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Substance Name: Metronidazole [USAN:USP:INN:BAN:JAN]
RN: 443-48-1
UNII: 140QMO216E
InChIKey: VAOCPAMSLUNLGC-UHFFFAOYSA-N
Note
- 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 (NTP 85-002, 1985, p133), this substance may reasonably be anticipated to be a carcinogen (Merck, 11th ed).
Molecular Formula
- C6-H9-N3-O3
Molecular Weight
- 171.1551
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antiparasitic Agents
- Antiprotozoal (Trichomonas)
- Antiprotozoal Agents
- Drug / Therapeutic Agent
- Human Data
- Mutation Data
- Radiation-Sensitizing Agents
- Reproductive Effect
- Slimicide
- Tumor Data
Superlist Classification Codes
- Overall Carcinogenic Evaluation: Group 2B
- Reasonably Anticipated to be a Carcinogen
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Names and Synonyms
Name of Substance
- Metronidazole
- Metronidazole [USAN:USP:INN:BAN:JAN]
MeSH Heading
- Metronidazole
Synonyms
- 1-(2-Hydroxy-1-ethyl)-2-methyl-5-nitroimidazole
- 1-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole
- 1-(beta-Ethylol)-2-methyl-5-nitro-3-azapyrrole
- 1-(beta-Hydroxyethyl)-2-methyl-5-nitroimidazole
- 1-(beta-Oxyethyl)-2-methyl-5-nitroimidazole
- 2-Methyl-1-(2-hydroxyethyl)-5-nitroimidazole
- 2-Methyl-3-(2-hydroxyethyl)-4-nitroimidazole
- 2-Methyl-5-nitroimidazole-1-ethanol
- 5-23-05-00063 (Beilstein Handbook Reference)
- Acromona
- Anagiardil
- Arilin
- Atrivyl
- Bayer 5360
- Bexon
- BRN 0611683
- Caswell No. 579AA
- CCRIS 410
- Clont
- CONT
- Danizol
- Deflamon
- Deflamon-wirkstoff
- Efloran
- EINECS 207-136-1
- Elyzol
- Entizol
- EPA Pesticide Chemical Code 120401
- Eumin
- Flagemona
- Flagesol
- Flagil
- Flagyl
- Flagyl ER
- Flagyl I.V. rtu in plastic container
- Fossyol
- Giatricol
- Gineflavir
- HSDB 3129
- Klion
- Klont
- Meronidal
- Metro Gel
- Metro I.V.
- Metro I.V. in plastic container
- Metrocream
- Metrogel
- MetroGel-Vaginal
- Metrolotion
- Metromidol
- Metronidaz
- Metronidazol
- Metronidazol [INN-Spanish]
- Metronidazole
- Metronidazole in plastic container
- Metronidazolo
- Metronidazolo [DCIT]
- Metronidazolum
- Metronidazolum [INN-Latin]
- Mexibol
- Mexibol 'silanes'
- Monagyl
- Monasin
- Nalox
- Neo-tric
- NIDA
- Noritate
- Novonidazol
- NSC 50364
- NSC 69587
- NSC-50364
- Orvagil
- Protostat
- RP 8823
- Sanatrichom
- Satric
- SC 10295
- Takimetol
- Trichazol
- Trichex
- Trichocide
- Trichomol
- Trichomonacid 'pharmachim'
- Trichopol
- Tricocet
- Tricom
- Tricowas B
- Trikacide
- Trikamon
- Trikojol
- Trikozol
- Trimeks
- Trivazol
- UNII-140QMO216E
- Vagilen
- Vagimid
- Vandazole
- Vertisal
- Wagitran
Systematic Names
- 1H-Imidazole-1-ethanol, 2-methyl-5-nitro-
- Imidazole-1-ethanol, 2-methyl-5-nitro-
- Metronidazole
Superlist Names
- 1H-Imidazole-1-ethanol, 2-methyl-5-nitro-
- 2-Methyl-5-nitroimidazole-1-ethanol
- Metronidazole
Mixture Names
- Flagyl I.V. RTU
- Helidac
Registry Numbers
CAS Registry Number
- 443-48-1
FDA UNII
- 140QMO216E
Related Registry Number
- 69198-10-3 (mono-hydrochloride)
System Generated Number
- 0000443481
Structure Descriptors
InChI
InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3InChIKey
VAOCPAMSLUNLGC-UHFFFAOYSA-NSmiles
Cc1ncc([N+](=O)Toxicity
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. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 160.5 | deg C | EXP | |
log P (octanol-water) | -0.02 | (none) | EXP | |
Water Solubility | 9500 | mg/L | 25 | EXP |
Vapor Pressure | 3.05E-07 | mm Hg | 25 | EST |
Henry's Law Constant | 1.69E-11 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 9.30E-12 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.