Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H26O2 |
| Molecular Weight | 274.3978 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@H]2O
InChI
InChIKey=NPAGDVCDWIYMMC-IZPLOLCNSA-N
InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
Nandrolone, also known as 19-nortestosterone or 19-norandrostenolone, is a semisynthetic anabolic-androgenic steroid derived from testosterone. Nandrolone is used in the form of a variety of long-acting prodrug esters for intramuscular injection, the most common of which are nandrolone decanoate. Nandrolone decanoate is indicated for the management of the anemia of renal insufficiency and has been shown to increase hemoglobin and red cell mass. Certain clinical effects and adverse reactions demonstrate the androgenic properties of this class of drugs. Complete dissociation of anabolic and androgenic effects has not been achieved. The actions of anabolic steroids are therefore similar to those of male sex hormones with the possibility of causing serious disturbances of growth and sexual development if given to young children. Anabolic steroids suppress the gonadotropic functions of the pituitary and may exert a direct effect upon the testis. Anabolic steroids have been reported to increase low-density lipoproteins and decrease high-density lipoproteins. Synthetic version of nandrolone was developed in 1950. But nandrolone for sale appeared later only in 1962 in the form of decanoate under the trade name Deca-Durabolin (Organon company).
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The effect of anabolic steroid on the distribution of muscle fiber in rat hind limb. | 2001 |
|
| Consequence of boar edible tissue consumption on urinary profiles of nandrolone metabolites. II. Identification and quantification of 19-norsteroids responsible for 19-norandrosterone and 19-noretiocholanolone excretion in human urine. | 2001 |
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| [What is the role of hormonal treatments in acne?]. | 2001 Apr |
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| Human cell lines as an in vitro/in vivo model for prostate carcinogenesis and progression. | 2001 Apr |
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| Effects of nandrolone treatment on recovery in horses after strenuous physical exercise. | 2001 Aug |
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| Gas chromatography-combustion-isotope ratio mass spectrometry analysis of 19-norsteroids: application to the detection of a nandrolone metabolite in urine. | 2001 Aug 15 |
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| Measurement of androgen and estrogen receptors in breast tissue from subjects with anabolic steroid-dependent gynecomastia. | 2001 Aug 17 |
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| The effects of postmenopausal hormone replacement therapy and oral contraceptives on the endogenous estradiol metabolism. | 2001 Dec |
|
| Suppression of spermatogenesis to azoospermia by combined administration of GnRH antagonist and 19-nortestosterone cannot be maintained by this non-aromatizable androgen alone. | 2001 Dec |
|
| Expression of the human androgen receptor in eukaryotic cells using a recombinant adenovirus vector yields high levels of the soluble, functional receptor protein. | 2001 Dec |
|
| Detection and determination of anabolic steroids in nutritional supplements. | 2001 Jul |
|
| Novel amino acid substitutional mutation, tyrosine-739-aspartic acid, in the androgen receptor gene in complete androgen insensitivity syndrome. | 2001 Jun |
|
| Comparison of the efficiences of enzymatic and chemical hydrolysis of (nortestosterone and diethylstilboestrol) glucuronides in bovine urine. | 2001 Jun 15 |
|
| Recombinant expression and purification of human androgen receptor in a baculovirus system. | 2001 Jun 15 |
|
| Differential effects of nandrolone decanoate in fast and slow rat skeletal muscles. | 2001 Mar |
|
| Doping control for nandrolone using hair analysis. | 2001 Mar |
|
| Aggression in male rats receiving anabolic androgenic steroids: effects of social and environmental provocation. | 2001 Nov |
|
| Detection of nandrolone metabolites in urine after a football game in professional and amateur players: a Bayesian comparison. | 2001 Nov 1 |
|
| [New gestagens--advantages and disadvantages]. | 2001 Sep |
|
| Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women. | 2001 Sep |
|
| Silymarin inhibits function of the androgen receptor by reducing nuclear localization of the receptor in the human prostate cancer cell line LNCaP. | 2001 Sep |
|
| Effect of combined treatment with nandrolone and cocaine on the NMDA receptor gene expression in the rat nucleus accumbens and periaqueductal gray. | 2002 |
|
| Role of androgens in female genital sexual arousal: receptor expression, structure, and function. | 2002 Apr |
|
| Dienogest is as effective as triptorelin in the treatment of endometriosis after laparoscopic surgery: results of a prospective, multicenter, randomized study. | 2002 Apr |
|
| Aromatase and breast cancer: W39R, an inactive protein. | 2002 Apr |
|
| The popliteal-artery entrapment syndrome in a patient using anabolic steroids. | 2002 Apr 18 |
|
| Suppression of spermatogenesis to azoospermia by combined administration of GnRH antagonist and 19-nortestosterone cannot be maintained by this non-aromatizable androgen alone. | 2002 Aug |
|
| Nandrolone: generic now in stock. | 2002 Aug 9 |
|
| Metabolic effects of nandrolone decanoate and resistance training in men with HIV. | 2002 Dec |
|
| The anabolic androgenic steroid, nandrolone decanoate, increases the density of Fos-like immunoreactive neurons in limbic regions of guinea-pig brain. | 2002 Feb |
|
| Physical provocation potentiates aggression in male rats receiving anabolic androgenic steroids. | 2002 Feb |
|
| Endogenous nandrolone metabolites in human urine: preliminary results to discriminate between endogenous and exogenous origin. | 2002 Feb |
|
| Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol. | 2002 Jan |
|
| Misuse of androgenic-anabolic steroids and human deltoid muscle fibers: differences between polydrug regimens and single drug administration. | 2002 Jan |
|
| Inhibition of oestrone sulphatase activity by tibolone and its metabolites. | 2002 Jan |
|
| The effects of nandrolone decanoate on nutritional parameters in hemodialysis patients. | 2002 Jul |
|
| Treatment for HIV wasting withdrawn. | 2002 Jun |
|
| Effect of dienogest-containing oral contraceptives on lipid metabolism. | 2002 Mar |
|
| Characterization of bone mineral composition in the proximal tibia of cynomolgus monkeys: effect of ovariectomy and nandrolone decanoate treatment. | 2002 Mar |
|
| The human ovarian surface epithelium is an androgen responsive tissue. | 2002 Mar 18 |
|
| Anti-androgenic and hair growth promoting activities of Lygodii spora (spore of Lygodium japonicum) I. Active constituents inhibiting testosterone 5alpha-reductase. | 2002 May |
|
| Twenty-one day administration of dienogest reversibly suppresses gonadotropins and testosterone in normal men. | 2002 May |
|
| Evaluation of human hepatocyte incubation as a new tool for metabolism study of androstenedione and norandrostenedione in a doping control perspective. | 2002 Nov 15 |
|
| Urine nandrolone metabolites: false positive doping test? | 2002 Oct |
|
| Synthesis of nitrile derivatives of estrogens. | 2002 Oct 21 |
|
| Impact of hormone replacement therapy on endogenous estradiol metabolism in postmenopausal women. | 2002 Oct 25 |
|
| Repeated anabolic-androgenic steroid treatment during adolescence increases vasopressin V(1A) receptor binding in Syrian hamsters: correlation with offensive aggression. | 2002 Sep |
|
| Successful DNA typing of a urine sample in a doping control case using human mitochondrial DNA analysis. | 2002 Sep |
|
| Effects of adjuvant androgen on anemia and nutritional parameters in chronic hemodialysis patients using low-dose recombinant human erythropoietin. | 2002 Sep |
|
| Nandrolone excretion is not increased by exhaustive exercise in trained athletes. | 2002 Sep |
Patents
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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WHO-VATC |
QA14AB01
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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LIVERTOX |
667
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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NDF-RT |
N0000175824
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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NCI_THESAURUS |
C243
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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DEA NO. |
4000
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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WHO-ATC |
A14AB01
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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NCI_THESAURUS |
C2360
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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WHO-ATC |
S01XA11
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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WHO-VATC |
QS01XA11
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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D009277
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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434-22-0
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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NANDROLONE
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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7244
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | RxNorm | ||
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DB00984
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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434-22-0
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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207-101-0
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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C29279
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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6949
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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9904
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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295
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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434-22-0
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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M7720
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | Merck Index | ||
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CHEMBL2104906
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY | |||
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SUB09148MIG
Created by
admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE LESS ACTIVE (PARENT)
