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Apronal

Names

[ CAS No. ]:
528-92-7

[ Name ]:
Apronal

[Synonym ]:
APRONALIDE
Allylisopropylacetylurea
Sedormid
Allylisopropylacetylcarbamide
Isopropylallylessigsaeure-ureid
(2-Isopropyl-4-pentenoyl)urea
2-Isopropyl-pent-4-ensaeure-ureid
Allylisoprorylacetylurea
EINECS 208-443-3
Apronal
Isodormid

Biological Activity

[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Apronal (Allylisopropylacetylurea, Apronalide) is a hypnotic and sedative drug that has been withdrawn in several countries due to side effects.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.


[Related Small Molecules]

Captisol | Cyclosporin A | H2DCFDA | 0MPTP hydrochloride | GW4869 | Etomoxir | TD139 | Mitoquinone mesylate | GSK2795039 | JC-1 | BAPTA-AM | AP 20187 | Setanaxib (GKT137831) | D-Luciferin | Crotaline

Chemical & Physical Properties

[ 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

Toxicological Information

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

Safety Information

[ HS Code ]:
2924210090

Synthetic Route

Customs

[ 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%


Related Compounds