ChemFOnt: Showing chemical card for Fluoxymesterone (CFc000009596)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:47 UTC

Chemfont ID

CFc000009596

Molecule Identification

Common Name

Fluoxymesterone

Definition

Fluoxymesterone is only found in individuals that have used or taken this drug. It is 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]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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
11beta,17beta-Dihydroxy-9alpha-fluoro-17alpha-methyl-4-androster-3-one	ChEBI
17alpha-Methyl-9alpha-fluoro-11beta-hydroxytesterone	ChEBI
9-Fluoro-11beta,17beta-dihydroxy-17-methylandrost-4-en-3-one	ChEBI
9alpha-Fluoro-11beta-hydroxy-17-methyltestosterone	ChEBI
Fluoximesterona	ChEBI
Fluoxymesteronum	ChEBI
Androxy	Kegg
Halotestin	Kegg
11b,17b-Dihydroxy-9a-fluoro-17a-methyl-4-androster-3-one	Generator
11Β,17β-dihydroxy-9α-fluoro-17α-methyl-4-androster-3-one	Generator
17a-Methyl-9a-fluoro-11b-hydroxytesterone	Generator
17Α-methyl-9α-fluoro-11β-hydroxytesterone	Generator
9-Fluoro-11b,17b-dihydroxy-17-methylandrost-4-en-3-one	Generator
9-Fluoro-11β,17β-dihydroxy-17-methylandrost-4-en-3-one	Generator
9a-Fluoro-11b-hydroxy-17-methyltestosterone	Generator
9Α-fluoro-11β-hydroxy-17-methyltestosterone	Generator
Androfluorene	HMDB
Androfluorone	HMDB
Fluossimesterone	HMDB
Fluoximesterone	HMDB
Fluoximesteronum	HMDB
Fluoxymestrone	HMDB
Fluoximesteron	HMDB
Android-F	HMDB
Android F	HMDB
Atlantis brand OF fluoxymesterone	HMDB
Pharmacia brand OF fluoxymesterone	HMDB
Stenox	HMDB

Chemical Formula

C₂₀H₂₉FO₃

Average Molecular Weight

336.4409

Monoisotopic Molecular Weight

336.210072999

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

Traditional Name

fluoxymesterone

CAS Registry Number

76-43-7

SMILES

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

InChI Identifier

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

InChI Key

YLRFCQOZQXIBAB-RBZZARIASA-N

Chemical Taxonomy

Description

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

Substituents

Androgen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
9-halo-steroid
Halo-steroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Fluorohydrin
Halohydrin
Ketone
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Organooxygen compound
Organofluoride
Organohalogen compound
Alkyl fluoride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

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

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015316)

Process

Not Available

Role

Industrial application

Antineoplastic agent (HMDB: HMDB0015316)

Biological role

Anabolic agent (HMDB: HMDB0015316)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.045 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015316

DrugBank ID

DB01185

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fluoxymesterone

METLIN ID

Not Available

PubChem Compound

6446

PDB ID

Not Available

ChEBI ID

5120

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Fluoxymesterone (CFc000009596)

MOL for CFc000009596 (Fluoxymesterone)

3D MOL for CFc000009596 (Fluoxymesterone)

3D SDF for CFc000009596 (Fluoxymesterone)

3D-SDF for CFc000009596 (Fluoxymesterone)

PDB for CFc000009596 (Fluoxymesterone)

3D PDB for CFc000009596 (Fluoxymesterone)

SMILES for CFc000009596 (Fluoxymesterone)

INCHI for CFc000009596 (Fluoxymesterone)

Structure for CFc000009596 (Fluoxymesterone)

3D Structure for CFc000009596 (Fluoxymesterone)