Metronidazole
Names
[ CAS No. ]:
443-48-1
[ Name ]:
Metronidazole
[Synonym ]:
Eumin
Bexon
Klont
2-(2-Methyl-4-nitro-1H-imidazol-1-yl)ethanol
Elyzol
2-(2-Methyl-5-nitro-1-imidazolyl)ethanol
Cont
Klion
EINECS 207-136-1
2-Methyl-5-nitroimidazole-1-ethanol
1h-imidazole-1-ethanol, 2-methyl-4-nitro-
Nalox
Metronidazole
MFCD00009750
2-(2-Methyl-4-nitro-imidazol-1-yl)-ethanol
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethanol
Flagil
Nida
CLONT
Biological Activity
[Description]:
[Related Catalog]:
[References]
[Related Small Molecules]
Chemical & Physical Properties
[ Density]:
1.5±0.1 g/cm3
[ Boiling Point ]:
405.4±25.0 °C at 760 mmHg
[ Melting Point ]:
159-161 °C(lit.)
[ Molecular Formula ]:
C6H9N3O3
[ Molecular Weight ]:
171.154
[ Flash Point ]:
199.0±23.2 °C
[ Exact Mass ]:
171.064392
[ PSA ]:
83.87000
[ LogP ]:
-0.01
[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C
[ Index of Refraction ]:
1.612
[ Storage condition ]:
2-8°C
[ Stability ]:
Stable. Incompatible with strong oxidizing agents.
[ Water Solubility ]:
acetic acid: 0.1 M, clear, faintly yellow | <0.1 g/100 mL at 20 ºC
MSDS
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- NI5600000
- CHEMICAL NAME :
- Imidazole-1-ethanol, 2-methyl-5-nitro-
- CAS REGISTRY NUMBER :
- 443-48-1
- BEILSTEIN REFERENCE NO. :
- 0611683
- LAST UPDATED :
- 199801
- DATA ITEMS CITED :
- 77
- MOLECULAR FORMULA :
- C6-H9-N3-O3
- MOLECULAR WEIGHT :
- 171.18
- WISWESSER LINE NOTATION :
- T5N CNJ A2Q B1 ENW
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 40 mg/kg
- TOXIC EFFECTS :
- Behavioral - hallucinations, distorted perceptions
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 3570 ug/kg/D
- TOXIC EFFECTS :
- Liver - jaundice, other or unclassified Liver - other changes Nutritional and Gross Metabolic - body temperature increase
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 12 mg/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - tremor
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 1030 mg/kg/8W
- TOXIC EFFECTS :
- Peripheral Nerve and Sensation - paresthesis Peripheral Nerve and Sensation - structural change in nerve or sheath
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 100 mg/kg/5D-I
- TOXIC EFFECTS :
- Behavioral - hallucinations, distorted perceptions Behavioral - toxic psychosis Behavioral - irritability
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 3 gm/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - cyanosis Nutritional and Gross Metabolic - body temperature decrease
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 3800 mg/kg
- TOXIC EFFECTS :
- Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other oxidoreductases
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 870 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 3640 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - tremor Behavioral - convulsions or effect on seizure threshold
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 34 gm/kg/34D-C
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - hematuria Related to Chronic Data - death Related to Chronic Data - changes in testicular weight
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 6500 mg/kg/26D-I
- TOXIC EFFECTS :
- Brain and Coverings - other degenerative changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 219 gm/kg/2Y-C
- TOXIC EFFECTS :
- Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors Skin and Appendages - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 181 gm/kg/72W-C
- TOXIC EFFECTS :
- Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors Blood - lymphoma, including Hodgkin's disease
- TYPE OF TEST :
- TD - Toxic dose (other than lowest)
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 27 gm/kg/35W-C
- TOXIC EFFECTS :
- Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors Reproductive - Tumorigenic effects - uterine tumors
- TYPE OF TEST :
- TD - Toxic dose (other than lowest)
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 8 gm/kg/14W-C
- TOXIC EFFECTS :
- Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors Blood - lymphoma, including Hodgkin's disease
- TYPE OF TEST :
- TD - Toxic dose (other than lowest)
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 3 gm/kg/14W-C
- TOXIC EFFECTS :
- Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors
- TYPE OF TEST :
- TD - Toxic dose (other than lowest)
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 21800 mg/kg/2Y-I
- TOXIC EFFECTS :
- Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors
- TYPE OF TEST :
- TD - Toxic dose (other than lowest)
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1680 mg/kg female 1-21 day(s) after conception
- TOXIC EFFECTS :
- Tumorigenic - Carcinogenic by RTECS criteria Reproductive - Tumorigenic effects - transplacental tumorigenesis Lungs, Thorax, or Respiration - tumors
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 16800 mg/kg
- SEX/DURATION :
- male 42 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 22400 mg/kg
- SEX/DURATION :
- male 56 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- DOSE :
- 750 mg/kg
- SEX/DURATION :
- female 30 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - uterus, cervix, vagina
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 60 mg/kg
- SEX/DURATION :
- female 8-14 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- TYPE OF TEST :
- Cytogenetic analysis
- TYPE OF TEST :
- Cytogenetic analysis
- TYPE OF TEST :
- Cytogenetic analysis
- TYPE OF TEST :
- Sister chromatid exchange
MUTATION DATA
- TYPE OF TEST :
- DNA adduct
- TEST SYSTEM :
- Mammal - species unspecified Lymphocyte
- DOSE/DURATION :
- 60 umol/L
- REFERENCE :
- MOPMA3 Molecular Pharmacology. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1965- Volume(issue)/page/year: 13,872,1977 *** REVIEWS *** IARC Cancer Review:Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,113,1977 IARC Cancer Review:Human Inadequate Evidence IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,250,1987 IARC Cancer Review:Group 2B IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,250,1987 TOXICOLOGY REVIEW JACHDX Journal of Antimicrobial Chemotherapy. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1975- Volume(issue)/page/year: 3,205,1977 TOXICOLOGY REVIEW ADCMAZ Advances in Chemotherapy. (New York, NY) V.1-3, 1964-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 3,39,1968 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4277 No. of Facilities: 216 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 5262 (estimated) No. of Female Employees: 2655 (estimated)
Safety Information
[ Symbol ]:
GHS08
[ Signal Word ]:
Warning
[ Hazard Statements ]:
H351
[ Precautionary Statements ]:
P281
[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves
[ Hazard Codes ]:
T:Toxic
[ Risk Phrases ]:
R40;R46;R45
[ Safety Phrases ]:
36/37-45-53
[ RIDADR ]:
NONH for all modes of transport
[ WGK Germany ]:
3
[ RTECS ]:
NI5600000
[ HS Code ]:
2933990090
Synthetic Route
Precursor & DownStream
Precursor
DownStream
Customs
[ HS Code ]: 2933290090
[ Summary ]:
2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
Articles
PLoS ONE 9(4) , e93953, (2014)
Trisubstituted benzimidazoles have demonstrated potency against Gram-positive and Gram-negative bacterial pathogens. Previously, a library of novel trisubstituted benzimidazoles was constructed for hi...
Indirect electroreduction as pretreatment to enhance biodegradability of metronidazole.J. Hazard. Mater. 278 , 172-9, (2014)
The removal of metronidazole, a biorecalcitrant antibiotic, by coupling an electrochemical reduction with a biological treatment was examined. Electroreduction was performed in a home-made flow cell a...
Carrier Mediated Distribution System (CAMDIS): a new approach for the measurement of octanol/water distribution coefficients.Eur. J. Pharm. Sci. 68 , 68-77, (2015)
Here we present a miniaturized assay, referred to as Carrier-Mediated Distribution System (CAMDIS) for fast and reliable measurement of octanol/water distribution coefficients, log D(oct). By introduc...