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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H32N2O
Molecular Weight 388.546
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALETERONE

SMILES

C[C@@]12CC[C@@]([H])(CC2=CC[C@@]3([H])[C@]4([H])CC=C([C@@]4(C)CC[C@@]31[H])n5cnc6ccccc65)O

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 388.546
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25591066 https://www.ncbi.nlm.nih.gov/pubmed/27486306

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2528 ng × h/mL
3400 mg single, oral
dose: 3400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GALETERONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2646 ng × h/mL
1700 mg single, oral
dose: 1700 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GALETERONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2684 ng × h/mL
2550 mg single, oral
dose: 2550 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GALETERONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Synergistic effect of a novel antiandrogen, VN/124-1, and signal transduction inhibitors in prostate cancer progression to hormone independence in vitro.
2008 Jan
Patents

Sample Use Guides

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
Galeterone (VN/124-1) dose-dependently inhibits prostate cancer cell growth (LNCaP and LAPC4 cells).
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:08:59 UTC 2021
Edited
by admin
on Sat Jun 26 06:08:59 UTC 2021
Record UNII
WA33E149SW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GALETERONE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
VN 124
Code English
TOK 001
Code English
VN/124-1
Code English
GALETERONE [USAN]
Common Name English
GALETERONE [WHO-DD]
Common Name English
VN-124
Code English
GALETERONE [INN]
Common Name English
TOK-001
Code English
VN/124
Code English
ANDROSTA-5,16-DIEN-3-OL, 17-(1H-BENZIMIDAZOL-1-YL)-, (3.BETA.)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
Code System Code Type Description
EVMPD
SUB124320
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
INN
9423
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
DRUG BANK
DB12415
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
CAS
851983-85-2
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
NCI_THESAURUS
C84866
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
PUBCHEM
11188409
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL2105738
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
FDA UNII
WA33E149SW
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
WIKIPEDIA
GALETERONE
Created by admin on Sat Jun 26 06:08:59 UTC 2021 , Edited by admin on Sat Jun 26 06:08:59 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDING
Related Record Type Details
ACTIVE MOIETY