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Triparanol

Names

[ CAS No. ]:
78-41-1

[ Name ]:
Triparanol

[Synonym ]:
Metasqualene
MER 29
EINECS 201-115-0
triparanolum
valip
TRIPARANOL

Biological Activity

[Description]:

Triparanol (MER-29) is a potent cholesterol biosynthesis inhibitor blocking the 24-dehydrocholesterol reductase (24-DHCR). Triparanol can interfere with posttranslational modification of Hedgehog signaling molecules as well as the sterol sensing domain of its receptor PTCH1, leading to down-regulation of Hh signaling. Triparanol suppresses human tumor growth[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Stem Cell/Wnt >> Hedgehog

[In Vitro]

Triparanol can block proliferation and induce apoptosis in multiple human cancer cells including lung, breast, liver, pancreatic, prostate cancer and melanoma cells, and growth inhibition can be rescued by exogenous addition of cholesterol[2].

[References]

[1]. AVIGAN J, et al. The mechanism of action of MER-29. Prog Cardiovasc Dis. 1960;2:525-530.

[2]. Bi X, et al. Triparanol suppresses human tumor growth in vitro and in vivo [published correction appears in Biochem Biophys Res Commun. 2012 Nov 2;427(4):808]. Biochem Biophys Res Commun. 2012;425(3):613-618.

Chemical & Physical Properties

[ Density]:
1.133g/cm3

[ Boiling Point ]:
546.9ºC at 760 mmHg

[ Melting Point ]:
102.9-103.7ºC

[ Molecular Formula ]:
C27H32ClNO2

[ Molecular Weight ]:
438.00100

[ Flash Point ]:
284.5ºC

[ Exact Mass ]:
437.21200

[ PSA ]:
32.70000

[ LogP ]:
5.84760

[ Index of Refraction ]:
1.582

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KK2400000
CHEMICAL NAME :
Ethanol, 2-(p-chlorophenyl)-1-(p-(2-(diethylamino)ethoxy)pheny l)-1-p-tolyl-
CAS REGISTRY NUMBER :
78-41-1
LAST UPDATED :
199612
DATA ITEMS CITED :
13
MOLECULAR FORMULA :
C27-H32-Cl-N-O2
MOLECULAR WEIGHT :
438.05
WISWESSER LINE NOTATION :
GR D1XQR D1&R DO2N2&2

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 :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 155,2255,1961 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
14 mg/kg
SEX/DURATION :
female 1-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 10,565,1967
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
450 mg/kg
SEX/DURATION :
female 6-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - homeostasis Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 10,565,1967
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
350 mg/kg
SEX/DURATION :
female 2-15 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: 167,1523,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
350 mg/kg
SEX/DURATION :
female 2-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion 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: 167,1523,1973
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
70 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - live birth index (measured after birth)
REFERENCE :
ENDOAO Endocrinology (Baltimore). (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21203) V.1- 1917- Volume(issue)/page/year: 74,64,1964
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
70 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear
REFERENCE :
ENDOAO Endocrinology (Baltimore). (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21203) V.1- 1917- Volume(issue)/page/year: 74,64,1964
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
2800 mg/kg
SEX/DURATION :
female 1-14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - eye/ear 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: 160,923,1966
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
2800 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: 160,923,1966 *** REVIEWS *** TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 1(1),93,1971 TOXICOLOGY REVIEW CLPTAT Clinical Pharmacology and Therapeutics (St. Louis). (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1960- Volume(issue)/page/year: 5,480,1964 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H318

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-41

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
KK2400000

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