AY9944

Names

[ CAS No. ]:
366-93-8

[ Name ]:
AY9944

[Synonym ]:
N,N'-[1,4-Cyclohexanediylbis(methylene)]bis[1-(2-chlorophenyl)methanamine] dihydrochloride
N,N'-[Cyclohexane-1,4-diylbis(methylene)]bis[1-(2-chlorophenyl)methanamine] dihydrochloride
1,4-bis(2-chlorobenzylaminomethyl)cyclohexane dihydrochloride
1,4-Cyclohexandiylbis[N-(2-chlorbenzyl)methanamin]dihydrochlorid
1,4-Cyclohexanediylbis[N-(2-chlorobenzyl)methanamine] dihydrochloride
1,4-Cyclohexanediylbis[N-(2-chlorobenzyl)méthanamine] dichlorhydrate
trans-1,4-Cyclohexanediylbis[N-(2-chlorobenzyl)methanamine] dihydrochloride
trans-N,N'-bis((2-chlorophenyl)methyl)-1,4-Cyclohexanedimethanamine dihydrochloride
1,4-Cyclohexanedimethanamine, N,N-bis[(2-chlorophenyl)methyl]-, hydrochloride (1:2)
1,4-Cyclohexanedimethanamine, N,N-bis[(2-chlorophenyl)methyl]-, trans-, hydrochloride (1:2)
AY9944

Biological Activity

[Description]:

AY 9944 is a specific cholesterol biosynthesis inhibitor. AY 9944 inhibits the 7-dehydro cholesterol Δ7-reductase (DHCR7) enzyme (IC50=13 nM). AY 9944 causes hypocholesterolemia and accumulation of 7DHC. At high doses, AY 9944 inhibits also in cultured embryos sterol Δ7-Δ8 isomerase, which causes the accumulation of cholest-8-en-3β-ol[1][2][3].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[References]

[1]. Dvornik D, et al. Effect of long-term administration of AY-9944, an inhibitor of 7-dehydrocholesterol delta 7-reductase, on serum and tissue lipids in the rat. J Lipid Res. 1968 Sep;9(5):587-95.

[2]. Moebius FF, et al. Molecular cloning and expression of the human delta7-sterol reductase. Proc Natl Acad Sci U S A. 1998 Feb 17;95(4):1899-902.

[3]. Chevy F, et al. Limb malformations of rat fetuses exposed to a distal inhibitor of cholesterol biosynthesis. J Lipid Res. 2002 Aug;43(8):1192-200.

Chemical & Physical Properties

[ Boiling Point ]:
497.7ºC at 760mmHg

[ Molecular Formula ]:
C₂₂H₃₀Cl₄N₂

[ Molecular Weight ]:
464.299

[ Flash Point ]:
254.8ºC

[ Exact Mass ]:
462.116302

[ PSA ]:
24.06000

[ LogP ]:
8.06500

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GU7025000

CHEMICAL NAME :: 1,4-Cyclohexanebis(methylamine), N,N'-bis(2-chlorobenzyl)-, dihydrochloride, (E)-

CAS REGISTRY NUMBER :: 366-93-8

LAST UPDATED :: 199709

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C22-H28-Cl2-N2.2Cl-H

MOLECULAR WEIGHT :: 464.34

WISWESSER LINE NOTATION :: L6TJ A1M1R BG& D1M1R BG &GH 2 -E

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 155 mg/kg

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

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 139,100,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 360 mg/kg/6D-C

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 69,12,1983 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 2-4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - homeostasis Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Specific Developmental Abnormalities - eye/ear

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 171,15,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 50 mg/kg

SEX/DURATION :: female 4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 176,54,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 2-4 day(s) after conception

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

REFERENCE :: JONUAI Journal of Nutrition. (Subscription Dept., 9650 Rockville Pike, Bethesda, MD 20014) V.1- 1928- Volume(issue)/page/year: 110,2310,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 75 mg/kg

SEX/DURATION :: female 3 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 54,115,1996

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 75 mg/kg

SEX/DURATION :: female 1-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - urogenital system

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 160,1353,1966

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 225 mg/kg

SEX/DURATION :: female 2-4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Effects on Newborn - biochemical and metabolic

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 29(3),32A,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 50 mg/kg

SEX/DURATION :: female 4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 29(3),19A,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 150 mg/kg

SEX/DURATION :: female 2-4 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Specific Developmental Abnormalities - homeostasis

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 166,1233,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 70 mg/kg

SEX/DURATION :: female 1-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 163,327,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 mg/kg

SEX/DURATION :: female 1-14 day(s) after conception

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

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 163,327,1969

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 650 mg/kg

SEX/DURATION :: female 1-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 163,327,1969

Safety Information

[ Hazard Codes ]:
Xi