Chemistry:Drostanolone

From HandWiki
Short description: Chemical compound
Drostanolone
Drostanolone Structural Formula V2.svg
Clinical data
Trade namesDrolban, Masteril, Masteron, others (all as drostanolone propionate)
Other namesDromostanolone; 2α-Methyl-4,5α-dihydrotestosterone; 2α-Methyl-DHT; 2α-Methyl-5α-androstan-17β-ol-3-one
Routes of
administration
Intramuscular injection (as drostanolone propionate)
Drug classAndrogen; Anabolic steroid
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC20H32O2
Molar mass304.474 g·mol−1
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed.[1][2][3] An androgen ester prodrug of drostanolone, drostanolone propionate, was formerly used in the treatment of breast cancer in women under brand names such as Drolban, Masteril, and Masteron.[1][2][3][4] This has also been used non-medically for physique- or performance-enhancing purposes.[3]

Pharmacology

Pharmacodynamics

v · d · e Androgenic vs. anabolic activity
of androgens/anabolic steroids
Medication Ratioa
Testosterone ~1:1
Androstanolone (DHT) ~1:1
Methyltestosterone ~1:1
Methandriol ~1:1
Fluoxymesterone 1:1–1:15
Metandienone 1:1–1:8
Drostanolone 1:3–1:4
Metenolone 1:2–1:30
Oxymetholone 1:2–1:9
Oxandrolone 1:3–1:13
Stanozolol 1:1–1:30
Nandrolone 1:3–1:16
Ethylestrenol 1:2–1:19
Norethandrolone 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

Like other AAS, drostanolone is an agonist of the androgen receptor (AR).[3] It is not a substrate for 5α-reductase and is a poor substrate for 3α-hydroxysteroid dehydrogenase (3α-HSD), and therefore shows a high ratio of anabolic to androgenic activity.[3] As a DHT derivative, drostanolone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites.[3] While no data are available on the progestogenic activity of drostanolone, it is thought to have low or no such activity similarly to other DHT derivatives.[3] Since the drug is not 17α-alkylated, it is not known to cause hepatotoxicity.[3]

Chemistry

Drostanolone, also known as 2α-methyl-5α-dihydrotestosterone (2α-methyl-DHT) or as 2α-methyl-5α-androstan-17β-ol-3-one, is a synthetic androstane steroid and a derivative of DHT.[1][2][3] It is specifically DHT with a methyl group at the C2α position.[1][2][3]

History

Drostanolone and its ester drostanolone propionate were first described in 1959.[3][5] Drostanolone propionate was first introduced for medical use in 1961.[6]

Society and culture

Generic names

Drostanolone is the generic name of the drug and its INN, BAN, and DCF.[1][2] It has also been referred to as dromostanolone.[1][2]

Legal status

Drostanolone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[7]

Synthesis

Bolazine is when react 2 eq. with hydrazine to give dimer

Treatment of DHT (androstan-17β-ol-3-one, stanolone) [521-18-6] (1) with methyl formate and the strong base sodium methoxide gives [4033-95-8] (2). The newly added formyl function in the product is shown in the enol form. Catalytic hydrogenation reduces that function to a methyl group (3). The addition of hydrogen from the bottom face of the molecule leads to the formation of β-methyl isomer where the methyl group occupies the higher-energy axial position. Strong base-induced equilibration of the methyl group leads to the formation of the sterically favoured equatorial α-methyl isomer, affording dromostanolone (4).

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 652–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA652. 
  2. 2.0 2.1 2.2 2.3 2.4 2.5 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 377–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA377. 
  3. 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 Llewellyn, William (2011). Anabolics. Molecular Nutrition Llc. pp. 517–. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT517. 
  4. "Hormonal therapy of breast cancer with special reference to Masteril therapy". South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde 49 (49): 2036–40. November 1975. PMID 1242823. 
  5. "Steroids. CV.12-Methyl and 2-Hydroxymethylene-androstane Derivatives". Journal of the American Chemical Society 81 (2): 427–432. 1959. doi:10.1021/ja01511a040. ISSN 0002-7863. 
  6. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1402–. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1402. 
  7. Karch, Steven B. (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8. https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30. 
  8. "Steroids. CV. 1 2-Methyl and 2-hydroxymethylene-androstane derivatives". Journal of the American Chemical Society 81 (2): 427–432. January 1959. doi:10.1021/ja01511a040. 
  9. Volovel'skii, L.N. et al, Zh. Obschch. Khim., 1966, 46, 1772.
  10. Ringold HJ, Rosenkranz G, US patent 2908693, issued 1959, assigned to Syntex SA
  11. Ringold HJ, Rosenkranz G, US patent 3118915, issued 1964, assigned to Roche Palo Alto LLC
  12. GB patent 1005896 US patent 3249627, issued 1966, assigned to Ormonoterapia Richter Spa

External links

{{Navbox

| name = Androgens and antiandrogens
| title = Androgens and antiandrogens
| state = collapsed
| listclass = hlist
| groupstyle = text-align:center;
| group1 = Androgens
(incl. AAS)

| list1 =

  | group3 = Antigonadotropins
  | list3 =
  | group4 = Others
  | list4 =
}}
| liststyle = background:#DDDDFF;
| list3 =
See also
Androgen receptor modulators
Estrogens and antiestrogens
Progestogens and antiprogestogens
List of androgens/anabolic steroids

}}