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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26O2
Molecular Weight 298.4192
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATAMESTANE

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C(C)[C@]34C

InChI

InChIKey=PEPMWUSGRKINHX-TXTPUJOMSA-N
InChI=1S/C20H26O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10-11,15-17H,4-9H2,1-3H3/t15-,16-,17-,19-,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H26O2
Molecular Weight 298.4192
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Atamestane is a new, competitive, and irreversible inhibitor of estrogen biosynthesis. It is an aromatase inhibitor. Atamestane lacks other intrinsic hormonal or antihormonal activities and shows no inhibition of other cytochrome-P450 dependent enzymes of adrenal steroidogenesis. It had been in phase III clinical trial for the treatment of breast cancer and phase II for the treatment of benign prostatic hyperplasia. It was discontinued from development after an 865-patient trial in breast cancer showed no improvement in efficacy over letrozole.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.4 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Atamestane is administered over 48 weeks as a daily dose of 100 mg or 300 mg.
Route of Administration: Oral
In Vitro Use Guide
The levels of aromatase mRNA was 6.31 amol/ug total RNA in JEG-3 cells, cultured in the presence or absence of 10 uM Atamestane at 37°C for 24 h.
Substance Class Chemical
Record UNII
62GA3K28B6
Record Status Validated (UNII)
Record Version