Finibax

Base Information

• Chemical Name: Finibax
• CAS No.: 148016-81-3
• Molecular Formula: C15H24N4O6S2
• Molecular Weight: 420.511
• Pharos Ligand ID: PGFBFNGJ8MXR
• Mol file: 148016-81-3.mol

Synonyms:Finibax;(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-1-ium-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Chemical Property of Finibax

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: >186 °C dec.
• Refractive Index: 1.68
• Boiling Point: 694.8 °C at 760 mmHg
• PKA: 4.27±0.60(Predicted)
• Flash Point: 374 °C
• PSA: 195.74000
• Density: 1.59 g/cm³
• LogP: 0.83560
• Storage Temp.: -20°C Freezer
• Solubility.: In water, not known, in DMSO 20 mg/ml, in pBS 3 mg/ml
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 420.11372685
• Heavy Atom Count: 27
• Complexity: 774

Purity/Quality:

99% ^*data from raw suppliers

Doripenem Monohydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(C(=O)N2C(=C1SC3CC([NH2+]C3)CNS(=O)(=O)N)C(=O)[O-])C(C)O
• Isomeric SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H]([NH2+]C3)CNS(=O)(=O)N)C(=O)[O-])[C@@H](C)O
• Recent EU Clinical Trials: A Randomized, Open-Label, Multicenter Study to Assess the Safety and Tolerability of Doripenem Compared With Imipenem in the Treatment of Subjects With Complicated Intra-Abdominal Infections or Ventilator-Associated Pneumonia
• Description: Doripenem monohydrate is an ultra-broad-spectrum injectable β-lactam antibiotic and belongs to the subgroup of carbapenems. It was introduced by Shionogi Co. of Japan under the brand name Finibax in 2005 and is being marketed outside Japan by Johnson & Johnson. Doripenem act by decreases the process of cell wall growth, which eventually leads to elimination of the infectious cell bacteria together. It is used for treatment of bacterial respiratory and urinary tract infections. Doripenem 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.
• Uses: Doripenem hydrate is used to treat complicated urinary infection including Pyelonephritis caused by E.coli. Doripenem hydrate is promoted in the United States as DORIBAX(R). This drug is synthesized from p-nitrobenzyl-protected enolphosphate 2b and N-(p-nitrobenzyloxycarbonyl)-protected aminomethylpyrrolidine.
• Clinical Use: Doripenem is indicated for use for the treatment of intra-abdominal infections, and complicated urinary tract infections.Complicated urinary tract infections, including pyelonephritisNosocomial pneumonia, including ventilator-associated pneumonia (Europe)

Technology Process of Finibax

There total 62 articles about Finibax 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: 97.0%

(+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3S,5S)-5-[(aminosulfonylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrobenzyl ester acetate → doripenem (148016-81-3)

Guidance literature:

With 2,6-dimethylpyridine; platinum on activated charcoal; hydrogen; In ethanol; water; at 20 - 30 ℃; for 1h; under 19001.3 Torr; pH=5 - 6;

Reference yield: 94.0%

(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(N-sulfamoylamino) methylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid allyl ester (148017-61-2) → doripenem (148016-81-3)

Guidance literature:

With N-ethyl-N-phenylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; isopropyl alcohol; at 25 ℃; for 4.5h; Product distribution / selectivity;

Reference yield: 90.0%

(+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(3S,5S)-5-[(aminosulfonylamino)-methyl]-3-pyrrolidinyl]thio]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrobenzyl ester sulfate → doripenem (148016-81-3)

Guidance literature:

With 4-methyl-morpholine; hydrogenchloride; 10 wt% Pd(OH)2 on carbon; hydrogen; In tetrahydrofuran; water; at 30 - 40 ℃; for 5h; under 760.051 Torr; pH=7 - 8;

upstream raw materials:

C₄₁H₄₈N₄O₁₃S₂

diphenylmethyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(3S,5S)-1-(tert-butoxycarbonyl)-5-[N-sulfamoyl-N-(tert-butoxycarbonyl)aminomethyl]pyrrolidin-3-yl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(1R,5S,6S)-2-[(3S,5S)-1-allyloxycarbonyl-5-(N-sulfamoylamino) methylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid allyl ester

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Refernces

• 1、 Raju, K. Rajasekhara,Mahesh,Reddy, B. Shankar,Raju, K. Mohana. "Improved Large-scale One-pot Synthesis of Pure Doripenem Hydrate (S-4661)". . p. 342 - 349. Retrieved 2016.
• 2、 -. "A method for preparing Doripenem (by machine translation)". Paragraph 0007; 0017. . Retrieved 2016/10/08.