Chemistry:Mebolazine

Mebolazine
Clinical data
Trade names	Dostalon, Roxilon
Other names	Dimethazine; Dymethazine; Dimethasterone azine; Di(methasterone) azine; 2α,17α-Dimethyl-5α-androstan-17β-ol-3-one azine
Identifiers
	IUPAC name (3Z)-3-[(Z)-(17-Hydroxy-2,10,13,17-tetramethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-ylidene)hydrazinylidene]-2,10,13,17-tetramethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol;
CAS Number	3625-07-8 ;
PubChem CID	9571069;
ChemSpider	16736946 ;
UNII	69C642I19V;
Chemical and physical data
Formula	C42H68N2O2
Molar mass	633.018 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@]23[C@](CC[C@]4([H])[C@@]([H])3CC[C@@]5(C)[C@]([H])4CC[C@@](C)5O)([H])C/C([C@H](C)C2)=N/N=C1[C@H](C)C[C@@]6(C)[C@](CC[C@]7([H])[C@@]([H])6CC[C@@]8(C)[C@]([H])7CC[C@@](C)8O)([H])C/1;
	InChI InChI=1S/C42H68N2O2/c1-25-23-37(3)27(9-11-29-31(37)13-17-39(5)33(29)15-19-41(39,7)45)21-35(25)43-44-36-22-28-10-12-30-32(38(28,4)24-26(36)2)14-18-40(6)34(30)16-20-42(40,8)46/h25-34,45-46H,9-24H2,1-8H3/b43-35-,44-36-/t25-,26-,27+,28+,29-,30-,31+,32+,33+,34+,37+,38+,39+,40+,41+,42+/m1/s1 ; Key:POPWFGNRCCUJGU-QQZDHCPGSA-N ;
	(what is this?) (verify)

Short description: Chemical compound

Mebolazine (INN; brand names Dostalon and Roxilon; also known as dimethazine, dymethazine, di(methasterone) azine, or 2α,17α-dimethyl-5α-androstan-17β-ol-3-one azine) is a synthetic, orally active androgen/anabolic steroid (AAS) and a 17α-alkylated derivative of dihydrotestosterone (DHT) which is no longer marketed.^[1]^[2] It has a unique and unusual chemical structure, being a dimer of methasterone linked at the 3-position of the A-ring by an azine group, and reportedly acts as a prodrug of methasterone.^[3]

Since 2008, mebolazine has been used illegally as an ingredient is some dietary supplements,^[4] including vitamin B supplements, and in the United States the Food and Drug Administration has taken legal action against such manufacturers.^[5]^[6]

References

↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 756–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA756.
↑ "In vitro and in vivo metabolism studies of dimethazine". Biomedical Chromatography 30 (8): 1202–1209. August 2016. doi:10.1002/bmc.3668. PMID 26663462.
↑ "Nutritional and Dietary Supplements: Code or Concern". Preventive Nutrition. Nutrition and Health. 2015. pp. 47–62. doi:10.1007/978-3-319-22431-2_3. ISBN 978-3-319-22430-5.
↑ "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology 3 (2): 150–155. March 2015. doi:10.1111/andr.307. PMID 25684733.
↑ See, for example: "FDA Warns Consumers About Health Risks With Healthy Life Chemistry Dietary Supplement". Food and Drug Administration. https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm362799.htm.
↑ "Criminal Investigations (2011) Dietary Supplements Manufacturer Sentenced". Department of Justice. https://www.fda.gov/ICECI/CriminalInvestigations/ucm254526.htm.

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| title = Androgens and antiandrogens
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| group1 = Androgens
(incl. AAS)

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| group2 = Antiandrogens
| list2 = {{Navbox|child
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| groupwidth = 9em;

  | group1 = AR antagonists
  | list1 =

  | group2 = Steroidogenesis
inhibitors

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  | group3 = Antigonadotropins
  | list3 =

D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
Estrogens (e.g., bifluranol, [[diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
GnRH agonists (e.g., leuprorelin)
GnRH antagonists (e.g., cetrorelix)
Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

  | group4 = Others
  | list4 =

Androstenedione immunogens: Androvax (androstenedione albumin)
Ovandrotone albumin (Fecundin)

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| liststyle = background:#DDDDFF;

| list3 =

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgen receptor modulators; Estrogens and antiestrogens; Progestogens and antiprogestogens; List of androgens/anabolic steroids

}}

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Original source: https://en.wikipedia.org/wiki/Mebolazine. Read more

[Elks2014-1] The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 756–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA756.

[pmid26663462-2] "In vitro and in vivo metabolism studies of dimethazine". Biomedical Chromatography 30 (8): 1202–1209. August 2016. doi:10.1002/bmc.3668. PMID 26663462.

[ClemensPressman2015-3] "Nutritional and Dietary Supplements: Code or Concern". Preventive Nutrition. Nutrition and Health. 2015. pp. 47–62. doi:10.1007/978-3-319-22431-2_3. ISBN 978-3-319-22430-5.

[4] "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology 3 (2): 150–155. March 2015. doi:10.1111/andr.307. PMID 25684733.

[5] See, for example: "FDA Warns Consumers About Health Risks With Healthy Life Chemistry Dietary Supplement". Food and Drug Administration. https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm362799.htm.

[6] "Criminal Investigations (2011) Dietary Supplements Manufacturer Sentenced". Department of Justice. https://www.fda.gov/ICECI/CriminalInvestigations/ucm254526.htm.

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5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel^† Spironolactone

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