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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 of APOPTONE

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

PubMed

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
Record UNII
891O182ZP5
Record Status Validated (UNII)
Record Version