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Basic Information
CAS No.: 16773-42-5
Name: Ornidazole
Article Data: 19
Molecular Structure:
Molecular Structure of 16773-42-5 (Ornidazole)
Formula: C7H10ClN3O3
Molecular Weight: 219.628
Synonyms: Tiberal;1-Chloro-3-(5-(hydroxy(oxido)amino)-2-methyl-1H-imidazol-1-yl)-2-propanol;Ornidazol [INN-Spanish];alpha-(Chloromethyl)-2-methyl-5-nitro-1H-imidazole-1-ethanol (9CI);Madelen;Imidazole-1-ethanol, .alpha.- (chloromethyl)-2-methyl-5-nitro-;Prestwick_584;Ornidazolum [INN-Latin];1H-Imidazole-1-ethanol, .alpha.-(chloromethyl)-2-methyl-5-nitro-;Ormidazole;S-(-)-ornidazole;
EINECS: 240-826-0
Density: 1.53 g/cm3
Melting Point: 85-90 ºC
Boiling Point: 443.2 ºC at 760 mmHg
Flash Point: 221.9 ºC
Solubility: 4330 mg/L at 25 ºC in water
Appearance: Crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
PSA: 83.87000
LogP: 1.22260
Synthetic route
696-23-1

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

106-89-8

epichlorohydrin

16773-42-5

ornidazole

Conditions
ConditionsYield
With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(dimethylamino)cyclohexyl]thiourea In ethyl acetate at 25 - 30℃; for 6h; Solvent; Temperature; Reagent/catalyst;85.2%
Stage #1: 2-methyl-5-nitro-1H-imidazole With aluminum (III) chloride In ethyl acetate at 0℃; for 0.25h;
Stage #2: epichlorohydrin In ethyl acetate
79%
With aluminum (III) chloride In ethyl acetate at 45 - 50℃; for 1.5h;78%
16773-42-5

ornidazole

16773-52-7

(±)-2-methyl-5-nitro-1-(oxiran-2-ylmethyl)-1H-imidazole

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 0℃; for 1h; Inert atmosphere;97.2%
With sodium hydroxide In dichloromethane; water at 0℃;91%
With sodium hydroxide In dichloromethane at 0℃; for 3h;90%
With sodium hydroxide for 0.25h;82%
16773-42-5

ornidazole

1-cyclopropyl-6-fluoro-7-(4-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)-3-methylpiperazin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 12h; Reflux;93%
10025-99-7

potassium tetrachloroplatinate(II)

16773-42-5

ornidazole

84431-20-9

(NO2CCHNC(CH3)N(CH2CH(OH)CH2Cl))2PtCl2

Conditions
ConditionsYield
In water solid ligand added to aq. soln. of K2(PtCl4), stirred at 50 °C for 1 h; ppt. filtered, washed with EtOH/Et2O, Et2O, dried in vac.; elem. anal.;91%
16773-42-5

ornidazole

1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(3-methylaminopiperidin-1-yl)-3-quinolinecarboxylic acid

1-cyclopropyl-6-fluoro-7-(3-((2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)(methyl)amino)piperidin-1-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 12h; Reflux;91%

moxifloxacin hydrochloride

16773-42-5

ornidazole

1-cyclopropyl-6-fluoro-7-((4aS,7aS)-1-(2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl)hexahydro-1H-pyrrolo[3,4-b]pyridin-6(2H)-yl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 12h; Reflux;87%
16773-42-5

ornidazole

C14H19Cl2N6O8P

Conditions
ConditionsYield
With trichlorophosphate In acetonitrile Reflux;87%
108-24-7

acetic anhydride

16773-42-5

ornidazole

57939-59-0

1-(2-acetoxypropyl-3-chloro)-2-methyl-5-nitroimidazole

Conditions
ConditionsYield
With pyridine for 1h; Ambient temperature;84%
16773-42-5

ornidazole

potassium 4-benzylpiperidinedithiocarbamate

(±)-2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl 4-benzylpiperidine-1-carbodithioate

Conditions
ConditionsYield
In acetone for 4h; Alkylation; Heating;81%
16773-42-5

ornidazole

4-phenyl-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

1-(2-methyl-5-nitro-imidazol-1-yl)-3-(4-phenyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propan-2-ol

Conditions
ConditionsYield
With potassium carbonate In acetone for 21h; Alkylation; Heating;81%
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Chemistry

Molecular Structure of Ornidazole (CAS NO.16773-42-5):

IUPAC Name: 1-Chloro-3-(2-methyl-5-nitroimidazol-1-yl)propan-2-ol
Canonical SMILES: CC1=NC=C(N1CC(CCl)O)[N+](=O)[O-]
InChI: InChI=1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3
InChIKey: IPWKIXLWTCNBKN-UHFFFAOYSA-N
Molecular Weight: 219.6256 [g/mol]
Molecular Formula: C7H10ClN3O3
XLogP3: 0.6
H-Bond Donor: 1
H-Bond Acceptor: 4 
Index of Refraction: 1.617
Molar Refractivity: 50.19 cm3
Molar Volume: 143.3 cm3
Surface Tension: 58.2 dyne/cm
Density: 1.53 g/cm3
Flash Point: 221.9 °C
Enthalpy of Vaporization: 73.86 kJ/mol
Boiling Point: 443.2 °C at 760 mmHg
Vapour Pressure: 1.23E-08 mmHg at 25 °C
Appearance: Crystalline Solid
Melting Point: 85-90 °C
Water Solubility: 4330 mg/L at 25 °C
Classification Code: Amebicides; Anti-Infective Agents; Anti-infective; Antiparasitic Agents; Antiprotozoal Agents; Antitrichomonal agents; Drug / Therapeutic Agent; Mutation data; Radiation-sensitizing agents; Reproductive Effect

Uses

 Ornidazole (CAS NO.16773-42-5) is a drug that cures some protozoan infections. It is used by the poultry industry. It has been investigated for use in Crohn's disease after bowel resection.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1120mg/kg (1120mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 612, 1978.
mouse LD50 intravenous 375mg/kg (375mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 612, 1978.
mouse LD50 oral 1139mg/kg (1139mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 612, 1978.
rabbit LD50 oral > 2gm/kg (2000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 612, 1978.
rat LD50 oral 1780mg/kg (1780mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 612, 1978.

Safety Profile

Safety Information of Ornidazole (CAS NO.16773-42-5):
Hazard Codes : HarmfulXn
Risk Statements : 22 
R22:Harmful if swallowed.
Safety Statements : 36 
S36:Wear suitable protective clothing.
WGK Germany : 3
RTECS : NI5460000
Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl and NOx.

Specification

 Ornidazole (CAS NO.16773-42-5), its Synonyms are 1-(2-Hydroxy-3-chloropropyl)-2-methyl-5-nitroimidazole ; 1-(3-Chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole ; Madelen ; Ornidazolum ; alpha-(Chlormethyl)-2-methyl-5-nitro-imidazol-1-aethanol ; alpha-(Chloromethyl)-2-methyl-5-nitroimidazole-1-ethanol ; 1H-Imidazole-1-ethanol, alpha-(chloromethyl)-2-methyl-5-nitro- ; Imidazole-1-ethanol, alpha-(chloromethyl)-2-methyl-5-nitro- .