Fluoxymesterone - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (5)Carriers (1)

Targets (5)Carriers (1)Biointeractions (4)

Identification

Name

Fluoxymesterone

Accession Number

DB01185 (APRD00981)

Type

Small Molecule

Groups

Approved, Illicit

Description

An anabolic steroid that has been used in the treatment of male hypogonadism, delayed puberty in males, and in the treatment of breast neoplasms in women. [PubChem]

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one

17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesterone

17α-Methyl-9α-fluoro-11β-hydroxytesterone

9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one

9alpha-Fluoro-11beta-hydroxy-17-methyltestosterone

Fluoximesterona

Fluoxymesteronum

Testosterone, 9-fluoro-11beta-hydroxy-17-methyl-

External IDs

NSC-12165

Product Ingredients

Not Available

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Halotestin	Tablet	5 mg	Oral	Pfizer	1962-12-31	2006-08-02	Canada

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Androxy	Tablet	10 mg/1	Oral	Upsher Smith Laboratories	1983-10-21	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Ora-Testryl	Bristol-Myers Squibb
Testoral	Midy
U-Gono	Upjohn
UItandren	Ciba

Brand mixtures

Not Available

Categories

UNII

9JU12S4YFY

CAS number

76-43-7

Weight

Average: 336.4409
Monoisotopic: 336.210072999

Chemical Formula

C₂₀H₂₉FO₃

InChI Key

YLRFCQOZQXIBAB-RBZZARIASA-N

InChI

InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1

IUPAC Name

(1R,2S,10S,11S,14S,15S,17S)-1-fluoro-14,17-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[[email protected]](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Pharmacology

Indication

In males, used as replacement therapy in conditions associated with symptoms of deficiency or absence of endogenous testosterone. In females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal.

Structured Indications

Pharmacodynamics

Fluoxymesterone is a synthetic androgen, or male hormone, similar to testosterone. Fluoxymesterone works by attaching itself to androgen receptors; this causes it to interact with the parts of the cell involved in the making of proteins. It may cause an increase in the synthesis of some proteins or a decrease in the synthesis of others. These proteins have a variety of effects, including blocking the growth of some types of breast cancer cells, stimulating cells that cause male sexual characteristics, and stimulating the production of red blood cells.

Mechanism of action

Fluoxymesterone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, fluoxymesterone binds to the androgen receptor. It produces retention of nitrogen, sodium, potassium, and phosphorus; increases protein anabolism; decreases amino acid catabolism and decreased urinary excretion of calcium. The antitumour activity of fluoxymesterone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Androgen receptor	Protein	yes	agonist	Human	P10275	details
Estrogen receptor alpha	Protein	yes	antagonist	Human	P03372	details
Prolactin receptor	Protein	yes	antagonist	Human	P16471	details
Glucocorticoid receptor	Protein	unknown	antagonist	Human	P04150	details
Corticosteroid 11-beta-dehydrogenase isozyme 2	Protein	unknown	inhibitor	Human	P80365	details

Absorption

Oral absorption is less than 44%.

Volume of distribution

Not Available

Protein binding

Very high (99%) with 80% to sex hormone binding globulin, 19% to albumin.

Metabolism

Presence of 17-alpha alkyl group reduces susceptibility to hepatic enzyme degradation, which slows metabolism and allows oral administration. Inactivation of testosterone occurs primarily in the liver

Route of elimination

Not Available

Half life

9.2 hours

Clearance

Not Available

Toxicity

Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
16-Bromoepiandrosterone	16-Bromoepiandrosterone may increase the fluid retaining activities of Fluoxymesterone.	Investigational
19-norandrostenedione	19-norandrostenedione may increase the fluid retaining activities of Fluoxymesterone.	Experimental, Illicit
5-androstenedione	5-androstenedione may increase the fluid retaining activities of Fluoxymesterone.	Experimental, Illicit
Acarbose	Fluoxymesterone may increase the hypoglycemic activities of Acarbose.	Approved, Investigational
Acenocoumarol	Fluoxymesterone may increase the anticoagulant activities of Acenocoumarol.	Approved
Albiglutide	Fluoxymesterone may increase the hypoglycemic activities of Albiglutide.	Approved
Alclometasone	Alclometasone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Aldosterone	Aldosterone may increase the fluid retaining activities of Fluoxymesterone.	Experimental
Alogliptin	Fluoxymesterone may increase the hypoglycemic activities of Alogliptin.	Approved
Amcinonide	Amcinonide may increase the fluid retaining activities of Fluoxymesterone.	Approved
Androstenedione	4-Androstenedione may increase the fluid retaining activities of Fluoxymesterone.	Experimental, Illicit
Anecortave	Anecortave may increase the fluid retaining activities of Fluoxymesterone.	Investigational
Beclomethasone dipropionate	Beclomethasone dipropionate may increase the fluid retaining activities of Fluoxymesterone.	Approved, Investigational
Betamethasone	Betamethasone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Vet Approved
Bromocriptine	Fluoxymesterone may increase the hypoglycemic activities of Bromocriptine.	Approved, Investigational
Budesonide	Budesonide may increase the fluid retaining activities of Fluoxymesterone.	Approved
Canagliflozin	Fluoxymesterone may increase the hypoglycemic activities of Canagliflozin.	Approved
Chlorpropamide	Fluoxymesterone may increase the hypoglycemic activities of Chlorpropamide.	Approved
Ciclesonide	Ciclesonide may increase the fluid retaining activities of Fluoxymesterone.	Approved, Investigational
Clobetasol	Clobetasol may increase the fluid retaining activities of Fluoxymesterone.	Investigational
Clobetasol propionate	Clobetasol propionate may increase the fluid retaining activities of Fluoxymesterone.	Approved
Clocortolone	Clocortolone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Conestat alfa	Fluoxymesterone may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).	Approved
Cortisone acetate	Cortisone acetate may increase the fluid retaining activities of Fluoxymesterone.	Approved
Cyclosporine	Fluoxymesterone may increase the hepatotoxic activities of Cyclosporine.	Approved, Investigational, Vet Approved
Dapagliflozin	Fluoxymesterone may increase the hypoglycemic activities of Dapagliflozin.	Approved
Desoximetasone	Desoximetasone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Desoxycorticosterone Pivalate	Desoxycorticosterone Pivalate may increase the fluid retaining activities of Fluoxymesterone.	Experimental, Vet Approved
Dexamethasone	Dexamethasone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Investigational, Vet Approved
Dicoumarol	Fluoxymesterone may increase the anticoagulant activities of Dicoumarol.	Approved
Diflorasone	Diflorasone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Difluocortolone	Difluocortolone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Difluprednate	Difluprednate may increase the fluid retaining activities of Fluoxymesterone.	Approved
Disopyramide	Fluoxymesterone may increase the hypoglycemic activities of Disopyramide.	Approved
Dulaglutide	Fluoxymesterone may increase the hypoglycemic activities of Dulaglutide.	Approved
Empagliflozin	Fluoxymesterone may increase the hypoglycemic activities of Empagliflozin.	Approved
Equilenin	Equilenin may increase the fluid retaining activities of Fluoxymesterone.	Experimental
Equilin	Equilin may increase the fluid retaining activities of Fluoxymesterone.	Approved
Estrone	Estrone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Estrone sulfate	Estrone sulfate may increase the fluid retaining activities of Fluoxymesterone.	Approved
Ethyl biscoumacetate	Fluoxymesterone may increase the anticoagulant activities of Ethyl biscoumacetate.	Withdrawn
Exenatide	Fluoxymesterone may increase the hypoglycemic activities of Exenatide.	Approved, Investigational
Fludrocortisone	Fludrocortisone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Fluindione	Fluoxymesterone may increase the anticoagulant activities of Fluindione.	Investigational
Flumethasone	Flumethasone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Vet Approved
Flunisolide	Flunisolide may increase the fluid retaining activities of Fluoxymesterone.	Approved, Investigational
Fluocinolone Acetonide	Fluocinolone Acetonide may increase the fluid retaining activities of Fluoxymesterone.	Approved, Investigational, Vet Approved
Fluocinonide	Fluocinonide may increase the fluid retaining activities of Fluoxymesterone.	Approved, Investigational
Fluocortolone	Fluocortolone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Withdrawn
Fluorometholone	Fluorometholone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Fluprednidene	Fluprednidene may increase the fluid retaining activities of Fluoxymesterone.	Approved, Withdrawn
Flurandrenolide	Flurandrenolide may increase the fluid retaining activities of Fluoxymesterone.	Approved
Fluticasone furoate	Fluticasone furoate may increase the fluid retaining activities of Fluoxymesterone.	Approved
Fluticasone propionate	Fluticasone Propionate may increase the fluid retaining activities of Fluoxymesterone.	Approved
Formestane	Formestane may increase the fluid retaining activities of Fluoxymesterone.	Approved, Investigational, Withdrawn
Gliclazide	Fluoxymesterone may increase the hypoglycemic activities of Gliclazide.	Approved
Glimepiride	Fluoxymesterone may increase the hypoglycemic activities of Glimepiride.	Approved
Glipizide	Fluoxymesterone may increase the hypoglycemic activities of Glipizide.	Approved
Glyburide	Fluoxymesterone may increase the hypoglycemic activities of Glyburide.	Approved
HE3286	HE3286 may increase the fluid retaining activities of Fluoxymesterone.	Investigational
Human C1-esterase inhibitor	Fluoxymesterone may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).	Approved
Hydrocortisone	Hydrocortisone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Vet Approved
Insulin Aspart	Fluoxymesterone may increase the hypoglycemic activities of Insulin Aspart.	Approved
Insulin Detemir	Fluoxymesterone may increase the hypoglycemic activities of Insulin Detemir.	Approved
Insulin Glargine	Fluoxymesterone may increase the hypoglycemic activities of Insulin Glargine.	Approved
Insulin Glulisine	Fluoxymesterone may increase the hypoglycemic activities of Insulin Glulisine.	Approved
Insulin Human	Fluoxymesterone may increase the hypoglycemic activities of Insulin Human.	Approved, Investigational
Insulin Lispro	Fluoxymesterone may increase the hypoglycemic activities of Insulin Lispro.	Approved
Lanreotide	Fluoxymesterone may increase the hypoglycemic activities of Lanreotide.	Approved
Liraglutide	Fluoxymesterone may increase the hypoglycemic activities of Liraglutide.	Approved
ME-609	ME-609 may increase the fluid retaining activities of Fluoxymesterone.	Investigational
Mecasermin	Fluoxymesterone may increase the hypoglycemic activities of Mecasermin.	Approved, Investigational
Medrysone	Medrysone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Metformin	Fluoxymesterone may increase the hypoglycemic activities of Metformin.	Approved
Methylprednisolone	Methylprednisolone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Vet Approved
Mifepristone	Fluoxymesterone may increase the hypoglycemic activities of Mifepristone.	Approved, Investigational
Miglitol	Fluoxymesterone may increase the hypoglycemic activities of Miglitol.	Approved
Mometasone	Mometasone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Vet Approved
Nateglinide	Fluoxymesterone may increase the hypoglycemic activities of Nateglinide.	Approved, Investigational
NCX 1022	NCX 1022 may increase the fluid retaining activities of Fluoxymesterone.	Investigational
Octreotide	Fluoxymesterone may increase the hypoglycemic activities of Octreotide.	Approved, Investigational
Oleoyl-estrone	Oleoyl estrone may increase the fluid retaining activities of Fluoxymesterone.	Investigational
Paramethasone	Paramethasone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Pasireotide	Fluoxymesterone may increase the hypoglycemic activities of Pasireotide.	Approved
Pentamidine	Fluoxymesterone may increase the hypoglycemic activities of Pentamidine.	Approved
Phenindione	Fluoxymesterone may increase the anticoagulant activities of Phenindione.	Approved
Phenprocoumon	Fluoxymesterone may increase the anticoagulant activities of Phenprocoumon.	Approved
Pioglitazone	Fluoxymesterone may increase the hypoglycemic activities of Pioglitazone.	Approved, Investigational
Pramlintide	Fluoxymesterone may increase the hypoglycemic activities of Pramlintide.	Approved, Investigational
Prasterone	Prasterone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Nutraceutical
Prasterone sulfate	dehydroepiandrosterone sulfate may increase the fluid retaining activities of Fluoxymesterone.	Investigational
Prednicarbate	Prednicarbate may increase the fluid retaining activities of Fluoxymesterone.	Approved
Prednisolone	Prednisolone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Vet Approved
Prednisone	Prednisone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Vet Approved
Pregnenolone	Pregnenolone may increase the fluid retaining activities of Fluoxymesterone.	Experimental
Quinine	Fluoxymesterone may increase the hypoglycemic activities of Quinine.	Approved
Repaglinide	Fluoxymesterone may increase the hypoglycemic activities of Repaglinide.	Approved, Investigational
Rimexolone	Rimexolone may increase the fluid retaining activities of Fluoxymesterone.	Approved
Rosiglitazone	Fluoxymesterone may increase the hypoglycemic activities of Rosiglitazone.	Approved, Investigational
Saxagliptin	Fluoxymesterone may increase the hypoglycemic activities of Saxagliptin.	Approved
Sitagliptin	Fluoxymesterone may increase the hypoglycemic activities of Sitagliptin.	Approved, Investigational
Sulfadiazine	Fluoxymesterone may increase the hypoglycemic activities of Sulfadiazine.	Approved, Vet Approved
Sulfamethoxazole	Fluoxymesterone may increase the hypoglycemic activities of Sulfamethoxazole.	Approved
Sulfisoxazole	Fluoxymesterone may increase the hypoglycemic activities of Sulfisoxazole.	Approved, Vet Approved
Sunitinib	Fluoxymesterone may increase the hypoglycemic activities of Sunitinib.	Approved, Investigational
Tixocortol	Tixocortol may increase the fluid retaining activities of Fluoxymesterone.	Approved
Tolazamide	Fluoxymesterone may increase the hypoglycemic activities of Tolazamide.	Approved
Tolbutamide	Fluoxymesterone may increase the hypoglycemic activities of Tolbutamide.	Approved
Triamcinolone	Triamcinolone may increase the fluid retaining activities of Fluoxymesterone.	Approved, Vet Approved
Warfarin	Fluoxymesterone may increase the anticoagulant activities of Warfarin.	Approved

Food Interactions

Take with food.

References

Synthesis Reference

U.S. Patent 2,793,218 U.S. Patent 2,813,881

General References

Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, Lopez FJ, Marschke KB, Rosen J, Schrader W, Turner R, van Oeveren A, Viveros H, Zhi L, Negro-Vilar A: An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Epub 2006 Oct 5. [PubMed:17023534 ]

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15316
KEGG Drug	D00327
PubChem Compound	6446
PubChem Substance	46508867
ChemSpider	6205
BindingDB	18189
ChEBI	5120
ChEMBL	CHEMBL1445
Therapeutic Targets Database	DAP000904
PharmGKB	PA164744518
IUPHAR	2861
Guide to Pharmacology	2861
Drug Product Database	7460
RxList	http://www.rxlist.com/cgi/generic2/fluoxy.htm
Drugs.com	http://www.drugs.com/cdi/fluoxymesterone.html
Wikipedia	Fluoxymesterone

ATC Codes

G03BA01 — Fluoxymesterone

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (75.7 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Terminated	Treatment	Metastatic Breast Cancer (MBC)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Dosage forms

Form	Route	Strength
Tablet	Oral	10 mg/1
Tablet	Oral	5 mg

Prices

Unit description	Cost	Unit
Fluoxymesterone powder	391.79USD	g
Android 10 mg capsule	11.35USD	each

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	265	U.S. Patent 2,793,218 U.S. Patent 2,813,881
water solubility	67.5 mg/L	Not Available
logP	2.38	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	0.0452 mg/mL	ALOGPS
logP	2.5	ALOGPS
logP	2.38	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.19 m³·mol^-1	ChemAxon
Polarizability	36.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9633
Caco-2 permeable	+	0.8586
P-glycoprotein substrate	Substrate	0.7505
P-glycoprotein inhibitor I	Non-inhibitor	0.7583
P-glycoprotein inhibitor II	Non-inhibitor	0.87
Renal organic cation transporter	Non-inhibitor	0.8136
CYP450 2C9 substrate	Non-substrate	0.862
CYP450 2D6 substrate	Non-substrate	0.8773
CYP450 3A4 substrate	Substrate	0.7669
CYP450 1A2 substrate	Non-inhibitor	0.9041
CYP450 2C9 inhibitor	Non-inhibitor	0.8159
CYP450 2D6 inhibitor	Non-inhibitor	0.9286
CYP450 2C19 inhibitor	Non-inhibitor	0.917
CYP450 3A4 inhibitor	Non-inhibitor	0.8354
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8585
Ames test	Non AMES toxic	0.8777
Carcinogenicity	Non-carcinogens	0.9242
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.7028 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.943
hERG inhibition (predictor II)	Non-inhibitor	0.5784

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available
MS	Mass Spectrum (Electron Ionization)	splash10-006x-5951000000-4c37d94fe4ed0b343941	View in MoNA

Taxonomy

Description

This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Halogenated steroids / 3-oxo delta-4-steroids / 17-hydroxysteroids / 11-beta-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Tertiary alcohols / Secondary alcohols / Fluorohydrins / Cyclic alcohols and derivatives

Substituents

Androgen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / 17-hydroxysteroid / 11-hydroxysteroid / 11-beta-hydroxysteroid / Oxosteroid / 9-halo-steroid / Halo-steroid / Hydroxysteroid

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid, fluorinated steroid, anabolic androgenic steroid (CHEBI:5120 ) / C19 steroids (androgens) and derivatives (LMST02020025 )

Targets

Details

1. Androgen receptor

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: agonist

General Function:: Zinc ion binding
Specific Function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:: AR
Uniprot ID:: P10275
Uniprot Name:: Androgen receptor
Molecular Weight:: 98987.9 Da

References

Fernandez L, Chirino R, Boada LD, Navarro D, Cabrera N, del Rio I, Diaz-Chico BN: Stanozolol and danazol, unlike natural androgens, interact with the low affinity glucocorticoid-binding sites from male rat liver microsomes. Endocrinology. 1994 Mar;134(3):1401-8. [PubMed:8119180 ]
Kasperk CH, Wergedal JE, Farley JR, Linkhart TA, Turner RT, Baylink DJ: Androgens directly stimulate proliferation of bone cells in vitro. Endocrinology. 1989 Mar;124(3):1576-8. [PubMed:2521824 ]
Smallridge RC, Vigersky R, Glass AR, Griffin JE, White BJ, Eil C: Androgen receptor abnormalities in identical twins with oligospermia. Clinical and biochemical studies. Am J Med. 1984 Dec;77(6):1049-54. [PubMed:6439037 ]
Miner JN, Chang W, Chapman MS, Finn PD, Hong MH, Lopez FJ, Marschke KB, Rosen J, Schrader W, Turner R, van Oeveren A, Viveros H, Zhi L, Negro-Vilar A: An orally active selective androgen receptor modulator is efficacious on bone, muscle, and sex function with reduced impact on prostate. Endocrinology. 2007 Jan;148(1):363-73. Epub 2006 Oct 5. [PubMed:17023534 ]
Kemppainen JA, Langley E, Wong CI, Bobseine K, Kelce WR, Wilson EM: Distinguishing androgen receptor agonists and antagonists: distinct mechanisms of activation by medroxyprogesterone acetate and dihydrotestosterone. Mol Endocrinol. 1999 Mar;13(3):440-54. [PubMed:10077001 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Details

2. Estrogen receptor alpha

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: antagonist

General Function:: Zinc ion binding
Specific Function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:: ESR1
Uniprot ID:: P03372
Uniprot Name:: Estrogen receptor
Molecular Weight:: 66215.45 Da

References

Ingle JN, Suman VJ, Mailliard JA, Kugler JW, Krook JE, Michalak JC, Pisansky TM, Wold LE, Donohue JH, Goetz MP, Perez EA: Randomized trial of tamoxifen alone or combined with fluoxymesterone as adjuvant therapy in postmenopausal women with resected estrogen receptor positive breast cancer. North Central Cancer Treatment Group Trial 89-30-52. Breast Cancer Res Treat. 2006 Jul;98(2):217-22. Epub 2006 Mar 15. [PubMed:16538529 ]
Sledge GW Jr, Hu P, Falkson G, Tormey D, Abeloff M: Comparison of chemotherapy with chemohormonal therapy as first-line therapy for metastatic, hormone-sensitive breast cancer: An Eastern Cooperative Oncology Group study. J Clin Oncol. 2000 Jan;18(2):262-6. [PubMed:10637238 ]
Pearson OH, Manni A, Arafah BM: Antiestrogen treatment of breast cancer: an overview. Cancer Res. 1982 Aug;42(8 Suppl):3424s-3429s. [PubMed:7044524 ]
Perloff M, Norton L, Korzun AH, Wood WC, Carey RW, Gottlieb A, Aust JC, Bank A, Silver RT, Saleh F, Canellos GP, Perry MC, Weiss RB, Holland JF: Postsurgical adjuvant chemotherapy of stage II breast carcinoma with or without crossover to a non-cross-resistant regimen: a Cancer and Leukemia Group B study. J Clin Oncol. 1996 May;14(5):1589-98. [PubMed:8622076 ]
Swain SM, Steinberg SM, Bagley C, Lippman ME: Tamoxifen and fluoxymesterone versus tamoxifen and danazol in metastatic breast cancer--a randomized study. Breast Cancer Res Treat. 1988 Sep;12(1):51-7. [PubMed:3058238 ]

Details

3. Prolactin receptor

Kind: Protein
Organism: Human
Pharmacological action: yes
Actions: antagonist

General Function:: Protein homodimerization activity
Specific Function:: This is a receptor for the anterior pituitary hormone prolactin (PRL). Acts as a prosurvival factor for spermatozoa by inhibiting sperm capacitation through suppression of SRC kinase activation and stimulation of AKT. Isoform 4 is unable to transduce prolactin signaling. Isoform 6 is unable to transduce prolactin signaling.
Gene Name:: PRLR
Uniprot ID:: P16471
Uniprot Name:: Prolactin receptor
Molecular Weight:: 69505.045 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Details

4. Glucocorticoid receptor

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: antagonist

General Function:: Zinc ion binding
Specific Function:: Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon grow...
Gene Name:: NR3C1
Uniprot ID:: P04150
Uniprot Name:: Glucocorticoid receptor
Molecular Weight:: 85658.57 Da

References

Mayer M, Rosen F: Interaction of anabolic steroids with glucocorticoid receptor sites in rat muscle cytosol. Am J Physiol. 1975 Nov;229(5):1381-6. [PubMed:173192 ]

Details

5. Corticosteroid 11-beta-dehydrogenase isozyme 2

Kind: Protein
Organism: Human
Pharmacological action: unknown
Actions: inhibitor

General Function:: Steroid binding
Specific Function:: Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Gene Name:: HSD11B2
Uniprot ID:: P80365
Uniprot Name:: Corticosteroid 11-beta-dehydrogenase isozyme 2
Molecular Weight:: 44126.06 Da

References

Furstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A: The anabolic androgenic steroid fluoxymesterone inhibits 11beta-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation. Toxicol Sci. 2012 Apr;126(2):353-61. doi: 10.1093/toxsci/kfs022. Epub 2012 Jan 23. [PubMed:22273746 ]

Carriers

Details

1. Sex hormone-binding globulin

Kind: Protein
Organism: Human
Pharmacological action: unknown

General Function:: Androgen binding
Specific Function:: Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration.
Gene Name:: SHBG
Uniprot ID:: P04278
Uniprot Name:: Sex hormone-binding globulin
Molecular Weight:: 43778.755 Da

References

Smallridge RC, Vigersky R, Glass AR, Griffin JE, White BJ, Eil C: Androgen receptor abnormalities in identical twins with oligospermia. Clinical and biochemical studies. Am J Med. 1984 Dec;77(6):1049-54. [PubMed:6439037 ]
Pugeat MM, Dunn JF, Nisula BC: Transport of steroid hormones: interaction of 70 drugs with testosterone-binding globulin and corticosteroid-binding globulin in human plasma. J Clin Endocrinol Metab. 1981 Jul;53(1):69-75. [PubMed:7195405 ]
Vigersky RA, Easley RB, Loriaux DL: Effect of fluoxymesterone on the pituitary-gonadal axis: the role of testosterone-estradiol-binding globulin. J Clin Endocrinol Metab. 1976 Jul;43(1):1-9. [PubMed:947929 ]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:31

Structure for DB01185 (Fluoxymesterone)

Targets

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Carriers

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