Loracarbef

Base Information

• Chemical Name: Loracarbef
• CAS No.: 76470-66-1
• Molecular Formula: C16H16 Cl N3 O4
• Molecular Weight: 349.774
• UNII: W72I5ZT78Z
• DSSTox Substance ID: DTXSID7023223
• Nikkaji Number: J362.169C
• Wikipedia: Loracarbef
• Wikidata: Q979521
• NCI Thesaurus Code: C61815
• Metabolomics Workbench ID: 42802
• ChEMBL ID: CHEMBL1013
• Mol file: 76470-66-1.mol

Synonyms:Carbac;KT 3777;KT-3777;Lorabid;loracarbef;loracarbef monohydrate;Lorafem;Lorax;LY 163892;LY-163892;LY163892

Chemical Property of Loracarbef

Chemical Property:

• Vapor Pressure: 1.95E-18mmHg at 25°C
• Melting Point: >196°C (dec.)
• Boiling Point: 662.2°C at 760 mmHg
• Flash Point: 354.3°C
• PSA: 112.73000
• Density: 1.52g/cm³
• LogP: 1.73990
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Acid (slightly)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 349.0829337
• Heavy Atom Count: 24
• Complexity: 600

Purity/Quality:

98%Min ^*data from raw suppliers

Loracarbef ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=C(N2C1C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)Cl
• Isomeric SMILES: C1CC(=C(N2[C@H]1[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)Cl
• Description: Loracarbef is a synthetic C-5 “carba” analogue of cefaclor. The smaller methylene moiety (as compared to sulfur) would be expected to make loracarbef more reactive/potent, and this seems to be the case. It is more stable chemically, however, and this adds to its virtues.
• Uses: An antibiotic, a synthetic carbacephem analogue of cefaclor, and is more stable chemically.
• Therapeutic Function: Antibiotic
• Clinical Use: Loracarbef (Lorabid) is the first of a series of carbacephemsprepared by total synthesis to be introduced. Carbacephemsare isosteres of the cephalosporin (or △ 3-cephem) antibioticsin which the 1-sulfur atom has been replaced by a methylene(CH2) group. Loracarbef is isosteric with cefaclor and hassimilar pharmacokinetic and microbiological properties.Thus, the antibacterial spectrum of activity resembles thatof cefaclor, but it has somewhat greater potency againstH. influenzae and M. catarrhalis, including β-lactamase–producing strains. Unlike cefaclor, which undergoes degradationin human serum, loracarbef is chemically stable inplasma. It is absorbed well orally. Oral absorption is delayedby food. The half-life in plasma is about 1 hour.

Technology Process of Loracarbef

There total 23 articles about Loracarbef 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: 78.2%

(R)-Phenylglycine methyl ester (24461-61-8) + (6R*,7S*)-3-chloro-7-amino-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid (76497-76-2) → loracarbef (76470-66-1)

Guidance literature:

In water; at 20 ℃; for 8.5h; Kluyvera citrophila KY-7844, phosphate buffer (pH 6.75);

DOI:10.1248/cpb.37.1239

Reference yield:

mono N,N-DMAc solvate of loracarbef → loracarbef (76470-66-1)

Guidance literature:

mono N,N-DMAc solvate of loracarbef; With hydrogenchloride; pyrographite; In water; for 0.5 - 0.666667h;

With ammonia; In water; at 50 - 55 ℃; for 1h; pH=1.8 - 1.9;

Reference yield:

mono N-methylpyrrolidone solvate of loracarbef → loracarbef (76470-66-1)

Guidance literature:

mono N-methylpyrrolidone solvate of loracarbef; With hydrogenchloride; pyrographite; In water; for 0.5 - 0.666667h;

With ammonia; In water; at 50 - 55 ℃; for 1 - 1.08333h; pH=1.8 - 4.8;

upstream raw materials:

(R)-Phenylglycine methyl ester

(6R*,7S*)-3-chloro-7-amino-8-oxo-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid

(6R,7S)-3-Chloro-7-[(R)-2-((E)-2-methoxycarbonyl-1-methyl-vinylamino)-2-phenyl-acetylamino]-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(6R,7S)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Downstream raw materials:

3-chloro-7-[2-(5-methyl-3,4-dioxocyclohexa-1,5-dienylamino)-2-phenylacetylamino]-8-oxo-5-azabicyclo[4.2.0]oct-3-ene-4-carboxylic acid

C₄₁H₄₀ClN₃O₅S

Refernces

• 1、 Matsukuma,Yoshiye,Mochida,Hashimoto,Sato,Okachi,Hirata. "Synthesis and biological evaluation of 3-chloro-1-carbacephem compounds". . p. 1239 - 1244. Retrieved 2007/10/02.