U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C5H6N2OS
Molecular Weight 142.179
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLTHIOURACIL

SMILES

CC1=CC(=O)NC(=S)N1

InChI

InChIKey=HWGBHCRJGXAGEU-UHFFFAOYSA-N
InChI=1S/C5H6N2OS/c1-3-2-4(8)7-5(9)6-3/h2H,1H3,(H2,6,7,8,9)

HIDE SMILES / InChI
Methylthiouracil is an orally active thyroid enzyme activity inhibitor. Methylthiouracil was introduced in the mid-1940s for the treatment of hyperthyroidism. Methylthiouracil is no longer in clinical use in most countries, although it may be used to a limited degree in some eastern European countries. Methylthiouracil possess anti-inflammatory effects in vitro and in vivo and was found effective in a murine model of sepsis.

Originator

Curator's Comment: Wheeler, H. L., and D. F. McFarland. 'Action of methyl iodide and of benzyl chloride upon 2-oxy-4-methyl-6-methylmercaptopyrimidine.' Am Chem J 42 (1909): 431-440.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P49895|||Q6Q4C6
Gene ID: 1733.0
Gene Symbol: DIO1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

For the treatment of low-grade thyrotoxicosis, methylthiouracil is administered at 0.05 g/day in combination with low doses of iodine. For the treatment of medium and high-grade thyrotoxicosis, methylthiouracil is administered at 0.05-0.25 g 1-3 times/day for 15-25 days.
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The in-vitro effect of methylthiouracil and oestradiol monophosphate on the conversion of thyroxine to triiodothyronine by kidney slices.
1955 Oct 29
Aplastic anaemia after propylthiouracil.
1968 Jun 22
Thiouracil antithyroid drugs as a new class of neuronal nitric oxide synthase inhibitors.
2001 Apr 6
Method for the analysis of thyreostats in meat tissue using gas chromatography with nitrogen phosphorus detection and tandem mass spectrometric confirmation.
2001 May
First example of mu(3)-sulfido bridged mixed-valent triruthenium complex triangle Ru(III)(2)Ru(II)(O,O-acetylacetonate)(3)(mu-O,O,gamma-C-acetylacetonate)(3)(mu(3)-S) (1) incorporating simultaneous O,O- and gamma-C-bonded bridging acetylacetonate units. Synthesis, crystal structure, and spectral and redox properties.
2003 Feb 24
Determination of thyreostatics in animal feeds by CE with electrochemical detector.
2009 Oct
Interaction of antithyroid drugs with bovine serum albumin: electrophoretic and fluorimetric study.
2010 Mar
Antithyroid drugs and their analogues: synthesis, structure, and mechanism of action.
2013 Nov 19
Methylthiouracil, a new treatment option for sepsis.
2017 Jan
Patents

Sample Use Guides

For the treatment of low-grade thyrotoxicosis, methylthiouracil is administered at 0.05 g/day in combination with low doses of iodine. For the treatment of medium and high-grade thyrotoxicosis, methylthiouracil is administered at 0.05-0.25 g 1-3 times/day for 15-25 days.
Route of Administration: Oral
The effect of methylthiouracil on the conversion of thyroxine to triiodothyronine in kidney tissue slices was investigated using a transformation of chromatically pure l-thyroxine labeled with 131I. Methylthiouracil 15 ug dissolved in an alkaline medium was added to the kidney preparations before incubation. The butanol extracts were analyzed by paper chromatography and radioactivity was registered on the chromatogram.
Name Type Language
METHYLTHIOURACIL
HSDB   INN   MART.   MI   WHO-DD  
INN  
Official Name English
METHYLTHIOURACIL [MI]
Common Name English
4(1H)-PYRIMIDINONE, 2,3-DIHYDRO-6-METHYL-2-THIOXO-
Systematic Name English
methylthiouracil [INN]
Common Name English
NSC-193526
Code English
METHYLTHIOURACIL [MART.]
Common Name English
THIMECIL
Brand Name English
METHYLTHIOURACIL [HSDB]
Common Name English
Methylthiouracil [WHO-DD]
Common Name English
6-Methyl-2-thiouracil
Systematic Name English
METHYLTHIOURACIL [IARC]
Common Name English
Classification Tree Code System Code
IARC Methylthiouracil
NCI_THESAURUS C885
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
WHO-ATC H03BA01
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
WHO-VATC QH03BA01
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
Code System Code Type Description
FDA UNII
QW24888U5F
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY
SMS_ID
100000080909
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY
CAS
56-04-2
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
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NSC
193526
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
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MESH
D008779
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
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ECHA (EC/EINECS)
200-252-3
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY
NCI_THESAURUS
C81590
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
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DRUG CENTRAL
1773
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
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HSDB
3366
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
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WIKIPEDIA
METHYLTHIOURACIL
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
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DRUG BANK
DB13644
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY
MERCK INDEX
m7471
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY Merck Index
INN
4150
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID2020890
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL1330588
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY
PUBCHEM
667493
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY
EVMPD
SUB08878MIG
Created by admin on Fri Dec 15 15:13:20 UTC 2023 , Edited by admin on Fri Dec 15 15:13:20 UTC 2023
PRIMARY