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Basic Information

Molecular Structure:
CAS No.:	16773-42-5
Name:	Ornidazole
Article Data:	19

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:	Xn
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

Conditions	Yield
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

Conditions	Yield
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

: 160738-57-8, 112811-59-3
gatifloxacin

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide In ethanol; water for 12h; Reflux;	87%

: 16773-42-5
ornidazole

: C14H19Cl2N6O8P

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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)	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 : Harmful Xn
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 NO_x.

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- .