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443-48-1 1261392-47-5
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443-48-1

443-48-1 structure
443-48-1 structure
  • Name: Metronidazole
  • Chemical Name: metronidazole
  • CAS Number: 443-48-1
  • Molecular Formula: C6H9N3O3
  • Molecular Weight: 171.154
  • Catalog: API Antiparasitic drug Anti-amebiasis and anti-trichomoniasis drugs
  • Create Date: 2018-02-04 08:00:00
  • Modify Date: 2024-01-02 00:27:04
  • 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]
Name metronidazole
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
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
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,
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

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)
Symbol GHS08
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
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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