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

• ChemBase ID: 44451
• Molecular Formular: C16H18ClNO6S2
• Molecular Mass: 419.90022
• Monoisotopic Mass: 419.02640698
• SMILES: C1CN(Cc2c1scc2)[C@@H](c1c(cccc1)Cl)C(=O)OC.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.COC(=O)[C@H](c1ccccc1Cl)N1CCc2c(C1)ccs2
• InChI: InChI=1S/C16H16ClNO2S.H2O4S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14;1-5(2,3)4/h2-5,7,9,15H,6,8,10H2,1H3;(H2,1,2,3,4)/t15-;/m0./s1
• InChIKey: FDEODCTUSIWGLK-RSAXXLAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sulfuric acid methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate
• IUPAC Traditional name: clopidogrel; sulfuric acid
• Synonyms: (S)-(+)-Clopidogrel bisulfate; (S)-(+)-Methyl 2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)-2-(2-chlorophenyl)acetate hydrogensulfate; Clopidogrel Bisulphate; (S)-(+)-Clopidogrel hydrogensulfate; (S)-methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate sulfate; Clopidogrel bisulfate; sulfuric acid methyl (2S)-2-(2-chlorophenyl)-2-{4H,5H,6H,7H-thieno[3,2-c]pyridin-5-yl}acetate; Clopidogrel Hemisulfate; Iscover; Myogrel; Plavix; (S)-(+)-Methyl 2-(2-Chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate Hydrogen Sulfate; Clopidogrel Bisulfate; SR 25990C; Stroka; S-(+)-Clopidogrel Hydrogen Sulfate

Database IDs

• CAS Number: 135046-48-9; 120202-66-6
• MDL Number: MFCD00876395
• PubChem SID: 162049214
• PubChem CID: 115366

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL (warmed); Methanol; Water
• Apperance: Off-White Solid; white to tan powder
• Melting Point: 174-176°C (Transition), >210°C (dec.)
• Optical Rotation: [α]/D +54 to +70°, c = 0.5 in methanol
• Hydrophobicity(logP): 4.208

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: P450

Product Information

• Purity: >98%; ≥98% (HPLC); 95%
• Salt Data: Bisulfate; H2SO4
• Empirical Formula (Hill Notation): C16H16ClNO2S · H2SO4

DETAILS

Selleck Chemicals - S1415

Research Area: Cardiovascular Disease
Biological Activity:
Clopidogrel (Plavix) is an oral, thienopyridine class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease. Clopidogrel works by irreversibly inhibiting a receptor called P2Y12, an adenosine diphosphate ADP chemoreceptor. [1]

Sigma Aldrich - SML0004

Biochem/physiol Actions
(S)-(+)-Clopidogrel hydrogen sulfate is an antithrombotic antiplatelet agent. It specifically and irreversibly inhibits the Purinoceptor P2Y12 subtype which inhibits ADP-induced platelet aggregation. (S)-(+)-Clopidogrel hydrogen sulfate is the active isomer.

Toronto Research Chemicals - C587250

Used as an antithrombotic.

REFERENCES

• http://en.wikipedia.org/wiki/Clopidogrel
• Mills, D.C.B., et al.: Arterioscler. Thromb., 12, 430 (1992)
• Feuerstein, G., et al.: Exp. Opin. Invest. Drugs, 4, 425 (1995)