Iclaprim

Base Information

• Chemical Name: Iclaprim
• CAS No.: 192314-93-5
• Molecular Formula: C₁₉H₂₂N₄O₃
• Molecular Weight: 354.409
• European Community (EC) Number: 606-269-6
• UNII: 42445HUU0O
• DSSTox Substance ID: DTXSID70870191
• Nikkaji Number: J1.180.368G
• Wikipedia: Iclaprim
• Wikidata: Q907480
• NCI Thesaurus Code: C65877
• Pharos Ligand ID: 3SG4TTYVPRCW
• Metabolomics Workbench ID: 149749
• ChEMBL ID: CHEMBL134561
• Mol file: 192314-93-5.mol

Synonyms:AR 100;AR-100;iclaprim

Chemical Property of Iclaprim

Chemical Property:

• Vapor Pressure: 3.84E-15mmHg at 25°C
• Boiling Point: 616.7°Cat760mmHg
• PKA: 7.07±0.10(Predicted)
• Flash Point: 326.8°C
• PSA: 105.51000
• Density: 1.332g/cm³
• LogP: 3.59560
• Water Solubility.: 14g/L at 20℃
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 354.16919058
• Heavy Atom Count: 26
• Complexity: 515

Purity/Quality:

99.9% ^*data from raw suppliers

Iclaprim ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C(C=CC(O2)C3CC3)C(=C1)CC4=CN=C(N=C4N)N)OC
• Recent ClinicalTrials: Phase 3 Study to Evaluate Safety and Efficacy of Iclaprim Versus Vancomycin for ABSSSI: REVIVE-2
• Recent EU Clinical Trials: Randomized, double-blind, multicenter study to evaluate efficacy and safety of intravenous iclaprim versus vancomycin in the treatment of hospital-acquired, ventilator-associated, or health-care-associated pneumonia suspected or confirmed to be due to Gram-positive pathogens
• Uses: Iclaprim is a novel antibacterial agent that is currently in development for the treatment of complicated skin and skin structure infections (cSSSI). Iclaprim is a novel antibacterial agent that is currently in development for the treatment of complicated skin and skin structure infections (cSSSI). Antibiotics.

Technology Process of Iclaprim

There total 37 articles about Iclaprim 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: 98.87%

(2-cyclopropyl-5-((2,4-diaminopyrimidin-5-yl)methyl)-7,8-dimethoxy-3,4-dihydrobenzopyran-4-ol) → iclaprim (192314-93-5)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; for 15h; Reagent/catalyst; Reflux;

Reference yield: 92.0%

N-[5-((R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-ylmethyl)-4-(2,2-dimethyl-propionylamino)-pyrimidin-2-yl]-2,2-dimethyl-propionamide (1228103-71-6) → 5-((R)-2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-ylmethyl)-pyrimidine-2,4-diamine (1208116-65-7,192314-93-5)

Guidance literature:

With methanol; sodium hydroxide; at 80 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo100566c

Reference yield: 90.37%

C19H22N4O3*H2O4S → iclaprim (192314-93-5)

Guidance literature:

With sodium carbonate; for 1h;

upstream raw materials:

(RS)-3-anilino-2-(2-cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-yl-methyl)acrylonitrile

potassium tert-butylate

guanidine hydrochloride