Conditions | Yield |
---|---|
With formic acid; sulfuric acid at 80℃; for 12h; Temperature; | 88% |
With formic acid at 50 - 60℃; for 0.5h; Reagent/catalyst; Temperature; | 74.9% |
With phosphoric acid; acetic anhydride In water at 25 - 30℃; for 2.5h; Yield given; | |
With sulfuric acid; acetic acid at 90℃; for 0.5h; Concentration; Temperature; Cooling; | |
With formic acid; sulfuric acid Large scale; |
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate
benzoic acid
metronidazole
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 71% |
metronidazole phosphate
metronidazole
Conditions | Yield |
---|---|
With human serum In water at 37℃; human serum hydrolysis of metronidazole phosphate; pH dependence of solubility of metronidazole and metronidazole phosphate; |
Conditions | Yield |
---|---|
With aqueous buffer Rate constant; pHs 0.83-8.82, half-life times for the hydrolysis, also in simulated intestinal fluid (pH 7.55), Jones medium (pH 6.69) and Kupferberg medium (pH 6.11); |
Conditions | Yield |
---|---|
With aqueous buffer Rate constant; pHs 0.83-8.82, half-life times for the hydrolysis, also in simulated intestinal fluid (pH 7.55), Jones medium (pH 6.69) and Kupferberg medium (pH 6.11); |
Conditions | Yield |
---|---|
With aqueous buffer Rate constant; pHs 0.83-8.82, half-life times for the hydrolysis, also in simulated intestinal fluid (pH 7.55), Jones medium (pH 6.69) and Kupferberg medium (pH 6.11); |
metronidazole glycyl glycinate hydrochloride
A
Glycine anhydride
B
glycylglycine
C
metronidazole
Conditions | Yield |
---|---|
With aqueous buffer Rate constant; pHs 0.83-8.82, half-life times for the hydrolysis, also in simulated intestinal fluid (pH 7.55), Jones medium (pH 6.69) and Kupferberg medium (pH 6.11); |
metronidazole glycyl phenylalaninate hydrochloride
A
Gly-Phe-OH
B
metronidazole
C
cyclo(Gly-Phe)
Conditions | Yield |
---|---|
With aqueous buffer Rate constant; pHs 0.83-8.82, half-life times for the hydrolysis, also in simulated intestinal fluid (pH 7.55), Jones medium (pH 6.69) and Kupferberg medium (pH 6.11); |
Conditions | Yield |
---|---|
In water at 20℃; under 735.5 Torr; Rate constant; also in the presence of enzymes or cellular extracts with nitroreductase, oxygen reductase, superoxide dismutase or nitrite raductase activity, variation of pH; also the radical anion of 5-nitro-2-furaldoxime; | |
In water at 20℃; under 735.5 Torr; Rate constant; also in the presence of a copper oxidase (laccase or ceruloplasmin); also the radical anion of misonidazole; |
Conditions | Yield |
---|---|
With sodium chloride at 25℃; Rate constant; rate constant of hydrolysis; pH 4.5; other pH, buffers; | |
With water at 37℃; Rate constant; rate constant of hydrolysis; |
Conditions | Yield |
---|---|
With sodium chloride at 25℃; Rate constant; rate constant of hydrolysis; pH 4.5; other pH, buffers; | |
With water at 37℃; Rate constant; rate constant of hydrolysis; |
Conditions | Yield |
---|---|
With sodium chloride at 25℃; Rate constant; rate constant of hydrolysis; pH 4.5; other pH, buffers; | |
With water at 37℃; Rate constant; rate constant of hydrolysis; |
Conditions | Yield |
---|---|
With water at 37℃; Rate constant; rate constant of hydrolysis; | |
With sodium chloride at 25℃; Rate constant; rate constant of hydrolysis; pH 4.5; other pH, buffers; |
Conditions | Yield |
---|---|
With sodium chloride at 25℃; Rate constant; rate constant of hydrolysis; pH 4.5; other pH, buffers; | |
With water at 37℃; Rate constant; rate constant of hydrolysis; |
Conditions | Yield |
---|---|
With sodium chloride at 25℃; Rate constant; rate constant of hydrolysis; pH 4.5; other pH, buffers; | |
With water at 37℃; Rate constant; rate constant of hydrolysis; |
Conditions | Yield |
---|---|
With sodium chloride at 25℃; Rate constant; rate constant of hydrolysis; pH 4.5; other pH, buffers; | |
With water at 37℃; Rate constant; rate constant of hydrolysis; |
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate
A
metronidazole
B
benzoic acid
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.); |
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.); |
2-Formyl-benzoic acid 2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl ester
A
metronidazole
B
o-carboxybenzaldehyde
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; Mechanism; |
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.); |
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.); |
A
2,6-diformylbenzoic acid
B
metronidazole
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; |
A
2,6-diformylbenzoic acid
B
metronidazole
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.); |
A
metronidazole
B
2-(2,2,2-trifluoroacetyl)benzoic acid
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; Thermodynamic data; var. temp., ΔH(excit.), ΔS)(excit.); |
Conditions | Yield |
---|---|
With hydroxide In 1,4-dioxane; water at 30℃; Rate constant; |
succinic acid bis-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl] ester
A
succinic acid
B
metronidazole
C
4-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy]-4-oxobutanoic acid
Conditions | Yield |
---|---|
With phosphate buffer pH 7.4 In methanol; water at 37℃; Rate constant; var. pH, also in human plasma, Wistar rat liver homogenate; |
phthalic acid bis-[2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl] ester
A
benzene-1,2-dicarboxylic acid
B
metronidazole
C
1,2-benzenedicarboxylic acid, mono[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]ester
Conditions | Yield |
---|---|
With phosphate buffer pH 7.4 In methanol; water at 37℃; Rate constant; var. pH, also in human plasma, Wistar rat liver homogenate; |
Conditions | Yield |
---|---|
With phosphate buffer pH 7.4 In methanol; water at 37℃; for 48h; Rate constant; Kinetics; var. pH, also in human plasma, Wistar rat liver homogenate; |
Conditions | Yield |
---|---|
With phosphate buffer pH 7.4 In methanol; water at 37℃; Rate constant; Kinetics; var. pH, also in human plasma, Wistar rat liver homogenate; |
methanesulfonyl chloride
metronidazole
2-(5-nitro-2-methyl-1-imidazolyl)ethyl methanesulfonate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 100% |
With triethylamine In dichloromethane at 10 - 20℃; for 4h; | 97% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 97.5% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at -10 - 20℃; | 99.1% |
metronidazole
1-(2-chloroethyl)-2-methyl-5-nitro-1H-imidazole
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 50℃; for 2h; | 99% |
With thionyl chloride In dichloromethane at 20℃; | 96% |
With thionyl chloride for 3h; Heating; | 90% |
Conditions | Yield |
---|---|
In methanol at 65℃; for 0.25h; | 99% |
Conditions | Yield |
---|---|
In methanol at 20 - 40℃; | 99% |
Conditions | Yield |
---|---|
In methanol at 20 - 40℃; | 99% |
Conditions | Yield |
---|---|
In methanol at 20 - 40℃; | 99% |
Conditions | Yield |
---|---|
In methanol at 20 - 40℃; | 99% |
nickel diacetate
metronidazole
Conditions | Yield |
---|---|
In methanol at 20 - 40℃; | 99% |
metronidazole
Cysteamine
4-<(2-aminoethyl)thio>-2-methylimidazole-1-ethanol
Conditions | Yield |
---|---|
With pH 5.0 In water at 37℃; for 120h; | 98% |
With pH 5.0 at 37℃; for 120h; Product distribution; Mechanism; other reaction conditions; |
metronidazole
Conditions | Yield |
---|---|
With thionyl chloride In chloroform at 20℃; for 12h; | 98% |
With thionyl chloride In benzene for 2h; Heating; |
Conditions | Yield |
---|---|
In chloroform at 20℃; Product distribution / selectivity; | 98% |
In dichloromethane at 20℃; Product distribution / selectivity; | |
In N,N-dimethyl-formamide for 12h; | 7.32 g |
Conditions | Yield |
---|---|
In methanol at 20 - 40℃; | 98% |
Conditions | Yield |
---|---|
In methanol at 20 - 40℃; | 98% |
Conditions | Yield |
---|---|
In methanol at 20 - 40℃; | 98% |
metronidazole
Conditions | Yield |
---|---|
With potassium fluoride; 1,3-bis(2,6-diisopropylphenyl)-2-fluoroimidazolium tetrafluoroborate In 1,4-dioxane at 40℃; for 17h; Inert atmosphere; Schlenk technique; Sealed tube; | 98% |
Stage #1: metronidazole With copper(l) chloride; diisopropyl-carbodiimide at 60℃; for 1h; Sealed tube; Microwave irradiation; Stage #2: With copper (II)-fluoride In water at 100℃; for 24h; Microwave irradiation; | 61% |
benzoyl chloride
metronidazole
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate
Conditions | Yield |
---|---|
With dmap; ammonium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In chloroform at 5℃; for 3h; pH=9; Reagent/catalyst; Temperature; Solvent; pH-value; | 97.38% |
With pyridine In dichloromethane at 20℃; | 85.12% |
With triethylamine In 1,4-dioxane; chloroform 1.) r.t., 30 min, 2.) reflux, 4 h; |
succinic acid anhydride
metronidazole
4-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy]-4-oxobutanoic acid
Conditions | Yield |
---|---|
With dmap In acetonitrile for 48h; Ambient temperature; | 95% |
With pyridine at 20℃; for 24h; Inert atmosphere; Cooling with ice; | 95% |
With sodium hydroxide In methanol; water at 60℃; for 2h; | 94% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; | 95% |
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 4h; Esterification; | 72% |
potassium tetrachloroplatinate(II)
metronidazole
cis-Pt(metronidazole)2Br2
Conditions | Yield |
---|---|
With KBr In water 20-fold excess of KBr added to aq. soln. of K2(PtCl4), added solid ligand, stirred at 50 °C for 1 h; ppt. filtered, washed with EtOH/Et2O, Et2O, dried in vac.; elem. anal.; | 95% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; | 95% |
metronidazole
Conditions | Yield |
---|---|
Stage #1: metronidazole With potassium hexamethylsilazane In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique; | 95% |
metronidazole
Conditions | Yield |
---|---|
In benzene byproducts: pyridine; soln. of metronidazole (excess) and Pd compd. in benzene stirred for ca. 12 h at ca. 25 °C; evapn. in vac.; residue chromd. (TLC) on silica gel eluting with ethyl acetate; | 94.8% |
p-toluenesulfonyl chloride
metronidazole
toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 5h; | 94% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3h; | 90% |
With pyridine | 85% |
(9R,12Z )-9-hydroxyoctadec-12-enoic acid
metronidazole
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; | 92% |
Conditions | Yield |
---|---|
With potassium iodide In ethanol; water aq. soln. of KI was added to a soln. of Pt-complex in H2O, stirred for 1 min at room temp., a soln. of ligand in EtOH was added, stirred for 30min, stored at ca. 2°C overnight; elem. anal.; | 91% |
potassium tetrachloroplatinate(II)
metronidazole
cis-Pt(metronidazole)2Cl2
Conditions | Yield |
---|---|
In water 50°C, 1 h (crystn.); recrystn. (Me2CO/H2O); | 91% |
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.; | 90% |
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1.75h; | 91% |
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 1.75h; | 91% |
With sulfuric acid; ammonium bromide In water at 120℃; for 12h; | 87.6% |
Stage #1: metronidazole With bromine; phosphorus trichloride In ethyl acetate for 3h; Reflux; Stage #2: With sodium hydroxide pH=5 - 6; |
metronidazole
m-Toluic acid
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-methylbenzoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 91% |
phthalic anhydride
metronidazole
1,2-benzenedicarboxylic acid, mono[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]ester
Conditions | Yield |
---|---|
With dmap In acetonitrile Ambient temperature; | 90% |
With dmap In acetonitrile at 20℃; | 87.1% |
With dmap In acetonitrile at 20℃; | 87.1% |
With dmap In acetonitrile |
NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 250.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 ,1977,p. 113.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program.
Metronidazole (CAS NO.443-48-1) is a prodrug. It is converted in anaerobic organisms by the redox enzyme pyruvate-ferredoxin oxidoreductase. The nitro group of metronidazole is chemically reduced by ferredoxin and the products are responsible for disrupting the DNA helical structure, thus inhibiting nucleic acid synthesis. Metronidazole is selectively taken up by anaerobic bacteria and sensitive protozoal organisms because of the ability of these organisms to reduce metronidazole to its active form intracellularly.
Metronidazole is an antibiotic especially effective against anaerobic infections (infections that grow without the presence of oxygen.) With the CAS NO. 443-48-1, it also can be called Acromona; Anagiardil; Arilin; Atrivyl. It should be stored below 25ºC and protect from light. Metronidazole suppositories should be stored below 20ºC.A nitroimidazole used to treat AMEBIASIS; VAGINITIS; TRICHOMONAS INFECTIONS; GIARDIASIS; ANAEROBIC BACTERIA; and TREPONEMAL INFECTIONS. It has also been proposed as a radiation sensitizer for hypoxic cells. According to the Fourth Annual Report on Carcinogens this substance may reasonably be anticipated to be a carcinogen.
Physical properties about Metronidazole are:
(1)ACD/LogP: -0.548; (2)ACD/LogD (pH 5.5): -0.55; (3)ACD/LogD (pH 7.4): -0.55; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 12.00 ; (7)ACD/KOC (pH 7.4): 12.00; (8)#H bond acceptors: 6 ; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.612 ; (12)Molar Refractivity: 40.981 cm3; (13)Molar Volume: 117.867 cm3; (14)Polarizability: 16.246 10-24cm3; (15)Surface Tension: 60.4799995422363 dyne/cm; (16)Density: 1.452 g/cm3; (17)Flash Point: 198.975 °C ; (18)Enthalpy of Vaporization: 69.277 kJ/mol; (19)Boiling Point: 405.394 °C at 760 mmHg
Uses of Metronidazole:
Metronidazole is used also as a gel preparation in the treatment of the dermatological conditions such as rosacea (Rozex and MetroGel by Galderma) and fungating tumours (Anabact, Cambridge Healthcare Supplies).
When you are using Metronidazole, please be cautious about it as the following:
1. Wear suitable protective clothing and gloves;
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
3. Avoid exposure - obtain special instruction before use;
You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3;
(2)InChIKey=VAOCPAMSLUNLGC-UHFFFAOYSA-N;
(3)SmilesCc1ncc(n1CCO)[N+](=O)[O-];
The toxiciy data of Metronidazole is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | oral | 39600mg/kg/4W (39600mg/kg) | PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE BEHAVIORAL: HEADACHE | International Journal of Clinical Pharmacology Research. Vol. 19, Pg. 83, 1999. |
man | TDLo | oral | 3570ug/kg/D (3.57mg/kg) | JAMA, Journal of the American Medical Association. Vol. 193, Pg. 1128, 1965. | |
man | TDLo | oral | 3570ug/kg/D (3.57mg/kg) | LIVER: OTHER CHANGES LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" | JAMA, Journal of the American Medical Association. Vol. 193, Pg. 1128, 1965. |
man | TDLo | oral | 1030mg/kg/8W (1030mg/kg) | PERIPHERAL NERVE AND SENSATION: STRUCTURAL CHANGE IN NERVE OR SHEATH PERIPHERAL NERVE AND SENSATION: PARESTHESIS | British Medical Journal. Vol. 2, Pg. 610, 1977. |
mouse | LD50 | intraperitoneal | 870mg/kg (870mg/kg) | Polish Journal of Pharmacology and Pharmacy. Vol. 42, Pg. 471, 1990. | |
mouse | LD50 | oral | 3800mg/kg (3800mg/kg) | Journal of Medicinal Chemistry. Vol. 20, Pg. 1522, 1977. | |
mouse | LD50 | subcutaneous | 3640mg/kg (3640mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: TREMOR BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 1089, 1974. |
rat | LD50 | oral | 3gm/kg (3000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 1089, 1974. |
women | TDLo | intravenous | 100mg/kg/5D-I (100mg/kg) | BEHAVIORAL: IRRITABILITY BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TOXIC PSYCHOSIS | American Journal of Psychiatry. Vol. 154, Pg. 1169, 1997. |
women | TDLo | oral | 12mg/kg (12mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: TREMOR | British Medical Journal. Vol. 292, Pg. 174, 1986. |
women | TDLo | oral | 40mg/kg (40mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Southern Medical Journal. Vol. 78, Pg. 627, 1985. |
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View