Ornidazole

Names

[ Name ]:
Ornidazole

[Synonym ]:
1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole
α-(Chloromethyl)-2-methyl-5-nitro-1H-imidazole-1-ethanol
α-(Chloromethyl)-2-methyl-5-nitroimidazole-1-ethanol
UNII:62XCK0G93T
Imidazole-1-ethanol, α- (chloromethyl)-2-methyl-5-nitro-
Ornidazole
1-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
Imidazole-1-ethanol, α-(chloromethyl)-2-methyl-5-nitro-
α-(Chloromethyl)-2-methyl-5-nitro-1H-imidazole-1-ethanol (9CI)
MFCD00057960
1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)-2-propanol
1H-Imidazole-1-ethanol, α-(chloromethyl)-2-methyl-5-nitro-
a-(Chloromethyl)-2-methyl-5-nitro-1H-imidazole-1-ethanol
1H-Imidazole-1-ethanol, α- (chloromethyl)-2-methyl-5-nitro-
1-chloro-3-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol
EINECS 240-826-0

Biological Activity

[Description]:

Ornidazole(Ro 7-0207) is a 5-nitroimidazole derivative with antiprotozoal and antibacterial properties against anaerobic bacteria. Target: Antibacterial; AntiparasiticOrnidazole is a drug that cures some protozoan infections. Ornidazole 1 g/day is effective for the prevention of recurrence of Crohn's disease after ileocolonic resection [1]. Ornidazole is converted to reduction products that interact with DNA to cause destruction of helical DNA structure and strand leading to a protein synthesis inhibition and cell death in susceptible organisms [2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

Natural Products >> Others

[References]

[1]. Rutgeerts, P., et al., Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial. Gastroenterology, 2005. 128(4): p. 856-61.

[2]. Goldstein, E.J., V.L. Sutter, and S.M. Finegold, Comparative susceptibilities of anaerobic bacteria to metronidazole, ornidazole, and SC-28538. Antimicrob Agents Chemother, 1978. 14(4): p. 609-13.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
443.2±40.0 °C at 760 mmHg

[ Melting Point ]:
85-90°C

[ Molecular Formula ]:
C₇H₁₀ClN₃O₃

[ Molecular Weight ]:
219.626

[ Flash Point ]:
221.9±27.3 °C

[ Exact Mass ]:
219.041061

[ PSA ]:
83.87000

[ LogP ]:
0.69

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

[ Index of Refraction ]:
1.617

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI5460000

CHEMICAL NAME :: Imidazole-1-ethanol, alpha-(chloromethyl)-2-methyl-5-nitro-

CAS REGISTRY NUMBER :: 16773-42-5

BEILSTEIN REFERENCE NO. :: 0614299

LAST UPDATED :: 199612

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C7-H10-Cl-N3-O3

MOLECULAR WEIGHT :: 219.65

WISWESSER LINE NOTATION :: T5N CNJ A1YQ1G B1 ENW

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 :: 1780 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 :: 1139 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 :: 1120 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 375 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 - rabbit

DOSE/DURATION :: >2 gm/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 :: 36400 mg/kg/13W-C

TOXIC EFFECTS :: Related to Chronic Data - changes in prostate weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 6500 mg/kg/26D-I

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 292 gm/kg/2Y-C

TOXIC EFFECTS :: Brain and Coverings - changes in brain weight Blood - changes in erythrocyte (RBC) count Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 25600 mg/kg

SEX/DURATION :: male 64 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 35 gm/kg

SEX/DURATION :: male 61 day(s) pre-mating female 14 day(s) pre-mating - 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 11200 mg/kg

SEX/DURATION :: male 4 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 5600 mg/kg

SEX/DURATION :: male 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

MUTATION DATA

TYPE OF TEST :: Host-mediated assay

TEST SYSTEM :: Rodent - mouse Bacteria - Salmonella typhimurium

DOSE/DURATION :: 50 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 86,243,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
NI5460000

[ HS Code ]:
2933290090

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%

Articles

Determination of nitroimidazole residues in aquaculture tissue using ultra high performance liquid chromatography coupled to tandem mass spectrometry.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 960 , 105-15, (2014)

An UHPLC-MS/MS method was developed for the quantitative confirmatory analysis of residues of nitroimidazole drugs (dimetridazole, ipronidazole, metronidazole, ornidazole and ronidazole) and their cor...

Phenotypic and transcriptional profiling in Entamoeba histolytica reveal costs to fitness and adaptive responses associated with metronidazole resistance.

Front. Microbiol. 6 , 354, (2015)

Antimicrobial chemotherapy is critical in the fight against infectious diseases caused by Entamoeba histolytica. Among the drugs available for the treatment of amebiasis, metronidazole (MTZ) is consid...

Genetically different clonal isolates of Trichomonas gallinae, obtained from the same bird, can vary in their drug susceptibility, an in vitro evidence.

Parasitol. Int. 60(2) , 213-5, (2011)

Trichomonas gallinae is a flagellated protozoon which parasitizes in the upper digestive tract of different birds, especially columbiformes (doves and pigeons) and falconiformes. The parasite is also ...

Related Compounds

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