methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate

• ChemBase ID: 638
• Molecular Formular: C16H16ClNO2S
• Molecular Mass: 321.82174
• Monoisotopic Mass: 321.05902744
• SMILES: Clc1c([C@H](N2CCc3sccc3C2)C(=O)OC)cccc1
• Canonical SMILES: COC(=O)[C@H](c1ccccc1Cl)N1CCc2c(C1)ccs2
• InChI: InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1
• InChIKey: GKTWGGQPFAXNFI-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
• IUPAC Traditional name: clopidogrel
• Brand Name: Clopidogrel sulfate; Clopidogrel [Ban:Inn]; Plavix
• Synonyms: Clopidogrel

Database IDs

• CAS Number: 113665-84-2
• PubChem SID: 160964101; 46507295
• PubChem CID: 60606

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.875259
• LogD (pH = 7.4): 4.029398
• Log P: 4.031764
• Molar Refractivity: 84.927 cm^3
• Polarizability: 32.98264 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.84
• LOG S: -4.43
• Solubility (Water): 1.18e-02 g/l

PROPERTIES

Physical Property

• Solubility: 50.78 mg/L
• Hydrophobicity(logP): 2.5

DETAILS

DrugBank - DB00758

• Drug Groups: approved; nutraceutical
• Description: Clopidogrel, an antiplatelet agent structurally and pharmacologically similar to ticlopidine, is used to reduce atherosclerotic events such as myocardial infarction, stroke, and vascular death in patients who have had a recent stroke, recent MI, or have established peripheral vascular disease.
• Indication: For the reduction of atherosclerotic events (myocardial infarction, stroke, and vascular death) in patients with atherosclerosis documented by recent stroke, recent myocardial infarction, or established peripheral arterial disease
• Pharmacology: Clopidogrel, an antiplatelet agent structurally and pharmacologically similar to ticlopidine, is used to reduce atherosclerotic events such as myocardial infarction, stroke, and vascular death in patients who have had a recent stroke, recent MI, or have established peripheral vascular disease.
• Toxicity: Symptoms of acute toxicity include vomiting (in baboons), prostration, difficult breathing, and gastrointestinal hemorrhage.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, extensive and rapid, by hydrolysis to the main circulating metabolite, a carboxylic acid derivative, which accounts for approximately 85% of the circulating drug-related compounds. A glucuronic acid derivative of the carboxylic acid derivative has also been found in plasma and urine. Neither the parent compound nor the carboxylic acid derivative has a platelet inhibiting effect.
• Absorption: Absorption is at least 50% based on urinary excretion of clopidogrel-related metabolites. Bioavailability has not been found to be affected by food.
• Half Life: Carboxylic acid derivative: 8 hours (after single and multiple doses). Covalent binding to platelets has accounted for 2% of radiolabeled clopidogrel with a half-life of 11 days.
• Protein Binding: 98%
• Elimination: Following an oral dose of 14C-labeled clopidogrel in humans, approximately 50% of total radioactivity was excreted in urine and approximately 46% in feces over the 5 days post-dosing.
• References: Chan FK, Ching JY, Hung LC, Wong VW, Leung VK, Kung NN, Hui AJ, Wu JC, Leung WK, Lee VW, Lee KK, Lee YT, Lau JY, To KF, Chan HL, Chung SC, Sung JJ: Clopidogrel versus aspirin and esomeprazole to prevent recurrent ulcer bleeding. N Engl J Med. 2005 Jan 20;352(3):238-44. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Chan FK, Ching JY, Hung LC, Wong VW, Leung VK, Kung NN, Hui AJ, Wu JC, Leung WK, Lee VW, Lee KK, Lee YT, Lau JY, To KF, Chan HL, Chung SC, Sung JJ: Clopidogrel versus aspirin and esomeprazole to prevent recurrent ulcer bleeding. N Engl J Med. 2005 Jan 20;352(3):238-44. Pubmed