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

Molecular Formula	C5H6N2OS
Molecular Weight	142.179
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thyrotoxicosis 6 Sources: https://monographs.iarc.fr/ENG/Monographs/vol79/mono79-7.pdf	Primary		Approved 8583	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 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26239884	Primary		Preclinical	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 activator 150 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 OATP1B3 961 OATP1B1 1079 BSEP 550 BCRP 910 CYP19A1 429 P-gp 1741	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 10.0	inconclusive [IC50 56.3813 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 11.0	inconclusive [IC50 80.1608 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 5.0	no [IC50 23.7101 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEzMzA1ODgifX0=	no [IC50 >1000 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 61.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 461.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 453.0	no
CYP3A4 2633	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 35.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 440.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 35.0	no
MRP1 232	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 29.0	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 63.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEzMzA1ODgifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEzMzA1ODgifX0	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 439.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/667493#section=Biological-Test-Results Page: 462.0

PubMed

Title	Date	PubMed
Methylthiouracil, a new treatment option for sepsis.	2017-01	26239884
Anti-inflammatory effects of methylthiouracil in vitro and in vivo.	2015-11-01	26298005
Antithyroid drugs and their analogues: synthesis, structure, and mechanism of action.	2013-11-19	23883148
Vasculoprotective effects of rosiglitazone through modulating renin-angiotensin system in vivo and vitro.	2011-01-26	21269478
Interaction of antithyroid drugs with bovine serum albumin: electrophoretic and fluorimetric study.	2010-03	19774650
Antithyroid drugs and their analogues protect against peroxynitrite-mediated protein tyrosine nitration--a mechanistic study.	2010-01-25	20029917
Determination of thyreostatics in animal feeds by CE with electrochemical detector.	2009-10	19728303
Influence of thioketo substitution on the properties of uracil and its noncovalent interactions with alkali metal ions: threshold collision-induced dissociation and theoretical studies.	2006-02-02	16435805
Bioinorganic chemistry in thyroid gland: effect of antithyroid drugs on peroxidase-catalyzed oxidation and iodination reactions.	2006	17497002
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.	2003-02-24	12588171
Carbon fiber cylindrical microelectrode-based detector for the determination of antithyroid drugs.	2002-03-04	18968531
Method for the analysis of thyreostats in meat tissue using gas chromatography with nitrogen phosphorus detection and tandem mass spectrometric confirmation.	2001-05	11348029
Thiouracil antithyroid drugs as a new class of neuronal nitric oxide synthase inhibitors.	2001-04-06	11401533
Structure-activity relationship of ligands of uracil phosphoribosyltransferase from Toxoplasma gondii.	1994-08-17	8080452
Aplastic anaemia after propylthiouracil.	1968-06-22	4172680
The in-vitro effect of methylthiouracil and oestradiol monophosphate on the conversion of thyroxine to triiodothyronine by kidney slices.	1955-10-29	13264643

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:50:42 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:42 GMT 2025`
Record UNII	QW24888U5F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIMECIL

Preferred Name

English

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

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