Basic information
- CAS
16773-42-5- Standard SMILES
Cc1ncc([N+](=O)[O-])n1CC(O)CCl- InChIKey
IPWKIXLWTCNBKN-UHFFFAOYSA-N- Molecular formula
- C7H10ClN3O3
- Average molar mass
- 219.62 g/mol
- Monoisotopic mass
- 219.0410689
Overview
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 antiamoebic agent, an antiinfective agent, an antiprotozoal drug, an antibacterial drug, an antitrichomonal drug and an epitope. It is a member of imidazoles, a secondary alcohol, a C-nitro compound and an organochlorine compound.
Names & identifiers
- Preferred name
- Ornidazole
- IUPAC
- 1-chloro-3-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol
- English name
- Ornidazole
- Molecular formula
- C7H10ClN3O3
- Molecular weight
- 219.63
Names & synonyms
Ornidazole16773-42-5TiberalRo 7-02071-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-olOrnidazolOrnidazolum1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazoleRo-702071-(2-Hydroxy-3-chloropropyl)-2-methyl-5-nitroimidazoleDTXSID4045420alpha-(Chloromethyl)-2-methyl-5-nitro-1H-imidazole-1-ethanol
Show more names
OPSSOrnidazol a-(ChloroMethyl)-2-Methyl-5-nitro-1H-iMidazole-1-ethanolMadelenOrnidalro7-0207NSC 95075
1H-Imidazole-1-ethanol, alpha-(chloromethyl)-2-methyl-5-nitro-CHEBI:75176NSC-95075alpha-(Chlormethyl)-2-methyl-5-nitro-imidazol-1-aethanol62XCK0G93TRO-7-0207DTXCID20254201-[3-Chloro-2-hydroxypropyl]-2-methyl-5-nitroimidazole
Database identifiers
- CAS
16773-42-5- PubChem CID
- 28061
- DTXSID
DTXSID4045420
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 83.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 211
Experimental & physicochemical properties
LogP0.58
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Antiprotozoal Agents; Nitroimidazoles
Pharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
141.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
144.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
140.17 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 85 · 85-90°C
- Boiling point
- 443.2 · 443.2±40.0 °C(Predicted)
- Density
- 1.6545 · 1.6545 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 97 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Other Safety InformationIMAP assessments - 1H-Imidazole-1-ethanol, .alpha.-(chloromethyl)-2-methyl-5-nitro-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- rtecs
- NI5460000
- hs_code
- 2933.29.4300
- Toxicity
- LD50 in rats, mice (mg/kg): 1780, 1420 orally (Grunberg); LD50 in mice (mg/kg): >2000 orally, >2000 i.p. (Hoffer, Grunberg)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- hazard_class
- IRRITANT
Chemistry & industry
Pharmacology
ATC Code
J01XD03
J - Antiinfectives for systemic use
P - Antiparasitic products, insecticides and repellents
G - Genito urinary system and sex hormones
QP - Antiparasitic products, insecticides and repellents
QG - Genito urinary system and sex hormones
Metabolism/MetabolitesOrnidazole 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 Pharmacological Classification
Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal.
Agents used to treat trichomonas infections.
Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
DescriptionOrnidazole 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.
DescriptionOrnidazole 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.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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