Triparanol

Modify Date: 2024-01-05 16:50:22

Triparanol structure	Common Name	Triparanol
	CAS Number	78-41-1	Molecular Weight	438.00100
	Density	1.133g/cm3	Boiling Point	546.9ºC at 760 mmHg
	Molecular Formula	C₂₇H₃₂ClNO₂	Melting Point	102.9-103.7ºC
	MSDS	Chinese USA	Flash Point	284.5ºC
	Symbol	GHS05, GHS07	Signal Word	Danger

Use of Triparanol

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].

Name	2-(4-chlorophenyl)-1-[4-[2-(diethylamino)ethoxy]phenyl]-1-(4-methylphenyl)ethanol
Synonym	More Synonyms

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.

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

Triparanol MSDS(Chinese)

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

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

Transcriptional Regulation of Cytosolic Sulfotransferase 1C2 by Intermediates of the Cholesterol Biosynthetic Pathway in Primary Cultured Rat Hepatocytes.

J. Pharmacol. Exp. Ther. 355 , 429-41, (2015)

Cytosolic sulfotransferase 1C2 (SULT1C2) is expressed in the kidney, stomach, and liver of rats; however, the mechanisms regulating expression of this enzyme are not known. We evaluated transcriptiona...

Teratogen-mediated inhibition of target tissue response to Shh signaling.

Science 280(5369) , 1603-7, (1998)

Veratrum alkaloids and distal inhibitors of cholesterol biosynthesis have been studied for more than 30 years as potent teratogens capable of inducing cyclopia and other birth defects. Here, it is sho...

Triggering of Erythrocyte Death by Triparanol.

Toxins (Basel.) 7 , 3359-71, (2015)

The cholesterol synthesis inhibitor Triparanol has been shown to trigger apoptosis in several malignancies. Similar to the apoptosis of nucleated cells, erythrocytes may enter eryptosis, the suicidal ...

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MER 29

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TRIPARANOL

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Triparanol

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