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

C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@H]3CC[C@@]4(C)[C@@H](CC[C@]4(C)O)[C@H]13

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

Molecular Formula	C20H30O2
Molecular Weight	302.451
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 169 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 2752		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 2752		5.9 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Effects of treatment with androgen receptor ligands on microRNA expression of prostate cancer cells.	2015-07-03	25846647
A novel anticancer agent, retigeric acid B, displays proliferation inhibition, S phase arrest and apoptosis activation in human prostate cancer cells.	2010-12-05	20692244
Androgens modulate autophagy and cell death via regulation of the endoplasmic reticulum chaperone glucose-regulated protein 78/BiP in prostate cancer cells.	2010-09-09	21364676
Androgen receptor mutations associated with androgen insensitivity syndrome: a high content analysis approach leading to personalized medicine.	2009-12-09	20011049
Manipulating prohibitin levels provides evidence for an in vivo role in androgen regulation of prostate tumours.	2009-12	19635783
Regulation of growth hormone receptors in human prostate cancer cell lines.	2009-10-15	19540305
Novel C-6 substituted and unsubstituted pregnane derivatives as 5alpha-reductase inhibitors and their effect on hamster flank organs diameter size.	2009-10	19406144
Aromatic esters of progesterone as 5alpha-reductase and prostate growth inhibitors.	2009-06	18825535
In vivo and in vitro effect of novel 4,16-pregnadiene-6,20-dione derivatives, as 5alpha-reductase inhibitors.	2008-09	18644453
Synthesis and biological effect of halogen substituted phenyl acetic acid derivatives of progesterone as potent progesterone receptor antagonists.	2008-09	18625316
Biological activity of novel progesterone derivatives having a bulky ester side chains at C-3.	2008-09	18472120
Antiproliferative actions of the synthetic androgen, mibolerone, in breast cancer cells are mediated by both androgen and progesterone receptors.	2008-06	18515094
Steroid and beta-adrenergic receptor modifications in target organs of broiler chickens fed with a diet containing beta2-adrenergic agents.	2008-06	18407392
Androgen receptor functional analyses by high throughput imaging: determination of ligand, cell cycle, and mutation-specific effects.	2008	18978937
Steroids with a carbamate function at C-17, a novel class of inhibitors for human and hamster steroid 5alpha-reductase.	2007-10	17629476
Oriental herbs as a source of novel anti-androgen and prostate cancer chemopreventive agents.	2007-09	17723170
Expression and function of the human androgen-responsive gene ADI1 in prostate cancer.	2007-08	17786183
Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs.	2007-07-17	17606915
Estrogen signaling and disruption of androgen metabolism in acquired androgen-independence during cadmium carcinogenesis in human prostate epithelial cells.	2007-02-01	17075824
Contraception in felids.	2006-07-01	16626799
Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells.	2006-05-18	16029925
COMPRENDO: Focus and approach.	2006-04	16818253
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.	2006-04	16488153
[Regulation of expression of pituitary tumor transforming gene 1 (PTTG1) by androgen in prostate cancer].	2005-12-18	16378119
Stem/progenitor and intermediate cell types and the origin of human prostate cancer.	2005-12	16351690
Acquisition of androgen independence by human prostate epithelial cells during arsenic-induced malignant transformation.	2005-09	16140617
Involvement of transcription factor Sp1 in quercetin-mediated inhibitory effect on the androgen receptor in human prostate cancer cells.	2005-04	15661808
The Estradiol-Dihydrotestosterone model of prostate cancer.	2005-03-18	15777479
Androgen-induced mineralization by MC3T3-E1 osteoblastic cells reveals a critical window of hormone responsiveness.	2005-03-18	15694414
Studies of targeting and intracellular trafficking of an anti-androgen doxorubicin-formaldehyde conjugate in PC-3 prostate cancer cells bearing androgen receptor-GFP chimera.	2004-11-04	15509168
Changes in androgen receptor nongenotropic signaling correlate with transition of LNCaP cells to androgen independence.	2004-10-01	15466214
Estimation of estrogenic and antiestrogenic activities of selected pesticides by MCF-7 cell proliferation assay.	2004-05	15253041
Methyl selenium metabolites decrease prostate-specific antigen expression by inducing protein degradation and suppressing androgen-stimulated transcription.	2004-05	15141018
Dexamethasone enhances the cytotoxic effect of radioiodine therapy in prostate cancer cells expressing the sodium iodide symporter.	2004-03	15001595
Forced expression of heat-shock protein 70 increases the secretion of Hsp70 and provides protection against tumour growth.	2004-02-23	14970875
Probasin promoter (ARR(2)PB)-driven, prostate-specific expression of the human sodium iodide symporter (h-NIS) for targeted radioiodine therapy of prostate cancer.	2003-11-15	14633711
Androgens inhibit estradiol-17beta synthesis in Atlantic croaker (Micropogonias undulatus) ovaries by a nongenomic mechanism initiated at the cell surface.	2003-11	12855603
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003-10	14565775
Suppression of prostate tumor growth by U19, a novel testosterone-regulated apoptosis inducer.	2003-08-01	12907652
The use of androgen receptor amino/carboxyl-terminal interaction assays to investigate androgen receptor gene mutations in subjects with varying degrees of androgen insensitivity.	2003-05	12727974
Effects of a diphenyl ether-type herbicide, chlornitrofen, and its amino derivative on androgen and estrogen receptor activities.	2003-04	12676605
The F-box protein SKP2 mediates androgen control of p27 stability in LNCaP human prostate cancer cells.	2002-08-20	12188931
Role of androgens in female genital sexual arousal: receptor expression, structure, and function.	2002-04	12007897
The human ovarian surface epithelium is an androgen responsive tissue.	2002-03-18	11953818
Effect of geldanamycin on androgen receptor function and stability.	2002-01	11894840
Expression of the human androgen receptor in eukaryotic cells using a recombinant adenovirus vector yields high levels of the soluble, functional receptor protein.	2001-12	11719284
Regulation of u-PA gene expression in human prostate cancer.	2001-11-01	11745419
Melatonin elicits nuclear exclusion of the human androgen receptor and attenuates its activity.	2001-10-01	11582594
Characterization of intracellular aggregates using fluorescently-tagged polyglutamine-expanded androgen receptor.	2001-07	15111251
Activation of androgen receptor in epidermal growth factor modulation of fetal mouse sexual differentiation.	1996-10-14	8912815

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:04:39 GMT 2025` Edited by `admin` on `Wed Apr 02 07:04:39 GMT 2025`
Record UNII	9OGY4BOR8D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MIBOLERONE CIII

Preferred Name

English

MIBOLERONE

Official Name

English

NSC-72260

Code

English

MIBOLERONE [GREEN BOOK]

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