ChemFOnt: Showing chemical card for Drostanolone (CFc000009311)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:24 UTC

Chemfont ID

CFc000009311

Molecule Identification

Common Name

Drostanolone

Definition

Drostanolone is only found in individuals that have used or taken this drug. It is a potent synthetic androgenic anabolic steroid similar to testosterone. Drostanolone is indicated in postmenopausal women with recurrent breast cancer, in a combined hormone therapy.Dromostanolone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, dromostanolone binds to the androgen receptor. This causes downstream genetic transcriptional changes. This ultimately causes retention of nitrogen, potassium, and phosphorus; increases protein anabolism; and decreases amino acid catabolism. The antitumour activity of dromostanolone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17beta-Hydroxy-2alpha-methyl-5alpha-androstan-3-one	ChEBI
2alpha-Methyldihydrotestosterone	ChEBI
Dihydro-2alpha-methyltestosterone	ChEBI
Dromostanolone	ChEBI
Drostanolona	ChEBI
Drostanolonum	ChEBI
Medrosteron	ChEBI
Medrotestron	ChEBI
17b-Hydroxy-2a-methyl-5a-androstan-3-one	Generator
17Β-hydroxy-2α-methyl-5α-androstan-3-one	Generator
2a-Methyldihydrotestosterone	Generator
2Α-methyldihydrotestosterone	Generator
Dihydro-2a-methyltestosterone	Generator
Dihydro-2α-methyltestosterone	Generator
Drolban	HMDB
Metholone	HMDB
Dromostanolone, (5alpha,17beta)-isomer	HMDB
Prometholone	HMDB
Drostanolon	HMDB
17 beta-Hydroxy-2 alpha-methyl-5 alpha-androstan-3-one	HMDB
Methalone	HMDB
Drostanolone	ChEBI

Chemical Formula

C₂₀H₃₂O₂

Average Molecular Weight

304.4669

Monoisotopic Molecular Weight

304.240230268

IUPAC Name

(1S,2S,4R,7S,10R,11S,14S,15S)-14-hydroxy-2,4,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

drostanolone

CAS Registry Number

58-19-5

SMILES

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

InChI Identifier

InChI=1S/C20H32O2/c1-12-11-20(3)13(10-17(12)21)4-5-14-15-6-7-18(22)19(15,2)9-8-16(14)20/h12-16,18,22H,4-11H2,1-3H3/t12-,13+,14+,15+,16+,18+,19+,20+/m1/s1

InChI Key

IKXILDNPCZPPRV-RFMGOVQKSA-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-oxosteroid
3-oxo-5-alpha-steroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:34838 )
17beta-hydroxy steroid (CHEBI:34838 )
anabolic androgenic steroid (CHEBI:34838 )

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: HMDB0014996)

Process

Not Available

Role

Industrial application

Antineoplastic agent (HMDB: HMDB0014996)

Biological role

Anabolic agent (HMDB: HMDB0014996)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	3.81	ALOGPS
logP	3.95	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	19.38	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.18 m³·mol⁻¹	ChemAxon
Polarizability	36.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon