Mesterolone: Difference between revisions

Mesterolone
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	G03BB01 (WHO) ;
Legal status
Legal status	Prescription Only (AU);
Pharmacokinetic data
Metabolism	Liver
Identifiers
	IUPAC name 1 alpha-methyl-17 beta-hydroxy-5 alpha-androstan-3-one;
CAS Number	1424-00-6;
PubChem CID	15020;
ChemSpider	14296 ;
UNII	0SRQ75X9I9;
KEGG	D04947 ;
ChEMBL	ChEMBL258918 ;
CompTox Dashboard (EPA)	DTXSID90878533 ;
ECHA InfoCard	100.014.397
Chemical and physical data
Formula	C20H32O2
Molar mass	304.467 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)[C@@H](C)C4;
	InChI InChI=1S/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-/m0/s1 ; Key:UXYRZJKIQKRJCF-TZPFWLJSSA-N ;
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Revision as of 05:43, 31 August 2011

Mesterolone is an orally applicable androgen, and DHT derivative. It is sold under the brand name Proviron, by Schering. In the late 70's and early 80's it was used with some success in controlled studies of men suffering from various forms of depression.

In one randomized, double-blind 4-week trial, 38 dysthymic men were administered 75mg daily. Itil & Colleagues reported an improvement of symptoms which included anxiety, lack of drive and desire. Next, they administered a high dose (450mg/day) or placebo in a 6-week randomized trial of 52 men with a mean age of 40 years, suffering from dysthymia, unipolar and bipolar depression. Both the mesterolone and placebo groups improved significantly and there were no statistically significant differences between the two groups. In this series of studies mesterolone lead to a significant decrease in LH and testosterone levels. This is probably as a result of the extremely high dose used. In another, 100mg mesterolone cipionate was administered twice monthly. With regards to plasma T levels, there was no difference between the treated vs untreated group, and baseline LH levels were minimally affected.^[1]

Mesterolone is a relatively weak androgen and rarely used for replacement therapies.^[2]

References

^ Kövary PM, Lenau H, Niermann H, Zierden E, Wagner H (1977). "Testosterone levels and gonadotrophins in Klinefelter's patients treated with injections of mesterolone cipionate". Arch Dermatol Res. 258 (3): 289–94. PMID 883846. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Nieschlag E, Behre HM, Bouchard P; et al. (2004). "Testosterone replacement therapy: current trends and future directions". Hum. Reprod. Update. 10 (5): 409–19. doi:10.1093/humupd/dmh035. PMID 15297434. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

Morrison, Mary Chase (2000). Hormones, Gender and the Aging Brain: The Endocrine Basis of Geriatric Psychiatry. Cambridge, UK: Cambridge University Press. p. 134. ISBN 0-521-65304-5.

Itil TM, Michael ST, Shapiro DM, Itil KZ (1984). "The effects of mesterolone, a male sex hormone in depressed patients (a double blind controlled study)". Methods Find Exp Clin Pharmacol. 6 (6): 331–7. PMID 6431212. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[1] Kövary PM, Lenau H, Niermann H, Zierden E, Wagner H (1977). "Testosterone levels and gonadotrophins in Klinefelter's patients treated with injections of mesterolone cipionate". Arch Dermatol Res. 258 (3): 289–94. PMID 883846. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[2] Nieschlag E, Behre HM, Bouchard P; et al. (2004). "Testosterone replacement therapy: current trends and future directions". Hum. Reprod. Update. 10 (5): 409–19. doi:10.1093/humupd/dmh035. PMID 15297434. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

[1]

[2]

@@ Line 1: / Line 1: @@
-{{drugbox
+{{Drugbox
 | Verifiedfields = changed
-| UNII_Ref = {{fdacite|changed|FDA}}
-| UNII = 0SRQ75X9I9
 | verifiedrevid = 415698619
+| IUPAC_name = 1 alpha-methyl-17 beta-hydroxy-5 alpha-androstan-3-one
-|
+| image = Mesterolone.svg
-|IUPAC_name =1 alpha-methyl-17 beta-hydroxy-5 alpha-androstan-3-one
-| image= Mesterolone.svg
+<!--Clinical data-->
+| tradename =
+| Drugs.com = {{drugs.com|international|mesterolone}}
+| pregnancy_category =
+| legal_status = Prescription Only (AU)
+| routes_of_administration =
+<!--Pharmacokinetic data-->
+| bioavailability =
+| metabolism = Liver
+| excretion =
+<!--Identifiers-->
+| CAS_number = 1424-00-6
+| ATC_prefix = G03
+| ATC_suffix = BB01
+| PubChem = 15020
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 14296
+| UNII_Ref = {{fdacite|changed|FDA}}
-| 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-/m0/s1
+| UNII = 0SRQ75X9I9
-| InChIKey = UXYRZJKIQKRJCF-TZPFWLJSBH
+| KEGG_Ref = {{keggcite|correct|kegg}}
-| smiles = O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)[C@@H](C)C4
+| KEGG = D04947
 | ChEMBL_Ref = {{ebicite|correct|EBI}}
 | ChEMBL = 258918
+<!--Chemical data-->
+| C=20 | H=32 | O=2
+| molecular_weight = 304.467 g/mol
+| smiles = O=C4C[C@@H]3CC[C@@H]2[C@H](CC[C@]1(C)[C@@H](O)CC[C@H]12)[C@@]3(C)[C@@H](C)C4
+| 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-/m0/s1
+| InChIKey = UXYRZJKIQKRJCF-TZPFWLJSBH
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/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-/m0/s1
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = UXYRZJKIQKRJCF-TZPFWLJSSA-N
-| CAS_number=1424-00-6
-| ATC_prefix=G03
-| ATC_suffix=BB01
-| ATC_supplemental=
-| PubChem=15020
-| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
-| DrugBank=
-| KEGG_Ref = {{keggcite|correct|kegg}}
-| KEGG = D04947
-| C = 20 | H = 32 | O = 2
-| molecular_weight = 304.467 g/mol
-| bioavailability=
-| metabolism =Liver
-| elimination_half-life=
-| excretion =
-| pregnancy_category =
-| legal_status =Prescription Only (AU)
-| routes_of_administration=
 }}
 '''Mesterolone''' is an orally applicable [[androgen]], and [[Dihydrotestosterone|DHT]] derivative. It is sold under the brand name '''Proviron''', by [[Schering]]. In the late 70's and early 80's it was used with some success in controlled studies of men suffering from various forms of depression.