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| CAS No.: | 443-48-1 |
|---|---|
| Name: | Metronidazole |
| Molecular Structure: | |
|
|
|
| Formula: | C6H9N3O3 |
| Molecular Weight: | 171.156 |
| Synonyms: | Bexon;Vagilen;1-(2-Hydroxy-1-ethyl)-2-methyl-5-nitroimidazole;Meronidal;Trikojol;Novonidazol;RP 8823;Eumin;Metronidazole (JP14/USP);Bayer 5360;Trichopol;Trichex;Sanatrichom;Nalox;Trikamon;1-Hydroxyethyl-2-methyl-5-nitroimidazole;Metric 21;Monasin;Giatricol;Orvagil;MTZ;Metronidazol;NIDA;Trichazol;Flagyl;Deflamon;Entizol;2-Methyl-1-(2-hydroxyethyl)-5-nitroimidazole;1-(.beta.-Hydroxyethyl)-2-methyl-5-nitroimidazole;Trikozol;1H-Imidazole-1-ethanol,2-methyl-5-nitro-;1-(.beta.-Ethylol)-2-methyl-5-nitro-3-azapyrrole;Klion;Arilin;Clont;Trimeks;Danizol;Efloran;Methronidazole;Trivazol;Acromona;1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole;Flagesol;Tricocet;Monagyl;Vertisal;Prestwick_334;Klont;Flegyl;Tricowas B;Trichomonacid pharmachim;Trichopal;Trichocide;Flagemona;Trichomol;Metronidaz;1H-Imidazole-1-ethanol, 2-methyl-5-nitro-;1-(β-Ethylol)-2-methyl-5-nitro-3-azapyrrole;1-(β-Hydroxyethyl)-2-methyl-5-nitroimidazole;NSC-50364;1-(β-Oxyethyl)-2-methyl-5-nitroimidaz-ole;2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-ol; |
| EINECS: | 207-136-1 |
| Density: | 1.45 g/cm3 |
| Melting Point: | 159-161 °C(lit.) |
| Boiling Point: | 405.4 °C at 760 mmHg |
| Flash Point: | 199 °C |
| Solubility: | <0.1 g/100 mL at 20 °C in water |
| Appearance: | white to slightly yellow crystalline powder |
| Hazard Symbols: |
 Xn,  T
|
| Risk Codes: | 40-46-45 |
| Safety: | 36/37-45-53 |
| PSA: | 83.87000 |
| LogP: | 0.61520 |
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| 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; |
- 13182-89-3
2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate
- 65-85-0
benzoic acid
- 443-48-1
metronidazole
| Conditions | Yield |
|---|---|
| With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 71% |
- 73334-05-1
metronidazole phosphate
- 443-48-1
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); |
- 145615-34-5
metronidazole glycyl glycinate hydrochloride
A
- 106-57-0
Glycine anhydride
B
- 556-50-3
glycylglycine
C
- 443-48-1
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); |
- 145615-35-6
metronidazole glycyl phenylalaninate hydrochloride
A
- 3321-03-7
Gly-Phe-OH
B
- 443-48-1
metronidazole
C
- 5037-75-2, 10125-07-2, 23927-19-7
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; |
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Consensus Reports
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.
Analytical Methods
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.
Specification
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. |