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Mibolerone

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Identification

Generic Name
Mibolerone
DrugBank Accession Number
DB11429
Background

Mibolerone is a potent anabolic steroid which is both higher affinity and more selective for the androgen receptor than metribolone.

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 302.458
Monoisotopic: 302.224580206
Chemical Formula
C20H30O2
Synonyms
  • (7α,17β)-17-hydroxy-7,17-dimethylestr-4-en-3-one
  • 17-beta-Hydroxy-7-alpha,17-dimethylestr-4-en-3-one
  • 7α-17α-dimethyl-19-nortestosterone
  • Mibolerona
  • Mibolerone
  • Miboleronum
External IDs
  • U 10997
  • U-10-997
  • U-10,997
  • U-10997
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AAndrogen receptor
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbciximabMibolerone may increase the anticoagulant activities of Abciximab.
AcenocoumarolMibolerone may increase the anticoagulant activities of Acenocoumarol.
AlteplaseMibolerone may increase the anticoagulant activities of Alteplase.
AncrodMibolerone may increase the anticoagulant activities of Ancrod.
AnistreplaseMibolerone may increase the anticoagulant activities of Anistreplase.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Tertiary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone / Delta-4-steroid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo Delta(4)-steroid, 17beta-hydroxy steroid (CHEBI:34849)
Affected organisms
Not Available

Chemical Identifiers

UNII
9OGY4BOR8D
CAS number
3704-09-4
InChI Key
PTQMMNYJKCSPET-OMHQDGTGSA-N
InChI
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
IUPAC Name
(1S,3aS,3bR,4R,9aR,9bS,11aS)-1-hydroxy-1,4,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3C[C@@H](C)[C@@]21[H]

References

General References
  1. Amin MI, Koshy KT, Bryan JT: Stability of aqueous solutions of mibolerone. J Pharm Sci. 1976 Dec;65(12):1777-9. [Article]
  2. Kakuk TJ, Frank FR, Weddon TE: Avian lymphoid leukosis prophylaxis with mibolerone. Avian Dis. 1977 Apr-Jun;21(2):280-9. [Article]
  3. Romero CH, Purchase HG, Frank F, Burmester BR, Kakuk TJ, Chang TS: Immune responses of chickens fed the androgen analog mibolerone. Avian Dis. 1977 Apr-Jun;21(2):264-79. [Article]
  4. Seaman WJ: Canine ovarian fibroma associated with prolonged exposure to mibolerone. Toxicol Pathol. 1985;13(3):177-80. [Article]
  5. Gardner HM, Hueston WD, Donovan EF: Use of mibolerone in wolves and in three Panthera species. J Am Vet Med Assoc. 1985 Dec 1;187(11):1193-4. [Article]
  6. Lucio B, Hitchner SB: Response of mibolerone-treated chickens to infectious bursal disease virus. Avian Dis. 1980 Apr-Jun;24(2):334-44. [Article]
  7. Murthy LR, Johnson MP, Rowley DR, Young CY, Scardino PT, Tindall DJ: Characterization of steroid receptors in human prostate using mibolerone. Prostate. 1986;8(3):241-53. [Article]
  8. Sokolowski JH, Geng S: Biological evaluation of mibolerone in the female Beagle. Am J Vet Res. 1977 Sep;38(9):1371-6. [Article]
  9. Burke TJ, Reynolds HA, Sokolowski JH: A 280-day tolerance-efficacy study with mibolerone for suppression of estrus in the cat. Am J Vet Res. 1977 Apr;38(4):469-77. [Article]
  10. Cops EJ, Bianco-Miotto T, Moore NL, Clarke CL, Birrell SN, Butler LM, Tilley WD: Antiproliferative actions of the synthetic androgen, mibolerone, in breast cancer cells are mediated by both androgen and progesterone receptors. J Steroid Biochem Mol Biol. 2008 Jun;110(3-5):236-43. doi: 10.1016/j.jsbmb.2007.10.014. Epub 2008 Apr 20. [Article]
  11. Romero CH, Purchase HG, Frank F, Crittenden LB, Chang TS: The prevention of natural and experimental avian lymphoid leukosis with the androgen analogue mibolerone. Avian Pathol. 1978 Jan;7(1):87-103. [Article]
  12. Romero CH, Claflin W, Frank F, Chang TS, Purchase HG: Vaccination immunity to selected diseases in chickens fed the androgen analog mibolerone. Poult Sci. 1978 Jan;57(1):74-9. [Article]
  13. Schulz P, Wolf D, Arbusow V, Bojar H, Klobeck HG, Fittler F: The synthetic androgen mibolerone induces transient suppression of the transformed phenotype in an androgen responsive human prostatic carcinoma cell line. Andrologia. 1990;22 Suppl 1:56-66. [Article]
  14. Akimoto S, Fuse H, Sato R, Zama S, Shimazaki J: Binding of mibolerone to androgen receptor of benign hypertrophic human prostate. Comparison with R1881. Endocrinol Jpn. 1985 Feb;32(1):141-52. [Article]
  15. Bhanushali JK, Ragland WL: Chickens bursectomized with mibolerone have Ig-positive cells which lack bursal cell specific antigens. Vet Immunol Immunopathol. 1985 Nov;10(2-3):189-203. [Article]
  16. Miki H, Oshimo K, Inoue H, Sumi T, Yamashita K, Morimoto T, Monden Y: [Comparison of the binding nature of mibolerone to androgen receptor of human prostate with that of R1881]. Nihon Naibunpi Gakkai Zasshi. 1988 Aug 20;64(8):655-65. [Article]
  17. Bhanushali JK, Murthy KK, Ragland WL: Delayed development of humoral immunity in chickens following in ovo treatment with mibolerone. Dev Comp Immunol. 1985 Summer;9(3):453-63. [Article]
  18. Bhanushali JK, Murthy KK, Ragland WL: The effects of in ovo mibolerone treatment on the bursa of Fabricius and the humoral system of chickens: a dose-response study. Immunopharmacology. 1985 Oct;10(2):99-110. [Article]
  19. Krzeminski LF, Sokolowski JH, Dunn GH, VanRavenswaay F, Pineda M: Serum concentrations of mibolerone in Beagle bitches as influenced by time, dosage form, and geographic location. Am J Vet Res. 1978 Apr;39(4):567-72. [Article]
  20. Winters SJ, Keeping HS, Troen P: Assay of primate seminiferous tubule androgen receptors using [3H]mibolerone. J Steroid Biochem. 1986 May;24(5):963-9. [Article]
KEGG Drug
D05025
KEGG Compound
C14255
ChemSpider
220460
BindingDB
26258
ChEBI
34849
ChEMBL
CHEMBL425863
ZINC
ZINC000004216936
Wikipedia
Mibolerone

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0194 mg/mLALOGPS
logP3.11ALOGPS
logP3.63Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.34Chemaxon
pKa (Strongest Basic)-0.53Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity89.14 m3·mol-1Chemaxon
Polarizability35.86 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0192000000-5b0f97db8e6a25587ecc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-b89b3ccbadd6f728ec11
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0019000000-12aacb1a3cc30e8e5d23
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zg1-3984000000-e51399f38841d10d1acc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ukl-0092000000-cf7d9897dfa39fcd6ce7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-3900000000-b494b8aa5e7a48444684
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-182.9998164
predicted
DarkChem Lite v0.1.0
[M-H]-165.59132
predicted
DeepCCS 1.0 (2019)
[M+H]+183.2982164
predicted
DarkChem Lite v0.1.0
[M+H]+167.91637
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.7878164
predicted
DarkChem Lite v0.1.0
[M+Na]+173.65678
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues (PubMed:19022849). Transcription factor activity is modulated by bound coactivator and corepressor proteins like ZBTB7A that recruits NCOR1 and NCOR2 to the androgen response elements/ARE on target genes, negatively regulating androgen receptor signaling and androgen-induced cell proliferation (PubMed:20812024). Transcription activation is also down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3
Specific Function
androgen binding
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
99187.115 Da
References
  1. Kojima H, Iida M, Katsura E, Kanetoshi A, Hori Y, Kobayashi K: Effects of a diphenyl ether-type herbicide, chlornitrofen, and its amino derivative on androgen and estrogen receptor activities. Environ Health Perspect. 2003 Apr;111(4):497-502. [Article]
  2. Okubo T, Yokoyama Y, Kano K, Soya Y, Kano I: Estimation of estrogenic and antiestrogenic activities of selected pesticides by MCF-7 cell proliferation assay. Arch Environ Contam Toxicol. 2004 May;46(4):445-53. [Article]
  3. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at February 25, 2016 18:42 / Updated at August 26, 2024 19:21