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:: Description was created based on several sources, including https://empower.pharmacy/drugs/nandrolone-decanoate-injection.html 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: 367.0 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 2470
Androgen Receptor 163 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18809391	Agonist 2470
Androgen receptor 42 Target ID: P10275 Gene ID: 367.0 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 2470

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 8043	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 1.28312646E12

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 n = 5 Health Status: unhealthy Condition: Anemias Age Group: adult Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/318825	Sources: https://pubmed.ncbi.nlm.nih.gov/318825

PubMed

Title	Date	PubMed
A report on alterations to the speaking and singing voices of four women following hormonal therapy with virilizing agents.	1999 Dec	10622516
Detection of nandrolone, testosterone, and their esters in rat and human hair samples.	1999 Oct	10517545
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
[The combined effect of retabolile and support loads on the post-traumatic reparation process in suspended rat muscles].	2001	11589151
Double-blind, placebo-controlled psychometric studies on the effects of a combined estrogen-progestin regimen versus estrogen alone on performance, mood and personality of menopausal syndrome patients.	2001	11304940
[What is the role of hormonal treatments in acne?].	2001 Apr	11450396
Steroidal control of male hamster sexual behavior in Me and MPOA: effects of androgen dose and tamoxifen.	2001 Apr	11337005
Human cell lines as an in vitro/in vivo model for prostate carcinogenesis and progression.	2001 Apr	11304724
The inhibitory effect of dienogest, a synthetic steroid, on the growth of human endometrial stromal cells in vitro.	2001 Apr	11279296
15N NMR relaxation studies of backbone dynamics in free and steroid-bound Delta 5-3-ketosteroid isomerase from Pseudomonas testosteroni.	2001 Apr 3	11300777
Effects of nandrolone treatment on recovery in horses after strenuous physical exercise.	2001 Aug	11554492
Measurement of androgen and estrogen receptors in breast tissue from subjects with anabolic steroid-dependent gynecomastia.	2001 Aug 17	11554608
The effects of postmenopausal hormone replacement therapy and oral contraceptives on the endogenous estradiol metabolism.	2001 Dec	11753761
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
Anabolic steroid abuse and cardiac sudden death: a pathologic study.	2001 Feb	11175645
Urinary nandrolone metabolites of endogenous origin in man: a confirmation by output regulation under human chorionic gonadotropin stimulation.	2001 Jan	11231992
The anabolic-androgenic steroid nandrolone decanoate affects the density of dopamine receptors in the male rat brain.	2001 Jan	11168533
Assessment of hormonally active agents in the reproductive tract of female nonhuman primates.	2001 Jan-Feb	11215689
Novel amino acid substitutional mutation, tyrosine-739-aspartic acid, in the androgen receptor gene in complete androgen insensitivity syndrome.	2001 Jun	11380707
Differential effects of nandrolone decanoate in fast and slow rat skeletal muscles.	2001 Mar	11252066
[Treatment of endometriosis with dienogest: preliminary report].	2001 May	11526761
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.	2001 May	11331656
Aggression in male rats receiving anabolic androgenic steroids: effects of social and environmental provocation.	2001 Nov	11673914
Effect of nandrolone decanoate on the lipid profile of male peritoneal dialysis patients.	2001 Nov-Dec	11783772
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
Melatonin elicits nuclear exclusion of the human androgen receptor and attenuates its activity.	2001 Oct 1	11582594
[Urinary nandrolone metabolites in antidoping control].	2001 Sep	11787429
Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women.	2001 Sep	11588945
Silymarin inhibits function of the androgen receptor by reducing nuclear localization of the receptor in the human prostate cancer cell line LNCaP.	2001 Sep	11532861
Determination of nandrolone and metabolites in urine samples from sedentary persons and sportsmen.	2001 Sep 25	11587353
Effect of combined treatment with nandrolone and cocaine on the NMDA receptor gene expression in the rat nucleus accumbens and periaqueductal gray.	2002	12072144
Role of androgens in female genital sexual arousal: receptor expression, structure, and function.	2002 Apr	12007897
Randomized prospective comparison between erythropoietin and androgens in CAPD patients.	2002 Apr	11918762
Aromatase and breast cancer: W39R, an inactive protein.	2002 Apr	11916629
Effects of withdrawal from anabolic androgenic steroids on aggression in adult male rats.	2002 Apr 1	12062318
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
Metabolic effects of nandrolone decanoate and resistance training in men with HIV.	2002 Dec	12388173
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
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.	2002 Jan	12064656
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
The effects of nandrolone decanoate on nutritional parameters in hemodialysis patients.	2002 Jul	12141405
Steroid receptor concentration in aged rat hindlimb muscle: effect of anabolic steroid administration.	2002 Jul	12070211
Treatment for HIV wasting withdrawn.	2002 Jun	12141285
Anabolic androgenic steroid affects competitive behaviour, behavioural response to ethanol and brain serotonin levels.	2002 Jun 15	12048171
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
Successful DNA typing of a urine sample in a doping control case using human mitochondrial DNA analysis.	2002 Sep	12356033

Patents

Sample Use Guides

In Vivo Use Guide

50 to 100 mg per week (women) 100 to 200 mg per week (men) For children from 2 to 13 years of age, the average dose is 25 to 50 mg every 3 to 4 weeks.

Route of Administration: Intramuscular

In Vitro Use Guide

Unknown

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