Chemistry:Methandriol bisenanthoyl acetate

Short description: Chemical compound

Methandriol bisenanthoyl acetate

Clinical data
Trade names	Notandron-Depot
Other names	Methandriol dioxononanoate; Methylandrostenediol dioxononanoate; Methandriol bisoxononanoate; Methylandrostenediol bisoxononanoate; 17α-Methylandrost-5-ene-3,17β-diol 3,17β-di(3-oxononanoate)
Routes of administration	Intramuscular injection
Identifiers
IUPAC name (1S,2R,10R,11S,14R,15S)-2,14,15-Trimethyl-5-[(3-oxononanoyl)oxy]tetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-yl 3-oxononanoate
CAS Number	94030-88-3
PubChem CID	44150473
ChemSpider	21166566
Chemical and physical data
Formula	C38H60O6
Molar mass	612.892 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCCC(=O)CC(=O)OC1CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@]4(C)OC(=O)CC(=O)CCCCCC)[C@@H]3CC=C2C1
InChI InChI=1S/C38H60O6/c1-6-8-10-12-14-28(39)25-34(41)43-30-18-21-36(3)27(24-30)16-17-31-32(36)19-22-37(4)33(31)20-23-38(37,5)44-35(42)26-29(40)15-13-11-9-7-2/h16,30-33H,6-15,17-26H2,1-5H3/t30?,31-,32+,33+,36?,37?,38-/m1/s1 Key:ASAWDXJIGAVOBY-JXCMQCOYSA-N

Methandriol bisenanthoyl acetate (brand name Notandron-Depot), or methylandrostenediol bisenanthoyl acetate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β,17β-di(3-oxononanoate), is a synthetic, injected anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of 5-androstenediol. It is an androgen ester—specifically, the C3β,17β di(3-oxononanoate) (or dienanthoylacetate) ester of methandriol (17α-methyl-5-androstenediol)—and acts as a prodrug of methandriol in the body. Methandriol bisenanthoyl acetate is administered by intramuscular injection and, relative to methandriol, has an extended duration via this route due to a depot effect afforded by its ester.

See also

• Methandriol diacetate
• Methandriol dipropionate
• Methandriol propionate
• Bolandiol dipropionate

References

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

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AR agonists

Testosterone derivatives: Androstenediol dipropionate Boldenone undecylenate Clostebol Clostebol acetate Clostebol caproate Clostebol propionate Cloxotestosterone acetate Prasterone (dehydroepiandrosterone, DHEA) Prasterone enanthate (DHEA enanthate) Prasterone sulfate (DHEA sulfate) Quinbolone Testosterone# Testosterone esters (e.g., testosterone cypionate, testosterone enanthate]], testosterone propionate]], testosterone undecanoate]], testosterone ester mixture]]s (Deposterona, Omnadren, Sustanon, Testoviron Depot)) Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT) Androstanolone esters Bolazine capronate Drostanolone propionate (dromostanolone propionate) Epitiostanol Mepitiostane Mesterolone Metenolone acetate (methenolone acetate) Metenolone enanthate (methenolone enanthate) Stenbolone acetate 19-Nortestosterone derivatives: Bolandiol dipropionate Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norclostebol Norclostebol acetate Oxabolone cipionate (oxabolone cypionate) Trenbolone acetate Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate) 17α-Alkylated testosterone derivatives: Bolasterone Calusterone Chlorodehydromethyltestosterone (CDMT) Fluoxymesterone Formebolone Metandienone (methandienone, methandrostenolone) Methandriol (methylandrostenediol) Methandriol bisenanthoyl acetate Methandriol dipropionate Methandriol propionate Methyltestosterone Methyltestosterone 3-hexyl ether Oxymesterone Penmesterol Tiomesterone (thiomesterone) 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole Furazabol Mebolazine (dimethazine) Mestanolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol Mibolerone Norethandrolone Normethandrone (methylestrenolone, normethisterone) Propetandrol (propethandrol) 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone) 17α-Ethynyltestosterone derivatives: Danazol Gestrinone Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), [[Chemistry:Lynestrlynestrenol, Norgestrienone|norgestrienone]]) Tibolone Progesterone derivatives: Medroxyprogesterone acetate

Progonadotropins

Antiestrogens (e.g., tamoxifen, Chemistry:Clomifene

| group2 = Antiandrogens
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  | group1 = AR antagonists
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• Steroidal: Abiraterone acetate
• Canrenone
• Chlormadinone acetate
• Cyproterone acetate
• Delmadinone acetate
• Dienogest
• Drospirenone
• Medrogestone
• Megestrol acetate
• Nomegestrol acetate
• Osaterone acetate
• Oxendolone
• Potassium canrenoate
• Spironolactone

• Nonsteroidal: Apalutamide
• Bicalutamide
• Cimetidine
• Darolutamide
• Enzalutamide
• Flutamide
• Ketoconazole
• Nilutamide
• Seviteronel^†
• Topilutamide (fluridil)

  | group2 = Steroidogenesis
inhibitors

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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

  | group3 = Antigonadotropins
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• 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
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• Androstenedione immunogens: Androvax (androstenedione albumin)
• Ovandrotone albumin (Fecundin)

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• ^#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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