FLUOXYMESTERONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H29FO3
Molecular Weight	336.4409
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=YLRFCQOZQXIBAB-RBZZARIASA-N

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

HIDE SMILES / InChI

Molecular Formula	C20H29FO3
Molecular Weight	336.4409
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is a synthetic, orally active androgenic-anabolic steroid (AAS) and a 17α-alkylated derivative of testosterone developed by Pharmacia & Upjohn Company LLC, approved by FDA at 1956. Fluoxymesterone is used in the treatment of hypogonadism in males and breast cancer in women. Fluoxymesterone has a relatively high ratio of androgenic to anabolic activity similarly to testosterone. Like many 17α-alkylated AAS, it has a relatively low affinity for the androgen receptor (AR). However, its actions are mediated by the AR, most likely due to its relatively long elimination half-life of approximately 9.2 hours.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167	Agonist 2,678		0.3 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Male hypogonadism 1	Primary	Approved 8,429	HALOTESTIN
Delayed male puberty 1	Primary	Approved 8,429	HALOTESTIN
Inoperable metastatic female breast cancer 1	Primary	Approved 8,429	HALOTESTIN

C_max

Value	Dose	Co-administered	Analyte	Population
80 ng/mL	10 mg single, oral		FLUOXYMESTERONE serum	Homo sapiens
100 ng/mL	10 mg single, buccal		FLUOXYMESTERONE serum	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
306 ng × h/mL	10 mg single, oral		FLUOXYMESTERONE serum	Homo sapiens
391 ng × h/mL	10 mg single, buccal		FLUOXYMESTERONE serum	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h	10 mg single, oral		FLUOXYMESTERONE serum	Homo sapiens

Doses

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Dose	Population	Adverse events
40 mg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Peliosis hepatis...

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AEs

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AE	Significance	Dose	Population
Peliosis hepatis	grade 4-5 Disc. AE	40 mg 1 times / day multiple, oral Recommended	unhealthy

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5120	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5120
ChemicalBook	CB9258118	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9258118
ZINC	ZINC000003875484	http://zinc15.docking.org/substances/ZINC000003875484

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PubMed

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Title	Date	PubMed
Impotence therapy and cancer of the prostate.	1976 May	58562
Ataxia caused by fluoxymesterone therapy in breast cancer.	1981 Jun	7235823
Peliosis hepatis after long-term androgen therapy.	1985 May	3992778
A49T, V89L and TA repeat polymorphisms of steroid 5alpha-reductase type II and breast cancer risk in Japanese women.	2002	12100746
Factors affecting progression-free survival in hormone-dependent metastatic breast cancer patients receiving high-dose chemotherapy and hematopoietic progenitor cell transplantation: role of maintenance endocrine therapy.	2002 May	12058236

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Patents

Sample Use Guides

In Vivo Use Guide

Hypogonadism (Males): 5-20 mg daily Delayed puberty (Males): 2.5-20 mg daily for 4-6 months Inoperable breast carcinoma (Females): 10-40 mg daily in divided doses for ≥3 months

Route of Administration: Oral

In Vitro Use Guide

MDA-MB-453 cells were used for Androgen Receptor binding assays. Media containing 0.3 nM [3H]DHT and Fluoxymesterone in concentrations ranging from 10-10 to 10-6 M were added to the cells. Three replicates were used for each sample. After 3 h at 37 C, an aliquot of the total binding media at each concentration was removed to determine the amount of free [3H]DHT.