An active metabolite of exemestane
Related Products
Labeled Version(s)
2575617β-hydroxy Exemestane-d3
Parent Compound(s)
15008Exemestane
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17β-hydroxy Exemestane

Item No. 27989

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
17β-hydroxy-6-methylene-androsta-1,4-dien-3-one
CAS Number
122370-91-6
Molecular Formula
C20H26O2
Formula Weight
298.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly, heatedMethanol: slightly, heated
SMILES
C=C1C2=CC(C=C[C@]2(C)[C@]3([H])[C@@]([C@@](CC[C@@H]4O)([H])[C@]4(C)CC3)([H])C1)=O
InChi Code
InChI=1S/C20H26O2/c1-12-10-14-15-4-5-18(22)20(15,3)9-7-16(14)19(2)8-6-13(21)11-17(12)19/h6,8,11,14-16,18,22H,1,4-5,7,9-10H2,2-3H3/t14-,15-,16-,18-,19+,20-/m0/s1
InChi Key
NFDPYPMRHKQTDM-NHWXPXPKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    1 mg

    $336

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    Product Description

    17β-hydroxy Exemestane is the primary active metabolite of exemestane (Item No. 15008).1 It is formed by metabolism of exemestane by the cytochrome P450 (CYP) isoforms CYP1A and CYP4A11.2 17β-hydroxy Exemestane is an aromatase inhibitor (IC50 = 69 nM using human placental microsomes) and an androgen receptor (AR) agonist (IC50 = 39.6 nM) that is selective for AR over estrogen receptor α (ERα; IC50 = 21.2 μM).3,4 It stimulates growth of AR- and ERα-positive MCF-7 (EC50 = 2.7 μM) and T47D breast cancer cells (EC50s = 0.43 and 1,500 nM for AR- and ER-mediated growth, respectively) and inhibits proliferation of testosterone-treated aromatase-overexpressing MCF-7aro cells in a concentration-dependent manner.4,5 17β-hydroxy Exemestane (20 mg/kg) inhibits increases in serum cholesterol and LDL levels and prevents decreases in bone mineral density in the lumbar vertebrae and femur, as well as femoral bending strength and compressive strength of the fifth lumbar vertebrae, in ovariectomized rats.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Goss, P.E., Qi, S., Cheung, A.M., et al. Effects of the steroidal aromatase inhibitor exemestane and the nonsteroidal aromatase inhibitor letrozole on bone and lipid metabolism in ovariectomized rats. Clin. Cancer Res. 10(17), 5717-5723 (2004).

    2. Kamdem, L.K., Flockhart, D.A., and Desta, Z. In vitro cytochrome P450-mediated metabolism of exemestane. Drug Metab. Dispos. 39(1), 98-105 (2011).

    3. Buzzetti, F., Di Salle, E., Longo, A., et al. Synthesis and aromatase inhibition by potential metabolites of exemestane (6-methylenandrosta-1,4-diene-3,17-dione). Steroids 58(11), 527-532 (1993).

    4. Ariazi, E.A., Leitão, A., Oprea, T.I., et al. Exemestane’s 17-hydroxylated metabolite exerts biological effects as an androgen. Mol. Cancer Ther. 6(11), 2817-2827 (2007).

    5. Varela, C.L., Amaral, C., Tavares da Silva, E., et al. Exemestane metabolites: Synthesis, stereochemical elucidation, biochemical activity and anti-proliferative effects in a hormone-dependent breast cancer cell line. Eur. J. Med. Chem. 87, 336-345 (2014).