Ornidazole

Base Information

• Chemical Name: Ornidazole
• CAS No.: 16773-42-5
• Molecular Formula: C7H10ClN3O3
• Molecular Weight: 219.628
• Hs Code.: 2933290090
• European Community (EC) Number: 240-826-0
• NSC Number: 759295,95075
• UNII: 62XCK0G93T
• DSSTox Substance ID: DTXSID4045420
• Nikkaji Number: J2.746D
• Wikipedia: Ornidazole
• Wikidata: Q2358146
• NCI Thesaurus Code: C166891
• Metabolomics Workbench ID: 153903
• ChEMBL ID: CHEMBL1449676
• Mol file: 16773-42-5.mol

Synonyms:Ornidazole;Ro 7 0207;Ro 7-0207;Ro 70207;Ro-70207;Ro7 0207;Ro7-0207;Ro70207;Tiberal

Chemical Property of Ornidazole

Chemical Property:

• Appearance/Colour: Crystalline solid
• Vapor Pressure: 1.23E-08mmHg at 25°C
• Melting Point: 85-90 ºC
• Refractive Index: 1.617
• Boiling Point: 443.2 ºC at 760 mmHg
• PKA: 2.4 ± 0.1(at 25℃)
• Flash Point: 221.9 ºC
• PSA: 83.87000
• Density: 1.53 g/cm³
• LogP: 1.22260
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in ethanol at 50mg/ml
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 219.0410689
• Heavy Atom Count: 14
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

Ornidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NC=C(N1CC(CCl)O)[N+](=O)[O-]
• Recent ClinicalTrials: Intravenous Versus Combined Oral and Intravenous Antimicrobial Prophylaxis for the Prevention of Surgical Site Infection in Elective Colorectal Surgery
• Recent EU Clinical Trials: Préparation colique et antibiotiques oraux avant chirurgie du cancer colique: un essai randomisé multicentrique en double aveugle
• Description: 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 development of microorganisms. Ornidazole is available as an oral tablet that should be taken based on a pharmacist/doctor’s instructions. Prescriptions that include this drug should also take into consideration some of the patient’s specifications such as hypersensitivity and potential drug interactions. Ornidazole is an orally bioavailable 5-nitroimidazole derivative with antibacterial and antiprotozoal activities. Ornidazole inhibits the growth of clinical isolates of B. fragilis (MICs = 0.5-5 μM) and various anaerobic bacteria when used at concentrations ranging from less than 0.1 to 3.2 μg/ml. It also inhibits the growth of Giardia isolates (IC50s = 0.01-0.47 μg/ml). Oral administration of ornidazole reduces T. vaginalis and T. foetus infection in mice and E. histolytica infection in rats with curative dose (CD50) values of 37, 3, and 10 mg/kg, respectively. Ornidazole (400 mg/kg per day) induces infertility in male rats within 7 days and inhibits spermatozoa binding to rat oocyte zona pellucida.
• Indications: Ornidazole is given to patients who have vaginal infections such as bacterial vaginitis, post-surgical infections, anaerobic bacterial infections, skin infections, trichomonas vaginitis, intestinal infections, stomach infections, parasitic infections and bacterial infections. It is highly recommended that this drug is taken under appropriate diagnosis and medical indication.
• Drug Interactions: Some medications have a higher probability of interacting with other prescription drugs hence the doctor should approve any medication adjustments. It is essential for a patient to notify their doctor of any medication, herbal treatments and vitamin supplements that they may be taking before the administration of Ornidazole. A prompt notification may minimize the probability of occurrence of specific side effects. Ornidazole may interact with warfarin and vecuronium.
• Uses: Ornidazole is a drug that cures some protozoan infections. It has been investigated for use in Crohn's disease after bowel resection. It is indicated in treatment of mixed amoebiasis, mixed amoebic dysentery, mixed giardiasis, trichomoniasis, bacterial vaginosis, Sexually transmitted diseases, infections of gynaecology, lower respiratory tract infections, ENT, surgical and dental infections. Anti-infective estrogen
• Therapeutic Function: Antiinfective

Technology Process of Ornidazole

There total 6 articles about Ornidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.2%

(S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + 2-methyl-5-nitro-1H-imidazole (696-23-1,88054-22-2) → (S)-(-)-1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (16773-42-5,166734-83-4)

Guidance literature:

With aluminum (III) chloride; In ethyl acetate; at 3 - 5 ℃;

Reference yield: 85.2%

2-methyl-5-nitro-1H-imidazole (696-23-1,88054-22-2) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → ornidazole (16773-42-5,166734-83-4)

Guidance literature:

With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(dimethylamino)cyclohexyl]thiourea; In ethyl acetate; at 25 - 30 ℃; for 6h; Solvent; Temperature; Reagent/catalyst;

Reference yield: 60.0%

S-(-)-1-(2-acetoxypropyl-3-chloro)-2-methyl-5-nitroimidazole → (S)-(-)-1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (16773-42-5,166734-83-4)

Guidance literature:

With hydrogenchloride; for 5h;

DOI:10.1016/S0957-4166(97)00260-7

upstream raw materials:

2-methyl-5-nitro-1H-imidazole

epichlorohydrin

ornidazole

(S)-epichlorohydrin

Downstream raw materials:

1-(2-methyl-5-nitro-imidazol-1-yl)-3-o-tolyloxy-propan-2-ol

Refernces

• 1、 -. "Process for preparing 5-nitroimidazole medicine through catalysis of small organic molecules". Paragraph 0035-0040; 0047-0050. . Retrieved 2020/08/09.
• 2、 -. "Nitroimidazole derivative, preparation method and applications thereof". Paragraph 0139-0146. . Retrieved 2020/02/29.