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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H32N2O
Molecular Weight 388.5451
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALETERONE

SMILES

[H][C@@]12CC=C(N3C=NC4=C3C=CC=C4)[C@@]1(C)CC[C@@]5([H])[C@@]2([H])CC=C6C[C@@H](O)CC[C@]56C

InChI

InChIKey=PAFKTGFSEFKSQG-PAASFTFBSA-N
InChI=1S/C26H32N2O/c1-25-13-11-18(29)15-17(25)7-8-19-20-9-10-24(26(20,2)14-12-21(19)25)28-16-27-22-5-3-4-6-23(22)28/h3-7,10,16,18-21,29H,8-9,11-15H2,1-2H3/t18-,19-,20-,21-,25-,26-/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H32N2O
Molecular Weight 388.5451
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Galeterone (TOK-001, formerly called VN/124-1) is a potent anti-androgen with three modes of action. The compound acts as a specific androgen receptor antagonist, inhibits CYP17 lyase while conserving CYP17 hydroxylase function, and decreases overall androgen receptor levels in prostate cancer cells. Galeterone is a first in class, multi-targeted small-molecule drug that disrupts the growth and survival of prostate cancer cells. Tokai Pharmaceuticals is developing galeterone as an oral treatment for castration-resistant prostate cancer. Phase III clinical development of galeterone is underway in the US, Canada, Australia, Western Europe, Spain and the United Kingdom.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
384.0 nM [IC50]
300.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

AUC

ValueDoseCo-administeredAnalytePopulation
2684 ng × h/mL
2550 mg single, oral
GALETERONE plasma
Homo sapiens
2646 ng × h/mL
1700 mg single, oral
GALETERONE plasma
Homo sapiens
2528 ng × h/mL
3400 mg single, oral
GALETERONE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
A once-daily galeterone dose of 2550mg was recommended for use in patients with castration-resistant prostate cancer based on results from part 1 of the phase II trial.
Route of Administration: Oral
In Vitro Use Guide
Galeterone (VN/124-1) dose-dependently inhibits prostate cancer cell growth (LNCaP and LAPC4 cells).
Substance Class Chemical
Record UNII
WA33E149SW
Record Status Validated (UNII)
Record Version