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Drostanolone

May 03, 2024

Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed.[2][3][4] 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.[2][3][4][5] This has also been used non-medically for physique- or performance-enhancing purposes.[4]

Drostanolone
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
  • (2R,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy- 2,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17- tetradecahydrocyclopenta[a]phenanthren-3-one
CAS Number
  • 58-19-5 Y
PubChem CID
  • 6011
ChemSpider
  • 5789 N
UNII
  • 7DR7H00HDT
ChEMBL
  • ChEMBL1582 N
CompTox Dashboard (EPA)
  • DTXSID6022971
ECHA InfoCard100.000.334
Chemical and physical data
FormulaC20H32O2
Molar mass304.474 g·mol−1
3D model (JSmol)
  • Interactive image
  • C[C@@H]1C[C@]2([C@@H](CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)CC1=O)C
  • 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 N
  • Key:IKXILDNPCZPPRV-RFMGOVQKSA-N N
 NY (what is this?)  (verify)

Pharmacology edit

Pharmacodynamics edit

Androgenic vs. anabolic activity ratio
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).[4] 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.[4] As a DHT derivative, drostanolone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites.[4] 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.[4] Since the drug is not 17α-alkylated, it is not known to cause hepatotoxicity.[4]

Chemistry edit

See also: List of androgens/anabolic steroids

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.[2][3][4] It is specifically DHT with a methyl group at the C2α position.[2][3][4]

History edit

Drostanolone and its ester drostanolone propionate were first described in 1959.[4][6] Drostanolone propionate was first introduced for medical use in 1961.[7]

Society and culture edit

Generic names edit

Drostanolone is the generic name of the drug and its INNTooltip International Nonproprietary Name, BANTooltip British Approved Name, and DCFTooltip Dénomination Commune Française.[2][3] It has also been referred to as dromostanolone.[2][3]

Legal status edit

Drostanolone, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act.[8]

Potential side effects edit

Like other AAS, drostanolone can cause a variety of side effects, including:

  • Virilization: This refers to the development of masculine characteristics in women, such as deepening of the voice, increased body hair growth, and clitoral enlargement.
  • Acne: AAS can increase sebum production, leading to acne.
  • Hair loss: Drostanolone can accelerate male pattern baldness.
  • Cardiovascular issues: AAS can negatively affect cholesterol levels and increase the risk of cardiovascular disease.
  • Liver damage: Although drostanolone is not 17α-alkylated, high doses or prolonged use can still potentially damage the liver.
  • Mood swings: AAS can cause aggression, irritability, and mood swings.

Non-medical uses edit

Drostanolone is used by some bodybuilders and athletes to increase muscle mass and strength. It is often used during "cutting cycles" to help preserve muscle mass while losing body fat. However, the use of AAS for non-medical purposes is not recommended due to the potential for serious side effects.

Synthesis edit

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

 
Thieme Synthesis:[9][10][11][12][13]

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 edit

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^ a b c d e f Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 652–. ISBN 978-1-4757-2085-3.
  3. ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 377–. ISBN 978-3-88763-075-1.
  4. ^ a b c d e f g h i j k Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 517–. ISBN 978-0-9828280-1-4.
  5. ^ Bennett MB, Helman P, Palmer P (November 1975). "Hormonal therapy of breast cancer with special reference to Masteril therapy". South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde. 49 (49): 2036–40. PMID 1242823.
  6. ^ Ringold HJ, Batres E, Halpern O, Necoechea E (1959). "Steroids. CV.12-Methyl and 2-Hydroxymethylene-androstane Derivatives". Journal of the American Chemical Society. 81 (2): 427–432. doi:10.1021/ja01511a040. ISSN 0002-7863.
  7. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1402–. ISBN 978-0-8155-1856-3.
  8. ^ Karch SB (21 December 2006). Drug Abuse Handbook, Second Edition. CRC Press. pp. 30–. ISBN 978-1-4200-0346-8.
  9. ^ Ringold HJ, Batres E, Halpern O, Necoechea E (January 1959). "Steroids. CV. 1 2-Methyl and 2-hydroxymethylene-androstane derivatives". Journal of the American Chemical Society. 81 (2): 427–432. doi:10.1021/ja01511a040.
  10. ^ Volovel'skii, L.N. et al, Zh. Obschch. Khim., 1966, 46, 1772.
  11. ^ US 2908693, Ringold HJ, Rosenkranz G, issued 1959, assigned to Syntex SA 
  12. ^ US 3118915, Ringold HJ, Rosenkranz G, issued 1964, assigned to Roche Palo Alto LLC 
  13. ^ GB 1005896  US 3249627, issued 1966, assigned to Ormonoterapia Richter Spa 

External links edit

  • Masteron (drostanolone propionate) - William Llewellyn's Anabolic.org 2016-09-26 at the Wayback Machine

May 03, 2024
drostanolone, dromostanolone, anabolic, androgenic, steroid, dihydrotestosterone, group, which, never, marketed, androgen, ester, prodrug, drostanolone, drostanolone, propionate, formerly, used, treatment, breast, cancer, women, under, brand, names, such, drol. Drostanolone or dromostanolone is an anabolic androgenic steroid AAS of the dihydrotestosterone DHT group which was never marketed 2 3 4 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 2 3 4 5 This has also been used non medically for physique or performance enhancing purposes 4 DrostanoloneClinical dataTrade namesDrolban Masteril Masteron others all as drostanolone propionate Other namesDromostanolone 2a Methyl 4 5a dihydrotestosterone 2a Methyl DHT 2a Methyl 5a androstan 17b ol 3 oneRoutes ofadministrationIntramuscular injection as drostanolone propionate Drug classAndrogen Anabolic steroidLegal statusLegal statusBR Class C5 Anabolic steroids 1 CA Schedule IV US Schedule IIIIdentifiersIUPAC name 2R 5S 8R 9S 10S 13S 14S 17S 17 hydroxy 2 10 13 trimethyl 1 2 4 5 6 7 8 9 11 12 14 15 16 17 tetradecahydrocyclopenta a phenanthren 3 oneCAS Number58 19 5 YPubChem CID6011ChemSpider5789 NUNII7DR7H00HDTChEMBLChEMBL1582 NCompTox Dashboard EPA DTXSID6022971ECHA InfoCard100 000 334Chemical and physical dataFormulaC 20H 32O 2Molar mass304 474 g mol 13D model JSmol Interactive imageSMILES C C H 1C C 2 C H CC C H 3 C H 2CC C 4 C H 3CC C H 4O C CC1 O CInChI 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 NKey IKXILDNPCZPPRV RFMGOVQKSA N N N Y what is this verify Contents 1 Pharmacology 1 1 Pharmacodynamics 2 Chemistry 3 History 4 Society and culture 4 1 Generic names 4 2 Legal status 5 Potential side effects 6 Non medical uses 7 Synthesis 8 References 9 External linksPharmacology editPharmacodynamics edit vte Androgenic vs anabolic activity ratioof 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 4 It is not a substrate for 5a reductase and is a poor substrate for 3a hydroxysteroid dehydrogenase 3a HSD and therefore shows a high ratio of anabolic to androgenic activity 4 As a DHT derivative drostanolone is not a substrate for aromatase and hence cannot be aromatized into estrogenic metabolites 4 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 4 Since the drug is not 17a alkylated it is not known to cause hepatotoxicity 4 Chemistry editSee also List of androgens anabolic steroids Drostanolone also known as 2a methyl 5a dihydrotestosterone 2a methyl DHT or as 2a methyl 5a androstan 17b ol 3 one is a synthetic androstane steroid and a derivative of DHT 2 3 4 It is specifically DHT with a methyl group at the C2a position 2 3 4 History editDrostanolone and its ester drostanolone propionate were first described in 1959 4 6 Drostanolone propionate was first introduced for medical use in 1961 7 Society and culture editGeneric names edit Drostanolone is the generic name of the drug and its INNTooltip International Nonproprietary Name BANTooltip British Approved Name and DCFTooltip Denomination Commune Francaise 2 3 It has also been referred to as dromostanolone 2 3 Legal status edit Drostanolone along with other AAS is a schedule III controlled substance in the United States under the Controlled Substances Act 8 Potential side effects editLike other AAS drostanolone can cause a variety of side effects including Virilization This refers to the development of masculine characteristics in women such as deepening of the voice increased body hair growth and clitoral enlargement Acne AAS can increase sebum production leading to acne Hair loss Drostanolone can accelerate male pattern baldness Cardiovascular issues AAS can negatively affect cholesterol levels and increase the risk of cardiovascular disease Liver damage Although drostanolone is not 17a alkylated high doses or prolonged use can still potentially damage the liver Mood swings AAS can cause aggression irritability and mood swings Non medical uses editDrostanolone is used by some bodybuilders and athletes to increase muscle mass and strength It is often used during cutting cycles to help preserve muscle mass while losing body fat However the use of AAS for non medical purposes is not recommended due to the potential for serious side effects Synthesis editBolazine is when react 2 eq with hydrazine to give dimer nbsp Thieme Synthesis 9 10 11 12 13 Treatment of DHT androstan 17b 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 b 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 a methyl isomer affording dromostanolone 4 References edit Anvisa 2023 03 31 RDC Nº 784 Listas de Substancias Entorpecentes Psicotropicas Precursoras e Outras sob Controle Especial Collegiate Board Resolution No 784 Lists of Narcotic Psychotropic Precursor and Other Substances under Special Control in Brazilian Portuguese Diario Oficial da Uniao published 2023 04 04 Archived from the original on 2023 08 03 Retrieved 2023 08 15 a b c d e f Elks J 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer pp 652 ISBN 978 1 4757 2085 3 a b c d e f Index Nominum 2000 International Drug Directory Taylor amp Francis January 2000 pp 377 ISBN 978 3 88763 075 1 a b c d e f g h i j k Llewellyn W 2011 Anabolics Molecular Nutrition Llc pp 517 ISBN 978 0 9828280 1 4 Bennett MB Helman P Palmer P November 1975 Hormonal therapy of breast cancer with special reference to Masteril therapy South African Medical Journal Suid Afrikaanse Tydskrif vir Geneeskunde 49 49 2036 40 PMID 1242823 Ringold HJ Batres E Halpern O Necoechea E 1959 Steroids CV 12 Methyl and 2 Hydroxymethylene androstane Derivatives Journal of the American Chemical Society 81 2 427 432 doi 10 1021 ja01511a040 ISSN 0002 7863 William Andrew Publishing 22 October 2013 Pharmaceutical Manufacturing Encyclopedia 3rd Edition Elsevier pp 1402 ISBN 978 0 8155 1856 3 Karch SB 21 December 2006 Drug Abuse Handbook Second Edition CRC Press pp 30 ISBN 978 1 4200 0346 8 Ringold HJ Batres E Halpern O Necoechea E January 1959 Steroids CV 1 2 Methyl and 2 hydroxymethylene androstane derivatives Journal of the American Chemical Society 81 2 427 432 doi 10 1021 ja01511a040 Volovel skii L N et al Zh Obschch Khim 1966 46 1772 US 2908693 Ringold HJ Rosenkranz G issued 1959 assigned to Syntex SA US 3118915 Ringold HJ Rosenkranz G issued 1964 assigned to Roche Palo Alto LLC GB 1005896 US 3249627 issued 1966 assigned to Ormonoterapia Richter Spa External links editMasteron drostanolone propionate William Llewellyn s Anabolic org Archived 2016 09 26 at the Wayback Machine Retrieved from https en wikipedia org w index php title Drostanolone amp oldid 1211097609, wikipedia, wiki, book, books, library,

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