Colestolone

Colestolone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name), also known as 5α-cholest-8(14)-en-3β-ol-15-one, is a potent inhibitor of sterol biosynthesis which is described as a hypocholesterolemic (lipid-lowering) agent.^{[1][2][3][4][5]} It was first reported in 1977 and was studied until at least 1988, but was never introduced for medical use.^[1][3][4]

Other names5α-Cholest-8(14)-en-3β-ol-15-one; 3β-Hydroxy-5α-cholest-8(14)-en-15-one

CAS Number

• 50673-97-7

PubChem CID

• 39756

ChemSpider

• 39756

Quick facts Clinical data, Other names ...

Colestolone

Clinical data
Other names	5α-Cholest-8(14)-en-3β-ol-15-one; 3β-Hydroxy-5α-cholest-8(14)-en-15-one
Identifiers
IUPAC name (3S,5S,10S,13R,17R)-3-Hydroxy-10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-15-one
CAS Number	50673-97-7
PubChem CID	39756
ChemSpider	39756
UNII	5P8396T5XF
CompTox Dashboard (EPA)	DTXSID6046212
Chemical and physical data
Formula	C27H44O2
Molar mass	400.647 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)CCCC(C)[C@H]1CC(=O)C2=C3CC[C@H]4C[C@H](CC[C@@]4(C3CC[C@]12C)C)O
InChI InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)23-16-24(29)25-21-10-9-19-15-20(28)11-13-26(19,4)22(21)12-14-27(23,25)5/h17-20,22-23,28H,6-16H2,1-5H3/t18?,19-,20-,22?,23+,26-,27+/m0/s1 Key:LINVVMHRTUSXHL-NDNSGUFDSA-N

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Colestolone has been found to significantly reduce serum levels of cholesterol both in animals and in humans.^[3][4][5] It inhibits multiple relatively early-stage steps in cholesterol biosynthesis such as HMG-CoA reductase^[6] and does not appear to affect any late-stage steps (after squalene, specifically).^[5] Unlike late-stage cholesterol biosynthesis inhibitors like triparanol and azacosterol, no accumulation of sterols has been observed in animals treated with colestolone, suggesting that it does not share the toxicity of late-stage cholesterol biosynthesis inhibitors.^[5]

In addition to its potent inhibition of cholesterol biosynthesis, it is notable that colestolone also happens to serve as a precursor of cholesterol, and is efficiently converted into it in rat liver homogenates and upon oral administration to rats.^[5]