Cangrelor

Base Information

• Chemical Name: Cangrelor
• CAS No.: 163706-06-7
• Molecular Formula: C₁₇H₂₅Cl₂F₃N₅O₁₂P₃S₂
• Molecular Weight: 776.366
• UNII: 6AQ1Y404U7
• DSSTox Substance ID: DTXSID90167651
• Nikkaji Number: J1.089.474C
• Wikipedia: Cangrelor
• Wikidata: Q3655338
• NCI Thesaurus Code: C76395
• RXCUI: 1656052
• Pharos Ligand ID: 2PP7NP1N8QA6
• Metabolomics Workbench ID: 149779
• ChEMBL ID: CHEMBL334966
• Mol file: 163706-06-7.mol

Synonyms:AR C69931MX;AR-C69931MX;cangrelor;cangrelor tetrasodium;Kengreal;N(6)-(2-methylthioethyl)-2-(3,3,3-trifluoropropylthio)-5'-adenylic acid monoanhydride with dichloromethylenebis(phosphonic acid)

Chemical Property of Cangrelor

Chemical Property:

• Boiling Point: 979.0±75.0 °C(Predicted)
• PKA: 0.82±0.50(Predicted)
• Flash Point: 545.882oC
• PSA: 335.94000
• Density: 2.08
• LogP: 2.92350
• XLogP3: -1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 21
• Rotatable Bond Count: 15
• Exact Mass: 774.9483145
• Heavy Atom Count: 44
• Complexity: 1140

Purity/Quality:

99% ^*data from raw suppliers

Cangrelor ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antithrombotic Agents
• Canonical SMILES: CSCCNC1=C2C(=NC(=N1)SCCC(F)(F)F)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=O)(C(P(=O)(O)O)(Cl)Cl)O)O)O
• Isomeric SMILES: CSCCNC1=C2C(=NC(=N1)SCCC(F)(F)F)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(C(P(=O)(O)O)(Cl)Cl)O)O)O
• Recent ClinicalTrials: Dual Antiplatelet Therapy For Shock Patients With Acute Myocardial Infarction
• Recent EU Clinical Trials: Preclinical antiplatelet treatment with Cangrelor in patients presenting with ST-Elevation myocardial infarction: a randomized, double-blind, placebo-controlled pilot trial
• Uses: Anti-platelet agent. Cangrelor is a P2Y12 inhibitor used as an antiplatelet drug for intravenous application.
• Clinical Use: Direct P2Y12 platelet receptor antagonist: Antiplatelet for patients undergoing a PCI
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Cangrelor

There total 6 articles about Cangrelor 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:

2-Mercaptoadenosine (43157-50-2) → cangrelor (163706-06-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, 2.) DMF, 36 h

2: 73 percent / AcONa / 7 h / 80 °C

3: NaH / dimethylformamide / 24 h / 60 °C

4: 0.1 M NaOH / methanol / 0.5 h / Heating

5: 1.) POCl₃, (Et₃O)3PO, 2.) aq. NaHCO₃ / 1.) 0 deg C, 5 h, 2.) 0 deg C, 45 min

6: 1.) tri-n-butylamine, pyridine, 2.) CDI, 3.) MeOH

With pyridine; methanol; sodium hydroxide; tributyl-amine; triethyl phosphate; sodium acetate; sodium hydride; sodium hydrogencarbonate; 1,1'-carbonyldiimidazole; trichlorophosphate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm981072s

Reference yield:

2-[(3,3,3-trifluoropropyl)thio]adenosine (163706-51-2) → cangrelor (163706-06-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 73 percent / AcONa / 7 h / 80 °C

2: NaH / dimethylformamide / 24 h / 60 °C

3: 0.1 M NaOH / methanol / 0.5 h / Heating

4: 1.) POCl₃, (Et₃O)3PO, 2.) aq. NaHCO₃ / 1.) 0 deg C, 5 h, 2.) 0 deg C, 45 min

5: 1.) tri-n-butylamine, pyridine, 2.) CDI, 3.) MeOH

With pyridine; methanol; sodium hydroxide; tributyl-amine; triethyl phosphate; sodium acetate; sodium hydride; sodium hydrogencarbonate; 1,1'-carbonyldiimidazole; trichlorophosphate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm981072s

Reference yield:

(2R,3R,4R,5R)-2-{6-acetylamino-2-[(3,3,3-trifluoropropyl)thio]-9H-purin-9-yl}-5-(acetoxymethyl)-3,4-bis(acetoxy)tetrahydrofuran (163706-52-3) → cangrelor (163706-06-7)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 24 h / 60 °C

2: 0.1 M NaOH / methanol / 0.5 h / Heating

3: 1.) POCl₃, (Et₃O)3PO, 2.) aq. NaHCO₃ / 1.) 0 deg C, 5 h, 2.) 0 deg C, 45 min

4: 1.) tri-n-butylamine, pyridine, 2.) CDI, 3.) MeOH

With pyridine; methanol; sodium hydroxide; tributyl-amine; triethyl phosphate; sodium hydride; sodium hydrogencarbonate; 1,1'-carbonyldiimidazole; trichlorophosphate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm981072s

upstream raw materials:

dichloromethylenebis(phosphonic acid) mono(tri-n-butylammonium) salt

N-[2-(methylthio)ethyl]-2-[(3,3,3-trifluoropropyl)thio]-5'-adenylic acid

2-Mercaptoadenosine

2-[(3,3,3-trifluoropropyl)thio]adenosine