• Melting Point: 173°C(dec.)(lit.)
• Boiling Point: 694.8 °C at 760 mmHg
• Flash Point: 374 °C
• Appearance: white to beige/
• Vapor Pressure: 2.49E-22mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble5mg/mL, clear (warmed)
• BRN: 15340136
• CAS DataBase Reference: Doripenem hydrate(CAS DataBase Reference)
• NIST Chemistry Reference: Doripenem hydrate(364622-82-2)
• EPA Substance Registry System: Doripenem hydrate(364622-82-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 364622-82-2(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Doripenem hydrate is used as a broad-spectrum antibiotic for the treatment of various infections, such as hospital-acquired pneumonia, complicated intra-abdominal or urinary-tract infections, and pyelonephritis.
2. Used in Analytical Chemistry:
Doripenem monohydrate can be used as a precursor for the preparation of doripenem, which may be used as an analytical reference standard for the determination of doripenem in various matrices:
a. Bovine muscle by liquid chromatography combined with tandem mass spectrometry (LC-MS/MS).
b. Bulk drug and formulations by high-performance thin-layer chromatography (HPTLC).
c. Medicinal products by capillary electrophoresis coupled to an ultraviolet (UV) detector, as well as micellar electrokinetic chromatography (MEKC) with UV detection.
3. Used in Antimicrobial Research:
Doripenem hydrate is used as an ultra-broad-spectrum injectable antibiotic, particularly active against Pseudomonas aeruginosa, for research and development in the field of antimicrobial agents.
4. Used in Drug Development:
Doripenem hydrate serves as a key component in the development of new antibiotics and drug formulations, targeting resistant bacterial strains and improving the efficacy of existing treatments.

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.

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

Upstream product

• 491878-07-0 (4R,5S,6S)-3-[[(3S,5S)-5-[[(aminosulfonyl)amino]methyl]-1-[[(4-nitrophenyl)methoxy]carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester 

Relevant articles and documents

Crystalline form doripenem monohydrate and preparation method thereof

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.