Methimazole

Modify Date: 2024-01-02 17:35:01

Methimazole Structure
Methimazole structure
Common Name Methimazole
CAS Number 60-56-0 Molecular Weight 114.169
Density 1.3±0.1 g/cm3 Boiling Point 280.0±9.0 °C at 760 mmHg
Molecular Formula C4H6N2S Melting Point 144-147 °C(lit.)
MSDS Chinese USA Flash Point 123.1±18.7 °C
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning

 Use of Methimazole


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.

 Names

Name methimazole
Synonym More Synonyms

 Methimazole 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
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.

 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

 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
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

~%

Methimazole Structure

Methimazole

CAS#:60-56-0

Literature: Heterocycles, , vol. 17, p. 125 - 138

~%

Methimazole Structure

Methimazole

CAS#:60-56-0

Literature: European Journal of Inorganic Chemistry, , # 13 p. 2502 - 2511

~%

Methimazole Structure

Methimazole

CAS#:60-56-0

Literature: Journal of the American Chemical Society, , vol. 71, p. 4000

~%

Methimazole Structure

Methimazole

CAS#:60-56-0

Literature: Journal of the Chemical Society, , p. 1806,1809

 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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 Synonyms

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
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