MIBOLERONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H30O2
Molecular Weight	302.451
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4C[C@@H](C)[C@@]23[H]

InChI

InChIKey=PTQMMNYJKCSPET-OMHQDGTGSA-N

InChI=1S/C20H30O2/c1-12-10-13-11-14(21)4-5-15(13)16-6-8-19(2)17(18(12)16)7-9-20(19,3)22/h11-12,15-18,22H,4-10H2,1-3H3/t12-,15+,16-,17+,18-,19+,20+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2422638
Curator's Comment: Description was created based on several sources, including http://www.skylocke.com/pdf_txt/CHEQUE-Drops.PDF | https://www.ncbi.nlm.nih.gov/pubmed/18515094 | https://anabolic.org/cheque-drops-mibolerone/

Mibolerone is a synthetic anabolic steroid. It binds both androgen and progesterone receptors and exerts both androgenic and progestagenic actions. Mibolerone (CHEQUE® Drops) was used in veterinary for estrous (heat) prevention in adult female dogs not intended primarily for breeding purposes. No prescription preparation, human or veterinary, is currently known to contain mibolerone worldwide.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2422638 \| https://www.ncbi.nlm.nih.gov/pubmed/10077001 \| https://www.ncbi.nlm.nih.gov/pubmed/18515094	Agonist 2678		1.5 nM [Kd]
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2422638 \| https://www.ncbi.nlm.nih.gov/pubmed/18515094 \| https://www.ncbi.nlm.nih.gov/pubmed/9228646	Agonist 2678		5.9 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Resveratrol inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells.	1999 Dec 1	10606230
Preserved male fertility despite decreased androgen sensitivity caused by a mutation in the ligand-binding domain of the androgen receptor gene.	2000 Jun	10852459
Expression of the human androgen receptor in eukaryotic cells using a recombinant adenovirus vector yields high levels of the soluble, functional receptor protein.	2001 Dec	11719284
Mass spectrometric characterization of the human androgen receptor ligand-binding domain expressed in Escherichia coli.	2001 Sep 11	11535050
The F-box protein SKP2 mediates androgen control of p27 stability in LNCaP human prostate cancer cells.	2002 Aug 20	12188931
Changes in androgen receptor nongenotropic signaling correlate with transition of LNCaP cells to androgen independence.	2004 Oct 1	15466214
Acquisition of androgen independence by human prostate epithelial cells during arsenic-induced malignant transformation.	2005 Sep	16140617
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.	2006 Apr	16488153
Androgen receptor functional analyses by high throughput imaging: determination of ligand, cell cycle, and mutation-specific effects.	2008	18978937
Synthesis and biological effect of halogen substituted phenyl acetic acid derivatives of progesterone as potent progesterone receptor antagonists.	2008 Sep	18625316
Aromatic esters of progesterone as 5alpha-reductase and prostate growth inhibitors.	2009 Jun	18825535
Novel C-6 substituted and unsubstituted pregnane derivatives as 5alpha-reductase inhibitors and their effect on hamster flank organs diameter size.	2009 Oct	19406144
A novel anticancer agent, retigeric acid B, displays proliferation inhibition, S phase arrest and apoptosis activation in human prostate cancer cells.	2010 Dec 5	20692244
Androgens modulate autophagy and cell death via regulation of the endoplasmic reticulum chaperone glucose-regulated protein 78/BiP in prostate cancer cells.	2010 Sep 9	21364676

Patents

Sample Use Guides

In Vivo Use Guide

CHEQUE® DROPS mibolerone 100 ug/ml female dogs: 1 to 25 lbs - 30 ug, 26 to 50 lbs - 60 ug, 51 to 100 lbs - 120 ug, 101 and over lbs - 180 ug orally once each day by adding to a small amount of food or directly to the mouth

Route of Administration: Oral

In Vitro Use Guide

Whereas high physiological doses (10-100nM) of 5alpha-dihydrotestosterone reduced E(2)-mediated induction of the estrogen-regulated gene progesterone receptor (PR) to basal levels, mibolerone at lower doses (1nM) eliminated PR expression, suggesting that mibolerone may also act via the PR.

Name

Type

Language

MIBOLERONE

Official Name

English

NSC-72260

Code

English

MIBOLERONE [GREEN BOOK]

Common Name

English

MIBOLERONE CIII

Common Name

English

MIBOLERONE [MI]

Common Name

English

U-10,997

Code

English

U-10997

Code

English

17β-Hydroxy-7α,17-dimethylestr-4-en-3-one

Systematic Name

English

MIBOLERONE [USP MONOGRAPH]

Common Name

English

MIBOLERONE [USAN]

Common Name

English

MIBOLERONE [MART.]

Common Name

English

MIBOLERONE CIII [USP-RS]

Common Name

English

U-10-997

Code

English

MATENON

Brand Name

English

ESTR-4-EN-3-ONE, 17-HYDROXY-7,17-DIMETHYL-, (7.ALPHA.,17.BETA.)-

Common Name

English

DIHYDROLONE

Common Name

English

CHEQUE DROPS

Brand Name

English

CHEQUE

Brand Name

English

mibolerone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C243