U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of MIBOLERONE

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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Activation of androgen receptor in epidermal growth factor modulation of fetal mouse sexual differentiation.
1996 Oct 14
Resveratrol inhibits the expression and function of the androgen receptor in LNCaP prostate cancer cells.
1999 Dec 1
A nonsteroidal anti-inflammatory drug, flufenamic acid, inhibits the expression of the androgen receptor in LNCaP cells.
1999 Nov
Characterization of intracellular aggregates using fluorescently-tagged polyglutamine-expanded androgen receptor.
2001 Jul
Regulation of u-PA gene expression in human prostate cancer.
2001 Nov 1
Melatonin elicits nuclear exclusion of the human androgen receptor and attenuates its activity.
2001 Oct 1
Silymarin inhibits function of the androgen receptor by reducing nuclear localization of the receptor in the human prostate cancer cell line LNCaP.
2001 Sep
Role of androgens in female genital sexual arousal: receptor expression, structure, and function.
2002 Apr
The human ovarian surface epithelium is an androgen responsive tissue.
2002 Mar 18
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 Nov 15
Forced expression of heat-shock protein 70 increases the secretion of Hsp70 and provides protection against tumour growth.
2004 Feb 23
Dexamethasone enhances the cytotoxic effect of radioiodine therapy in prostate cancer cells expressing the sodium iodide symporter.
2004 Mar
Methyl selenium metabolites decrease prostate-specific antigen expression by inducing protein degradation and suppressing androgen-stimulated transcription.
2004 May
Stem/progenitor and intermediate cell types and the origin of human prostate cancer.
2005 Dec
[Regulation of expression of pituitary tumor transforming gene 1 (PTTG1) by androgen in prostate cancer].
2005 Dec 18
The Estradiol-Dihydrotestosterone model of prostate cancer.
2005 Mar 18
COMPRENDO: Focus and approach.
2006 Apr
Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry.
2006 Apr
Contraception in felids.
2006 Jul 1
Perillyl alcohol inhibits the expression and function of the androgen receptor in human prostate cancer cells.
2006 May 18
Expression and function of the human androgen-responsive gene ADI1 in prostate cancer.
2007 Aug
Estrogen signaling and disruption of androgen metabolism in acquired androgen-independence during cadmium carcinogenesis in human prostate epithelial cells.
2007 Feb 1
Discovery of antiandrogen activity of nonsteroidal scaffolds of marketed drugs.
2007 Jul 17
Steroids with a carbamate function at C-17, a novel class of inhibitors for human and hamster steroid 5alpha-reductase.
2007 Oct
Oriental herbs as a source of novel anti-androgen and prostate cancer chemopreventive agents.
2007 Sep
Steroid and beta-adrenergic receptor modifications in target organs of broiler chickens fed with a diet containing beta2-adrenergic agents.
2008 Jun
Synthesis and biological effect of halogen substituted phenyl acetic acid derivatives of progesterone as potent progesterone receptor antagonists.
2008 Sep
Biological activity of novel progesterone derivatives having a bulky ester side chains at C-3.
2008 Sep
Manipulating prohibitin levels provides evidence for an in vivo role in androgen regulation of prostate tumours.
2009 Dec
Androgen receptor mutations associated with androgen insensitivity syndrome: a high content analysis approach leading to personalized medicine.
2009 Dec 9
Regulation of growth hormone receptors in human prostate cancer cell lines.
2009 Oct 15
A novel anticancer agent, retigeric acid B, displays proliferation inhibition, S phase arrest and apoptosis activation in human prostate cancer cells.
2010 Dec 5
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
Effects of treatment with androgen receptor ligands on microRNA expression of prostate cancer cells.
2015 Jul 3
Patents

Sample Use Guides

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
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
GREEN BOOK   INN   MART.   MI   USAN   USP  
INN   USAN  
Official Name English
NSC-72260
Code English
MIBOLERONE [GREEN BOOK]
Common Name English
MIBOLERONE CIII
USP-RS  
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
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
CFR 21 CFR 520.1430
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
WIKIPEDIA Designer-drugs-Mibolerone
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
DEA NO. 4000
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
CFR 21 CFR 558.348
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
Code System Code Type Description
EVMPD
SUB08941MIG
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
INN
3203
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
PUBCHEM
251636
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
DRUG BANK
DB11429
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
MESH
C100075
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL425863
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
SMS_ID
100000081184
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
NSC
72260
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
CAS
3704-09-4
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
CHEBI
34849
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID4036489
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
RS_ITEM_NUM
1443362
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
NCI_THESAURUS
C72100
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
ECHA (EC/EINECS)
223-046-5
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
FDA UNII
9OGY4BOR8D
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
WIKIPEDIA
MIBOLERONE
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY
MERCK INDEX
M7523
Created by admin on Thu Jul 06 21:34:40 UTC 2023 , Edited by admin on Thu Jul 06 21:34:40 UTC 2023
PRIMARY Merck Index