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Details

Stereochemistry RACEMIC
Molecular Formula C27H32ClNO2
Molecular Weight 438.0024
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIPARANOL

SMILES

CCN(CC)CCOc1ccc(cc1)C(Cc2ccc(cc2)Cl)(c3ccc(C)cc3)O

InChI

InChIKey=SYHDSBBKRLVLFF-UHFFFAOYSA-N
InChI=1S/C27H32ClNO2/c1-4-29(5-2)18-19-31-26-16-12-24(13-17-26)27(30,23-10-6-21(3)7-11-23)20-22-8-14-25(28)15-9-22/h6-17,30H,4-5,18-20H2,1-3H3

HIDE SMILES / InChI

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26305256 | https://www.ncbi.nlm.nih.gov/pubmed/22877755 | https://www.ncbi.nlm.nih.gov/pubmed/13852510 |

Triparanol (brand and developmental code names MER/29) is a 24-dehydro cholesterol reductase inhibitor, which is an enzyme involved in the biosynthesis of cholesterol. It has antitumor properties, such as decreasing proliferation and inducing apoptosis in many cancer cell lines and slowing tumor growth in a mouse xenograft model. It can also decrease Hedgehog pathway signaling in cancer cells. Triparanol was the first synthetic cholesterol-lowering drug. It was withdrawn in 1962 due to severe adverse effects such as nausea and vomiting, vision loss due to irreversible cataracts, alopecia, skin disorders (e.g., dryness, itching, peeling, and "fish-scale" texture), and accelerated atherosclerosis and is now considered to be obsolete.

Originator

Sources: Archivio Italiano di Scienze Mediche Tropicali e di Parassitologia (1957), 38, 611-24.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
11.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MER-29

Approved Use

Unknown
Primary
MER-29

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
1500 mg 1 times / day multiple, oral
Highest studied dose
Dose: 1500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 1 times / day
Sources:
unhealthy, 23 years
n = 1
Health Status: unhealthy
Age Group: 23 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Cataracts...
AEs leading to
discontinuation/dose reduction:
Cataracts (severe, 1 patient)
Sources:
250 mg 1 times / day multiple, oral (starting)
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Sources:
unhealthy, 42-66 years
n = 15
Health Status: unhealthy
Age Group: 42-66 years
Sex: M+F
Population Size: 15
Sources:
Disc. AE: Angina pectoris...
AEs leading to
discontinuation/dose reduction:
Angina pectoris (2 patients)
Sources:
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Sources:
unhealthy, 6-59 years
n = 8
Health Status: unhealthy
Age Group: 6-59 years
Sex: M+F
Population Size: 8
Sources:
Disc. AE: Cataracts...
AEs leading to
discontinuation/dose reduction:
Cataracts (severe, 8 patients)
Sources:
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Age Group: 70 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Malabsorption syndrome, Mucosal atrophy...
AEs leading to
discontinuation/dose reduction:
Malabsorption syndrome (1 patient)
Mucosal atrophy (severe, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Cataracts severe, 1 patient
Disc. AE
1500 mg 1 times / day multiple, oral
Highest studied dose
Dose: 1500 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1500 mg, 1 times / day
Sources:
unhealthy, 23 years
n = 1
Health Status: unhealthy
Age Group: 23 years
Sex: M
Population Size: 1
Sources:
Angina pectoris 2 patients
Disc. AE
250 mg 1 times / day multiple, oral (starting)
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Sources:
unhealthy, 42-66 years
n = 15
Health Status: unhealthy
Age Group: 42-66 years
Sex: M+F
Population Size: 15
Sources:
Cataracts severe, 8 patients
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Sources:
unhealthy, 6-59 years
n = 8
Health Status: unhealthy
Age Group: 6-59 years
Sex: M+F
Population Size: 8
Sources:
Malabsorption syndrome 1 patient
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Age Group: 70 years
Sex: F
Population Size: 1
Sources:
Mucosal atrophy severe, 1 patient
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Age Group: 70 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Experimental myopathy induced by amphiphilic cationic compounds including several psychotropic drugs.
1979
Dysregulation of hedgehog signalling predisposes to synovial chondromatosis.
2005 Jun
Constitutive hedgehog signaling in chondrosarcoma up-regulates tumor cell proliferation.
2006 Jan
Age estimation in 25-45 yrs. old females by physical and radiological methods.
2010 Jul
Different experimental approaches in modelling cataractogenesis: An overview of selenite-induced nuclear cataract in rats.
2010 Mar
Patents

Patents

Sample Use Guides

maximally effective dose of 250 mg. per day
Route of Administration: Oral
Lung cancer A549; breast cancer MCF7; hepatocellular carcinoma (liver cancer) HepG2; pancreatic cancer cell line bxpc3; prostate cancer cell line LnCAP; melanoma G361; and normal fibroblast were used for activity evaluation. One day before treatment, cells (5 _ 104) will be plated in 96-wells in growth medium without antibiotics and with reduced serum (2.5%). Cells will be incubated with Triparanol at different concentrations (0.5 and 1 mkM) as indicated with or without cholesterol (5 lM) in the same medium until ready for further analysis. Cells will be treated with Triparanol in 96-well plates for 6–7 days. Cell proliferation was assayed by MTS assay (Promega) according to the manufacturer’s protocol.
Name Type Language
TRIPARANOL
INN   MI   WHO-DD  
INN  
Official Name English
TRIPARANOL [INN]
Common Name English
TRIPARANOL [MI]
Common Name English
NSC-65345
Code English
2-P-CHLOROPHENYL-1-(P-(2-DIETHYLAMINOETHOXY)PHENYL)-1-P-TOLYLETHANOL
Common Name English
TRIPARANOL [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29703
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
Code System Code Type Description
PUBCHEM
6536
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
MERCK INDEX
M979
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
2761
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
NCI_THESAURUS
C152752
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
CAS
78-41-1
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
INN
1010
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
FDA UNII
63S8C3RXGS
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
EPA CompTox
78-41-1
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
MESH
D014308
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
EVMPD
SUB11321MIG
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-115-0
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY
ChEMBL
CHEMBL187709
Created by admin on Sat Jun 26 02:56:09 UTC 2021 , Edited by admin on Sat Jun 26 02:56:09 UTC 2021
PRIMARY