Misonidazole

Names

[ Name ]:
Misonidazole

[Synonym ]:
α-(Methoxymethyl)-2-nitroimidazole-1-ethanol
1-Methoxy-3-(2-nitro-1H-imidazol-1-yl)-2-propanol
misonidazol
1-Methoxy-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol
Misonidazole
a-(Methoxymethyl)-2-nitro-1H-imidazole-1-ethanol
Ro 7-0582
Imidazole-1-ethanol, α- (methoxymethyl)-2-nitro-
1H-Imidazole-1-ethanol, α- (methoxymethyl)-2-nitro-
EINECS 236-931-6
SRI 1354
1-Methoxy-3-(2-nitro-1-imidazolyl)-2-propanol
1H-Imidazole-1-ethanol, α-(methoxymethyl)-2-nitro-

Biological Activity

[Description]:

Misonidazole (Ro 7-0582; SR 1354) is a hypoxic tumor cell radiosensitizer[1]. Misonidazole also has antimicrobial effects[2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Bibo Li, et al. Preparation, Characterization, and In Vitro pH-sensitivity Evaluation of Superparamagnetic Iron Oxide Nanoparticle- Misonidazole pH-sensitive Liposomes. Curr Drug Deliv. 2019;16(3):254-267.

[2]. R C Knight, et al. Mechanism of action of nitroimidazole antimicrobial and antitumour radiosensitizing drugs. Effects of reduced misonidazole on DNA. Int J Radiat Biol Relat Stud Phys Chem Med. 1979 Oct;36(4):367-77.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
438.5±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₇H₁₁N₃O₄

[ Molecular Weight ]:
201.180

[ Flash Point ]:
219.0±31.5 °C

[ Exact Mass ]:
201.074951

[ PSA ]:
93.10000

[ LogP ]:
-0.28

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.583

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI5572000

CHEMICAL NAME :: Imidazole-1-ethanol, alpha-(methoxymethyl)-2-nitro-

CAS REGISTRY NUMBER :: 13551-87-6

BEILSTEIN REFERENCE NO. :: 0613655

LAST UPDATED :: 199612

DATA ITEMS CITED :: 36

MOLECULAR FORMULA :: C7-H11-N3-O4

MOLECULAR WEIGHT :: 201.21

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 228 mg/kg/3W-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, allergic (after systemic exposure)

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2131 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1 gm/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 :: 1869 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1340 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 :: 1414 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 :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1300 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 :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 1700 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5360 mg/kg/20D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 670 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 670 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 gm/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: Micronucleus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sister chromatid exchange

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 5 mmol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 78,289,1980

Safety Information

[ HS Code ]:
2933290090

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%