 Home > Encyclopedia > Thiouracil

Thiouracil

Thiouracil structure

CAS No:
141-90-2
Formula:
C4H4N2OS
Chemical Name:
Thiouracil
Synonyms:
4(1H)-Pyrimidinone,2,3-dihydro-2-thioxo-;Uracil,2-thio-;2,3-Dihydro-2-thioxo-4(1H)-pyrimidinone;6-Hydroxy-2-mercaptopyrimidine;2-Mercapto-4-hydroxypyrimidine;2-Thiouracil;Thiouracil;2-Mercapto-4-pyrimidinol;Antagothyroil;Deracil;Nobilen;4-Hydroxy-2-pyrimidinethiol;4-Hydroxy-2-mercaptopyrimidine;2-Mercapto-4-pyrimidinone;NSC 19473;NSC 290412;NSC 290413;NSC 290414;2-Thioxo-2,3-dihydropyrimidin-4(1H)-one;2-Sulfanyl-3,4-dihydropyrimidin-4-one;2-Sulfanylidene-1H-pyrimidin-4-one;2-Sulfanylpyrimidin-4-ol;2-Sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one;2-Mercapto-3H-pyrimidin-4-one;2-Thioxo-2,3-dihydro-1H-pyrimidin-4-one;107646-88-8;107646-89-9;156-82-1;4401-53-0;4401-54-1
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

white to cream fine crystalline powderChEBI: A nucleobase analogue that is uracil in which the oxo group at C-2 is replaced by a thioxo group.

Thiouracil is a nucleobase analogue that is uracil in which the oxo group at C-2 is replaced by a thioxo group. It has a role as an antithyroid drug and a metabolite. It is a thiocarbonyl compound and a nucleobase analogue. It derives from a uracil.|Thiouracil is a sulfur-containing uracil. An established antithyroid drug and highly selective inhibitor of nitric oxide synthase (NOS), thiouracil also covalently binds to dopaquinone, produced by tyrosinase catalyzed oxidation of tyrosine, thereby selectively accumulating in de novo-synthesized melanin in overactive melanin-producing cells and providing a means to localize melanoma cells. (NCI04)|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.

Thiouracil Basic Attributes

Molecular Weight：

128.15

Exact Mass：

128.15

EC Number：

205-508-8

UNII：

59X161SCYL

NSC Number：

758660|19473

DSSTox ID：

DTXSID4021347

NCI Thesaurus Code：

C29856

Color/Form：

MINUTE CRYSTALS, PRISMS, OR WHITE OR PALE CREAM-COLORED POWDER|PRISMS FROM WATER OR ALC

HScode：

29335995

Characteristics

PSA：

73.2

XLogP3：

-0.3

Appearance：

white to pale yellow crystalline powder

Density：

1.368 (estimate)

Melting Point：

>340 °C (decomp)

Boiling Point：

337.2ºC at 760mmHg

Flash Point：

157.7ºC

Refractive Index：

1.7000 (estimate)

Water Solubility：

H2O: 7.9g/l0.5 g/L

Storage Conditions：

2-8ºC

Vapor Pressure：

5.45E-05mmHg at 25°C

Odor：

ODORLESS

Taste：

BITTER TASTE

Collision Cross Section：

119.87 Å² [M+H]+

Experimental Properties：

FORMS PPT & COMPLEXES WITH HEAVY METALS & OTHER COMPD; REACTS WITH VARIOUS SULFHYDRYL REAGENTS

Safety Information

Packing level：

III

Hazard category：

Transport codes：

UN 3077 9/PG III

wgk germany：

hazard class code：

R40

safety instructions：

36/37-53-45

RTECS Number：

YR1575000

Marks：

Xn,T

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P281

Hazard Statements：

H351

GHS Classification：

|Warning|H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]|P201, P202, P281, P308+P313, P405, and P501|Aggregated GHS information provided by 51 companies from 3 notifications to the ECHA C&L Inventory.|Danger|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P281, P308+P313, P312, P314, P405, and P501

Toxicity

Natural Pollution Sources：

OCCURS IN SEEDS OF BRASSICA, CRUCIFERAE: PURVES, BRIT J EXP PATHOL 22, 241 (1941).

Drug Information

Therapeutic Uses：

Antimetabolites; Antithyroid Agents; Vasodilator Agents|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.|TREATMENT OF HYPERTHYROIDISM; ANGINA PECTORIS; CONGESTIVE HEART FAILURE /PRC: FORMER USES IN US/|MEDICATION (VET): THYROID DEPRESSANT; IN HYPERTHYROIDISM & TO PROMOTE FATTENING

Drug Warnings：

MAIN DRAWBACK TO THERAPY WITH ANTITHYROID DRUGS IS HIGH INCIDENCE OF RELAPSE WHEN TREATMENT IS STOPPED. /ANTITHYROID DRUGS/|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/|...WOMEN TAKING THESE AGENTS SHOULD NOT BREAST-FEED THEIR INFANTS. /ANTITHYROID DRUGS/|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/|For more Drug Warnings (Complete) data for 2-THIOURACIL (6 total), please visit the HSDB record page.

MeSH：

Agents that are used to treat hyperthyroidism by reducing the excessive production of thyroid hormones. (See all compounds classified as Antithyroid Agents.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

Absorption：

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/|/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...|...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/.|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.

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...

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/|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/

Antidote：

EARLIEST SIGN OF HYPOTHYROIDISM CALL FOR REDN IN DOSE; IF BY CHANCE THEY HAVE ADVANCED TO POINT OF DISCOMFORT, THYROID HORMONE CAN BE GIVEN TO HASTEN RECOVERY. FULL DOSE OF 120-180 MG DAILY OF THYROID OR EQUIV OF TYHROXINE OR TRIIODOTHYRONINE FOR WK WILL USUALLY SUFFICE. /ANTI-THYROID DRUGS/

Human Toxicity Excerpts：

HEMORRHAGE, PETECHIAE, PURPURA.|THIOURACIL CAN INDUCE HEPATIC INJURY. /FROM TABLE/|THESE DRUGS /WHICH INCL THIOURACIL/ HAVE CAUSED NUMEROUS TOXIC SIDE REACTIONS PRINCIPALLY...DRUG FEVER, SKIN ERUPTIONS, & ARTERITIS.|MATERNAL ANTI-THYROID MEDICATION...HAS RESULTED...IN DEVELOPMENT OF FETAL GOITER, & OCCASIONALLY IN HYPOTHYROIDISM IN SOME NEONATE LEADING TO MENTAL RETARDATION. ... JUST OCCASIONALLY, GOITER IN AFFECTED INFANTS MAY OBSTRUCT AIR PASSAGE, & CAUSE RESPIRATORY DISTRESS.|For more Human Toxicity Excerpts (Complete) data for 2-THIOURACIL (6 total), please visit the HSDB record page.

MeSH Entry Terms：

Thiouracil

Thiouracil Use and Manufacturing

Methods of Manufacturing

Thiourea (0.045 mol, 3.42 g) was weighed out, Crushed into the crude product obtained in Example 1, The reaction solution becomes thick, diluted with 15mL ethyl acetate reaction system, The reaction was stirred at 60 ° C for 2 hours and the reaction was completed by TLC.The reaction was concentrated to dryness, The resulting white solid was added 40mL hydrochloric acid solution (3mol / L) pulping 1 hour after filtration, Filter cake with 10mL water rinse, 50 ° C for 4 hours under vacuum to give a white solid powder 4.25g, Two-step combined yield of 74percent, purity: 98.97percent.(i) 2-[(4, 4-difluoro-3-butenyl)thio]-4(3H)-pyrimidinone (Compound No. 70). M+ =218; 1 H NMR (CDCl3): delta2.42(2H, m); 3.22(2H, t); 4.15-4.35(1H, m); 6.22(1H, d); 7.88(1H, d); (white solid mp 75.5-76.5 C.) from 2-thiouracil.

Uses

Reagent used in the preparation of Antithyroid agents. antiviral, thyroid depressant

Production

(1974) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Manufacturing Info：

4(1H)-Pyrimidinone, 2,3-dihydro-2-thioxo-: ACTIVE|THIOAMIDE DERIV USED IN THIS COUNTRY ARE PROPYLTHIOURACIL, METHIMAZOLE, & METHYLTHIOURACIL. THESE DRUGS HAVE REPLACED PARENT COMPD, THIOURACIL, WHICH IS MORE TOXIC.

Analytic Methods：

MERCURIMETRIC METHOD OF ABBOTT, CF, J PHARM PHARMACOL, 5, 53-59 (1953) HAS BEEN BASIS FOR DETERMINATION...IN PHARMACEUTICAL PREPN; MODIFICATION OF THIS METHOD...BY PINZAUTI ET AL, J PHARM SCI, 62, 997-999 (1973).|...IDENTIFIED BY USE OF 2,6-DICHLOROQUINONE CHLOROIMIDE REAGENT (MCALLISTER, 1951), BY NEGATIVE IODOBISMUTHOUS ACID TEST (MCALLISTER, 1952) OR BY MICROSCOPIC TESTS (ASHLEY, 1953; KOFLER & KOLSEK, 1970).|/SEVERAL REF ARE LISTED FOR DETERMINING THIOURACIL IN DRUGS/. BROMINATION METHOD. SEE 32.394, 10 EDITION.

Laboratory Methods：

...DETERMINED COLORIMETRICALLY IN SERUM, BLOOD & URINE.../BUT/ SINCE THESE COLORIMETRIC METHODS ARE NON-SPECIFIC, MORE RECENT DETERMINATIONS...HAVE EMPLOYED (35)S-LABELED THIOURACIL & SEPN BY CHROMATOGRAPHIC PROCEDURES (LEES ET AL, ENDOCRINOLOGY, 93, 162-171, 1953...)

Computed Properties

Molecular Weight:128.15
XLogP3:-0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:128.00443393
Monoisotopic Mass:128.00443393
Topological Polar Surface Area:73.2
Heavy Atom Count:8
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Thiouracil

Xi'an Honest BioEngr Co.,Ltd. Contact Supplier

CN
3 YRS

Business licensed

Trader Supplier of Estradiol,Progesterone,GS441524,4-Butylresorcinol,DeoxyArbutin,Coenzyme Q10,Piracetam,Pregabalin,Ketoprofen,omeprazole,Fullerene C60,Melatonin,Nicotinamide riboside chloride,lactoferrin,Tylosin tartrate,Gentamycin Sulfate,Levamisole HCl,Praziquantel,Ivermectin,GA3,Pepsin,MT2,5 amino 1MQ,selank,semax

100% Safe customs clearance high quality 2-Thiouracil CAS 141-90-2 with Best Price

CAS No.: 141-90-2

Grade: Pharmaceutical Grade

Content: 99%

Inquiry
Greenbo Biochem Contact Supplier

CN
4 YRS

Business licensed Certified factory

Manufactory Supplier of Active Pharm Ingredients,Chemical Catalyst,Pharmaceutical Intermediates,Flavors and Fragrances,Agrochemicals,Chemical Pesticides,Organic Intermediates,OLED Intermediates

2-Thiouracil 99% Powder Professional Producer Greenbo

CAS No.: 141-90-2

Grade: Pharmaceutical Grade

Content: 99%

Inquiry
Yangzhou Juhechang Technology Co., Ltd. Contact Supplier

CN
6 YRS

Business licensed Certified factory

Manufactory Supplier of 2-Butyl-5-ch,Uracil,Carbomer,allyl amyl glycolate

2-Thiouracil CAS 141-90-2 99% White Powder

CAS No.: 141-90-2

Grade: Pharmaceutical Grade

Content: 99%

Inquiry
HangzhouMeasureLifeTechnologyCo.,LTD Contact Supplier

CN
3 YRS

Business licensed

Trader Supplier of 2-Thiouracil

2-Thiouracil 98-99%

Unit Price: $120-140 /KG FOB

CAS No.: 141-90-2

Inquiry
NANTONG REFORM PETRO-CHEMICAL CO.,LTD Contact Supplier

CN
4 YRS

Business licensed Certified factory

Manufactory Supplier of Flavors & Fragrances,Catalyst & Auxiliary,Intermediates,Dyes & Pigments,Inorganic Chemistry,petro chemicals,Surfactant,Food Additives,Water Treatment Chemicals

2-Thiouracil CAS:141-90-2 organic chemical Intermediates Chemical Reagent Intermediates

Unit Price: $1 /KG FOB

CAS No.: 141-90-2

Grade: Industrial Grade

Content: 99%

Inquiry