CAS 443-48-1|Metronidazole
Introduction：Basic information about CAS 443-48-1|Metronidazole, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Metronidazole | ||
|---|---|---|---|
| CAS Number | 443-48-1 | Molecular Weight | 171.154 |
| Density | 1.5±0.1 g/cm3 | Boiling Point | 405.4±25.0 °C at 760 mmHg |
| Molecular Formula | C6H9N3O3 | Melting Point | 159-161 °C(lit.) |
| MSDS | ChineseUSA | Flash Point | 199.0±23.2 °C |
| Symbol | GHS08 | Signal Word | Warning |
Names
| Name | metronidazole |
|---|---|
| Synonym | More Synonyms |
Metronidazole BiologicalActivity
| Description | Metronidazole is a nitroimidazole antibiotic medication used particularly for anaerobic bacteria and protozoa.Target: Antibacterial; AntiparasiticMetronidazole is a nitroimidazole antibiotic medication used particularly for anaerobic bacteria and protozoa. Metronidazole is an antibiotic, amebicide, and antiprotozoal.[1] It is the drug of choice for first episodes of mild-to-moderate Clostridium difficile infection [2]. Metronidazole, taken up by diffusion, is selectively absorbed by anaerobic bacteria and sensitive protozoa. Once taken up by anaerobes, it is non-enzymatically reduced by reacting with reduced ferredoxin, which is generated by pyruvate oxido-reductase. Many of the reduced nitroso intermediates will form sulfinamides and thioether linkages with cysteine-bearing enzymes, thereby deactivating these critical enzymes. As many as 150 separate enzymes are affected.In addition or alternatively, the metronidazole metabolites are taken up into bacterial DNA, and form unstable molecules. This function only occurs when metronidazole is partially reduced, and because this reduction usually happens only in anaerobic cells, it has relatively little effect upon human cells or aerobic bacteria.[3] |
|---|---|
| Related Catalog | Signaling Pathways >>Anti-infection >>BacterialSignaling Pathways >>Anti-infection >>ParasiteResearch Areas >>Infection |
| References | [1]. In Schaechter, M.; Engleberg, N. C.; DiRita, V. J. et al. Schaechter's Mechanisms of Microbial Disease. Hagerstown, MD: Lippincott Williams & Wilkins. p. 28. [2]. http://www.drugs.com/monograph/metronidazole.html [3]. Cohen, S.H., et al., Clinical practice guidelines for Clostridium difficile infection in adults: 2010 update by the society for healthcare epidemiology of America (SHEA) and the infectious diseases society of America (IDSA). Infect Control Hosp Epidemiol, |
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 |
| InChIKey | VAOCPAMSLUNLGC-UHFFFAOYSA-N |
| SMILES | Cc1ncc([N+](=O)[O-])n1CCO |
| 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
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)
- 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 |
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% |
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Synonyms
| 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 |
