184972-12-1

Basic information

• Product Name: (8R,9S,10R,13S,14S)-10,13-Dimethylspiro[7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthrene-6,2'-oxirane]-3,17(10H,14H)-dione
• Synonyms: (8R,9S,10R,13S,14S)-10,13-Dimethylspiro[7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthrene-6,2'-oxirane]-3,17(10H,14H)-dione;Spiro[androsta-1,4-diene-6,2'-oxirane]-3,17-dione
• CAS NO: 184972-12-1
• Molecular Formula: C20H24O3
• Molecular Weight: 312.40276
• Mol File: 184972-12-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: (8R,9S,10R,13S,14S)-10,13-Dimethylspiro[7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthrene-6,2'-oxirane]-3,17(10H,14H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (8R,9S,10R,13S,14S)-10,13-Dimethylspiro[7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthrene-6,2'-oxirane]-3,17(10H,14H)-dione(184972-12-1)
• EPA Substance Registry System: (8R,9S,10R,13S,14S)-10,13-Dimethylspiro[7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthrene-6,2'-oxirane]-3,17(10H,14H)-dione(184972-12-1)

Safety Data

• Hazardous Substances Data: 184972-12-1(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

A metabolite of Exemestane (E957000).

Upstream product

• 122370-91-6 17β-hydroxy-6-methylen- androsta-1,4-dien-3-one 
• 846-48-0 1-dehydrotestosterone 
• 107868-30-4 exemestane 

Downstream Products

• 152764-26-6 6-hydroxymethylandrosta-1,4,6-triene-3,17-dione 
• 184972-11-0 6α/β-hydroxy-6α/β-hydroxymethylandrosta-1,4-diene-3,17-dione 

Relevant articles and documents

Synthesis and aromatase inhibition by potential metabolites of exemestane (6-methylenandrosta-1,4-diene-3,17-dione)

Exemestane (6-methylenandrosta-1,4-diene-3,17-dione; FCE 24304) is an orally active irreversible aromatase inhibitor which is in phase II clinical evaluation for the potential therapy of postmenopausal breast cancer. A series of exemestane analogs, with modifications at the 6-methylene group and with additional reduction at the 17-keto group, were synthesized as potential metabolites and tested in vitro for their effect on human placental aromatase. All these new analogs were found to be less potent in inhibiting aromatase than exemestane. The most effective compound was the 17β-hydroxy- derivative (compound 2), which is 2.6-fold less potent than exemestane [50% inhibitory concentration (IC50) 69 and 27 nM, respectively]. The various C- 6 modified derivatives of the 17-oxo series were found to inhibit the aromatase enzyme in the following descending order: 6-methylene (exemestane) > 6-spirooxirane (6) > 6β-hydroxymethyl (11) > 6-hydroxymethyl (7) > 6β- carboxy (13), showing IC50 values of 27, 206, 295, 2,300, and 7,200 nM, respectively. The 17β-hydroxy analogs of some of the above mentioned compounds were also synthesized (3, 4, 12) and found to be 3-8-fold less potent than the corresponding 17-keto analogs.