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 2637		1.5 nM [Kd]
Progesterone receptor 60 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 2637		5.9 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2554

PubMed

Title	Date	PubMed
Activation of androgen receptor in epidermal growth factor modulation of fetal mouse sexual differentiation.	1996 Oct 14	8912815
Characterization of intracellular aggregates using fluorescently-tagged polyglutamine-expanded androgen receptor.	2001 Jul	15111251
Novel amino acid substitutional mutation, tyrosine-739-aspartic acid, in the androgen receptor gene in complete androgen insensitivity syndrome.	2001 Jun	11380707
Silymarin inhibits function of the androgen receptor by reducing nuclear localization of the receptor in the human prostate cancer cell line LNCaP.	2001 Sep	11532861
Forced expression of heat-shock protein 70 increases the secretion of Hsp70 and provides protection against tumour growth.	2004 Feb 23	14970875
Dexamethasone enhances the cytotoxic effect of radioiodine therapy in prostate cancer cells expressing the sodium iodide symporter.	2004 Mar	15001595
[Regulation of expression of pituitary tumor transforming gene 1 (PTTG1) by androgen in prostate cancer].	2005 Dec 18	16378119
COMPRENDO: Focus and approach.	2006 Apr	16818253
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.	2006 Apr	16488153
Expression and function of the human androgen-responsive gene ADI1 in prostate cancer.	2007 Aug	17786183
Steroids with a carbamate function at C-17, a novel class of inhibitors for human and hamster steroid 5alpha-reductase.	2007 Oct	17629476
Oriental herbs as a source of novel anti-androgen and prostate cancer chemopreventive agents.	2007 Sep	17723170

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

17?-Hydroxy-7?,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