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Chemistry

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Also known as: 51-52-5, 6-propyl-2-thiouracil, Propacil, Procasil, Prothiurone, Prothyran
Molecular Formula
C7H10N2OS
Molecular Weight
170.23  g/mol
InChI Key
KNAHARQHSZJURB-UHFFFAOYSA-N
FDA UNII
721M9407IY

Propylthiouracil
A thiourea antithyroid agent. Propythiouracil inhibits the synthesis of thyroxine and inhibits the peripheral conversion of throxine to tri-iodothyronine. It is used in the treatment of hyperthyroidism. (From Martindale, The Extra Pharmacopeoia, 30th ed, p534)
Propylthiouracil is a Thyroid Hormone Synthesis Inhibitor. The mechanism of action of propylthiouracil is as a Thyroid Hormone Synthesis Inhibitor.
1 2D Structure

Propylthiouracil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-propyl-2-sulfanylidene-1H-pyrimidin-4-one
2.1.2 InChI
InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)
2.1.3 InChI Key
KNAHARQHSZJURB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCC1=CC(=O)NC(=S)N1
2.2 Other Identifiers
2.2.1 UNII
721M9407IY
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 6 Propyl 2 Thiouracil

2. 6-propyl-2-thiouracil

2.3.2 Depositor-Supplied Synonyms

1. 51-52-5

2. 6-propyl-2-thiouracil

3. Propacil

4. Procasil

5. Prothiurone

6. Prothyran

7. Propycil

8. 2-mercapto-6-propylpyrimidin-4-ol

9. Prothiucil

10. Protiural

11. Thiuragyl

12. 6-n-propylthiouracil

13. Prothycil

14. Propyl-thiorist

15. Propyl-thyracil

16. Thyreostat Ii

17. Propythiouracil

18. Propilthiouracil

19. 6-propylthiouracil

20. Propyl-thiorit

21. 6-propyl-2-thioxo-2,3-dihydropyrimidin-4(1h)-one

22. Propylthiorit

23. 6-thio-4-propyluracil

24. 6-n-propyl-2-thiouracil

25. Propylthiouracile

26. Ptu (thyreostatic)

27. 4-propyl-2-thiouracil

28. Propiltiouracilo

29. Propylthiouracilum

30. 2-mercapto-6-propyl-4-pyrimidone

31. 2-mercapto-6-propylpyrimid-4-one

32. 2-thio-6-propyl-1,3-pyrimidin-4-one

33. 2-thio-4-oxo-6-propyl-1,3-pyrimidine

34. 6-propil-tiouracile

35. Uracil, 6-propyl-2-thio-

36. 6-propyl-2-sulfanylidene-1h-pyrimidin-4-one

37. Nsc 6498

38. 2-mercapto-4-hydroxy-6-n-propylpyrimidine

39. 2,3-dihydro-6-propyl-2-thioxo-4(1h)-pyrimidinone

40. 6-propyl-2-thio-2,4(1h,3h)pyrimidinedione

41. 500-50-5

42. 4(1h)-pyrimidinone, 2,3-dihydro-6-propyl-2-thioxo-

43. Mfcd00006041

44. Chebi:8502

45. 6-propyl-2 Thiouracil

46. Nsc-6498

47. Nsc-70461

48. Mls000028494

49. 721m9407iy

50. Cas-51-52-5

51. Ncgc00022715-03

52. Smr000058275

53. Propiltiouracile

54. Dsstox_cid_1209

55. Propiltiouracile [dcit]

56. 6-n-propylthiouracil;6-propyl-2-thiouracil;ptu

57. Dsstox_rid_76011

58. Dsstox_gsid_21209

59. Wln: T6mymvj Bus F3

60. 4-hydroxy-2-mercapto-6-propylpyrimidine

61. 6-propil-tiouracile [italian]

62. Propiltiouracilo [inn-spanish]

63. Propyl Thiouracil

64. Propylthiouracile [inn-french]

65. Propylthiouracilum [inn-latin]

66. 6-propyl-2-thio-2,3h)-pyrimidinedione

67. Ccris 544

68. Hsdb 3390

69. Propylthiouracil (tn)

70. Sr-05000001706

71. 4(1h)-pyrimidinone,3-dihydro-6-propyl-2-thioxo-

72. Einecs 200-103-2

73. 6-(n-propyl)-2-thiouracil

74. Ai3-25477

75. Unii-721m9407iy

76. 6-propyl-2-sulfanylpyrimidin-4-ol

77. Prestwick_810

78. 6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one

79. Propylthiouracil [usp:inn:ban:jan]

80. 6-propyl-2-thioxo-1h-pyrimidin-4-one

81. 6-propyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1h)-one

82. Spectrum_000876

83. 2-mercapto-6-propylpyrimidin-4(3h)-one

84. Opera_id_530

85. 3cj

86. Prestwick0_000494

87. Prestwick1_000494

88. Prestwick2_000494

89. Prestwick3_000494

90. Spectrum2_001302

91. Spectrum3_001731

92. Spectrum4_000492

93. Spectrum5_001815

94. 6-propyl-2-thio-2,4(1h,3h)-pyrimidinedione

95. 2-thio-4-hydroxy-6-n-propyl-pyrimidine

96. Chembl1518

97. Schembl41239

98. Bspbio_000387

99. Bspbio_003402

100. Kbiogr_001003

101. Kbioss_001356

102. Propylthiouracil [mi]

103. Mls002303010

104. Mls006011901

105. Divk1c_000268

106. Propylthiouracil [inn]

107. Propylthiouracil [jan]

108. Spectrum1500515

109. Spbio_001363

110. Spbio_002308

111. Propylthiouracil [hsdb]

112. Propylthiouracil [iarc]

113. 6-propyl-2-thioxo-2, 3-dihydropyrimidin-4(1h)-one

114. Bpbio1_000427

115. Gtpl6650

116. Propylthiouracil [vandf]

117. Dtxsid5021209

118. Propylthiouracil [mart.]

119. Schembl17375339

120. Hms500n10

121. Kbio1_000268

122. Kbio2_001356

123. Kbio2_003924

124. Kbio2_006492

125. Kbio3_002622

126. Nsc6498

127. Propylthiouracil [usp-rs]

128. Propylthiouracil [who-dd]

129. Propylthiouracil [who-ip]

130. Ninds_000268

131. Hms1569d09

132. Hms1766d22

133. Hms1920l22

134. Hms2092e03

135. Hms2096d09

136. Hms2230b22

137. Hms3259m04

138. Hms3371d17

139. Hms3655j07

140. Hms3713d09

141. Pharmakon1600-01500515

142. Bcp22165

143. Hy-b0346

144. Nsc70461

145. Propylthiouracil (jp17/usp/inn)

146. Zinc4640636

147. Tox21_110882

148. Tox21_201741

149. Tox21_300280

150. 2-mercapto-6-propyl-pyrimidin-4-ol

151. Ac8761

152. Bdbm50133597

153. Ccg-39240

154. Nsc 70461

155. Nsc757302

156. S1988

157. Stl102645

158. Propylthiouracil [ep Impurity]

159. Propylthiouracil [orange Book]

160. 6-propyl-2-sulfanyl-4-pyrimidinol #

161. Akos000120319

162. Akos001053246

163. Akos015892537

164. Tox21_110882_1

165. 2-thio-4-hydroxy-6-n-propylpyrimidine

166. Bs-3928

167. Db00550

168. Nc00533

169. Nsc-757302

170. Propylthiouracil [ep Monograph]

171. Ps-3436

172. 4-hydroxy-6-n-propylpyrimidine-2-thiol

173. Idi1_000268

174. Propylthiouracil [usp Monograph]

175. 6-propyl-2-thiouracil, Enzyme Inhibitor

176. Ncgc00016229-01

177. Ncgc00016229-02

178. Ncgc00016229-03

179. Ncgc00016229-04

180. Ncgc00016229-05

181. Ncgc00016229-06

182. Ncgc00016229-07

183. Ncgc00016229-08

184. Ncgc00016229-09

185. Ncgc00016229-10

186. Ncgc00016229-11

187. Ncgc00016229-13

188. Ncgc00016229-14

189. Ncgc00090881-01

190. Ncgc00090881-02

191. Ncgc00090881-03

192. Ncgc00178089-01

193. Ncgc00178089-02

194. Ncgc00183321-01

195. Ncgc00254180-01

196. Ncgc00259290-01

197. 2-mercapto-4-hydroxy-6-propyl Pyrimidine

198. Ac-10795

199. Propylthiouracil / 6-propyl-2-thiouracil

200. Smr003317355

201. Sy038617

202. Sbi-0051497.p003

203. Bb 0242498

204. Ft-0621285

205. Ft-0695546

206. P0533

207. Sw196944-3

208. C07569

209. D00562

210. 6-propyl-2-sulfanyl-3,4-dihydropyrimidin-4-one

211. 6-propyl-2-thiouracil, Purum, >=98.0% (t)

212. Ab00052082_05

213. Ab00052082_06

214. Q377342

215. Sr-05000001706-1

216. Sr-05000001706-2

217. Sr-05000001706-3

218. W-105881

219. 6-propyl-2-thioxo-2,3-dihydro-1h-pyrimidin-4 -one

220. Brd-k48168960-001-04-4

221. Brd-k48168960-001-05-1

222. Brd-k48168960-001-08-5

223. Z56922173

224. F1967-1318

225. F2199-0035

226. F3097-4245

227. 4(1h)-pyrimidinone,6-butyl-2,3-dihydro-2-thioxo-

228. 6-propyl-2-thiouracil, Vetranal(tm), Analytical Standard

229. Propylthiouracil, European Pharmacopoeia (ep) Reference Standard

230. Propylthiouracil, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 170.23 g/mol
Molecular Formula C7H10N2OS
XLogP30.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass170.05138412 g/mol
Monoisotopic Mass170.05138412 g/mol
Topological Polar Surface Area73.2 Ų
Heavy Atom Count11
Formal Charge0
Complexity223
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NamePropylthiouracil
PubMed HealthPropylthiouracil (By mouth)
Drug ClassesAntithyroid Agent
Drug LabelPropylthiouracil, USP is one of the thiocarbamide compounds. It is a white, crystalline substance that has a bitter taste and is very slightly soluble in water. Propylthiouracil is an antithyroid drug administered orally. The structural formula is:Ea...
Active IngredientPropylthiouracil
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanyDava Pharms; Actavis Elizabeth

2 of 2  
Drug NamePropylthiouracil
PubMed HealthPropylthiouracil (By mouth)
Drug ClassesAntithyroid Agent
Drug LabelPropylthiouracil, USP is one of the thiocarbamide compounds. It is a white, crystalline substance that has a bitter taste and is very slightly soluble in water. Propylthiouracil is an antithyroid drug administered orally. The structural formula is:Ea...
Active IngredientPropylthiouracil
Dosage FormTablet
RouteOral
Strength50mg
Market StatusPrescription
CompanyDava Pharms; Actavis Elizabeth

4.2 Therapeutic Uses

Mesh Heading: Antimetabolites, Antithyroid Agents

National Library of Medicine, SIS; ChemIDplus Record for Propylthiouracil (51-52-5). Available from, as of April 17, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp


... Propylthiouracil /is/ indicated in the treatment of hyperthyroidism, including prior to surgery or radiotherapy, and as adjuncts in the treatment of thyrotoxicosis or thyroid storm. Propylthiouracil may be preferred over methimazole for use in thyroid storm, since propylthiouracil inhibits peripheral conversion of thyroxine (T4) to triiodothyronine (T3).

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 450


EXPTL USE: Paradoxically propylthiouracil has been shown to reverse histological changes of alcoholic hepatitis in rat and has been proposed as possible treatment for this condition in man.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 917


EXPTL USE: Twelve-day pretreatment with PTU prevented the tylenol-induced increase in transaminase activities. Increase in hepatic reduced glutathione levels and prevention of inflammatory response to necrotic liver tissue appeared to be mechanism in protective action of hypothyroidism.

PMID:7350016 LINSCHEER ET AL; GASTROENTEROLOGY 78 (1): 100 (1980)


For more Therapeutic Uses (Complete) data for PROPYL THIOURACIL (14 total), please visit the HSDB record page.


4.3 Drug Warning

Although reported much less frequently, severe adverse effects, including inhibition of myelopoiesis with resultant agranulocytosis, granulocytopenia, and thrombocytopenia; aplastic anemia; drug fever; lupus-like syndrome (including splenomegaly); severe hepatic reactions (including encephalopathy, fulminant hepatic necrosis, and death); periarteritis; and hypoprothrombinemia and bleeding, have been reported to occur in some patients receiving propylthiouracil. Nephritis and interstitial pneumonitis have also been reported. Cutaneous vasculitis, which may manifest as purpuric and/or bullous hemorrhagic lesions or erythema nodosum, and possibly may progress to necrotic ulcerations, and polymyositis also have occurred.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3192


Agranulocytosis is potentially the most serious adverse effect of propylthiouracil, and most cases of agranulocytosis appear to occur within the first 2 months of therapy, but rarely may occur after 4 months of therapy. The risk of propylthiouracil-induced agranulocytosis appears to be substantially increased in patients older than 40 years of age compared with younger patients, but, unlike methimazole, an association with dosage has not been established. Although the mechanism(s) of propylthiouracil-induced agranulocytosis has not been determined, antigranulocyte antibodies have been reported in some patients with thioamide-induced agranulocytosis; a direct toxic effect of these drugs on bone marrow has not been excluded as an additional possible cause.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3192


Propylthiouracil crosses the placenta and may cause fetal harm when administered to pregnant women; the drug can induce goiter and hypothyroidism (cretinism) in the developing fetus. If the drug is used during pregnancy for the management of hyperthyroidism, the manufacturer states that careful dosage adjustment, using a sufficient but not excessive dosage of propylthiouracil, is necessary. The manufacturer states that because thyroid dysfunction diminishes in many women as pregnancy proceeds, a reduction in dosage may be possible, and, in some patients, propylthiouracil can be discontinued 2 or 3 weeks before delivery. If propylthiouracil is used during pregnancy, or if a woman becomes pregnant while receiving the drug, she should be advised of the potential hazard to the fetus.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3192


... Disagreement about therapy of thyrotoxicosis during pregnancy. Antithyroid drugs cross placenta and can cause fetal hypothyroidism and goiter. ... There are 3 choices of therapy, each with its advocates: minimal doses of antithyroid drugs, full doses ... with thyroid hormone supplementation, or surgery. /Antithyroid drugs/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1375


For more Drug Warnings (Complete) data for PROPYL THIOURACIL (20 total), please visit the HSDB record page.


4.4 Drug Indication

Used to manage hyperthyroidism which is due to an overactive thyroid gland (Grave's disease).


5 Pharmacology and Biochemistry
5.1 Pharmacology

Propylthiouracil is a thiourea antithyroid agent. Grave's disease is the most common cause of hyperthyroidism. It is an autoimmune disease where an individual's own antibodies attach to thyroid stimulating hormone receptors within cells of the thyroid gland and then trigger overproduction of thyroid hormone. The two thyroid hormones manufactured by the thyroid gland, thyroxine (T4) and triiodothyronine (T3), are formed by combining iodine and a protein called thyroglobulin with the assistance of an enzyme called peroxidase. PTU inhibits iodine and peroxidase from their normal interactions with thyroglobulin to form T4 and T3. This action decreases thyroid hormone production. PTU also interferes with the conversion of T4 to T3, and, since T3 is more potent than T4, this also reduces the activity of thyroid hormones. The actions and use of propylthiouracil are similar to those of methimazole.


5.2 MeSH Pharmacological Classification

Antimetabolites

Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)


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 FDA Pharmacological Classification
5.3.1 Active Moiety
PROPYLTHIOURACIL
5.3.2 FDA UNII
721M9407IY
5.3.3 Pharmacological Classes
Thyroid Hormone Synthesis Inhibitors [MoA]; Thyroid Hormone Synthesis Inhibitor [EPC]
5.4 ATC Code

H03BA02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


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

H03 - Thyroid therapy

H03B - Antithyroid preparations

H03BA - Thiouracils

H03BA02 - Propylthiouracil


5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed following oral administration.


Route of Elimination

Propylthiouracil is readily absorbed and is extensively metabolized. Approximately 35% of the drug is excreted in the urine, in intact and conjugated forms, within 24 hours.


Elimination: Less than 1% is excreted in the urine unchanged. Total body clearance is approximately 7 L/hr. In dialysis: Elimination and pharmacokinetics are not significantly altered in hemodialysis. In one patient undergoing hemodialysis, 5% of a 200 mg oral dose was removed by 3 hours of hemodialysis; elimination rate was not significantly altered. Peak serum concentration was decreased (from 7.9 to 4.9 ug/mL), although it remained within an approximate therapeutic range.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 450


Although distribution of propylthiouracil into human body tissues and fluids has not been fully characterized, the drug appears to be concentrated in the thyroid gland. Propylthiouracil readily crosses the placenta. Propylthiouracil is distributed into milk; however, some studies indicate that the extent of distribution is only about 0.007-0.077% of a single dose.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3192


Propylthiouracil is rapidly and readily absorbed from the GI tract following oral administration with peak plasma concentrations of about 6-9 mcg/mL occurring within 1-1.5 hours after a single dose of 200-400 mg. In one study in which the drug was administered orally and IV, about 75% of the oral dose was absorbed. Plasma concentrations of the drug do not appear to correlate with the therapeutic effects.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3192


Time to peak effect: 17 weeks (average) to normalize serum T3 and T4 concentrations with use of 300 mg/day.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 450


For more Absorption, Distribution and Excretion (Complete) data for PROPYL THIOURACIL (19 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Propylthiouracil was concentrated by thyroid gland, and four sulfur-35 compounds were demonstrated by TLC in both rat and man: unchanged propylthiouracil, (35)-sulfate, unknown propylthiouracil metabolite and protein-bound sulfur-35...

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 73 (1974)


Biotransformation: Primarily undergoes glucuronidation. Approximately 33% of an orally administered dose is metabolized by a first-pass effect.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 450


Presence of more than one glucuronide conjugate of propylthiouracil ought to be expected, as it has four functional groups, each capable of conjugation with glucuronic acid ...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 307


Although the exact metabolic fate of propylthiouracil has not been fully established, the drug is rapidly metabolized to its glucuronide conjugate and other minor metabolites and requires frequent administration to maintain its antithyroid effect. The drug and its metabolites are excreted in urine, with about 35% of a dose excreted within 24 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3192


For more Metabolism/Metabolites (Complete) data for PROPYL THIOURACIL (8 total), please visit the HSDB record page.


5.7 Biological Half-Life

2 hours


The elimination half-life of propylthiouracil has generally been reported to be about 1-2 hours.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3192


The plasma half-life of propylthiouracil .../is/ 1 to 2 hours.

Haddad, L.M. (Ed). Clinical Management of Poisoning and Drug Overdose 3rd Edition. Saunders, Philadelphia, PA. 1998., p. 1141


/After GI absorption/ plasma half-lives of 2.5 hr (human) and 4.8 hr (rat) have been reported ... .

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 72 (1974)


The half-life of propylthiouracil in plasma is about 75 min ...

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1581


Propylthiouracil is rapidly absorbed from /orally/ dosed tablets in man, yielding max plasma levels at 60-120 min, and biological t/2 of about 60 min in euthyroid subjects.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 163


5.8 Mechanism of Action

Propylthiouracil binds to thyroid peroxidase and thereby inhibits the conversion of iodide to iodine. Thyroid peroxidase normally converts iodide to iodine (via hydrogen peroxide as a cofactor) and also catalyzes the incorporation of the resulting iodide molecule onto both the 3 and/or 5 positions of the phenol rings of tyrosines found in thyroglobulin. Thyroglobulin is degraded to produce thyroxine (T4) and tri-iodothyronine (T3), which are the main hormones produced by the thyroid gland. Therefore propylthiouracil effectively inhibits the production of new thyroid hormones.


Propylthiouracil inhibits the synthesis of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin; the drug also inhibits the coupling of these iodotyrosyl residues to form iodothyronine. Although the exact mechanism(s) has not been fully elucidated, propylthiouracil may interfere with the oxidation of iodide ion and iodotyrosyl groups. Based on limited evidence it appears that the coupling reaction is more sensitive to antithyroid agents than the iodination reaction. Propylthiouracil does not inhibit the action of thyroid hormones already formed and present in the thyroid gland or circulation nor does the drug interfere with the effectiveness of exogenously administered thyroid hormones. Patients whose thyroid gland contains relatively high concentration of iodine (e.g., from prior ingestion or from administration during diagnostic radiologic procedures) may respond relatively slowly to antithyroid agents. Unlike methimazole, propylthiouracil inhibits the peripheral deiodination of thyroxine to triiodothyronine. Although the importance of this inhibition has not been established, propylthiouracil has a theoretical advantage compared with methimazole or carbimazole in patients with thyrotoxic crisis, since a decreased rate of conversion of circulating thyroxine to triiodothyronine may be clinically beneficial in these patients.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 3192


The thionamide /propylthiouracil/ inhibit organification of iodide and the coupling of iodotyrosines to form hormonally active iodothyronines.

Haddad, L.M. (Ed). Clinical Management of Poisoning and Drug Overdose 3rd Edition. Saunders, Philadelphia, PA. 1998., p. 1141


Inhibit synthesis of thyroid hormone within the thyroid gland by serving as substrates for thyroid peroxidase, which catalyzes the incorporation of oxidized iodide into tyrosine residues in thyroglobulin molecules and couples iodotyrosines. This diverts iodine from the synthesis of thyroid hormones. Antithyroid agents do not interfere with the actions of exogenous thyroid hormone or inhibit the release of thyroid hormones. Therefore, stores of thyroid hormones must be depleted before clinical effects will be apparent. Antithyroid agents may also have moderating effects on the underlying immunologic abnormalities, in hyperthyroidism due to Graves' disease (toxic-diffuse goiter), but evidence on this point reported to date is inconclusive.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 450


Type I 5'-deiodinase (D1) is inhibited by ... the antithyroid drug propylthiouracil.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1567


For more Mechanism of Action (Complete) data for PROPYL THIOURACIL (9 total), please visit the HSDB record page.


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20-Nov-2024
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