Ritipenem

Base Information

• Chemical Name: Ritipenem
• CAS No.: 84845-57-8
• Molecular Formula: C₁₀H₁₂N₂O₆S
• Molecular Weight: 288.281
• UNII: D4SL77931L
• DSSTox Substance ID: DTXSID60868840
• Nikkaji Number: J554.937J
• Wikipedia: Ritipenem
• Wikidata: Q7336745
• NCI Thesaurus Code: C72840
• ChEMBL ID: CHEMBL70088
• Mol file: 84845-57-8.mol

Synonyms:FCE 22101;FCE-22101;ritipenem;ritipenem sodium

Chemical Property of Ritipenem

Chemical Property:

• Vapor Pressure: 3.42E-20mmHg at 25°C
• Boiling Point: 659.4°Cat760mmHg
• Flash Point: 352.6°C
• PSA: 155.46000
• Density: 1.71g/cm³
• LogP: -0.07180
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 288.04160728
• Heavy Atom Count: 19
• Complexity: 490

Purity/Quality:

98%min ^*data from raw suppliers

Ritipenem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C2N(C1=O)C(=C(S2)COC(=O)N)C(=O)O)O
• Isomeric SMILES: C[C@H]([C@@H]1[C@@H]2N(C1=O)C(=C(S2)COC(=O)N)C(=O)O)O
• Description: Ritipenem is a synthetic b-lactam antibiotic of the penem class that has a broad antimicrobial spectrum and high resistance to b-lactamases. Since it is stable in relation to renal dehydropeptidase-I, ritipenem does not require concomitant administration of an inhibitor of this enzyme.
• Uses: Ritipenem is a penem antibiotic.
• Clinical Use: Ritipenem has been used in a limited number of clinical conditions in which the use of a carbapenem that can be administered both parenterally and orally was considered a possible advantage. Ritipenem is not currently licensed for clinical use by the US FDA. Only a few clinical studies have assessed the role of ritipenem therapy, and these have been in the treatment of respiratory tract or urinary tract infections, but results appear generally disappointing.

Technology Process of Ritipenem

There total 3 articles about Ritipenem 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:

(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-carbamoyloxymethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid acetoxymethyl ester (138471-46-2) → ritipenem (84845-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / n-Bu₄NF / acetic acid; tetrahydrofuran / Ambient temperature

2: phosphate buffer (pH 7) / PLE

With phosphate buffer; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetic acid;

DOI:10.1016/S0040-4039(00)79192-1

Reference yield:

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-carbamoyloxy-acetylsulfanyl)-4-oxo-azetidin-1-yl]-oxo-acetic acid acetoxymethyl ester → ritipenem (84845-57-8)

Guidance literature:

Multi-step reaction with 3 steps

1: P(OEt)3 / Heating

2: 76 percent / n-Bu₄NF / acetic acid; tetrahydrofuran / Ambient temperature

3: phosphate buffer (pH 7) / PLE

With phosphate buffer; tetrabutyl ammonium fluoride; triethyl phosphite; In tetrahydrofuran; acetic acid;

DOI:10.1016/S0040-4039(00)79192-1

Reference yield:

[14C]-FCE22891 (87238-52-6,99376-22-4) → ritipenem (84845-57-8)

Guidance literature:

With phosphate buffer; Yield given; PLE;

DOI:10.1016/S0040-4039(00)79192-1

upstream raw materials:

[14C]-FCE₂₂₈₉₁

(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-carbamoyloxymethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid acetoxymethyl ester

Refernces