Doripenem hydrate

Base Information

• Chemical Name: Doripenem hydrate
• CAS No.: 364622-82-2
• Molecular Formula: C15H24N4O6S2^.H2O
• Molecular Weight: 438.526
• European Community (EC) Number: 680-392-3
• UNII: 4B035T6NKT
• DSSTox Substance ID: DTXSID60957788
• Wikidata: Q27259357
• ChEMBL ID: CHEMBL4303454
• Mol file: 364622-82-2.mol

Synonyms:Doripenem hydrate;364622-82-2;Doripenem monohydrate;Dripenem hydrate;Finibax;Doripenem (monohydrate);Doripenem hydrate [JAN];UNII-4B035T6NKT;4B035T6NKT;(4R,5S,6S)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((sulfamoylamino)methyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 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;hydrate;(4R,5S,6S)-6-((R)-1-Hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((sulfamoylamino)methyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid h2o;(4R,5beta)-3-(((3S)-5beta-((sulfamoylamino)methyl)pyrrolidine-3beta-yl)thio)-4alpha-Methyl-6beta-((1R)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hepta-2-ene-2-carboxylic acid hydrate;C15H24N4O6S2.H2O;Dripenem;Doribax (TN);S 4661 monohydrate;(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;Doripenem hydrate (JP17);SCHEMBL195434;DORIPENEM HYDRATE [MI];CHEMBL4303454;CHEBI:31518;HY-B0187A;DTXSID60957788;Doripenem hydrate, >=98% (HPLC);MFCD09749887;s1374;AKOS022186077;DORIPENEM MONOHYDRATE [WHO-DD];CCG-269113;CS-2076;KS-1446;A51073;D-9050;D01836;Doripenem, Antibiotic for Culture Media Use Only;Q27259357;Z2756516871;Doripenem monohydrate, VETRANAL(TM), analytical standard;(4R,5.BETA.)-3-(((3S)-5.BETA.-((SULFAMOYLAMINO)METHYL)PYRROLIDINE-3.BETA.-YL)THIO)-4.ALPHA.-METHYL-6.BETA.-((1R)-1-HYDROXYETHYL)-7-OXO-1-AZABICYCLO(3.2.0)HEPTA-2-ENE-2-CARBOXYLIC ACID HYDRATE;(4R,5S,6S)-6-((R)-1-Hydroxyethyl)-4-methyl-7-oxo-3-(((3S,5S)-5-((sulfamoylamino)methyl)pyrrolidin-3-yl)thio)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid h2o;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-, monohydrate, (4R,5S,6S)-;6-(1-Hydroxyethyl)-4-methyl-7-oxo-3-({5-[(sulfamoylamino)methyl]pyrrolidin-3-yl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid--water (1/1)

Chemical Property of Doripenem hydrate

Chemical Property:

• Appearance/Colour: white power
• Vapor Pressure: 2.49E-22mmHg at 25°C
• Melting Point: 173°C(dec.)(lit.)
• Boiling Point: 694.8 °C at 760 mmHg
• Flash Point: 374 °C
• PSA: 204.97000
• LogP: 0.77130
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble5mg/mL, clear (warmed)
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 438.12429153
• Heavy Atom Count: 28
• Complexity: 780

Purity/Quality:

99% ^*data from raw suppliers

Doripenem Monohydrate >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(C(=O)N2C(=C1SC3CC(NC3)CNS(=O)(=O)N)C(=O)O)C(C)O.O
• Isomeric SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)CNS(=O)(=O)N)C(=O)O)[C@@H](C)O.O
• Recent EU Clinical Trials: An Open-Label Study to Evaluate the Penetration of Doripenem in Cerebrospinal Fluid After Doripenem Administration in Pediatric Subjects Less Than 1 Year
• Recent NIPH Clinical Trials: None
• 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.
• Uses: Doripenem monohydrate is a broad spectrum antibiotic belonging to the class of antibiotics called carbapenems. 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

Technology Process of Doripenem hydrate

There total 1 articles about Doripenem hydrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(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 (491878-07-0) → (+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3S,5S)-5-(sulfamoylaminomethyl)pyrrolidin-3-yl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monohydrate (364622-82-2)

Guidance literature:

With potassium dihydrogenphosphate; water; zinc; In tetrahydrofuran; at 30 - 35 ℃; for 2h;

upstream raw materials:

(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

Refernces