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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
 

Classification Codes

Classification Codes

  • 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

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

1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3

InChIKey

VAOCPAMSLUNLGC-UHFFFAOYSA-N

Smiles

Cc1ncc(n1CCO)[N+](=O)[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.