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Home> Encyclopedia >Pharmaceutical Intermediates>Pharmaceuticals and Biochemicals>Blood System Agents
Clopidogrel structure
Clopidogrel structure

Clopidogrel

Iupac Name:methyl (2S)-2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate
CAS No.: 113665-84-2
Molecular Weight:321.819
Modify Date.: 2022-11-02 19:20
Introduction: Clopidogrel was launched in the US as a potent inhibitor of plateletaggregation for the preventive management of secondary ischemic events,including MI, stroke and vascular deaths. Clopidogrel can be synthesized in 4steps (including an optical resolution to the S active enantiomer) from 2-(2-ch1orophenyl)-glycine, the key step being the cyclization to thienopyridine withformaldehyde and acetic acid. Clopidogrel belongs to the original chemical classof Ticlopidine, but shows fewer side effects (in particular, bone-marrowsuppressingeffects) at the dosage generally used. Like Ticlopidine, it is anAdenosine diphosphate (ADP) antagonist acting at the purinergic P2y receptor.In in vivo experiments with rabbits, Clopidogrel shows a maximal antiaggreganteffect at 20mg/kg po, reducing adhesion of platelets to the vascularsubendothelium ; moreover, it reduces myointimal thickening occuring afterendothelial injury of rat carotid artery. Clopigrel does not affect plateletaggregation in vitro ; actually, its in vivo activity is highly dependent on hepaticmetabolism. The results of a CAPRIE trial (Clopidogrel versus Aspirin in patientsat risk of ischemic events) demonstrated that Clopidogrel was well tolerated andmore effective than aspirin. View more+
1. Names and Identifiers
1.1 Name
Clopidogrel
1.2 Synonyms

(+)-(S)-Clopidogrel (S)-(+)-Methyl (2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl)acetate (S)-Clopidogrel (S)-Methyl α-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)-α-(o-chlorophenyl)acetate Clopidogrel Pellets ClopidogrelHcl ClopidogrelHydrobromide ClopidogrelHydrogenSulfateBase Methyl (2S)-(2-chlorophenyl)(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate methyl (2s)-2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate R 130964 SR 25990 Thieno[3,2-c]pyridine-5(4H)-acetic acid, α-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (S)- Thieno[3,2-c]pyridine-5(4H)-acetic acid, α-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (αS)- Thrombo

1.3 CAS No.
113665-84-2
1.4 CID
60606
1.5 EINECS(EC#)
601-269-2; 601-679-1
1.6 Molecular Formula
C16H16ClNO2S (isomer)
1.7 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
1.8 InChkey
GKTWGGQPFAXNFI-HNNXBMFYSA-N
1.9 Canonical Smiles
COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3
1.10 Isomers Smiles
COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3
2. Properties
2.1 Density
1.317
2.1 Boiling point
423.7°Cat760mmHg
2.1 Refractive index
1.617
2.1 Flash Point
210°C
2.1 Precise Quality
321.05900
2.1 PSA
57.78000
2.1 logP
3.61180
2.1 Solubility
In water;, 51 mg/L at 25 deg C (est)
2.2 AnalyticLaboratory Methods
Analyte: clopidogrel;; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /clopidogrel bisulfate;/
2.3 Appearance
white powder
2.4 Color/Form
Colorless oil
2.5 Physical
Solid
2.6 pKa
4.56±0.20(Predicted)
2.7 Water Solubility
In water;, 51 mg/L at 25 deg C (est)
3. Use and Manufacturing
3.1 GHS Classification
GHS Hazard Statements
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

H362 (100%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

Precautionary Statement Codes
P201, P260, P263, P264, P270, P30, and P313
3.2 Methods of Manufacturing
Prepn: (unspec. stereochem.): D. Aubert et al., EP 99802; eidem, US patent 4529596 (1984, 1985 both to Sanofi). Prepn of (+)-form: A. Badorc, D. Frehel, EP 281459; eidem, US patent 4847265 (1988, 1989 both to Sanofi).
3.3 Usage
anthelmintic, antiparasitic, antimite
4. Safety and Handling
4.1 Hazard Codes
Xn
4.1 Risk Statements
R22
4.1 Safety Statements
26-36
4.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl clopidogrel bisulfate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Clopidogrel bisulfate/
4.2 Formulations/Preparations
Oral: Tablets: 75 mg (of clopidogrel) Plavix, (Sanofi-Aventis) (also promoted by Bristol-Myers Squibb). /Clopidogrel bisulfate/
Trade names (hydrogen sulfate): Iscover (Bristol-Myers Squibb), Plavix (Sanofi, Sanofi Winthrop, Sanofi Pharma Bristol-Myers Squibb SNC).
4.3 WGK Germany
3
4.3 Safety

Hazard Codes:?HarmfulXn
Risk Statements: 22-36/37/38
R22:? Harmful if swallowed?
R36/37/38:? Irritating to eyes, respiratory system and skin?
Safety Statements: 26-36
S26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
S36:? Wear suitable protective clothing?

4.4 Specification

? Clopidogrel (CAS NO.113665-84-2), its Synonyms are ( )-(S)-Clopidogrel ; (S)-Clopidogrel ; Clopidogrel 1A Pharma ; Clopidogrel Acino ; Clopidogrel BMS ; Clopidogrel Hexal ; Clopidogrel Teva (hydrogen sulphate) ; Clopidogrel Winthrop ; Clopidogrel ratiopharm GmbH ; HSDB 7430 ; Iscover ; Plavix ; Methyl (+)-(S)-alpha-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4H)-acetate ; Thieno(3,2-c)pyridine-5(4H)-acetic acid, alpha-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (S)- .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s) no data available
Signal word

no data available

Hazard statement(s)

no data available

Precautionary statement(s)
Prevention

no data available

Response

no data available

Storage

no data available

Disposal

no data available

2.3 Other hazards which do not result in classification

no data available

9. Other Information
9.0 Uses
anthelmintic, antiparasitic, antimite
9.1 Uses
Sertraline metabolite
9.2 Brand name
Plavix (Sanofi Aventis).
10. Computational chemical data
  • Molecular Weight: 321.819g/mol
  • Molecular Formula: C16H16ClNO2S
  • Compound Is Canonicalized: True
  • XLogP3-AA: 3.8
  • Exact Mass: 321.0590276
  • Monoisotopic Mass: 321.0590276
  • Complexity: 381
  • Rotatable Bond Count: 4
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 57.8
  • Heavy Atom Count: 21
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceB6MABEAAAAAAAAAAAAAAAAASAAAAA8QAAAAAAAAFgBwAAAHgYAAAAADCrF2CayCYMABAiMAiDSCACDAIAgDRBIiBmIBogKIDKhlzGFIAhkwAG4iAeYyKCOAAAAAAABAAAAAAAAAAIAAAAAAAAAAA==
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