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Also known as: 120202-66-6, Clopidogrel sulfate, Clopidogrel hydrogen sulfate, Iscover, Plavix, Clopidogrel bisulphate

Molecular Formula

C₁₆H₁₈ClNO₆S₂

Molecular Weight

419.9 g/mol

InChI Key

FDEODCTUSIWGLK-RSAXXLAASA-N

FDA UNII

08I79HTP27

A ticlopidine analog and platelet purinergic P2Y receptor antagonist that inhibits adenosine diphosphate-mediated PLATELET AGGREGATION. It is used to prevent THROMBOEMBOLISM in patients with ARTERIAL OCCLUSIVE DISEASES; MYOCARDIAL INFARCTION; STROKE; or ATRIAL FIBRILLATION.

1 2D Structure

CAS 120202-66-6

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 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

2.1.3 InChI Key

FDEODCTUSIWGLK-RSAXXLAASA-N

2.1.4 Canonical SMILES

COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O

2.1.5 Isomeric SMILES

COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

08I79HTP27

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Clopidogrel

2. Clopidogrel Besilate

3. Clopidogrel Besylate

4. Clopidogrel Hydrochloride

5. Clopidogrel Mepha

6. Clopidogrel Napadisilate

7. Clopidogrel Sandoz

8. Clopidogrel, (+)(s)-isomer

9. Clopidogrel-mepha

10. Iscover

11. Pcr 4099

12. Pcr-4099

13. Plavix

14. Sc 25989c

15. Sc 25990c

16. Sr 25989

2.3.2 Depositor-Supplied Synonyms

1. 120202-66-6

2. Clopidogrel Sulfate

3. Clopidogrel Hydrogen Sulfate

4. Iscover

5. Plavix

6. Clopidogrel Bisulphate

7. Clopidogrel Hemisulfate

8. (s)-methyl 2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4h)-yl)acetate Sulfate

9. Clopidogrel Hydrogen Sulphate

10. Clopidogrel Bms

11. Clopidogrel Sulphate

12. Sr 25990c

13. Clopidogrel (hydrogen Sulfate)

14. Isocover

15. Pidogrel

16. Clopidogrel-bgr

17. Clopidogrel-bms

18. Clopidogrel Teva

19. Clopidogrel Zentiva

20. Clopidogrel (plavix)

21. Clopidogrel Ratiopharm

22. Sr-25990c

23. S-(+)-clopidogrel Hydrogen Sulfate

24. Clopidogrel (as Bisulfate)

25. (s)-(+)-clopidogrel Sulfate

26. 08i79htp27

27. 120202-66-6 (sulfate)

28. Pm-103

29. Methyl (s)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4h)-yl)acetate Sulfate

30. 144077-07-6

31. Myogrel

32. Clopidogrel Hydrogensulfate

33. Plavix (tn)

34. Dsstox_cid_26024

35. Dsstox_rid_81297

36. Dsstox_gsid_46024

37. Plavitor

38. Osvix

39. Chebi:3759

40. Chembl1083385

41. Methyl (2s)-2-(2-chlorophenyl)-2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)acetate Sulfate

42. Methyl (2s)-2-(2-chlorophenyl)-2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)acetate;sulfuric Acid

43. Sulfuric Acid Methyl (2s)-2-(2-chlorophenyl)-2-{4h,5h,6h,7h-thieno[3,2-c]pyridin-5-yl}acetate

44. Clopidogrel Bisulfate [usan]

45. Cas-135046-48-9

46. Unii-08i79htp27

47. R-(-)-clopidogrel Hydrogen Sulfate

48. Clopidogrel Bisulfate [usan:usp]

49. Isocover (tn)

50. Clopidogrel Bisolfato

51. (s)-(+)-clopidogrel Hydrogen Sulfate

52. Bisulfato De Clopidogrel

53. Bissulfato De Clopidogrel

54. Ncgc00159321-02

55. (+)-clopidogrel Bisulfate

56. (+) Clopidogrel Bisulfate

57. Methyl Alphas-(2-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4h)-acetate Sulfate (1:1)

58. Clopidogrel Bisulfate (usp)

59. Clopidogrel Sulfate (jp17)

60. Schembl33556

61. Clopidogrel Hydrogen Sulphate

62. Spectrum1503710

63. Mdco-157

64. (+)-clopidogrel Hydrogen Sulfate

65. Clopidogrel Sulfate [jan]

66. Dtxsid601016080

67. Hms1922g16

68. Hms2093i13

69. Hms3884g15

70. Pharmakon1600-01503710

71. Amy40591

72. Clopidogrel Sulfate Tablets (jp17)

73. Tox21_111570

74. Ccg-39568

75. Clopidogrel Bisulfate [vandf]

76. Mfcd00876395

77. Nsc758613

78. S1415

79. Clopidogrel Bisulfate [mart.]

80. Akos015900408

81. Clopidogrel Bisulfate [usp-rs]

82. Clopidogrel Bisulfate [who-dd]

83. Tox21_111570_1

84. Ac-2135

85. Cs-1882

86. Dv-7314

87. Ks-1045

88. S65c842

89. Clopidogrel (as Hydrogen Sulfate)

90. Clopidogrel Hydrogen Sulfate [mi]

91. Ncgc00163329-03

92. 111ge004

93. Bc164326

94. Hy-17459

95. Methyl (+)-(s)-alpha-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4h)-acetate, Sulfate (1:1)

96. Thieno(3,2-c)pyridine-5(4h)-acetic Acid, 6,7-dihydro-alpha-(2-chlorophenyl)-, Methyl Ester, (s)-, Sulfate

97. Thieno(3,2-c)pyridine-5(4h)-acetic Acid, Alpha-(2-chlorophenyl)-6,7-dihydro-, Methyl Ester, (alphas)-, Sulfate (1:1)

98. Thieno(3,2-c)pyridine-5(4h)-acetic Acid, Alpha-(2-chlorophenyl)-6,7-dihydro-, Methyl Ester, (s)-, Sulfate (1:1)

99. Thieno[3,2-c]pyridine-5(4h)-acetic Acid,a-(2-chlorophenyl)-6,7-dihydro-, Methyl Ester, (as)-, Sulfate (1:1)

100. Clopidogrel Bisulfate [orange Book]

101. Clopidogrel Bisulfate [usp Monograph]

102. Sw219457-1

103. Clopidogrel Hydrogen Sulfate [ema Epar]

104. D00769

105. Duocover Component Clopidogrel Bisulfate

106. Duoplavin Component Clopidogrel Bisulfate

107. Clopidogrel Hydrogen Sulphate [ema Epar]

108. Clopidogrel Bisulfate Component Of Duocover

109. Clopidogrel Bisulfate Component Of Duoplavin

110. Clopidogrel Hydrogen Sulfate [ep Monograph]

111. Sr-05000002068

112. J-006637

113. Sr-05000002068-1

114. (+)-clopidogrel1r(-)camphor-10-sulphonic Acid Salt

115. (s)-(+)-clopidogrel Hydrogensulfate, >=98% (hplc)

116. Q27888063

117. Z1550648767

118. (s)-(+)-clopidogrel Bisulfate;(s)-(+)-clopidogrel Hydrogen Sulfate

119. Clopidogrel Bisulfate, United States Pharmacopeia (usp) Reference Standard

120. Clopidogrel Hydrogen Sulfate, European Pharmacopoeia (ep) Reference Standard

121. Clopidogrel/acetylsalicyclic Acid Teva Component Clopidogrel Bisulfate

122. (s)-(+)-methyl (2-chlorophenyl)(6,7-dihydro-4h-thieno(3,2-c)pyrid-5-yl)acetate Bisulfate

123. Clopidogrel Bisulfate Component Of Clopidogrel/acetylsalicyclic Acid Teva

124. Clopidogrel Bisulfate, Pharmaceutical Secondary Standard; Certified Reference Material

125. Clopidogrel For System Suitability, European Pharmacopoeia (ep) Reference Standard

126. Methyl(s)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4h)-yl)acetatesulfate

127. (s)-(+)-methyl 2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)-2-(2-chlorophenyl)acetate Hydrogen Sulfate

128. (s)-(2-chloro-phenyl)-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-acetic Acid Methyl Ester Sulfuric Acid Salt

129. (s)-methyl-(2-chloro-phenyl)-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-acetate H2so4

130. Methyl (+)-(s)-.alpha.-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4h)-acetate, Sulfate (1:1)

131. Methyl (+)-(s)-.alpha.-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4h)-acetate, Sulphate (1:1)

132. Methyl (2s)-2-(2-chlorophenyl)-2-{4h,5h,6h,7h-thieno[3,2-c]pyridin-5-yl}acetate; Sulfuric Acid

133. Methyl (s)-(+)-2-(2-chlorophenyl)-2-[6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl]acetate Sulfate

134. Thieno(3,2-c)pyridine-5(4h)-acetic Acid, .alpha.-(2-chlorophenyl)-6,7-dihydro-, Methyl Ester, (s)-, Sulfate (1:1)

135. Thieno(3,2-c)pyridine-5(4h)-acetic Acid, .alpha.-(2-chlorophenyl)-6,7-dihydro-, Methyl Ester, (s)-, Sulphate (1:1)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₈ClNO₆S₂
Molecular Weight	419.9 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	419.0264073 g/mol
Monoisotopic Mass	419.0264073 g/mol
Topological Polar Surface Area	141 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	463
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	CLOPIDOGREL BISULFATE
Active Ingredient	CLOPIDOGREL BISULFATE
Company	ACCORD HLTHCARE (Application Number: A202925); ACME LABS (Application Number: A078004); AMNEAL PHARMS (Application Number: A203751); APOTEX INC (Application Number: A076274); AUROBINDO PHARMA LTD (Application Number: A090540); CSPC OUYI PHARM CO (Application Number: A204359); DR REDDYS LABS INC (Application Number: A076273); DR REDDYS LABS LTD (Application Number: A091023); GATE PHARMS (Application Number: A091216); MACLEODS PHARMS LTD (Application Number: A202928); MYLAN PHARMS INC (Application Number: A077665); SCIEGEN PHARMS INC (Application Number: A204165); SUN PHARM INDUSTRIES (Application Number: A078133); SUN PHARMA GLOBAL (Application Number: A090494); TEVA PHARMS (Application Number: A090625); TEVA (Application Number: A076999); TORRENT PHARMS LTD (Application Number: A090844); WOCKHARDT LTD (Application Number: A202266); ZYDUS PHARMS USA INC (Application Number: A201686)

2 of 2
Drug Name	PLAVIX
Active Ingredient	CLOPIDOGREL BISULFATE
Company	SANOFI AVENTIS US (Application Number: N020839. Patents: 6429210, 6429210PED, 6504030, 6504030PED)

4.2 Drug Indication

Secondary prevention of atherothrombotic events Clopidogrel is indicated in:

- Adult patients suffering from myocardial infarction (from a few days until less than 35 days), ischaemic stroke (from 7 days until less than 6 months) or established peripheral arterial disease.

- Adult patients suffering from acute coronary syndrome:

- Non-ST segment elevation acute coronary syndrome (unstable angina or non-Q-wave myocardial infarction), including patients undergoing a stent placement following percutaneous coronary intervention, in combination with acetylsalicylic acid (ASA).

- ST segment elevation acute myocardial infarction, in combination with ASA in medically treated patients eligible for thrombolytic therapy.

Prevention of atherothrombotic and thromboembolic events in atrial fibrillation

In adult patients with atrial fibrillation who have at least one risk factor for vascular events, are not suitable for treatment with Vitamin K antagonists (VKA) and who have a low bleeding risk, clopidogrel is indicated in combination with ASA for the prevention of atherothrombotic and thromboembolic events, including stroke.

Secondary prevention of atherothrombotic events

Clopidogrel is indicated in:

- Adult patients suffering from myocardial infarction (from a few days until less than 35 days), ischaemic stroke (from 7 days until less than 6 months) or established peripheral arterial disease.

- Adult patients suffering from acute coronary syndrome:

- ST segment elevation acute myocardial infarction, in combination with ASA in medically treated patients eligible for thrombolytic therapy.

- Prevention of atherothrombotic and thromboembolic events in atrial fibrillation

* Secondary prevention of atherothrombotic events:

Clopidogrel is indicated in:

- Adult patients suffering from myocardial infarction (from a few days until less than 35 days), ischaemic stroke (from 7 days until less than 6 months) or established peripheral arterial disease.

- Adult patients suffering from acute coronary syndrome:

- ST segment elevation acute myocardial infarction, in combination with ASA in medically treated patients eligible for thrombolytic therapy.

In patients with moderate to high-risk Transient Ischemic Attack (TIA) or minor Ischemic Stroke (IS)

Clopidogrel in combination with ASA is indicated in:

- Adult patients with moderate to high-risk TIA (ABCD2 score 4) or minor IS (NIHSS 3) within 24 hours of either the TIA or IS event.

* Prevention of atherothrombotic and thromboembolic events in atrial fibrillation:

Prevention of atherothrombotic events Clopidogrel is indicated in:

Adult patients suffering from myocardial infarction (from a few days until less than 35 days), ischaemic stroke (from 7 days until less than 6 months) or established peripheral arterial disease.

Prevention Secondary prevention of atherothrombotic events Clopidogrel is indicated in:

- Adult patients suffering from myocardial infarction (from a few days until less than 35 days), ischaemic stroke (from 7 days until less than 6 months) or established peripheral arterial disease.

- Adult patients suffering from acute coronary syndrome:

- ST segment elevation acute myocardial infarction, in combination with ASA in medically treated patients eligible for thrombolytic therapy.

- Prevention of atherothrombotic and thromboembolic events in atrial fibrillation:

- In adult patients with atrial fibrillation who have at least one risk factor for vascular events, are not suitable for treatment with Vitamin K antagonists (VKA) and who have a low bleeding risk, clopidogrel is indicated in combination with ASA for the prevention of atherothrombotic and thromboembolic events, including stroke.

* Secondary prevention of atherothrombotic events:

Clopidogrel is indicated in:

- adult patients suffering from myocardial infarction (from a few days until less than 35 days), ischaemic stroke (from seven days until less than six months) or established peripheral arterial disease;

- adult patients suffering from acute coronary syndrome:

- non-ST-segment-elevation acute coronary syndrome (unstable angina or non-Q-wave myocardial infarction), including patients undergoing a stent placement following percutaneous coronary intervention, in combination with acetylsalicylic acid (ASA);

- ST-segment-elevation acute myocardial infarction, in combination with ASA in medically treated patients eligible for thrombolytic therapy.

- In patients with moderate to high-risk Transient Ischemic Attack (TIA) or minor Ischemic Stroke (IS)

Clopidogrel in combination with ASA is indicated in:

- Adult patients with moderate to high-risk TIA (ABCD2 score 4) or minor IS (NIHSS 3) within 24 hours of either the TIA or IS event.

* Prevention of atherothrombotic and thromboembolic events in atrial fibrillation:

In adult patients with atrial fibrillation who have at least one risk factor for vascular events, are not suitable for treatment with vitamin-K antagonists and who have a low bleeding risk, clopidogrel is indicated in combination with ASA for the prevention of atherothrombotic and thromboembolic events, including stroke.

Clopidogrel is indicated in adults for the prevention of atherothrombotic events in:

- patients suffering from myocardial infarction (from a few days until less than 35 days), ischaemic stroke (from 7 days until less than 6 months) or established peripheral arterial disease.

For further information please refer to section 5. 1.

Clopidogrel is indicated in adults for the prevention of atherothrombotic events in:

- Patients suffering from myocardial infarction (from a few days until less than 35 days), ischaemic stroke (from 7 days until less than 6 months) or established peripheral arterial disease.

- Patients suffering from acute coronary syndrome:

Non-ST segment elevation acute coronary syndrome (unstable angina or non-Q-wave myocardial infarction), including patients undergoing a stent placement following percutaneous coronary intervention, in combination with acetylsalicylic acid (ASA).

ST segment elevation acute myocardial infarction, in combination with ASA in medically treated patients eligible for thrombolytic therapy.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

Purinergic P2Y Receptor Antagonists

Compounds that bind to and block the stimulation of PURINERGIC P2Y RECEPTORS. Included under this heading are antagonists for specific P2Y receptor subtypes. (See all compounds classified as Purinergic P2Y Receptor Antagonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Decreased Platelet Aggregation [PE]; P2Y12 Platelet Inhibitor [EPC]; P2Y12 Receptor Antagonists [MoA]; Cytochrome P450 2C8 Inhibitors [MoA]

5.3 ATC Code

B01AC04

B01AC03

B01AC04