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Chemistry

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Also known as: Thiouracil, 141-90-2, 2-mercaptopyrimidin-4-ol, 4-hydroxy-2-mercaptopyrimidine, Deracil, Antagothyroid

Molecular Formula

C₄H₄N₂OS

Molecular Weight

128.15 g/mol

InChI Key

ZEMGGZBWXRYJHK-UHFFFAOYSA-N

FDA UNII

59X161SCYL

Occurs in seeds of Brassica and Crucifera species. Thiouracil has been used as antithyroid, coronary vasodilator, and in congestive heart failure although its use has been largely supplanted by other drugs. It is known to cause blood dyscrasias and suspected of terato- and carcinogenesis.

1 2D Structure

2-Thiouracil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-sulfanylidene-1H-pyrimidin-4-one

2.1.2 InChI

InChI=1S/C4H4N2OS/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)

2.1.3 InChI Key

ZEMGGZBWXRYJHK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CNC(=S)NC1=O

2.2 Other Identifiers

2.2.1 UNII

59X161SCYL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Thiouracil

2.3.2 Depositor-Supplied Synonyms

1. Thiouracil

2. 141-90-2

3. 2-mercaptopyrimidin-4-ol

4. 4-hydroxy-2-mercaptopyrimidine

5. Deracil

6. Antagothyroid

7. 2-thioxo-2,3-dihydropyrimidin-4(1h)-one

8. Antagothyroil

9. Nobilen

10. 2-mercapto-4-hydroxypyrimidine

11. 2-mercapto-4-pyrimidone

12. 80275-68-9

13. 2-mercapto-4-pyrimidinol

14. 6-thiouracil

15. 4-hydroxy-2-pyrimidinethiol

16. 4(1h)-pyrimidinone, 2,3-dihydro-2-thioxo-

17. Uracil, 2-thio-

18. 4-pyrimidinol, 2-mercapto-

19. 6-hydroxy-2-mercaptopyrimidine

20. 2-thio-1,3-pyrimidin-4-one

21. 2,3-dihydro-2-thioxo-4(1h)-pyrimidinone

22. 2-sulfanylidene-1h-pyrimidin-4-one

23. 2-tu

24. 2-sulfanylpyrimidin-4-ol

25. Mfcd00006039

26. 2-mercapto-4(1h)-pyrimidinone

27. 2-thio-2,4-(1h,3h)-pyrimidinedione

28. 4-hydroxy-2(1h)-pyrimidinethione

29. 156-82-1

30. Nsc 19473

31. 125220-28-2

32. 126160-72-3

33. 2-sulfanylpyrimidin-4(3h)-one

34. 4(1h)-pyrimidinone, 2-mercapto- (9ci)

35. 4-hydroxypyrimidine-2(1h)-thione

36. 2(1h)-pyrimidinethione, 4-hydroxy- (9ci)

37. 2-mercaptopyrimid-4-one

38. 124700-71-6

39. Tu

40. 2-mercapto-pyrimidin-4-ol

41. 4-hydroxypyrimidine-2-thiol

42. 2-thioxo-2,3-dihydro-1h-pyrimidin-4-one

43. 4(3h)-pyrimidinone, 2-mercapto- (9ci)

44. 59x161scyl

45. 2(1h)-pyrimidinethione, 6-hydroxy- (9ci)

46. Chebi:348530

47. Nsc-19473

48. 124700-72-7

49. 2-sulfanyl-3,4-dihydropyrimidin-4-one

50. Ncgc00095088-01

51. 2,3-dihydro-2-thioxopyrimidin-4(1h)-one

52. Dsstox_cid_1347

53. Dsstox_rid_76100

54. Dsstox_gsid_21347

55. Tiouracyl [polish]

56. 2-thiouracil (van)

57. Tiouracyl

58. 2-thio-4-oxypyrimidine

59. 2-thio-6-oxypyrimidine

60. Cas-141-90-2

61. Ccris 587

62. 2-thio-4-oxo-1,3-pyrimidine

63. Hsdb 2954

64. Nci-c01490

65. Einecs 205-508-8

66. Uracil, 2-thio- (van)

67. Unii-59x161scyl

68. 2-thioxo-1h-pyrimidin-4-one

69. Ai3-25474

70. 2-thio-4-pyrimidone

71. Spectrum_001652

72. Specplus_000746

73. 4-hydroxypyrimidinethione

74. Spectrum3_000979

75. Spectrum4_001104

76. Spectrum5_001378

77. Thiouracil [hsdb]

78. Thiouracil [iarc]

79. Wln: T6mymvj Bus

80. 2-mercaptopyrimidine-4-one

81. 2-thiouracil, >=99%

82. Schembl9172

83. 2-thiouracil [mi]

84. Thiouracil [who-dd]

85. 2-sulfanyl-4-pyrimidinol #

86. 6-hydroxypyrimidine-2-thione

87. Bspbio_002617

88. Kbiogr_001548

89. Kbioss_002132

90. Divk1c_000104

91. Divk1c_006842

92. Spectrum1503973

93. 2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one

94. Chembl345768

95. Dtxsid4021347

96. Hms500f06

97. Kbio1_000104

98. Kbio1_001786

99. Kbio2_002132

100. Kbio2_004700

101. Kbio2_007268

102. Kbio3_001837

103. Ninds_000104

104. Hms1922o08

105. Hms3651f22

106. Hms3885a09

107. Pharmakon1600-01503973

108. Hy-b0503

109. Nsc19473

110. Zinc5127810

111. Tox21_111418

112. Tox21_202418

113. Tox21_302955

114. Ab7033

115. Ccg-39926

116. Mfcd00044203

117. Mfcd09276345

118. Nsc758660

119. S3100

120. Stl011919

121. Stl134904

122. Stl168055

123. Stl185506

124. Akos000119226

125. Akos002303247

126. Akos005366847

127. Akos022061520

128. Tox21_111418_1

129. Am84374

130. Ccg-266107

131. Gs-6727

132. Nsc-758660

133. Sb57767

134. Idi1_000104

135. Smp1_000293

136. Ncgc00095088-02

137. Ncgc00095088-03

138. Ncgc00095088-04

139. Ncgc00095088-05

140. Ncgc00249223-01

141. Ncgc00256423-01

142. Ncgc00259967-01

143. Sy014748

144. 2-thioxo-2,3-dihydro-4(1h)-pyrimidinone

145. Sbi-0051878.p002

146. Db-004877

147. Db-028206

148. Cs-0369245

149. Ft-0613452

150. Ft-0725874

151. Sw220234-1

152. T0224

153. 2-thiouracil, Vetec(tm) Reagent Grade, 99%

154. C19304

155. T-3800

156. T-3808

157. Ab00052397_02

158. Ab00171996_02

159. 2-thiouracil, Vetranal(tm), Analytical Standard

160. Sr-01000872748

161. Sr-01000872748-1

162. Q20892027

163. Z56771015

164. F0001-0490

165. Tul

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₄H₄N₂OS
Molecular Weight	128.15 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	128.00443393 g/mol
Monoisotopic Mass	128.00443393 g/mol
Topological Polar Surface Area	73.2 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	163
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 Therapeutic Uses

Antimetabolites; Antithyroid Agents; Vasodilator Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

THIOURACIL HAS REPORTEDLY BEEN USED IN HUMAN MEDICINE AS ANTI-THYROID AGENT & IN TREATMENT OF ANGINA PECTORIS & CONGESTIVE HEART FAILURE... HOWEVER, NO EVIDENCE WAS FOUND THAT THIOURACIL PRESENTLY FINDS USE IN US IN THESE APPLICATIONS.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V7 86

TREATMENT OF HYPERTHYROIDISM; ANGINA PECTORIS; CONGESTIVE HEART FAILURE /PRC: FORMER USES IN US/

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 1210

MEDICATION (VET): THYROID DEPRESSANT; IN HYPERTHYROIDISM & TO PROMOTE FATTENING

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 1210

4.2 Drug Warning

MAIN DRAWBACK TO THERAPY WITH ANTITHYROID DRUGS IS HIGH INCIDENCE OF RELAPSE WHEN TREATMENT IS STOPPED. /ANTITHYROID DRUGS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1414

PT SHOULD IMMEDIATELY REPORT DEVELOPMENT OF SORE THROAT OR FEVER, WHICH USUALLY HERALDS ONSET OF.../AGRANULOCYTOSIS/. MILD GRANULOCYTOPENIA, IF NOTED, MAY BE SIGN OF THYROTOXICOSIS OR MAY BE FIRST SIGN OF THIS DANGEROUS DRUG REACTION. CAUTION & FREQUENT LEUKOCYTE COUNTS ARE THEN REQUIRED. /THIOAMIDE DERIV/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1413

...WOMEN TAKING THESE AGENTS SHOULD NOT BREAST-FEED THEIR INFANTS. /ANTITHYROID DRUGS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1413

AT WHAT STAGE IN PREGNANCY...TREATMENT MUST BE INITIATED FOR SUCH EFFECT /FETAL GOITER & HYPOTHYROIDISM/ ON FETUS TO DEVELOP IS NOT KNOWN PRECISELY, BUT IN SOME...INSTANCES MEDICATION WAS NOT BEGUN UNTIL TWO-THIRDS THROUGH PREGNANCY. IT IS FEASIBLE...MIGHT RESULT FROM EVEN LATER MATERNAL ADMIN. /ANTI-THYROID DRUGS/

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 669

For more Drug Warnings (Complete) data for 2-THIOURACIL (6 total), please visit the HSDB record page.

5 Pharmacology and Biochemistry

5.1 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.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

5.2 Absorption, Distribution and Excretion

DRUG TRANSMISSION TO FETUS: TIME TO APPEAR IN FETUS 10 MIN; TIME TO FETAL/MATERNAL CONCN EQUILIBRIUM 40 MIN; FETAL/MATERNAL CONCN RATIO 1.0 /FROM TABLE/

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 102

/IN RATS/ ACCUMULATION OF (35)S LABEL WAS FASTER & OCCURRED TO GREATER EXTENT FROM SMALLER DOSE, SUGGESTING PRESENCE OF SATURABLE TRANSPORT MECHANISM. SIMILAR STUDIES WITH (14)C-THIOURACIL HAVE SHOWN ACCUM OF RADIOACTIVITY IN BOTH MATERNAL & FETAL THYROID TISSUES OF RABBITS...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 162

...WITH BOTH LARGE (39 UMOL) & SMALL (1.2 UMOL) DOSES OF (35)S-THIOURACIL, CONSIDERABLE ACCUM OF BOTH TOTAL RADIOACTIVITY & UNMETABOLIZED (35)S-THIOURACIL OCCURS IN THYROID TISSUE RELATIVE TO PLASMA /IN RATS/.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 162

THIOURACIL IS ABSORBED FROM GI TRACT IN RATS... IN RATS ADMIN 5 MG BY IV INJECTION, 30% OF THIOURACIL...RECOVERED FROM CARCASSES AFTER 3 HR & ONLY TRACES AFTER 24 HR.

For more Absorption, Distribution and Excretion (Complete) data for 2-THIOURACIL (7 total), please visit the HSDB record page.

5.3 Metabolism/Metabolites

IN HOMOGENIZED RAT LIVER PREPN FROM FEMALE HOLTZMAN RATS, 28-35% OF THIOURACIL WAS METABOLIZED WITHIN 3 HR. PATHWAY FOR BREAKDOWN OF THIOURACIL WAS SUGGESTED TO BE AS FOLLOWS: URACIL; BETA-UREIDOPROPIONIC ACID, WHICH WAS FURTHER METABOLIZED TO BETA-ALANINE; AMMONIA & CARBON DIOXIDE...

5.4 Mechanism of Action

ANTITHYROID DRUGS INHIBIT FORMATION OF THYROID HORMONE LARGELY BY INTERFERING WITH INCORPORATION OF IODINE INTO ORGANIC FORM. THIS IMPLIES THAT THEY INTERFERE WITH OXIDN OF IODIDE ION, BUT ELUCIDATION OF DETAILED MECHANISM... HAMPERED BY INCOMPLETE UNDERSTANDING OF IODIDE-OXIDIZING SYSTEM OF...GLAND. /ANTITHYROID DRUGS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1411

THIOAMIDE DERIV DO NOT HAVE PERMANENT EFFECT UPON THYROID GLAND BUT INHIBIT HORMONE SYNTHESIS & SECRETION UNTIL SPONTANEOUS REMISSION OCCURS DURING COURSE OF DISEASE. /THIOAMIDE DERIV/

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 607

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