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Ornidazole

Ornidazole structure

CAS No:
16773-42-5
Formula:
C7H10ClN3O3
Chemical Name:
Ornidazole
Synonyms:
1H-Imidazole-1-ethanol,α-(chloromethyl)-2-methyl-5-nitro-;Imidazole-1-ethanol,α-(chloromethyl)-2-methyl-5-nitro-;α-(Chloromethyl)-2-methyl-5-nitro-1H-imidazole-1-ethanol;α-(Chloromethyl)-2-methyl-5-nitro-1-imidazoleethanol;Ro 7-0207;1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole;Ornidazole;Tiberal;(±)-Tiberal;Ornidal;Madelen;NSC 95075;(±)-Ornidazole;Ornisid;Ornidone;Ornitop;Giro;Ornilox;Dazolic;1-Chloro-3-(2-methyl-5-nitro-imidazol-1-yl)-propan-2-ol;1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol;1-Chloro-3-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol;95880-34-5;166734-79-8
Categories:
Active Pharmaceutical Ingredients > Antiparasitic Drugs

Description

Crystalline SolidChEBI: A C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by 3-chloro-2-hydroxypropyl and methyl groups, respectively. It is used in the treatment of susceptible protozoal infections and for thetreatment of anaerobic bacterial infections.Ornidazole is prescribed for the treatment of certain protozoan infections, post-surgery infections and bacterial infections. The action of this drug is based on its potential to inhibit the d

Ornidazole is a C-nitro compound that is 5-nitroimidazole in which the hydrogens at positions 1 and 2 are replaced by 3-chloro-2-hydroxypropyl and methyl groups, respectively. It is used in the treatment of susceptible protozoal infections and for the treatment of anaerobic bacterial infections. It has a role as an antiprotozoal drug, an antiinfective agent, an antibacterial drug, an antitrichomonal drug, an epitope and an antiamoebic agent. It is a member of imidazoles, a C-nitro compound, a secondary alcohol and an organochlorine compound.|Ornidazole has been used in trials studying the prevention of Elective Colorectal Surgery.|A nitroimidazole antiprotozoal agent used in ameba and trichomonas infections. It is partially plasma-bound and also has radiation-sensitizing action.

Ornidazole Basic Attributes

Molecular Weight：

219.63

Exact Mass：

219.63

EC Number：

240-826-0

NSC Number：

759295|95075

DSSTox ID：

DTXSID4045420

ATC Code：

J01XD03|G - Genito urinary system and sex hormones|J - Antiinfectives for systemic use|P - Antiparasitic products, insecticides and repellents

HScode：

2933290090

Characteristics

PSA：

83.9

XLogP3：

0.6

Appearance：

Crystalline Solid

Density：

1.497 g/cm³

Melting Point：

77-78 °C

Boiling Point：

443.2±40.0 °C(Predicted)

Flash Point：

221.9±27.3 °C

Refractive Index：

1.6000 (estimate)

Water Solubility：

Soluble in ethanol at 50mg/ml

Storage Conditions：

-20°C Freezer

Vapor Pressure：

1.23E-08mmHg at 25°C

Toxicity：

LD50 in rats, mice (mg/kg): 1780, 1420 orally (Grunberg); LD50 in mice (mg/kg): >2000 orally, >2000 i.p. (Hoffer, Grunberg)

Collision Cross Section：

141.7 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|144.6 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

RTECS Number：

NI5460000

Marks：

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 96 companies from 3 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)|Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)|Agents used to treat trichomonas infections. (See all compounds classified as Antitrichomonal Agents.)

Metabolism/Metabolites：

Ornidazole has known human metabolites that include (2S,3S,4S,5R)-6-[1-chloro-3-(2-methyl-5-nitroimidazol-1-yl)propan-2-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

MeSH Entry Terms：

Ornidazole

Ornidazole Use and Manufacturing

Methods of Manufacturing

A mixture of 2-methyl-4/5-nitro-1H-imidazole (1, 39.37mmol) and anhydrous aluminium chloride (39.37mmol) were dissolved in ethylacetate (50mL) at 0°C and stirred for 15min then added (±)-epichlorohydrin (78.74mmol) to the above reaction mixture and contents were further stirred for 15–20h. After completion of reaction (as monitored by TLC) 30mL of distilled water was added and further continued the stirring for 30min and stopped the reaction. Then EtOAc (20mL) and excess water (3×30mL) was added to the reaction mixture and organic layer was separated, dried (anhyd. NaTake 2-methyl-5-nitroimidazole 10g, After adding ethyl acetate 200ml dissolved, Then add anhydrous aluminum trichloride 10g, stirring and cooling, After cooling to 0°C, epichlorohydrin 20g was added dropwise.Insulation reaction, After the reaction is completed, the reaction solution is slowly added to water and hydrolyzed.Separate the ethyl acetate layerThe ethyl acetate layer was extracted with a 10percent hydrochloric acid solution.Finally, the acid-water layer was adjusted to pH 7 with ammonia, and a solid precipitated.Filter and dry to obtain compound 2 4.8g.

Uses

Antiparasitic drugs. Used as anti-anaerobic bacteria and antiprotozoal drugs

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:219.62
XLogP3:0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:219.0410689
Monoisotopic Mass:219.0410689
Topological Polar Surface Area:83.9
Heavy Atom Count:14
Complexity:211
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Through the nitro group in its molecule, it is reduced to amino group in an anaerobic environment or through the formation of free radicals, which interact with cell components and cause the death of microorganisms.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Ornidazole vaginal effervescent tablets
Indication	1. Compared with other nitroimidazole drugs, ornidazole has no inhibitory effect on acetaldehyde dehydrogenase. 2. Ornidazole can inhibit the metabolism of the anticoagulant warfarin, prolong its half-life, and enhance the efficacy of the anticoagulant. When used with warfarin, attention should be paid to observing the prothrombin time and adjusting the dosage. 3. Barbiturates, ranitidine, cimetidine and other drugs can accelerate the elimination of ornidazole and reduce its efficacy and affect coagulation, so their combined use should be contraindicated. 4. The simultaneous use of drugs that induce liver microsomal enzymes such as phenytoin sodium and phenobarbital can enhance the metabolism of ornidazole, reduce blood drug concentrations, and slow down the excretion of phenytoin sodium. 5. Ornidazole can delay the effect of the muscle relaxant vecuronium bromide.
Specifications	0.5g
Manufacturer	Xi'an Wan Long Pharmaceutical Co., Ltd.

Ornidazole Sodium Chloride Injection
Ingredients	Ornidazole. Chemical name: 1-(3-chloro-2-hydropropyl)-2-methyl-5-nitroimidazole.
Indication	1. Compared with other nitroimidazole drugs, this product has no inhibitory effect on acetaldehyde dehydrogenase. 2. Ornidazole can inhibit the metabolism of the anticoagulant warfarin, prolong its half-life, and enhance the efficacy of the anticoagulant. When used with warfarin, the prothrombin time should be observed and the dosage should be adjusted. 3. Since this product has many contraindications, it should be administered alone.
Specifications	100ml: Ornidazole 0.25g, Sodium chloride 0.86g
Manufacturer	Nanjing Sanhome Pharmaceutical Co., Ltd.

Ornidazole vaginal suppository
Ingredients	The main ingredient of this product is ornidazole, and its chemical name is: α-chloromethyl-2-methyl-5-nitroimidazole-1-ethanol. Its structural formula: Molecular formula: C7H10CIN3O3 Molecular weight: 219.63
Indication	1. Ornidazole can inhibit the metabolism of the anticoagulant warfarin and prolong its half-life. When used with warfarin, the prothrombin time should be observed and the dosage should be adjusted. 2. Cimetidine can accelerate the elimination of ornidazole. Therefore, cimetidine should be avoided when using ornidazole. 3. Compared with other nitroimidazole drugs, ornidazole has no inhibitory effect on acetyl dehydrogenase. 4. Ornidazole can prolong the muscle relaxant effect of vecuronium bromide.
Specifications	0.5g
Manufacturer	Harbin Reputation Scale Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Chengdu Jingxi Pharmaceutical Co., Ltd.

China
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Hunan Jiudian HONGYANG Pharmaceutical Co., Ltd.

China
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China
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