NANDROLONE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H26O2
Molecular Weight	274.3985
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]3([H])[C@]2([H])CC[C@]1([H])O

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

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/pro/nandrolone.html
Curator's Comment:: https://us.basicstero.info/nandrolones

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

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen receptor 42 Target ID: P10275 Gene ID: 367 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22093481 \| https://www.ncbi.nlm.nih.gov/pubmed/18809391	Agonist 2456
Androgen Receptor 163 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18809391	Agonist 2456
Androgen receptor 42 Target ID: P10275 Gene ID: 367 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00984 \| https://www.ncbi.nlm.nih.gov/pubmed/14303256 \| https://www.ncbi.nlm.nih.gov/pubmed/13572933	Agonist 2456

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anemia of renal insufficiency 11 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3f059e04-1ebc-40bb-a49c-f9d90d41b1cb	Primary		Approved 7997	NANDROLONE DECANOATE Approved Use Nandrolone decanoate is indicated for the management of the anemia of renal insufficiency and has been shown to increase hemoglobin and red cell mass. Surgically induced anephric patients have been reported to be less responsive. Launch Date 1283126400000

C_max

Value	Dose	Co-administered	Analyte	Population
36.1 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10435281	6 mL single, oral dose: 6 mL route of administration: Oral experiment type: SINGLE co-administered:		NANDROLONE PHENPROPIONATE blood	Sus scrofa population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
219.9 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10435281	6 mL single, oral dose: 6 mL route of administration: Oral experiment type: SINGLE co-administered:		NANDROLONE PHENPROPIONATE blood	Sus scrofa population: HEALTHY age: UNKNOWN sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
100 mg 1 times / week multiple, intramuscular Dose: 100 mg, 1 times / week Route: intramuscular Route: multiple Dose: 100 mg, 1 times / week Sources: https://pubmed.ncbi.nlm.nih.gov/318825	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/318825	Sources: https://pubmed.ncbi.nlm.nih.gov/318825

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7466	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7466
ZINC	ZINC000003814379	http://zinc15.docking.org/substances/ZINC000003814379

PubMed

Title	Date	PubMed
Sport nutritional supplements: quality and doping controls.	2001	11897888
The effect of anabolic steroid on the distribution of muscle fiber in rat hind limb.	2001	11729953
Advances in male hormonal contraception.	2001 Dec	11817653
Climodien (estradiol valerate 2 mg plus dienogest 2 mg) is safe and effective in the treatment of postmenopausal complaints.	2001 Dec	11770190
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	11726576
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	11719284
The metabolism of orally ingested 19-nor-4-androstene-3,17-dione and 19-nor-4-androstene-3,17-diol in healthy, resistance-trained men.	2001 Feb	11708699
Aggression in male rats receiving anabolic androgenic steroids: effects of social and environmental provocation.	2001 Nov	11673914
Detection of nandrolone metabolites in urine after a football game in professional and amateur players: a Bayesian comparison.	2001 Nov 1	11672966
Endogenous origin of norandrosterone in female urine: indirect evidence for the production of 19-norsteroids as by-products in the conversion from androgen to estrogen.	2001 Oct	11717005
Drugs and food supplements in sports. The nandrolone lessons.	2001 Oct	11668257
Effect of combined treatment with nandrolone and cocaine on the NMDA receptor gene expression in the rat nucleus accumbens and periaqueductal gray.	2002	12072144
Estradiol valerate/dienogest.	2002	11827562
Role of androgens in female genital sexual arousal: receptor expression, structure, and function.	2002 Apr	12007897
Dienogest is as effective as triptorelin in the treatment of endometriosis after laparoscopic surgery: results of a prospective, multicenter, randomized study.	2002 Apr	11937116
Randomized prospective comparison between erythropoietin and androgens in CAPD patients.	2002 Apr	11918762
Aromatase and breast cancer: W39R, an inactive protein.	2002 Apr	11916629
The popliteal-artery entrapment syndrome in a patient using anabolic steroids.	2002 Apr 18	11961162
In situ detection and quantification of bursa of fabricius cellular proliferation or apoptosis in normal or steroid-treated neonatal chicks.	2002 Aug	12211305
Molecular imprinted polymer coated QCM for the detection of nandrolone.	2002 Aug	12195940
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	12136833
Treatment of menstruation-associated recurrence of hereditary pancreatitis with pharmacologic ovarian suppression.	2002 Aug 1	12133758
The F-box protein SKP2 mediates androgen control of p27 stability in LNCaP human prostate cancer cells.	2002 Aug 20	12188931
Nandrolone: generic now in stock.	2002 Aug 9	12236206
Metabolic effects of nandrolone decanoate and resistance training in men with HIV.	2002 Dec	12388173
The anabolic androgenic steroid, nandrolone decanoate, increases the density of Fos-like immunoreactive neurons in limbic regions of guinea-pig brain.	2002 Feb	11876781
Abuse of performance-enhancing drugs in sport.	2002 Feb	11805741
Role of IGF-I and IGF-binding proteins within diaphragm muscle in modulating the effects of nandrolone.	2002 Feb	11788382
Endogenous nandrolone metabolites in human urine: preliminary results to discriminate between endogenous and exogenous origin.	2002 Feb	11755174
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.	2002 Jan	12064656
Misuse of androgenic-anabolic steroids and human deltoid muscle fibers: differences between polydrug regimens and single drug administration.	2002 Jan	11990732
Inhibition of oestrone sulphatase activity by tibolone and its metabolites.	2002 Jan	11832993
Human nutritional supplements in the horse: comparative effects of 19-norandrostenedione and 19-norandrostenediol on the 19-norsteroid profile and consequences for doping control.	2002 Jan 25	11824814
Endogenous nandrolone metabolites in human urine. Two-year monitoring of male professional soccer players.	2002 Jan-Feb	11888015
Nandrolone decanoate treatment induces changes in contractile responses of rat untrained fast-twitch skeletal muscle.	2002 Jul	12100358
Steroid receptor concentration in aged rat hindlimb muscle: effect of anabolic steroid administration.	2002 Jul	12070211
Treatment for HIV wasting withdrawn.	2002 Jun	12141285
Nandrolone (Deca Durabolin) disappears in U.S., generic may return in July.	2002 Jun 28	12161856
Effect of dienogest-containing oral contraceptives on lipid metabolism.	2002 Mar	11929644
Characterization of bone mineral composition in the proximal tibia of cynomolgus monkeys: effect of ovariectomy and nandrolone decanoate treatment.	2002 Mar	11882463
The human ovarian surface epithelium is an androgen responsive tissue.	2002 Mar 18	11953818
Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of methyltestosterone (17 alpha-methylandrost-4-en-17 beta-ol-3-one) and nandrolone (estr-4-en-17 beta-ol-3-one) metabolites.	2002 Mar-Apr	11906255
Anti-androgenic and hair growth promoting activities of Lygodii spora (spore of Lygodium japonicum) I. Active constituents inhibiting testosterone 5alpha-reductase.	2002 May	12033503
Twenty-one day administration of dienogest reversibly suppresses gonadotropins and testosterone in normal men.	2002 May	11994349
Evaluation of human hepatocyte incubation as a new tool for metabolism study of androstenedione and norandrostenedione in a doping control perspective.	2002 Nov 15	12383490
Synthesis of nitrile derivatives of estrogens.	2002 Oct 21	12270160
Impact of hormone replacement therapy on endogenous estradiol metabolism in postmenopausal women.	2002 Oct 25	12385856
Successful DNA typing of a urine sample in a doping control case using human mitochondrial DNA analysis.	2002 Sep	12356033
Effects of adjuvant androgen on anemia and nutritional parameters in chronic hemodialysis patients using low-dose recombinant human erythropoietin.	2002 Sep	12298427
Nandrolone excretion is not increased by exhaustive exercise in trained athletes.	2002 Sep	12218735

Patents

Sample Use Guides

In Vivo Use Guide

50 to 100 mg per week (women)

Route of Administration: Intramuscular

Name

Type

Language

NANDROLONE

Official Name

English

NORANDROSTENOLONE

Common Name

English

NANDROLONE CIII

Common Name

English

NANDROLONE [MI]

Common Name

English

17-HYDROXYESTR-4-EN-3-ONE

Systematic Name

English

MENIDRABOL

Brand Name

English

NANDROLONE [VANDF]

Common Name

English

NSC-3351

Code

English

19-NORTESTOSTERONE

Common Name

English

NANDROLONE CIII [USP-RS]

Common Name

English

BIOBOL

Brand Name

English

DECADURA

Brand Name

English

4-ESTREN-17.BETA.-OL-3-ONE

Systematic Name

English

NANDROLONE [MART.]

Common Name

English

HYBOLIN

Brand Name

English

NANDROLONE [WHO-DD]

Common Name

English

4-ESTREN-3-ONE-17.BETA.-OL

Systematic Name

English

NANDROLONE [HSDB]

Common Name

English

NANDROLONE [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA14AB01