2-티오우라실

Thiouracil

HCID 1269845CAS 141-90-2

기본 정보

표준 SMILES
O=c1cc[nH]c(=S)[nH]1
InChIKey
ZEMGGZBWXRYJHK-UHFFFAOYSA-N
분자식
C4H4N2OS
평균 분자량
128.15 g/mol
단동위원소 질량
128.00443375

개요

Thiouracil can cause cancer according to The World Health Organization's International Agency for Research on Cancer (IARC).

이름 및 식별자

우선 이름
Thiouracil
IUPAC
2-sulfanylidene-1H-pyrimidin-4-one
현지명
2-티오우라실
영어명
2-Thiouracil
분자식
C4H4N2OS
분자량
128.15

이름 및 동의어

2-thiouracilThiouracil141-90-2DeracilAntagothyroidAntagothyroilNobilen2-thioxo-2,3-dihydropyrimidin-4(1H)-one2-Mercapto-4-hydroxypyrimidine2-Mercapto-4-pyrimidone4(1H)-Pyrimidinone, 2,3-dihydro-2-thioxo-6-Thiouracil
이름 더 보기
2-티오우라실2-싸이오우라실TU2-Mercapto-4-pyriMidinone2-TU
2-Mercapto-4-pyrimidinolUracil, 2-thio-2-sulfanylidene-1H-pyrimidin-4-one4-Hydroxy-2-pyrimidinethiol2,3-Dihydro-2-thioxo-4(1H)-pyrimidinone6-Hydroxy-2-mercaptopyrimidine2-Thio-1,3-pyrimidin-4-one2-Mercapto-4(1H)-pyrimidinone

데이터베이스 식별자

CAS
141-90-2
PubChem CID
1269845
DTXSID
DTXSID4021347
ChEMBL
CHEMBL345768
ChEBI
CHEBI:348530
UNII
59X161SCYL
EC Number
205-508-8
Nikkaji
J9.741A

물성

구조 계산 물성

XLogP
-0.3
극성 표면적
73.2 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
8

실험 및 물리화학적 성질

SpringerMaterials PropertiesDensity
LogP-0.65
OdorODORLESS
TasteBITTER TASTE
Color/Form · 2건

MINUTE CRYSTALS, PRISMS, OR WHITE OR PALE CREAM-COLORED POWDER

PRISMS FROM WATER OR ALC

Solubility · 2건

VERY SLIGHTLY SOL IN WATER (1:2000); PRACTICALLY INSOL IN ETHER, ACIDS; READILY SOL IN ALKALINE SOLN

SLIGHTLY SOL IN ALC; SOL IN ANHYD HYDROGEN FLUORIDE

물리화학적 성질

녹는점
300 °C · >300 °C (lit.)
밀도
1.368 · 1.368 (estimate)
굴절률
1.7 · 1.7000 (estimate)
저장 조건
30 °C · Store below +30°C.
용해도
7.9 g/L · 7.9g/L
물리적 상태
미세 결정성 분말

화학적 성질

white to cream fine crystalline powder

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 5.6% (4 of 71) of reports.

Warning

H351 (94.4%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 71 reports by companies from 5 notifications to the ECHA C&L Inventory.

Danger

유해성 정보

Regulatory Information · 3건

Chemical: 4(1H)-Pyrimidinone, 2,3-dihydro-2-thioxo-

Hazard Traits - Carcinogenicity

4(1H)-Pyrimidinone, 2,3-dihydro-2-thioxo-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and Categories · 3건

Carc. 2 (94.4%)

Acute toxicity (Oral) - Category 5

Acute toxicity (Oral) - Category 5

독성 정보

Natural Pollution SourcesOCCURS IN SEEDS OF BRASSICA, CRUCIFERAE: PURVES, BRIT J EXP PATHOL 22, 241 (1941).
Human Toxicity Excerpts · 5건

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.

Carcinogen Classification · 5건

Thiouracil

Group 2B: Possibly carcinogenic to humans

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

2001

2000

Non-Human Toxicity Excerpts · 5건

DWARFISM & MENTAL RETARDATION...CAN BE PRODUCED IN RATS BY FEEDING DAMS...THIOURACIL...@ DIETARY LEVEL OF 1,000 PPM.

EIGHTY-ONE MICE OF 3 INBRED STRAINS (A, C57 & I) WERE ADMIN 0.1% THIOURACIL (TU) IN COMMERCIAL DIET FOR PERIODS OF UP TO 80 WK. IN 69 MICE EXAM, THYROIDAL FOLLICULAR CYSTS...FOUND & INTERPRETED BY AUTHORS AS NON-MALIGNANT LESIONS, SINCE THEY REGRESSED FOLLOWING WITHDRAWAL OF THIOURACIL...

OF 52 C STRAIN MICE (40 MALES & 12 FEMALES) ADMIN 0.37% THIOURACIL IN DIET FOR 6 MO FOLLOWED BY 0.5% FOR LIFE, LAST ANIMAL DIED @ 116 WK, & NODULAR HYPERPLASIS OF THYROID OCCURRED IN 28/39 MICE SURVIVING LONGER THAN 10 MO... IN (C57XCBA)F1 FEMALE MICE ADMIN 0.2% IN DIET...FROM 1-29 MO, HEPATOMAS...IN 6/21...ANIMALS.

NODULAR HYPERPLASIA OF THYROID WAS OBSERVED IN STANFORD ALBINO RATS OF BOTH SEXES AFTER ADMIN OF 0.1% THIOURACIL IN DIET FOR UP TO 45 WK. INCIDENCE IN MALES INCR FROM 3/10-11/20 AFTER TREATMENT FOR 29 & 45 WK, RESPECTIVELY. NO INCR...IN FEMALE RATS (3/10, COMPARED WITH 5/15) EXAM AFTER TREATMENT FOR 29 & 38 WK...

For more Non-Human Toxicity Excerpts (Complete) data for 2-THIOURACIL (9 total), please visit the HSDB record page.

Evidence for Carcinogenicity · 1건

Evaluation: There is inadequate evidence in humans for the carcinogenicity of thiouracil. There is sufficient evidence in experimental animals for the carcinogenicity of thiouracil. Overall evaluation: Thiouracil is probably carcinogenic to humans (Group 2B).

Antidote and Emergency Treatment · 1건

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/

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
YR1575000
HS 번호
29335995
risk_code
40-45-20/21/22
hazard_code
Xn,T

화학 및 산업

약리 정보

Mechanism of Action · 2건

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/

Metabolism/Metabolites · 1건

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...

MeSH Pharmacological Classification · 2건

Agents that are used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.

Drugs used to cause dilation of the blood vessels.

Absorption, Distribution and Excretion · 5건

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.

용도 및 제조

Uses · 3건

CHEM INT FOR IOTHIOURACIL SODIUM- AN ANTITHYROID AGENT

MEDICATION

MEDICATION (VET)

U.S. Exports · 2건

(1972) No Data

(1975) No Data

U.S. Imports · 2건

(1972) No Data

(1975) No Data

U.S. Production · 2건

(1974) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 2건

CONDENSATION OF ETHYL FORMYLACETATE WITH THIOUREA

PREPD BY CONDENSING ETHYL FORMYLACETATE WITH THIOUREA: WHEELER, LIDDLE, AM CHEM J 40, 550 (1908).

General Manufacturing Information · 2건

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.

응용 분야

용도2-Thiouracil has been used in the synthesis and characterization of silver colloid and film substrates and their applications in surface-enhanced Raman scattering (SERS)

공급사50 곳

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京兰亚化工贸易有限公司+86-25-8331-5620 · [email protected]

추가 설명

정의ChEBI: A nucleobase analogue that is uracil in which the oxo group at C-2 is replaced by a thioxo group.

관련 반응

23건

연결된 노트

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