Chemistry:Nandrolone sulfate

Short description: Synthetic androgen and anabolic steroid

Nandrolone sulfate

Clinical data
Trade names	Keratyl, Nandrol, Nandain, Colirio Ocul Nandrol
Other names	19-Nortestosterone 17β-sulfate
Routes of administration	Ophthalmic (eye drops)
Drug class	Androgen; Anabolic steroid; Androgen ester; Progestogen
Identifiers
IUPAC name [[(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] hydrogen sulfate
CAS Number	98804-55-8 60672-82-4 (sodium)
PubChem CID	3085201
DrugBank	DB14624
ChemSpider	23254851
UNII	2S202OX23O
Chemical and physical data
Formula	C18H26O5S
Molar mass	354.46 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OS(=O)(=O)O)CCC4=CC(=O)CC[C@H]34
InChI InChI=1S/C18H26O5S/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)23-24(20,21)22/h10,13-17H,2-9H2,1H3,(H,20,21,22)/t13-,14+,15+,16-,17-,18-/m0/s1 Key:SKZMVWBZTQNCKW-IZPLOLCNSA-N

Nandrolone sulfate, also known as 19-nortestosterone 17β-sulfate and used medically as the sodium salt nandrolone sodium sulfate (brand names Keratyl, Nandrol, Nandain, Colirio Ocul Nandrol), is a synthetic androgen and anabolic steroid and a nandrolone ester which is or has been used as an ophthalmic drug in the form of eye drops in Spain , Denmark , Switzerland , France , Portugal, and Belgium.

Relative affinities (%) of nandrolone and related steroids

Compound	PR	AR	ER	GR	MR	SHBG	CBG
Nandrolone	20	154–155	<0.1	0.5	1.6	1–16	0.1
Testosterone	1.0–1.2	100	<0.1	0.17	0.9	19–82	3–8
Estradiol	2.6	7.9	100	0.6	0.13	8.7–12	<0.1
Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, estradiol for the ER, dexamethasone for the GR, aldosterone]] for the MR, dihydrotestosterone for SHBG, and cortisol for CBG. Sources: See template.

See also

• List of androgen esters § Nandrolone esters

References

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| name = Androgens and antiandrogens
| title = 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
| list2 = {{Navbox|child
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| groupwidth = 9em;

  | group1 = AR antagonists
  | list1 =

• Steroidal: Abiraterone acetate
• Canrenone
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• 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

| list2 =

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)
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• 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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