Methimazole

Names

[ CAS No. ]:
60-56-0

[ Name ]:
Methimazole

[Synonym ]:
1-methyl-1H-imidazole-2(3H)-thione
Methimazole
2H-Imidazole-2-thione, 1,3-dihydro-1-methyl-
3-methyl-imidazole-2-thione
methyl-2-mercaptoimidazole
1-methyl-1H-imidazole-2-thiol
Thimazol
Merkastan
Frentirox
2-mercapto-1-methyl-imidazole
2-Mercapto-1-methylimidazole
Metazolo
Thymidazole
thioimidazole
1-Methyl-2-mercapto-1H-imidazole
mercaptomethylimidazole
Basolan
1-Methyl-1,3-dihydro-2H-imidazole-2-thione
1-Methyl-4-imidazoline-2-thione
Tapazole
Methiamazole
Methimazol
Metizol
Tapuzole
1-methylimidazole-2-thione
METAZOLE
thiamazole
1-methyl-2-mercapto-imidazole
N-METHYLIMIDAZOLETHIOL
Mercazole
Favistan
2-Mercapto-1-methyl-1H-imidazole
MFCD00179321
EINECS 200-482-4

Biological Activity

[Description]:

Methimazole(Tapazole, Northyx) is an antithyroid medicine.Target: OthersMethimazole is an antithyroid drug, and part of the thioamide group. Like its counterpart propylthiouracil, a major side effect of treatment is agranulocytosis. Methimazole is a drug used to treat hyperthyroidism, a condition that occurs when the thyroid gland begins to produce an excess of thyroid hormone. The drug may also be taken before thyroid surgery to lower thyroid hormone levels and minimize the effects of thyroid manipulation. Additionally, Methimazole is used in the veterinary setting to treat hyperthyroidism in cats.Methimazole inhibits the enzyme thyroperoxidase, which normally acts in thyroid hormone synthesis by oxidizing the anion iodide (I-) to iodine (I0), facilitating iodine's addition to tyrosine residues on the hormone precursor thyroglobulin, a necessary step in the synthesis of triiodothyronine (T3) and thyroxine. It does not inhibit the action of the sodium-dependent iodide transporter located on follicular cells' basolateral membranes. Inhibition of this step requires competitive inhibitors such as perchlorate and thiocyanate.It acts at CXCL10.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Endocrinology

[References]

[1]. Nakamura H, et al. Comparison of methimazole and propylthiouracil in patients with hyperthyroidism caused by Graves' disease. J Clin Endocrinol Metab. 2007 Jun;92(6):2157-62. Epub 2007 Mar 27.

[2]. Crescioli C, et al. Methimazole inhibits CXC chemokine ligand 10 secretion in human thyrocytes. J Endocrinol. 2007 Oct;195(1):145-55.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
280.0±9.0 °C at 760 mmHg

[ Melting Point ]:
144-147 °C(lit.)

[ Molecular Formula ]:
C₄H₆N₂S

[ Molecular Weight ]:
114.169

[ Flash Point ]:
123.1±18.7 °C

[ Exact Mass ]:
114.025169

[ PSA ]:
56.62000

[ LogP ]:
-0.34

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.633

[ Storage condition ]:
Refrigerator

[ Water Solubility ]:
soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI8615000

CHEMICAL NAME :: Imidazole-2-thiol, 1-methyl-

CAS REGISTRY NUMBER :: 60-56-0

LAST UPDATED :: 199710

DATA ITEMS CITED :: 29

MOLECULAR FORMULA :: C4-H6-N2-S

MOLECULAR WEIGHT :: 114.18

WISWESSER LINE NOTATION :: T5N CNJ A BSH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2250 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - somnolence (general depressed activity) Behavioral - tremor

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1050 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 860 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - somnolence (general depressed activity) Behavioral - tremor

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 345 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - somnolence (general depressed activity) Behavioral - tremor

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 580 mg/kg/1W-C

TOXIC EFFECTS :: Endocrine - evidence of thyroid hypofunction Endocrine - changes in thyroid weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2400 mg/kg/12D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1100 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors Endocrine - thyroid tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 33 gm/kg/1Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors Endocrine - thyroid tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2700 mg/kg/26W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Endocrine - thyroid tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 145 mg/kg

SEX/DURATION :: female 1-34 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 80 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 10 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 600 mg/kg

SEX/DURATION :: female 15-22 day(s) after conception lactating female 7 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - biochemical and metabolic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 320 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 10 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - endocrine system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1100 mg/kg

SEX/DURATION :: female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - parturition Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 160 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 10 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 567 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 10 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1530 ug/kg

SEX/DURATION :: female 18-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 320 mg/kg

SEX/DURATION :: female 16-21 day(s) after conception lactating female 10 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 320 mg/kg

SEX/DURATION :: female 16-21 day(s) after conception lactating female 10 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1152 mg/kg

SEX/DURATION :: female 16-21 day(s) after conception lactating female 10 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - behavioral

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 28 mg/kg/2W (Continuous)

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 326,193,1995 *** REVIEWS *** TOXICOLOGY REVIEW PCNAA8 Pediatric Clinics of North America. (W.B. Saunders Co., W. Washington Sq., Philadelphia, PA 19105) V.1- 1954- Volume(issue)/page/year: 8,413,1961 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83970 No. of Facilities: 33 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 297 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83970 No. of Facilities: 23 (estimated) No. of Industries: 2 No. of Occupations: 4 No. of Employees: 707 (estimated) No. of Female Employees: 239 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317-H361

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R43;R62;R63

[ Safety Phrases ]:
S26-S27-S36-S45-S36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NI8615000

[ HS Code ]:
2933290090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933290090

[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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