Apronal

Modify Date: 2024-01-06 18:25:06

Apronal Structure
Apronal structure
Common Name Apronal
CAS Number 528-92-7 Molecular Weight 184.23600
Density 1.025g/cm3 Boiling Point N/A
Molecular Formula C9H16N2O2 Melting Point 196 °C
MSDS N/A Flash Point N/A

 Use of Apronal


Apronal (Allylisopropylacetylurea, Apronalide) is a hypnotic and sedative drug that has been withdrawn in several countries due to side effects.

 Names

Name N-carbamoyl-2-propan-2-ylpent-4-enamide
Synonym More Synonyms

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Description Apronal (Allylisopropylacetylurea, Apronalide) is a hypnotic and sedative drug that has been withdrawn in several countries due to side effects.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

 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

~%

Apronal Structure

Apronal

CAS#:528-92-7

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

~%

Apronal Structure

Apronal

CAS#:528-92-7

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

~%

Apronal Structure

Apronal

CAS#: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

~%

Apronal Structure

Apronal

CAS#:528-92-7

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

 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%

 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
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