Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C27H32ClNO2 |
| Molecular Weight | 438.001 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CCOC1=CC=C(C=C1)C(O)(CC2=CC=C(Cl)C=C2)C3=CC=C(C)C=C3
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
| Molecular Formula | C27H32ClNO2 |
| Molecular Weight | 438.001 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/13852511Curator'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 |
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13852511
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 It was withdrawn in 1962 due to severe adverse effects such as nausea and vomiting, vision loss due to irreversible cataracts, alopecia, skin disorders (e.g., dryness, itching,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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2331059 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26789657 |
|||
Target ID: CHEMBL4931 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16033255 |
11.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | MER-29 Approved UseUnknown |
|||
| Primary | MER-29 Approved UseUnknown |
Doses
| Dose | Population | Adverse 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 |
Disc. AE: Cataracts... AEs leading to discontinuation/dose reduction: Cataracts (severe, 1 patient) 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, 42-66 years Health Status: unhealthy Age Group: 42-66 years Sex: M+F 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 Health Status: unhealthy Age Group: 6-59 years Sex: M+F 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 |
Disc. AE: Malabsorption syndrome, Mucosal atrophy... AEs leading to discontinuation/dose reduction: Malabsorption syndrome (1 patient) Sources: Mucosal atrophy (severe, 1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
| Angina pectoris | 2 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, 42-66 years Health Status: unhealthy Age Group: 42-66 years Sex: M+F 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 Health Status: unhealthy Age Group: 6-59 years Sex: M+F 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 |
| 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Age estimation in 25-45 yrs. old females by physical and radiological methods. | 2010-07 |
|
| Chemical combinations elucidate pathway interactions and regulation relevant to Hepatitis C replication. | 2010-06-08 |
|
| Different experimental approaches in modelling cataractogenesis: An overview of selenite-induced nuclear cataract in rats. | 2010-03 |
|
| A historical perspective on the discovery of statins. | 2010 |
|
| Inhibition of cholesterol biosynthesis disrupts lipid raft/caveolae and affects insulin receptor activation in 3T3-L1 preadipocytes. | 2009-09 |
|
| Constitutive hedgehog signaling in chondrosarcoma up-regulates tumor cell proliferation. | 2006-01 |
|
| Dysregulation of hedgehog signalling predisposes to synovial chondromatosis. | 2005-06 |
|
| Molecular mechanisms underlying limb anomalies associated with cholesterol deficiency during gestation: implications of Hedgehog signaling. | 2003-05-15 |
|
| Limb malformations of rat fetuses exposed to a distal inhibitor of cholesterol biosynthesis. | 2002-08 |
|
| Toxicologic lesions associated with two related inhibitors of oxidosqualene cyclase in the dog and mouse. | 2001-06-26 |
|
| Experimental myopathy induced by amphiphilic cationic compounds including several psychotropic drugs. | 1979 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13852511
maximally effective dose of 250 mg. per day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26305256
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:45:45 GMT 2025
by
admin
on
Mon Mar 31 17:45:45 GMT 2025
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| Record UNII |
63S8C3RXGS
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C29703
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6536
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m979
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100000076949
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C152752
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65345
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78-41-1
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SUB11321MIG
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201-115-0
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Triparanol
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CHEMBL187709
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