(1S,2R,10R,11S,15S)-6-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-dione

• ChemBase ID: 72899
• Molecular Formular: C19H26O3
• Molecular Mass: 302.40794
• Monoisotopic Mass: 302.18819469
• SMILES: C1C(=O)C(=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)C)O
• Canonical SMILES: O=C1CC[C@]2(C(=C1O)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H26O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,22H,3-10H2,1-2H3/t11-,12-,13-,18+,19-/m0/s1
• InChIKey: OSVMTWJCGUFAOD-KZQROQTASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-6-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione; (1S,2R,10R,11S,15S)-6-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
• IUPAC Traditional name: formestane
• Synonyms: 4-Hydroxyandrost-4-ene-3,17-dione, 4-OHA, CGP-32349, Lentaron; 4-Hydroxyandrost-4-ene-3,17-dione; Formestane; 4-Hydroxy-4-androstene-3,17-dione; 4-Androsten-4-ol-3,17-dione; Lentaron(R); 17-dione; CGP-32349; NSC 282175; Formestane

Database IDs

• CAS Number: 566-48-3
• MDL Number: MFCD00057814
• PubChem SID: 162037819; 24894827; 24278220
• PubChem CID: 11273

CALCULATED PROPERTIES

• Acid pKa: 9.209685
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.4102087
• LogD (pH = 7.4): 3.4036157
• Log P: 3.4102933
• Molar Refractivity: 85.5749 cm^3
• Polarizability: 33.33251 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: solid; White Solid
• Melting Point: 199-202°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: BV8152500
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Target: Aromatase
• Gene Information: human ... CYP19A1(1588)

Product Information

• Salt Data: Free Base
• Empirical Formula (Hill Notation): C19H26O3

DETAILS

Selleck Chemicals - S2208

Research Area: Breast cancer
Biological Activity:
Formestane(Lentaron(R)) is a second generation selective aromatase inhibitor with an IC50 of 80 nM. Formestane(Lentaron(R)) is used in the treatment of estrogen-receptor positive breast cancer in post-menopausal women. Formestane(Lentaron(R)) is often used to suppress estrogen production from anabolic steroids or prohormones. Formestane(Lentaron(R)) also acts as a prohormone to 4-hydroxytestosterone, an active steroid which displays weak androgenic activity in addition to acting as a mild aromatase inhibitor. Formestane has poor oral bioavailability and as such is no longer popular as many orally active aromatase inhibitors have been identified. Cells were treated with different aromatase inhibitors anastrozole, formestane, exemestane, and letrozole, or antiestrogens tamoxifen and fulvestrant. UMB-1Ca cells showed significant growth inhibition in response to fulvestrant (100 nM, P < 0.0005) and partial growth inhibition in response to letrozole (100 nM, P < 0.005). [1][2][3]References on Formestane[3] Ann Oncol., 1994, 5 Suppl 7:S15-7.[1] Cancer Res, 2005, 65:3903-3910[2] Journal of Steroid Biochemistry & Molecular Biology , 2001, 77 :39–47

Sigma Aldrich - F2552

Biochem/physiol Actions
Aromatase inhibitor used as an anti-cancer agent against estrogen-dependent tumors.

Toronto Research Chemicals - F692250

An antitumor drug. An aromatase inhibitor.

REFERENCES

• L??nning PE et al. J Steroid Biochem Mol Biol. 2001 Apr;77(1):39-47.
• Brodie, A.M. and Njar, V.C.: Steroids, 65, 171 (2000)
• Lonning, P.E., et al.: J. Steroid Biochem, 77, 39 (2001)