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Product Name: Allylisopropylacetylurea
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528-92-7

528-92-7 structure

Name: Apronal
Chemical Name: N-carbamoyl-2-propan-2-ylpent-4-enamide
CAS Number: 528-92-7
Molecular Formula: C₉H₁₆N₂O₂
Molecular Weight: 184.23600
Catalog: Research Areas Neurological Disease
Create Date: 2018-08-28 12:05:09
Modify Date: 2024-01-06 18:25:06
Apronal (Allylisopropylacetylurea, Apronalide) is a hypnotic and sedative drug that has been withdrawn in several countries due to side effects.

Name	N-carbamoyl-2-propan-2-ylpent-4-enamide
Synonyms	APRONALIDE Allylisopropylacetylurea Sedormid Allylisopropylacetylcarbamide Isopropylallylessigsaeure-ureid (2-Isopropyl-4-pentenoyl)urea 2-Isopropyl-pent-4-ensaeure-ureid Allylisoprorylacetylurea EINECS 208-443-3 Apronal Isodormid

Description	Apronal (Allylisopropylacetylurea, Apronalide) is a hypnotic and sedative drug that has been withdrawn in several countries due to side effects.
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Neurological Disease
In Vivo	Research shows that allylisopropylacetylurea not only increases the amount of porphyrins in the liver and urine of animals but also brings about a marked green pigmentation of the liver. Rats recover well from long-term treatment with high doses of allylisopropylacetylurea and revert to normal values for parameters measured. Lesions originated by long-term administration with allylisopropylacetylurea can be tolerated by rats and are reversible[1]. Fixed drug eruption and mucocutaneous ocular syndrome are reported due to apronal[2].
Animal Admin	Rats: Apronal is administered to male Sandoz OFA-SPF rats, weighing 140-150 g in two equal daily subcutaneous injections 8 h apart. The overall daily dose is 400 mg/kg and dosing is continued for 21 days. Control rats are similarly treated with propandiol only. Urine samples are collected in glass tubes at solid CO2, temperatures and stored frozen until analysis[1].
References	[1]. Rentsch G, et al. The effect of prolonged administration of allylisopropylacetylurea to rats on cytochrome P-450 and other liver haemoproteins. Xenobiotica. 1976 Mar;6(3):151-7. [2]. Fujimoto Y, et al. Fixed drug eruption due to allylisopropylacetylurea. Contact Dermatitis. 1993 May;28(5):282-4.

Density	1.025g/cm3
Melting Point	196 °C
Molecular Formula	C₉H₁₆N₂O₂
Molecular Weight	184.23600
Exact Mass	184.12100
PSA	72.19000
LogP	2.12080
Index of Refraction	1.474

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YT5775000

CHEMICAL NAME :: Urea, (2-isopropyl-4-pentenoyl)-

CAS REGISTRY NUMBER :: 528-92-7

BEILSTEIN REFERENCE NO. :: 1775529

LAST UPDATED :: 199612

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C9-H16-N2-O2

MOLECULAR WEIGHT :: 184.27

WISWESSER LINE NOTATION :: ZVMVY2U1&Y1&1

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 :: 1050 mg/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 19,323,1980

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 400 mg/kg

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

REFERENCE :: JPHAA3 Journal of the American Pharmaceutical Association. (Washington, DC) V.1-28, 1912-39; New series: V.1-17, 1961-77. Volume(issue)/page/year: 23,788,1934

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1220 mg/kg

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

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 19,323,1980

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 300 mg/kg

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

REFERENCE :: DMWOAX Deutsche Medizinische Wochenschrift. (Stuttgart, Fed. Rep. Ger.) V.1-104, 1875-1979. Volume(issue)/page/year: 54,1166,1928

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1250 mg/kg

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

REFERENCE :: DMWOAX Deutsche Medizinische Wochenschrift. (Stuttgart, Fed. Rep. Ger.) V.1-104, 1875-1979. Volume(issue)/page/year: 54,1166,1928

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 600 mg/kg

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

REFERENCE :: DMWOAX Deutsche Medizinische Wochenschrift. (Stuttgart, Fed. Rep. Ger.) V.1-104, 1875-1979. Volume(issue)/page/year: 54,1166,1928

HS Code	2924210090

77-02-1

528-92-7

Literature: Hoffmann-La Roche Patent: DE459903 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 15, p. 1478

420-05-3

299-78-5

528-92-7

Literature: Riedel,J.D. Patent: DE461814 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2476

99167-88-1

528-92-7

Literature: Aspelund; Skoglund Acta Academiae Aboensis, Series B: Mathematica et Physica, 1937 , vol. 10, # 10 p. 8,15,19,22 Chem. Zentralbl., 1937 , vol. 108, # II p. 2004

57-13-6

528-92-7

Literature: Riedel,J.D. Patent: DE461814 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2476

HS Code	2924210090
Summary	2924210090 other ureines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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