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443-48-1

Basic Information
CAS No.: 443-48-1
Name: Metronidazole
Article Data: 45
Molecular Structure:
Molecular Structure of 443-48-1 (Metronidazole)
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: HarmfulXn, ToxicT
Risk Codes: 40-46-45
Safety: 36/37-45-53
PSA: 83.87000
LogP: 0.61520
Synthetic route
75-21-8

oxirane

696-23-1

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

443-48-1

metronidazole

Conditions
ConditionsYield
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
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;71%
73334-05-1

metronidazole phosphate

443-48-1

metronidazole

Conditions
ConditionsYield
With human serum In water at 37℃; human serum hydrolysis of metronidazole phosphate; pH dependence of solubility of metronidazole and metronidazole phosphate;
89218-56-4

glycine ester of metronidaxole

A

443-48-1

metronidazole

B

56-40-6

glycine

Conditions
ConditionsYield
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);
98204-35-4

leucine ester of metronidaxole

A

61-90-5

L-leucine

B

443-48-1

metronidazole

Conditions
ConditionsYield
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);
98204-36-5

phenylalanine ester of metronidaxole

A

63-91-2

L-phenylalanine

B

443-48-1

metronidazole

Conditions
ConditionsYield
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
ConditionsYield
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

Conditions
ConditionsYield
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);

C6H9N3O3(1-)

A

443-48-1

metronidazole

B

2-(2-Methyl-5-nitroso-imidazol-1-yl)-ethanol

Conditions
ConditionsYield
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;

glycine ester of metronidaxole hydrochloride

A

443-48-1

metronidazole

B

56-40-6

glycine

Conditions
ConditionsYield
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.

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