Exemestane

Base Information

• Chemical Name: Exemestane
• CAS No.: 107868-30-4
• Molecular Formula: C20H24O2
• Molecular Weight: 296.409
• Hs Code.: 29372900
• European Community (EC) Number: 643-090-2
• NSC Number: 713563
• UNII: NY22HMQ4BX
• DSSTox Substance ID: DTXSID5023037
• Nikkaji Number: J367.471A
• Wikipedia: Exemestane
• Wikidata: Q418819
• NCI Thesaurus Code: C1097
• RXCUI: 258494
• Pharos Ligand ID: 1C9Y1PCACLQ5
• Metabolomics Workbench ID: 43239
• ChEMBL ID: CHEMBL1200374
• Mol file: 107868-30-4.mol

Synonyms:6-methyleneandrosta-1,4-diene-3,17-dione;Aromasil;Aromasin;Aromasine;examestane;exemestane;FCE 24304;FCE-24304

Chemical Property of Exemestane

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.02E-08mmHg at 25°C
• Melting Point: 155.13 ºC
• Refractive Index: 1.572
• Boiling Point: 453.7 ºC at 760 mmHg
• Flash Point: 169 ºC
• PSA: 34.14000
• Density: 1.13 g/cm³
• LogP: 4.02950
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 296.177630004
• Heavy Atom Count: 22
• Complexity: 653

Purity/Quality:

98% ^*data from raw suppliers

Exemestane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 60-61-51
• Safety Statements: 53-22-36/37-57

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CC12CCC3C(C1CCC2=O)CC(=C)C4=CC(=O)C=CC34C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC(=C)C4=CC(=O)C=C[C@]34C
• Recent ClinicalTrials: Exemestane With or Without Entinostat in Treating Patients With Recurrent Hormone Receptor-Positive Breast Cancer That is Locally Advanced or Metastatic
• Recent EU Clinical Trials: A PHASE III RANDOMIZED, OPEN-LABEL, MULTICENTER STUDY EVALUATING THE EFFICACY AND SAFETY OF GIREDESTRANT PLUS EVEROLIMUS COMPARED WITH EXEMESTANE PLUS EVEROLIMUS IN PATIENTS WITH ESTROGEN RECEPTOR-POSITIVE, HER2- NEGATIVE, LOCALLY ADVANCED OR METASTATIC BREAST CANCER
• Recent NIPH Clinical Trials: A Study of E7090 as Monotherapy and in Combination With Other Anticancer Agents in Participants With ER+ and HER2- Recurrent/Metastatic Breast Cancer
• Chemical Composition and Structure: Exemestane (EXE) is an irreversible steroidal aromatase inhibitor (AI) with the chemical formula 6-methylenandrosta-1,4-diene-3,17-dione. It belongs to the class of type I steroidal aromatase inhibitors.
• Uses: Exemestane is marketed under the tradename Aromasin?. It is primarily used as a first-line therapy for estrogen receptor-positive breast cancer in postmenopausal females. The US FDA approved exemestane in October 1999. It is also used for the treatment of advanced breast cancer in postmenopausal women whose disease has progressed following tamoxifen therapy. Exemestane is considered a safe therapeutic option for estrogen receptor-positive breast cancer at any stage in pre- and postmenopausal women.
• Mechanism of Action: Exemestane irreversibly binds to the active site of the aromatase enzyme, leading to its inactivation. This action reduces the production of estrogen, thereby inhibiting tumor growth. Additionally, exemestane can induce apoptosis and cell cycle arrest in cancer cells, further hindering cell proliferation.
• Pharmacokinetics: Exemestane has poor oral bioavailability due to its low aqueous solubility, extensive pre-systemic metabolism, and P-glycoprotein mediated efflux. Transdermal delivery has been explored as an alternative route to improve bioavailability by avoiding first-pass effects and P-glycoprotein-mediated efflux.
• Potential and Exploration: Various novel delivery approaches have been explored to enhance its bioavailability and anti-cancer efficacy, including lipid-based and polymeric nanoparticles, co-crystals, solid dispersion, and liquid crystalline gel formulations.; Co-delivery of exemestane with bioactive compounds, such as polyphenolic phytoestrogens, has shown synergistic anti-cancer activity and potential for overcoming resistance.

Technology Process of Exemestane

There total 16 articles about Exemestane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

17β-hydroxy-6-methylen- androsta-1,4-dien-3-one (122370-91-6) → exemestane (107868-30-4)

Guidance literature:

With Jones reagent; In acetone; at -20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.06.094

Reference yield: 90.0%

6α-hydroxymethylandrosta-1,4-diene-3,17-dione (933455-74-4) → exemestane (107868-30-4)

Guidance literature:

6α-hydroxymethylandrosta-1,4-diene-3,17-dione; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 30 ℃;

With methanol; potassium hydroxide; at 40 - 50 ℃;

Reference yield: 88.2%

17-hydroxyimino-6-methylenandrosta-1,4-diene-3-one → exemestane (107868-30-4)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; at 25 - 30 ℃; for 10h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;

upstream raw materials:

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

methanol

6β-hydroxymethylandrosta-1,4-diene-3,17-dione

Androsta-1,4-diene-3,17-dione

Downstream raw materials:

FCE₂₇₃₅₃

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

1α,2α-epoxy-6-methylenandrost-4-ene-3,17-dione

6β-spirooxiranandrosta-1,4-diene-3,17-dione

Refernces

• 1、 Chen, Kaixiong,Liu, Chang,Deng, Le,Xu, Guangyu. "A practical Δ1-dehydrogenation of Δ4-3-keto-steroids with DDQ in the presence of TBDMSCl at room temperature". . p. 513 - 516. Retrieved 2010.
• 2、 -. "Preparation method of exemestane". Paragraph 0010; 0011; 0013. . Retrieved 2018/07/30.
• 3、 -. "Industrial production method of exemestane". . . Retrieved 2017/02/09.