Cadralazine

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Names

[ Name ]:
Cadralazine

[Synonym ]:
DC-826
Cadralazine [INN:BAN:JAN]
2-[6-[Ethyl(2-Hydroxypropyl)Amino]-3-Pyridazinyl]-Hydrazinecarboxylic Acid Ethyl Ester
Cadralazina [INN-Spanish]
ISF 2469
Cadralazine
Cadralazina [Spanish]
Cadralazinum [INN-Latin]
N'-{6-[ethyl-(2-hydroxy-propyl)-amino]-pyridazin-3-yl}-hydrazinecarboxylic acid ethyl ester

Chemical & Physical Properties

[ Density]:
1.253 g/cm3

[ Boiling Point ]:
425.88°C (rough estimate)

[ Melting Point ]:
160-162°

[ Molecular Formula ]:
C₁₂H₂₁N₅O₃

[ Molecular Weight ]:
283.32700

[ Exact Mass ]:
283.16400

[ PSA ]:
99.61000

[ LogP ]:
1.22060

[ Index of Refraction ]:
1.59

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MV1720400

CHEMICAL NAME :: Hydrazinecarboxylic acid, 2-(6-(ethyl(2-hydroxypropyl)amino)-3-pyridazinyl)-, ethyl ester

CAS REGISTRY NUMBER :: 64241-34-5

BEILSTEIN REFERENCE NO. :: 0894631

LAST UPDATED :: 199612

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C12-H21-N5-O3

MOLECULAR WEIGHT :: 283.38

WISWESSER LINE NOTATION :: T6NNJ CN2&1YQ1 FMMVO2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2060 mg/kg

TOXIC EFFECTS :: Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section

REFERENCE :: JCPCDT Journal of Cardiovascular Pharmacology. (Raven Press, 1140 Ave. of the Americas, New York, NY 10036) V.1- 1979- Volume(issue)/page/year: 3,455,1981

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 440 mg/kg

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

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 7,382,1982

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex) Liver - other changes

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15,3839,1987

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 269 mg/kg

TOXIC EFFECTS :: Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section

REFERENCE :: JCPCDT Journal of Cardiovascular Pharmacology. (Raven Press, 1140 Ave. of the Americas, New York, NY 10036) V.1- 1979- Volume(issue)/page/year: 3,455,1981

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 825 mg/kg

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

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 7,382,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 362 mg/kg

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

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 7,382,1982

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1420 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15,3839,1987

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 162 mg/kg

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

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 7,382,1982

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

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

REFERENCE :: DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 7,382,1982

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section Kidney, Ureter, Bladder - changes in blood vessels or in circulation of kidney

REFERENCE :: JCPCDT Journal of Cardiovascular Pharmacology. (Raven Press, 1140 Ave. of the Americas, New York, NY 10036) V.1- 1979- Volume(issue)/page/year: 3,455,1981 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 36400 mg/kg/52W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes in urine composition Endocrine - changes in spleen weight Blood - changes in leukocyte (WBC) count

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15,3875,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9 gm/kg/30D-C

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - changes in spleen weight Blood - normocytic anemia

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15,3847,1987 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 132 mg/kg

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

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15,3913,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3300 mg/kg

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

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15,3913,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 910 mg/kg

SEX/DURATION :: female 17-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 15,3945,1987

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

3,6-Dichloropyridazine
1-Ethylamino-2-propanol
Ethyl hydrazinecarboxylate

DownStream

Related Compounds

6-(Butyl(methyl)amino)pyridazine-3-carboxylic acid
Carbamic acid, N-[(6-methyl-2-piperidinyl)methyl]-, methyl ester
3-Amino-3-(3-chloro-2-fluorophenyl)propan-1-ol
tert-butyl 2-(3-carbamoyl-1H-pyrazolo[3,4-c]pyridin-1-yl)acetate
4-Methyl-2-[(2-methylbutyl)amino]pentan-1-ol
4-Methyl-2-[(2-methylpentyl)amino]pentan-1-ol
(1H-indol-6-yl)-acetic acid tert-butyl ester
1-Carbamoyl-1H-indole-3-carboxylic acid benzyl ester
4-Methyl-2-{[1-(thiophen-2-yl)ethyl]amino}pentan-1-ol
2-Chloro-4-[[3-(1,3-dioxolan-2-yl)phenyl]sulfamoyl]benzoic acid

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