Metrizamide

Names

[ Name ]:
Metrizamide

[Synonym ]:
pyranose
Metrizamide
EINECS 250-475-5
D-Glucopyranose, 2-[[3-(acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoyl]amino]-2-deoxy-
2-[({3-(acetylamino)-5-[acetyl(methyl)amino]-2,4,6-triiodophenyl}carbonyl)amino]-2-deoxy-D-glucopyranose
Amipaque
2-[3-Acetamido-5-(N-methylacetamido)-2,4,6-triiodobenzamido]-2-deoxy-D-glucose
y-d-glucose
telebrix300
MFCD00010577
METRIZAMIDE,ULTRAPURE
no)-2-deoxy
2-(3-Acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzamido)-2-deoxy-D-glucopyranose
2-({3-(acetylamino)-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoyl}amino)-2-deoxy-D-glucopyranose
2-({3-Acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoyl}amino)-2-deoxy-D-glucopyranose
2-[3-Acetamido-2,4,6-triiodo-5-(N-methylacetamido)benzamido]-2-deoxy-D-glucopyranose

Biological Activity

[Description]:

Metrizamide (Amipaque) is used as the contrast medium for angiography in neuroradiological investigations[1]. Metrizamide inhibits human brain hexokinase[2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Hexokinase

Research Areas >> Neurological Disease

[In Vitro]

Metrizamide is a contrast medium possessing unique properties, one of which is that even in an isotonic solution it has a radiographic density sufficient for a diagnostic myelogram[3].

[References]

[1]. Vogelsang H, et al. Zerebrale und spinale Angiographie mit Metrizamid (Amipaque) [Cerebral and spinal angiography with metrizamide (amipaque) (author's transl)]. Rofo. 1978;129(5):559-561.

[2]. Bertoni JM. Metrizamide inhibits human brain hexokinase. Neurology. 1982;32(8):884-887.

[3]. Funkquist B. Myelographic localization of spinal cord compression in dogs. A comparison between cisternal and lumbar injections of metrizamide "Amipaque" in diagnosing and locating spinal cord compression. Acta Vet Scand. 1975;16(2):269-287.

Chemical & Physical Properties

[ Density]:
2.3±0.1 g/cm3

[ Boiling Point ]:
828.5±65.0 °C at 760 mmHg

[ Melting Point ]:
222-224ºC

[ Molecular Formula ]:
C₁₈H₂₂I₃N₃O₈

[ Molecular Weight ]:
789.096

[ Flash Point ]:
454.8±34.3 °C

[ Exact Mass ]:
788.854065

[ PSA ]:
168.66000

[ LogP ]:
-0.74

[ Vapour Pressure ]:
0.0±3.2 mmHg at 25°C

[ Index of Refraction ]:
1.761

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ6650000

CHEMICAL NAME :: D-Glucose, 2-(3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)ben zamido)-2-deoxy-

CAS REGISTRY NUMBER :: 31112-62-6

LAST UPDATED :: 199509

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C18-H22-I3-N3-O8

MOLECULAR WEIGHT :: 789.13

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraspinal

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 143 mg/kg

TOXIC EFFECTS :: Spinal Cord - meningeal changes

REFERENCE :: SMJOAV Southern Medical Journal. (Southern Medical Assoc., POB 2446, Birmingham, AL 35205) V.1- 1908- Volume(issue)/page/year: 77,88,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >20 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,842,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,842,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - hair

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 32,865,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 13100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,842,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 135 mg/kg

TOXIC EFFECTS :: Brain and Coverings - recordings from specific areas of CNS Behavioral - anticonvulsant Behavioral - changes in motor activity (specific assay)

REFERENCE :: RADLAX Radiology. (Radiological Soc. of North America, 20th & Northampton Sts., Easton, PA 18042) V.1- 1923- Volume(issue)/page/year: 140,713,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 160 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JACTDZ Journal of the American College of Toxicology. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1-12, 1982-1993. Discontinued. Volume(issue)/page/year: 9,563,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >20 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,842,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 9950 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4001323

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,842,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1534 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: INVRAV Investigative Radiology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1966- Volume(issue)/page/year: 15,S248,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2910 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4001323

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 21763 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARASA5 Acta Radiologica, Supplementum. (Acta Radiologica, POB 7449, S-10391 Stockholm, Sweden) No.1- 1921- Volume(issue)/page/year: 335,5,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 207 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4001323

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >622 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JACTDZ Journal of the American College of Toxicology. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1-12, 1982-1993. Discontinued. Volume(issue)/page/year: 9,563,1990 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 11456 mg/kg

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: NIIHAO Nichidoku Iho. Japanese-German Medical Reports. (Nihon Scheringu K.K, Gakujutsubu, 6-64, Nishimiyahara, 2-chome, Yodogawa-ku, Osaka 532, Japan) V.1- 1956- Volume(issue)/page/year: 24,277,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 34369 mg/kg

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: NIIHAO Nichidoku Iho. Japanese-German Medical Reports. (Nihon Scheringu K.K, Gakujutsubu, 6-64, Nishimiyahara, 2-chome, Yodogawa-ku, Osaka 532, Japan) V.1- 1956- Volume(issue)/page/year: 24,277,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 54008 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - other measures of fertility

REFERENCE :: NIIHAO Nichidoku Iho. Japanese-German Medical Reports. (Nihon Scheringu K.K, Gakujutsubu, 6-64, Nishimiyahara, 2-chome, Yodogawa-ku, Osaka 532, Japan) V.1- 1956- Volume(issue)/page/year: 24,287,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 18003 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: NIIHAO Nichidoku Iho. Japanese-German Medical Reports. (Nihon Scheringu K.K, Gakujutsubu, 6-64, Nishimiyahara, 2-chome, Yodogawa-ku, Osaka 532, Japan) V.1- 1956- Volume(issue)/page/year: 24,287,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5735 No. of Facilities: 234 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 9481 (estimated) No. of Female Employees: 6972 (estimated)

Safety Information

[ Safety Phrases ]:
22-24/25

[ RTECS ]:
LZ6650000

[ Packaging Group ]:
I; II; III

[ Hazard Class ]:
6.1

Synthetic Route

Click to get detail synthetic route

Related Compounds

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