NANDROLONE

US Previously Marketed

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

Structure Search

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

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

Molecular Formula	C18H26O2
Molecular Weight	274.3978
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 2678
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18809391	Agonist 2678
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 2678

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 8429	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 2010

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
Hair analysis and detectability of single dose administration of androgenic steroid esters.	2000 Jan 10	10689586
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
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	11507757
The role of nandrolone decanoate in patients with end stage renal disease in the erythropoietin era.	2001 Apr	11394696
Steroidal control of male hamster sexual behavior in Me and MPOA: effects of androgen dose and tamoxifen.	2001 Apr	11337005
15N NMR relaxation studies of backbone dynamics in free and steroid-bound Delta 5-3-ketosteroid isomerase from Pseudomonas testosteroni.	2001 Apr 3	11300777
Gas chromatography-combustion-isotope ratio mass spectrometry analysis of 19-norsteroids: application to the detection of a nandrolone metabolite in urine.	2001 Aug 15	11499480
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
Comparison of the efficiences of enzymatic and chemical hydrolysis of (nortestosterone and diethylstilboestrol) glucuronides in bovine urine.	2001 Jun 15	11417866
Doping control for nandrolone using hair analysis.	2001 Mar	11248508
[Endometriosis of the lungs: analysis of diagnosis and therapy].	2001 May	11526762
[Treatment of endometriosis with dienogest: preliminary report].	2001 May	11526761
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
[New gestagens--advantages and disadvantages].	2001 Sep	11594150
Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women.	2001 Sep	11588945
Estradiol valerate/dienogest.	2002	11827562
Dienogest is as effective as triptorelin in the treatment of endometriosis after laparoscopic surgery: results of a prospective, multicenter, randomized study.	2002 Apr	11937116
Aromatase and breast cancer: W39R, an inactive protein.	2002 Apr	11916629
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
The anabolic androgenic steroid, nandrolone decanoate, increases the density of Fos-like immunoreactive neurons in limbic regions of guinea-pig brain.	2002 Feb	11876781
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.	2002 Jan	12064656
Endogenous nandrolone metabolites in human urine. Two-year monitoring of male professional soccer players.	2002 Jan-Feb	11888015
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
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
Anti-androgenic and hair growth promoting activities of Lygodii spora (spore of Lygodium japonicum) I. Active constituents inhibiting testosterone 5alpha-reductase.	2002 May	12033503
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
Urine nandrolone metabolites: false positive doping test?	2002 Oct	12351328
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

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:59 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:59 GMT 2023`
Record UNII	6PG9VR430D
Record Status	`Validated (UNII)`
Record Version

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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

NANDROLONE DECANOATE IMPURITY D [EP IMPURITY]

Common Name

English

19-NORTESTOSTERONE

Common Name

English

NANDROLONE CIII [USP-RS]

Common Name

English

BIOBOL

Brand Name

English

DECADURA

Brand Name

English

Nandrolone [WHO-DD]

Common Name

English

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

Systematic Name

English

NANDROLONE [MART.]

Common Name

English

HYBOLIN

Brand 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