Mesterolone Chemical Properties

Melting point:

208 °C

alpha 

D20 +17.6° (c = 0.875 in CHCl3)

Boiling point:

420.3±45.0 °C(Predicted)

Density 

1.156 g/cm3

refractive index 

17.6 ° (C=0.9, CHCl3)

storage temp. 

2-8°C

solubility 

Practically insoluble in water, sparingly soluble in acetone, in ethyl acetate and in methanol

pka

15.09±0.70(Predicted)

Water Solubility 

3mg/L at 20℃

Merck 

5916

InChI

InChI=1/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/s3

InChIKey

UXYRZJKIQKRJCF-TZPFWLJSSA-N

SMILES

[C@@]12([H])CC[C@@]3([H])CC(=O)C[C@H](C)[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])O |&1:0,4,10,12,14,18,20,23,r|

CAS DataBase Reference

1424-00-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T,F

Risk Statements 

20/21/22-38-19-11-61-60

Safety Statements 

22-24/25-36/37/39-45-53

WGK Germany 

3

RTECS 

BV8063400

HS Code 

29372900

DEA Controlled Substances

CSCN: 4000
CSA SCH: Schedule III
NARC: No

MSDS

• Language:English Provider:1alpha-Methylandrostan-17beta-ol-3-one
• Language:English Provider:SigmaAldrich

Mesterolone Usage And Synthesis

Description

Mesterolone (Item No. 21171) is an analytical reference standard categorized as an anabolic androgenic steroid. Formulations containing mesterolone have been used in patients with low testosterone or symptoms of aging male syndrome. Mesterolone cannot be aromatized to estrogens, unlike other androgens. This compound is the active ingredient in different pharmaceutical preparations that have been used medically but have also been widely applied in sports in order to improve athlete performance. Mesterolone is regulated as a Schedule III drug in the United States. This product is intended for research and forensic applications.

Chemical Properties

White or yellowish crystalline powder.

Originator

Proviron,Schering,W. Germany,1967

Uses

Mesterolone is a synthetic androgen and a dihydrotestosterone derivative. Mesterolone is rarely used for replacement therapies due to its weak androgenic activity.

Definition

ChEBI: Mesterolone is a 3-oxo-5alpha-steroid. It is a structurally altered DHT hormone possessing the addition of a methyl group at the carbon one position. This allows the hormone to survive oral ingestion by protecting it from hepatic breakdown. This is one of the only oral anabolic steroids that is not C17-alpha alkylated (C17-aa) but instead carries the added methyl group.

Application

Mesterolone is a pharmacological agent that belongs to the group of androgens. It is an oral preparation and has been used in the treatment of infectious diseases, autoimmune diseases, and metabolic disorders. It has also been used as a matrix effect control in biological samples. The biological effects of it are mediated by its direct action on cells or through conversion to testosterone or dihydrotestosterone (DHT). These effects include increasing protein synthesis, promoting bone formation, lowering cholesterol levels, stimulating the production of red blood cells, and decreasing fat deposition.

Manufacturing Process

500 mg of 1α-methyl-androstan-17β-ol-3-one-17-acetate are heated under reflux for 90 minutes in a nitrogen atmosphere in 5 ml of 4% methanolic sodium hydroxide solution. The reaction mixture is then stirred into ice water,the precipitated product filtered with suction and recrystallized from isopropyl ether. 1α-Methyl-androstan-17β-ol-3-one melts at 203.5° to 205°C.

Therapeutic Function

Androgen

General Description

Mesterolone is a synthetic anabolic-androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT). It is inactivated by 3α-hydroxysteroid dehydrogenase in skeleta muscules so it is considered a weak androgen. It is not a substrate for aromatase so it is not converted into estrogen. Mesterolone demonstrated to have minimal effect on sperm counts and levels of FSH or LH. Experiments of mesterolone serving as a potential treatment of depression are still undergoing.

Side effects

The main side effects are acne vulgaris, male pattern baldness, prostate enlargement, increased risk for prostate cancer, and increased risk for developing breast cancer.

References

[1] MALCOLM CARRUTHERS  Mark R F  Paul Cathcart. Evolution of testosterone treatment over 25 years: symptom responses, endocrine profiles and cardiovascular changes.[J]. Aging Male, 2015, 18 4: 217-227. DOI: 10.3109/13685538.2015.1048218
[2] HARUN DUGEROGLU. Mesterolone treatment of aging male syndrome improves lower urinary tract symptoms.[J]. Journal of the Pakistan Medical Association, 2014: 1366-1369.
[3] GD LOWE. Mesterolone: thrombosis during treatment, and a study of its prothrombotic effects.[J]. British journal of clinical pharmacology, 1979, 7 1: 107-109. DOI: 10.1111/j.1365-2125.1979.tb00905.x
[4] M. DO?OWY. A Validated TLC-Densitometric Method for the Determination of Mesterolone in Bulk Material and in Tablets[J]. BioMed Research International, 2015, 2015 1. DOI: 10.1155/2015/230104

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