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122370-91-6

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122370-91-6 Usage

Description

17β-hydroxy Exemestane is the primary active metabolite of exemestane . It is formed by metabolism of exemestane by the cytochrome P450 (CYP) isoforms CYP1A and CYP4A11. 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). 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. 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.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 122370-91-6 differently. You can refer to the following data:
1. A metabolite of Exemestane; exerts biological effects as an androgen.
2. 17β-Hydroxy Exemestane Sulfamate is a metabolite of Exemestane (E957000).

Check Digit Verification of cas no

The CAS Registry Mumber 122370-91-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,2,3,7 and 0 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 122370-91:
(8*1)+(7*2)+(6*2)+(5*3)+(4*7)+(3*0)+(2*9)+(1*1)=96
96 % 10 = 6
So 122370-91-6 is a valid CAS Registry Number.
InChI:InChI=1/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

122370-91-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 17β-Hydroxy Exemestane

1.2 Other means of identification

Product number -
Other names (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-6-methylidene-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-3-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:122370-91-6 SDS

122370-91-6Synthetic route

6-methyleneandrosta-1,4-dien-3-one 17β-acetate
1160599-91-6

6-methyleneandrosta-1,4-dien-3-one 17β-acetate

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; Inert atmosphere;95%
With methanol; sodium hydroxide for 2h; Product distribution / selectivity;
17β-hydroxy-6-methyleneandrosta-4-ene-3-one
3347-73-7

17β-hydroxy-6-methyleneandrosta-4-ene-3-one

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

Conditions
ConditionsYield
With N,O-Bis(trimethylsilyl)trifluoroacetamide; chloranil; trifluorormethanesulfonic acid In toluene at 108 - 110℃; for 4h; Product distribution / selectivity; Heating / reflux;68.4%
With trifluorormethanesulfonic acid; N,O-Bis(trimethylsilyl)trifluoroacetamide; chloranil In toluene Inert atmosphere; Reflux;68%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; benzoic acid In benzene at 80 - 82℃; for 5h; Product distribution / selectivity; Heating / reflux;14%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane; ethyl acetate
exemestane
107868-30-4

exemestane

A

6-methylandrosta-1,4,6-trien-17β-ol

6-methylandrosta-1,4,6-trien-17β-ol

B

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

Conditions
ConditionsYield
With sodium tetrahydroborate; acetic acid; trifluoroacetic acid In dichloromethane; acetonitrile at 20℃; for 11h; Inert atmosphere;A 11.3 mg
B 39%
formaldehyd
50-00-0

formaldehyd

1-dehydrotestosterone
846-48-0

1-dehydrotestosterone

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

Conditions
ConditionsYield
With N,N-dimethylammonium chloride 1.) isoamyl alcohol, reflux, 2 h, 2.) isoamyl alcohol, reflux, 15 h; Multistep reaction;
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

exemestane
107868-30-4

exemestane

Conditions
ConditionsYield
With Jones reagent In acetone at -20℃; Jones oxidation; Inert atmosphere;100%
With jones reagent In acetone at -20℃; for 0.25h;85%
With Jones reagent In acetone at 0℃; Product distribution / selectivity;
L-Cysteine
52-90-4

L-Cysteine

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

6-methylcysteinylandrosta-1,4-diene-17β-hydroxy-3-one

6-methylcysteinylandrosta-1,4-diene-17β-hydroxy-3-one

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 24h; Inert atmosphere;13%
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

17β-hydroxy-6α/β-spirooxiranandrosta-1,4-dien-3-one

17β-hydroxy-6α/β-spirooxiranandrosta-1,4-dien-3-one

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 48h; Ambient temperature; Yield given;
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

17β-hydroxy-6-hydroxymethylandrosta-1,4,6-triene-3-one

17β-hydroxy-6-hydroxymethylandrosta-1,4,6-triene-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature
2: 35 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

6-Hydroxymethylexemestane

6-Hydroxymethylexemestane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / Jones reagent / acetone / 0.25 h / -20 °C
2: 80 percent / 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature
3: 38 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

6α/β,17β-dihydroxy-6α/β-hydroxymethylandrosta-1,4-diene-3-one

6α/β,17β-dihydroxy-6α/β-hydroxymethylandrosta-1,4-diene-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature
2: 45 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

FCE27353
184972-12-1

FCE27353

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / Jones reagent / acetone / 0.25 h / -20 °C
2: 80 percent / 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature
View Scheme
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

6α/β-hydroxy-6α/β-hydroxymethylandrosta-1,4-diene-3,17-dione

6α/β-hydroxy-6α/β-hydroxymethylandrosta-1,4-diene-3,17-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / Jones reagent / acetone / 0.25 h / -20 °C
2: 80 percent / 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature
3: 42 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature
View Scheme
propionyl chloride
79-03-8

propionyl chloride

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

6-methylenandrosta-1,4-diene-17β-ol-3-one-17-propionate
122396-87-6

6-methylenandrosta-1,4-diene-17β-ol-3-one-17-propionate

Conditions
ConditionsYield
In pyridine
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

6-methylenandrosta-1,4-diene-17β-ol-3-one-17-sulphate
122396-90-1

6-methylenandrosta-1,4-diene-17β-ol-3-one-17-sulphate

Conditions
ConditionsYield
With chlorosulfonic acid; dmap In pyridine
GLUTATHIONE
70-18-8

GLUTATHIONE

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

C30H43N3O8S

C30H43N3O8S

Conditions
ConditionsYield
Stage #1: 17β-hydroxy-6-methylen- androsta-1,4-dien-3-one With human liver cytosol; potassium phosphate at 37℃; for 0.05h; pH=7.4; Enzymatic reaction;
Stage #2: GLUTATHIONE at 37℃; for 2h;
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

C25H36N2O5S

C25H36N2O5S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium phosphate; human liver cytosol / 0.05 h / 37 °C / pH 7.4 / Enzymatic reaction
1.2: 2 h / 37 °C
2.1: potassium phosphate; D,L-dithiothreitol; glutamyl transpeptidase; glycylglycine / 37 °C / pH 7.4 / Enzymatic reaction
View Scheme
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
122370-91-6

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one

6-methylcysteinylandrosta-1,4-diene-17β-hydroxy-3-one

6-methylcysteinylandrosta-1,4-diene-17β-hydroxy-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium phosphate; human liver cytosol / 0.05 h / 37 °C / pH 7.4 / Enzymatic reaction
1.2: 2 h / 37 °C
2.1: potassium phosphate; D,L-dithiothreitol; glutamyl transpeptidase; glycylglycine / 37 °C / pH 7.4 / Enzymatic reaction
3.1: potassium phosphate; manganese(ll) chloride; D,L-dithiothreitol; human liver cytosol / 37 °C / pH 7.4 / Enzymatic reaction
View Scheme

122370-91-6Relevant articles and documents

Exemestane metabolites: Synthesis, stereochemical elucidation, biochemical activity and anti-proliferative effects in a hormone-dependent breast cancer cell line

Varela, Carla L.,Amaral, Cristina,Tavares Da Silva, Elisiário,Lopes, Andreia,Correia-Da-Silva, Georgina,Carvalho, Rui A.,Costa, Saul C.P.,Roleira, Fernanda M.F.,Teixeira, Natércia

, p. 336 - 345 (2014)

Exemestane is a third-generation steroidal aromatase inhibitor that has been used in clinic for hormone-dependent breast cancer treatment in post-menopausal women. It is known that exemestane undergoes a complex metabolization, giving rise to some already identified metabolites, the 17β-hydroxy-6-methylenandrosta-1,4-dien-3-one (17-βHE) and the 6-(hydroxymethyl)androsta-1,4,6-triene-3,17-dione (6-HME). In this study, four metabolites of exemestane have been analyzed, three of them were synthesized (6β-spirooxiranandrosta-1,4-diene-3,17-dione (2), 1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione (3) and 17-βHE (4)) while one was acquired, the 6-HME (6). The stereochemistry of the epoxide group of 2 and 3 has been unequivocally elucidated for the first time on the basis of NOESY experiments. New structure-activity relationships (SAR) have been established through the observation that the substitution of the double bonds by epoxide groups led to less potent derivatives in microsomes. However, the reduction of the C-17 carbonyl group to a hydroxyl group originating 17-βHE (4) resulted in a significant increase in activity in MCF-7aro cells when compared to exemestane (IC500.25 μM vs 0.90 μM, respectively). All the studied metabolites reduced MCF-7aro cells viability in a dose and time-dependent manner, and metabolite 3 was the most potent one. Altogether our results showed that not only exemestane but also its main metabolites are potent aromatase inhibitors and reduce breast cancer cells viability. This suggests that exemestane efficacy may also be due to the active metabolites that result from its metabolic transformation. Our results emphasize the importance of performing further studies to expand our understanding of exemestane actions in breast cancer cells.

Process for obtaining 6-Alkylidenandrost-1,4-diene-3one

-

Page/Page column 11-12, (2009/07/10)

6-alkylidenandrost-1,4-dien-3-ones of general formula (I), wherein R is H o alkyl; R1 y R2, independently of one another, represent H, OR3, OC(=O) R4 or O-(GPH), wherein R3 is H; C1-C6 alkyl or aryl; R4 is H or C1-C6 alkyl,; and GPH is a hydroxyl protecting group; or R1 and R2, together with the carbon atom to which they are bonded, form a carbonyl group or equivalent or a cyclic ketal; can be obtained by a process comprising subjecting the corresponding 6-alkyliden-4-androsten-3-one to a dehydrogenation reaction in the 1,2 position in the presence of a quinine, a silylating agent and a strong acid.

17-SUBSTITUTED ANDROSTA-1,4-DIEN-3-0NE DERIVATIVES

-

, (2008/06/13)

The invention relates to new 17-hydroxy androsta-1,4-diene-3-one derivatives of the following formula STR1 wherein each of R and R. sub. 3, independently, is hydrogen or C 1-C 6 alkyl; R 1 is hydrogen, halogen or C 1-C 6 alkyl; R 2 is hydrogen or C 1-C 6 alkyl;R. sub.4 is hydrogen or fluorine;R 5 is (a) hydrogen or C. sub. 1-C 6 alkyl; (b) phenyl unsubstituted or substituted by one or two substituents independently chosen from C 1-C 6 alkyl, halogen and amino; (c) an acyl group; or (d) a hydroxy protecting group; and the pharmaceutically acceptable salts thereof,which are useful in therapy, in particular as anti-cancer agents.

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