METHYLTHIOURACIL

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 Search

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

Description
Sources: https://monographs.iarc.fr/ENG/Monographs/vol79/mono79-7.pdf | http://www.medical-enc.ru/12/methylthiouracilum.shtml | https://www.ncbi.nlm.nih.gov/pubmed/26239884

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Type I iodothyronine deiodinase 1 Target ID: P49895\|\|\|Q6Q4C6 Gene ID: 1733.0 Gene Symbol: DIO1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23883148	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thyrotoxicosis 3 Sources: https://monographs.iarc.fr/ENG/Monographs/vol79/mono79-7.pdf	Primary		Approved 8429	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.
Sepsis 71 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26239884	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The in-vitro effect of methylthiouracil and oestradiol monophosphate on the conversion of thyroxine to triiodothyronine by kidney slices.	1955 Oct 29	13264643
Aplastic anaemia after propylthiouracil.	1968 Jun 22	4172680
Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.	1994 Aug 17	8080452
Thiouracil antithyroid drugs as a new class of neuronal nitric oxide synthase inhibitors.	2001 Apr 6	11401533
Method for the analysis of thyreostats in meat tissue using gas chromatography with nitrogen phosphorus detection and tandem mass spectrometric confirmation.	2001 May	11348029
Carbon fiber cylindrical microelectrode-based detector for the determination of antithyroid drugs.	2002 Mar 4	18968531
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	12588171
Bioinorganic chemistry in thyroid gland: effect of antithyroid drugs on peroxidase-catalyzed oxidation and iodination reactions.	2006	17497002
Influence of thioketo substitution on the properties of uracil and its noncovalent interactions with alkali metal ions: threshold collision-induced dissociation and theoretical studies.	2006 Feb 2	16435805
Determination of thyreostatics in animal feeds by CE with electrochemical detector.	2009 Oct	19728303
Antithyroid drugs and their analogues protect against peroxynitrite-mediated protein tyrosine nitration--a mechanistic study.	2010 Jan 25	20029917
Interaction of antithyroid drugs with bovine serum albumin: electrophoretic and fluorimetric study.	2010 Mar	19774650
Vasculoprotective effects of rosiglitazone through modulating renin-angiotensin system in vivo and vitro.	2011 Jan 26	21269478
Antithyroid drugs and their analogues: synthesis, structure, and mechanism of action.	2013 Nov 19	23883148
Anti-inflammatory effects of methylthiouracil in vitro and in vivo.	2015 Nov 1	26298005
Methylthiouracil, a new treatment option for sepsis.	2017 Jan	26239884

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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