APOPTONE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H32O2
Molecular Weight	316.4776
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@H](O)CC[C@]34C

InChI

InChIKey=CKAXZOYFIHQCBN-JRRMKBMNSA-N

InChI=1S/C21H32O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,14-18,22-23H,5-13H2,2-3H3/t14-,15+,16+,17-,18-,19-,20-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H32O2
Molecular Weight	316.4776
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20814732 | https://www.drugbank.ca/drugs/DB06307 | https://www.ncbi.nlm.nih.gov/pubmed/20814732

17α-ethynyl-5α-androstane-3α, 17β-diol (HE3235, Apoptone) is an orally bioavailable synthetic analogue of 3β-androstanediol, that is active in rodent models of prostate and breast cancer. HE3235 is a second generation antitumor agent that causes apoptosis. It is an androgen receptor antagonist. HE3235 inhibits the BCL2 gene which translates proteins that prevent apoptosis and stimulates the expression proteins that induce apoptosis. HE3235 also downregulates the gene that codes for the multi-drug resistant protein ABCG2 (BCRP1 – Breast Cancer Resistance Protein1). Apoptone was in Phase I/II trials to treat hormone-refractory prostate cancer. However, the development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19881957	Binding Agent 1064

PubMed

Title	Date	PubMed
HE3235 inhibits growth of castration-resistant prostate cancer.	2009 Nov	19881957
17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism.	2012 Feb	20814732

Patents

Sample Use Guides

In Vivo Use Guide

Mice were dosed IP with 200 ul HE3235 or vehicle once a day for 21 days.

Route of Administration: Intraperitoneal

In Vitro Use Guide

HE3235 inhibited LNCaP proliferation in the low nanomolar range (6 nM).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:26:21 GMT 2023` Edited by `admin` on `Sat Dec 16 01:26:21 GMT 2023`
Record UNII	891O182ZP5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APOPTONE

Common Name

English

HE 3235

Common Name

English

HE3235

Common Name

English

HE-3235

Code

English

PREGN-20-YNE-3,17-DIOL, (3.ALPHA.,5.ALPHA.,17.ALPHA.)-

Common Name

English

17.ALPHA.-ETHYNYL-5.ALPHA.-ANDROSTANE-3.ALPHA., 17.BETA.-DIOL

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL3545237