GALETERONE

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 Search

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

Description
Sources: http://adisinsight.springer.com/drugs/800031243
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15828836	Antagonist 2778		384.0 nM [IC50]
Cytochrome P450 17A1 8 Target ID: CHEMBL3522 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15828836	Inhibitor 8297		300.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 178 Sources: http://adisinsight.springer.com/drugs/800031243	Primary		Phase III 656	Unknown Approved Use Unknown

AUC

Value	Dose	Analyte	Population
2528 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527750	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527750	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26527750	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

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00G46X	https://www.1pchem.com/search?query=1P00G46X
A2B Chem	AH51129	http://a2bchem.com/prod/AH51129
AChemBlock	10322	http://www.achemblock.com/catalogsearch/result/?q=10322
AK Scientific	Y0281	https://aksci.com/item_detail.php?cat=Y0281
ApexBio Technology	A8623	https://www.apexbt.com/catalogsearch/result/?q=A8623
AstaTech	32688	http://astatechinc.com/CPSResult.php?CRNO=32688
BLD Pharm	BD165428	http://www.bldpharm.com/search/Search.html?keyword=BD165428
BioSynth	J-501178	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501178
Capot Chemical	28182	https://www.capotchem.com/search.do?q=28182
Cayman Chemical	17586	http://www.caymanchem.com/app/template/Product.vm/catalog/17586
Chem Scene	CS-0334	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0334
ChemShuttle	139029	https://www.chemshuttle.com/catalogsearch/result/?q=139029
Coresyn	CM11049	http://www.coresyn.com/search.do?q=CM11049
KeyOrganics	AS-56204	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-56204
Lab Network	LN01326675	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01326675
Lab Seeker	SC-96681	http://www.labseeker.com/search.php?keywords=SC-96681&category=0
LabSeeker	SC-96681	http://www.labseeker.com/search.php?keywords=SC-96681&category=0
MedChem Express	HY-70006	https://www.medchemexpress.com/search.html?q=HY-70006&ft=&fa=&fp=
MolPort	MolPort-009-682-975	https://www.molport.com/shop/molecule-link/MolPort-009-682-975
Molnova	M17617	https://www.molnova.com/en/serch-list.html?keywords=M17617
MuseChem	I005114	https://www.musechem.com/product/I005114.html
ShangHai Biochempartner	BCP02827	http://www.biochempartner.com/search_BCP02827
TargetMol	T6509	https://www.targetmol.com/search?keyword=T6509
Toronto Research Chemicals	G188200	https://www.trc-canada.com/product-detail/?CatNum=G188200
eMolecules	43473314	https://orderbb.emolecules.com/search/#?query=43473314
mcule	MCULE-1173407498	https://mcule.com/MCULE-1173407498/
mcule	MCULE-1880914691	https://mcule.com/MCULE-1880914691/

PubMed

Title	Date	PubMed
Novel C-17-heteroaryl steroidal CYP17 inhibitors/antiandrogens: synthesis, in vitro biological activity, pharmacokinetics, and antitumor activity in the LAPC4 human prostate cancer xenograft model.	2005 Apr 21	15828836
Androgen receptor inactivation contributes to antitumor efficacy of 17{alpha}-hydroxylase/17,20-lyase inhibitor 3beta-hydroxy-17-(1H-benzimidazole-1-yl)androsta-5,16-diene in prostate cancer.	2008 Aug	18723482
Synergistic effect of a novel antiandrogen, VN/124-1, and signal transduction inhibitors in prostate cancer progression to hormone independence in vitro.	2008 Jan	18202015
17alpha-Hydroxylase/17,20 lyase inhibitor VN/124-1 inhibits growth of androgen-independent prostate cancer cells via induction of the endoplasmic reticulum stress response.	2008 Sep	18790763
Discovery and development of Galeterone (TOK-001 or VN/124-1) for the treatment of all stages of prostate cancer.	2015 Mar 12	25591066
Galeterone and VNPT55 induce proteasomal degradation of AR/AR-V7, induce significant apoptosis via cytochrome c release and suppress growth of castration resistant prostate cancer xenografts in vivo.	2015 Sep 29	26196320
Galeterone for the treatment of advanced prostate cancer: the evidence to date.	2016	27486306

Patents

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).

Name

Type

Language

GALETERONE

Official Name

English

VN 124

Code

English

TOK 001

Code

English

VN/124-1

Code

English

GALETERONE [USAN]

Common Name

English

VN-124

Code

English

galeterone [INN]

Common Name

English

Galeterone [WHO-DD]

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