Fluoxymesterone

Structural formula
General
Surname	Fluoxymesterone
other names	9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta [ a ] phenanthren-3-one
Molecular formula	C 20 H 29 FO 3
Brief description	colorless solid
External identifiers / databases
EC number	200-961-8
ECHA InfoCard	100,000,875
PubChem	6446
DrugBank	DB01185
Wikidata	Q410663
Drug information
ATC code	G03 BA01
properties
Molar mass	336.44 g · mol -1
Physical state	firmly
Melting point	270 ° C (decomposition)
solubility	soluble in ethanol
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 361
	P: 281
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fluoxymesterone is a synthetically produced drug from the group of anabolic steroids with a strong androgenic effect. Today, fluoxymesterone is no longer important in human medicine, but is used improperly in sport to improve performance . It is known by the trade name Halotestin .

Fluoxymesterone is a testosterone derivative and is converted by the 5 α -reductase . The attached 11 β -hydroxy group prevents the conversion into estrogen . Fluoxymesterone stimulates the dihydrotestosterone receptors and thus ensures an increased willingness to exercise and an increase in strength when used by athletes. It also reduces the conversion of the catabolic cortisol into the weaker substances cortisone and 11-dehydrocorticosterone . In addition, fluoxymesterone shows a clinically significant affinity for the glucocorticoid receptor .

In Germany, possession of 150 mg or more is a criminal offense according to the doping agent quantity regulation .

Side effects

greatly increased aggressiveness and willingness to use violence
acne
Hair loss
Liver strain
Epistaxis
a headache
Gastrointestinal complaints
high blood pressure

source

The Black Book - Anabolic Steroids , 2007, ISBN 978-3-00-020944-4 , pp. 140/141.

Individual evidence

↑ ^a ^b ^c ^d Datasheet Fluoxymesterone, solid (photosensitive) from Sigma-Aldrich , accessed on December 27, 2011 ( PDF ).
^ ME Herr, JA Hogg, RH Levin: Synthesis of potent oral anabolic-androgenic steroids . In: Journal of the American Chemical Society . tape 78 , no. 2 , 1956, p. 500–501 , doi : 10.1021 / ja01583a072 .
↑ The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation

[Sigma-1] Datasheet Fluoxymesterone, solid (photosensitive) from Sigma-Aldrich , accessed on December 27, 2011 ( PDF ).

[2] ME Herr, JA Hogg, RH Levin: Synthesis of potent oral anabolic-androgenic steroids . In: Journal of the American Chemical Society . tape 78 , no. 2 , 1956, p. 500–501 , doi : 10.1021 / ja01583a072 .

[3] The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation