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Clinical data | |
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Trade names | MER/29 |
Other names | Metasqualene |
ATC code |
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Identifiers | |
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CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
ChEBI | |
CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.001.014 |
Chemical and physical data | |
Formula | C27H32ClNO2 |
Molar mass | 438.01 g·mol−1 |
3D model ( JSmol) | |
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Triparanol ( INN , BAN ; brand name and development code MER/29, as well as many other brand names) was the first synthetic cholesterol-lowering drug. [1] [2] It was patented in 1959 and introduced in the United States in 1960. [3] [4] The developmental code name of triparanol, MER/29, became so well known that it became the registered trade name of the drug. [5] It was withdrawn in 1962 due to severe adverse effects such as nausea and vomiting, vision loss due to irreversible cataracts, alopecia, skin disorders (e.g., dryness, itching,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. [3] [2] It is now considered to be obsolete. [3] [2]
The drug acts by inhibiting 24-dehydrocholesterol reductase, which catalyzes the final step of cholesterol biosynthesis, the conversion of desmosterol into cholesterol. [6] Although effective in reducing cholesterol levels, this results in tissue accumulation of desmosterol, which in turn is responsible for the side effects of triparanol. [2] Unlike statins, triparanol does not inhibit HMG-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis, [2] and in contrast to triparanol, statins can lower cholesterol levels without resulting in accumulation of intermediates like desmosterol. [2]
Estrogen is known to lower cholesterol levels, but produces side effects like gynecomastia and decreased libido in men. [3] It was hoped that a drug could be developed that lacked overt estrogenic effects but still lowered cholesterol levels. [3] Triparanol is a triphenylethanol and was derived from chlorotrianisene (TACE), a nonsteroidal triphenylethylene estrogen. [3] [7] The nonsteroidal triphenylethanol antiestrogen ethamoxytriphetol (MER-25) is a derivative of triparanol. [8] The selective estrogen receptor modulator clomifene is also structurally related to triparanol. [7] [9] The developers of triparanol jokingly referred to it as a "non-estrogenic estrogen" due to its lipid-lowering effects without other estrogenic effects. [3]
Recently, another laboratory code number, MER29, became so well known that it was adopted as the registered trademark for the anticholesterolemic drug concerned (triparanol).
![]() | |
Clinical data | |
---|---|
Trade names | MER/29 |
Other names | Metasqualene |
ATC code |
|
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
ChEBI | |
CompTox Dashboard ( EPA) | |
ECHA InfoCard | 100.001.014 |
Chemical and physical data | |
Formula | C27H32ClNO2 |
Molar mass | 438.01 g·mol−1 |
3D model ( JSmol) | |
| |
|
Triparanol ( INN , BAN ; brand name and development code MER/29, as well as many other brand names) was the first synthetic cholesterol-lowering drug. [1] [2] It was patented in 1959 and introduced in the United States in 1960. [3] [4] The developmental code name of triparanol, MER/29, became so well known that it became the registered trade name of the drug. [5] 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. [3] [2] It is now considered to be obsolete. [3] [2]
The drug acts by inhibiting 24-dehydrocholesterol reductase, which catalyzes the final step of cholesterol biosynthesis, the conversion of desmosterol into cholesterol. [6] Although effective in reducing cholesterol levels, this results in tissue accumulation of desmosterol, which in turn is responsible for the side effects of triparanol. [2] Unlike statins, triparanol does not inhibit HMG-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis, [2] and in contrast to triparanol, statins can lower cholesterol levels without resulting in accumulation of intermediates like desmosterol. [2]
Estrogen is known to lower cholesterol levels, but produces side effects like gynecomastia and decreased libido in men. [3] It was hoped that a drug could be developed that lacked overt estrogenic effects but still lowered cholesterol levels. [3] Triparanol is a triphenylethanol and was derived from chlorotrianisene (TACE), a nonsteroidal triphenylethylene estrogen. [3] [7] The nonsteroidal triphenylethanol antiestrogen ethamoxytriphetol (MER-25) is a derivative of triparanol. [8] The selective estrogen receptor modulator clomifene is also structurally related to triparanol. [7] [9] The developers of triparanol jokingly referred to it as a "non-estrogenic estrogen" due to its lipid-lowering effects without other estrogenic effects. [3]
Recently, another laboratory code number, MER29, became so well known that it was adopted as the registered trademark for the anticholesterolemic drug concerned (triparanol).