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Carbimazole

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ACTIVE PHARMA INGREDIENTS

10 API Suppliers, 1 USDMF, 4 CEP/COS, 3 EU WC, 1 VMF, 7 Listed Suppliers, $ API Reference Price

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1 USDMF
4 CEP/COS
3 EU WC
1 VMF
7 Listed Suppliers
$ API Reference Price

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32 FDF Dossiers, 2 Europe, 6 Australia, 3 South Africa, 21 Listed Dossiers

32 FDF Dossiers
2 Europe
6 Australia
3 South Africa
21 Listed Dossiers

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7 APIs, 5 FDF Dossiers

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7 APIs
5 FDF Dossiers

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1 EDQM

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Synopsis

ACTIVE PHARMA INGREDIENTS

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CEP/COS

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EU WC

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VMF

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$ 374

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Canada

Australia

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Chemistry

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Also known as: 22232-54-8, Athyromazole, Carbimazol, Neomercazole, Carbethoxymethimazole, Carbinazole

Molecular Formula

C₇H₁₀N₂O₂S

Molecular Weight

186.23 g/mol

InChI Key

CFOYWRHIYXMDOT-UHFFFAOYSA-N

FDA UNII

8KQ660G60G

An imidazole antithyroid agent. Carbimazole is metabolized to METHIMAZOLE, which is responsible for the antithyroid activity.

1 2D Structure

Carbimazole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl 3-methyl-2-sulfanylideneimidazole-1-carboxylate

2.1.2 InChI

InChI=1S/C7H10N2O2S/c1-3-11-7(10)9-5-4-8(2)6(9)12/h4-5H,3H2,1-2H3

2.1.3 InChI Key

CFOYWRHIYXMDOT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCOC(=O)N1C=CN(C1=S)C

2.2 Other Identifiers

2.2.1 UNII

8KQ660G60G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Carbimazole Henning

2. Neo Tomizol

3. Neo-mercazole

4. Neo-thyreostat

5. Neomercazole

2.3.2 Depositor-Supplied Synonyms

1. 22232-54-8

2. Athyromazole

3. Carbimazol

4. Neomercazole

5. Carbethoxymethimazole

6. Carbinazole

7. Neo-thyreostat

8. Basolest

9. Thyrostat

10. Carbimazolum

11. Tyrazol

12. Carbimazolum [inn-latin]

13. Ethyl 3-methyl-2-thioimidazoline-1-carboxylate

14. Carbimazol [inn-spanish, French]

15. Carbimazol Henning

16. 1-ethoxycarbonyl-3-methyl-2-thioxo-4-imidazoline

17. 1h-imidazole-1-carboxylic Acid, 2,3-dihydro-3-methyl-2-thioxo-, Ethyl Ester

18. Ethyl 3-methyl-2-thioxo-2,3-dihydro-1h-imidazole-1-carboxylate

19. Carbimazole (inn)

20. Neo-mercazole

21. Chebi:617099

22. Atirozidina

23. Carbotiroid

24. Mertiran

25. Cg1

26. 3-methyl-2-thioxo-4-imidazoline-1-carboxylic Acid Ethyl Ester

27. Nsc-758966

28. 4-imidazoline-1-carboxylic Acid, 3-methyl-2-thioxo-, Ethyl Ester

29. Carbimazol Spofa

30. Neo-tireol

31. Ethyl 3-methyl-2-sulfanylideneimidazole-1-carboxylate

32. Chembl508102

33. 8kq660g60g

34. Ethyl 3-methyl-2-thionoimidazoline-1-carboxylate

35. Ncgc00016760-01

36. Cas-22232-54-8

37. Carbimazole [inn]

38. Dsstox_cid_2736

39. Dsstox_rid_76708

40. Dsstox_gsid_22736

41. Carbimazole [inn:ban:dcf]

42. 1-ethoxycarbonyl-3-methyl-2-thioimidazol

43. Sr-01000872660

44. Carbimazol Henning (tn)

45. Einecs 244-854-4

46. Brn 0144339

47. Unii-8kq660g60g

48. Prestwick_788

49. 1h-imidazole-1-carboxylic Acid, 2,3-dihydro-3-methyl-2-thioxo, Ethyl Ester

50. Mfcd00027421

51. Fenobucarb Bassa Bpmc

52. Carbimazole [mi]

53. Prestwick0_000439

54. Prestwick1_000439

55. Prestwick2_000439

56. Prestwick3_000439

57. Spectrum2_001251

58. Spectrum3_001968

59. Epitope Id:116890

60. Carbimazole [mart.]

61. Schembl44211

62. Bspbio_000458

63. Bspbio_003568

64. Carbimazole [who-dd]

65. 4-24-00-00064 (beilstein Handbook Reference)

66. Mls004734638

67. Spectrum1505323

68. Spbio_001182

69. Spbio_002397

70. Bpbio1_000504

71. Zinc1091

72. Dtxsid9022736

73. Kbio3_002918

74. Carbimazole [ep Monograph]

75. Hms1569g20

76. Hms1922d12

77. Hms2096g20

78. Hms3652g04

79. Hms3713g20

80. Pharmakon1600-01505323

81. Bcp12935

82. Hy-b0558

83. Tox21_110596

84. Tox21_302320

85. Bdbm50275889

86. Ccg-39106

87. Ethyl 3-methyl-2-sulfanylidene-2,3-dihydro-1h-imidazole-1-carboxylate

88. Nsc758966

89. S4048

90. Akos001647527

91. Tox21_110596_1

92. Ac-8348

93. Am84794

94. Db00389

95. Nsc 758966

96. Ncgc00016760-02

97. Ncgc00016760-03

98. Ncgc00016760-04

99. Ncgc00016760-05

100. Ncgc00016760-08

101. Ncgc00095167-01

102. Ncgc00095167-02

103. Ncgc00177988-01

104. Ncgc00177988-02

105. Ncgc00255133-01

106. As-13267

107. Be164282

108. Smr001233183

109. Sbi-0207026.p001

110. Ft-0602919

111. Sw196926-3

112. A16427

113. C07615

114. C74138

115. D07616

116. 3-methyl-2-thioi-midazoline-1-carboxylate

117. A816030

118. Q414013

119. Sr-01000872660-1

120. Sr-01000872660-2

121. W-107493

122. Brd-k87156652-001-05-1

123. Brd-k87156652-001-06-9

124. Ethyl 3-methyl-2-thioxo-imidazole-1-carboxylate;carbimazole

125. Ethyl 3-methyl-2-thioxo-2,3-dihydro-1h-imidazole-1-carboxylate #

126. Carbimazole 3-methyl-2-thionoimidazoline-1-carboxylic Acid Ethyl Ester

127. Ethyl 3-methyl-2-thioxo-2,3-dihydro-1h-imidazole-1-carboxylate, Aldrichcpr

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₇H₁₀N₂O₂S
Molecular Weight	186.23 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	186.04629874 g/mol
Monoisotopic Mass	186.04629874 g/mol
Topological Polar Surface Area	64.9 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	240
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of hyperthyroidism and thyrotoxicosis. It is also used to prepare patients for thyroidectomy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Carbimazole is a carbethoxy derivative of methimazole. Its antithyroid action is due to its conversion to methimazole after absorption. It is used to treat hyperthyroidism and thyrotoxicosis.

5.2 MeSH Pharmacological Classification

Antithyroid Agents

Agents that are used to treat hyperthyroidism by reducing the excessive production of thyroid hormones. (See all compounds classified as Antithyroid Agents.)

5.3 ATC Code

H - Systemic hormonal preparations, excl. sex hormones and insulins

H03 - Thyroid therapy

H03B - Antithyroid preparations

H03BB - Sulfur-containing imidazole derivatives

H03BB01 - Carbimazole

5.4 Mechanism of Action

Carbimazole is an aitithyroid agent that decreases the uptake and concentration of inorganic iodine by thyroid, it also reduces the formation of di-iodotyrosine and thyroxine. Once converted to its active form of methimazole, it prevents the thyroid peroxidase enzyme from coupling and iodinating the tyrosine residues on thyroglobulin, hence reducing the production of the thyroid hormones T3 and T4.

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