Exemestane
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MedKoo CAT#: 100340

CAS#: 107868-30-4

Description: Exemestane is a synthetic androgen analogue. Exemestane binds irreversibly to and inhibits the enzyme aromatase, thereby blocking the conversion of cholesterol to pregnenolone and the peripheral aromatization of androgenic precursors into estrogens.


Chemical Structure

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Exemestane
CAS# 107868-30-4

Theoretical Analysis

MedKoo Cat#: 100340
Name: Exemestane
CAS#: 107868-30-4
Chemical Formula: C20H24O2
Exact Mass: 296.17763
Molecular Weight: 296.4
Elemental Analysis: C, 81.04; H, 8.16; O, 10.80

Price and Availability

Size Price Availability Quantity
200.0mg USD 90.0 Same day
500.0mg USD 150.0 Same day
1.0g USD 250.0 Same day
2.0g USD 450.0 Same day
5.0g USD 750.0 Same day
10.0g USD 1250.0 Same day
20.0g USD 1950.0 Same day
50.0g USD 4250.0 Same day
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Synonym: PNU155971; PNU-155971; PNU 155971; FCE24304; FCE-24304; FCE 24304; Exemestane; US brand name: Aromasin.

IUPAC/Chemical Name: (8R,9S,10R,13S,14S)-10,13-dimethyl-6-methylene-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione.

InChi Key: BFYIZQONLCFLEV-DAELLWKTSA-N

InChi Code: InChI=1S/C20H24O2/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/h6,8,11,14-16H,1,4-5,7,9-10H2,2-3H3/t14-,15-,16-,19+,20-/m0/s1

SMILES Code: O=C(C=C1C(C[C@@]2([H])[C@]3([H])CC4)=C)C=C[C@]1(C)[C@@]2([H])CC[C@]3(C)C4=O

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 296.4 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Gilabert M, Launay S, Gonçalves A. [Exemestane-everolimus in HER2-negative, hormonal receptor-positive, post-menopausal metastatic breast cancer with resistance to non-steroidal aromatase inhibitor: a new option]. Bull Cancer. 2014 Mar;101(3):325-33. doi: 10.1684/bdc.2014.1910. Review. French. PubMed PMID: 24691195.

2: Van Asten K, Neven P, Lintermans A, Wildiers H, Paridaens R. Aromatase inhibitors in the breast cancer clinic: focus on exemestane. Endocr Relat Cancer. 2014 Jan 16;21(1):R31-49. doi: 10.1530/ERC-13-0269. Print 2014 Feb. Review. PubMed PMID: 24434719.

3: Dunn BK, Cazzaniga M, DeCensi A. Exemestane: one part of the chemopreventive spectrum for ER-positive breast cancer. Breast. 2013 Jun;22(3):225-37. doi: 10.1016/j.breast.2013.02.015. Epub 2013 Mar 25. Review. PubMed PMID: 23535509.

4: Dhillon S. Everolimus in combination with exemestane: a review of its use in the treatment of patients with postmenopausal hormone receptor-positive, HER2-negative advanced breast cancer. Drugs. 2013 Apr;73(5):475-85. doi: 10.1007/s40265-013-0034-2. Review. PubMed PMID: 23529824.

5: Decensi A, Dunn BK, Puntoni M, Gennari A, Ford LG. Exemestane for breast cancer prevention: a critical shift? Cancer Discov. 2012 Jan;2(1):25-40. doi: 10.1158/2159-8290.CD-11-0248. Review. PubMed PMID: 22585166; PubMed Central PMCID: PMC3354700.

6: Santoro S, Santini M, Pepe C, Tognetti E, Cortelazzi C, Ficarelli E, De Panfilis G. Aromatase inhibitor-induced skin adverse reactions: exemestane-related cutaneous vasculitis. J Eur Acad Dermatol Venereol. 2011 May;25(5):596-8. doi: 10.1111/j.1468-3083.2010.03803.x. Review. PubMed PMID: 21492245.

7: Lintermans A, Neven P, Paridaens R. Drug safety evaluation of exemestane. Expert Opin Drug Saf. 2011 May;10(3):473-87. doi: 10.1517/14740338.2011.567264. Epub 2011 Mar 24. Review. PubMed PMID: 21428848.

8: Bertelli G, Gangadhara S. Exemestane in postmenopausal women with early or advanced breast cancer: a review. Expert Opin Pharmacother. 2010 Aug;11(11):1933-42. doi: 10.1517/14656566.2010.495945. Review. PubMed PMID: 20569090.

9: Macpherson IR, Lindsay C, Canney P. Adjuvant treatment of breast cancer in postmenopausal women: role of exemestane. Breast Cancer (Dove Med Press). 2010 Oct 14;2:59-70. doi: 10.2147/BCTT.S11835. Review. PubMed PMID: 24367167; PubMed Central PMCID: PMC3846455.

10: Glück S. Exemestane as first-line therapy in postmenopausal women with recurrent or metastatic breast cancer. Am J Clin Oncol. 2010 Jun;33(3):314-9. doi: 10.1097/COC.0b013e31819fdf9b. Review. PubMed PMID: 19730353.



Additional Information

DRUG DESCRIPTION
AROMASIN® Tablets for oral administration contain 25 mg of exemestane, an irreversible, steroidal aromatase inactivator. Exemestane is chemically described as 6-methylenandrosta-1,4-diene-3,17-dione. Its molecular formula is C20H24O2. The active ingredient is a white to slightly yellow crystalline powder with a molecular weight of 296.41. Exemestane is freely soluble in N, N-dimethylformamide, soluble in methanol, and practically insoluble in water. Each AROMASIN Tablet contains the following inactive ingredients: mannitol, crospovidone, polysorbate 80, hypromellose, colloidal silicon dioxide, microcrystalline cellulose, sodium starch glycolate, magnesium stearate, simethicone, polyethylene glycol 6000, sucrose, magnesium carbonate, titanium dioxide, methylparaben, and polyvinyl alcohol.
 
 
Mechanism of Action
Mechanism of Action
Breast cancer cell growth may be estrogen-dependent. Aromatase is the principal enzyme that converts androgens to estrogens both in pre- and postmenopausal women. While the main source of estrogen (primarily estradiol) is the ovary in premenopausal women, the principal source of circulating estrogens in postmenopausal women is from conversion of adrenal and ovarian androgens (androstenedione and testosterone) to estrogens (estrone and estradiol) by the aromatase enzyme in peripheral tissues. Estrogen deprivation through aromatase inhibition is an effective and selective treatment for some postmenopausal patients with hormone-dependent breast cancer. Exemestane is an irreversible, steroidal aromatase inactivator, structurally related to the natural substrate androstenedione. It acts as a false substrate for the aromatase enzyme, and is processed to an intermediate that binds irreversibly to the active site of the enzyme causing its inactivation, an effect also known as “suicide inhibition.” Exemestane significantly lowers circulating estrogen concentrations in postmenopausal women, but has no detectable effect on adrenal biosynthesis of corticosteroids or aldosterone. Exemestane has no effect on other enzymes involved in the steroidogenic pathway up to a concentration at least 600 times higher than that inhibiting the aromatase enzyme.
Breast cancer cell growth may be estrogen-dependent. Aromatase is the principal enzyme that converts androgens to estrogens both in pre- and postmenopausal women. While the main source of estrogen (primarily estradiol) is the ovary in premenopausal women, the principal source of circulating estrogens in postmenopausal women is from conversion of adrenal and ovarian androgens (androstenedione and testosterone) to estrogens (estrone and estradiol) by the aromatase enzyme in peripheral tissues. Estrogen deprivation through aromatase inhibition is an effective and selective treatment for some postmenopausal patients with hormone-dependent breast cancer. Exemestane is an irreversible, steroidal aromatase inactivator, structurally related to the natural substrate androstenedione. It acts as a false substrate for the aromatase enzyme, and is processed to an intermediate that binds irreversibly to the active site of the enzyme causing its inactivation, an effect also known as “suicide inhibition.” Exemestane significantly lowers circulating estrogen concentrations in postmenopausal women, but has no detectable effect on adrenal biosynthesis of corticosteroids or aldosterone. Exemestane has no effect on other enzymes involved in the steroidogenic pathway up to a concentration at least 600 times higher than that inhibiting the aromatase enzyme.