U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of NANDROLONE

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
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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P10275
Gene ID: 367.0
Gene Symbol: AR
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
36.1 μg/L
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

AUC

ValueDoseCo-administeredAnalytePopulation
219.9 μg × h/L
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

Doses

DosePopulationAdverse 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:
unhealthy, adult
n = 5
Health Status: unhealthy
Condition: Anemias
Age Group: adult
Population Size: 5
Sources:
PubMed

PubMed

TitleDatePubMed
A report on alterations to the speaking and singing voices of four women following hormonal therapy with virilizing agents.
1999 Dec
Detection of nandrolone, testosterone, and their esters in rat and human hair samples.
1999 Oct
Sport nutritional supplements: quality and doping controls.
2001
The effect of anabolic steroid on the distribution of muscle fiber in rat hind limb.
2001
[The combined effect of retabolile and support loads on the post-traumatic reparation process in suspended rat muscles].
2001
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
[What is the role of hormonal treatments in acne?].
2001 Apr
Steroidal control of male hamster sexual behavior in Me and MPOA: effects of androgen dose and tamoxifen.
2001 Apr
Human cell lines as an in vitro/in vivo model for prostate carcinogenesis and progression.
2001 Apr
The inhibitory effect of dienogest, a synthetic steroid, on the growth of human endometrial stromal cells in vitro.
2001 Apr
15N NMR relaxation studies of backbone dynamics in free and steroid-bound Delta 5-3-ketosteroid isomerase from Pseudomonas testosteroni.
2001 Apr 3
Effects of nandrolone treatment on recovery in horses after strenuous physical exercise.
2001 Aug
Measurement of androgen and estrogen receptors in breast tissue from subjects with anabolic steroid-dependent gynecomastia.
2001 Aug 17
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
Anabolic steroid abuse and cardiac sudden death: a pathologic study.
2001 Feb
Urinary nandrolone metabolites of endogenous origin in man: a confirmation by output regulation under human chorionic gonadotropin stimulation.
2001 Jan
The anabolic-androgenic steroid nandrolone decanoate affects the density of dopamine receptors in the male rat brain.
2001 Jan
Assessment of hormonally active agents in the reproductive tract of female nonhuman primates.
2001 Jan-Feb
Novel amino acid substitutional mutation, tyrosine-739-aspartic acid, in the androgen receptor gene in complete androgen insensitivity syndrome.
2001 Jun
Differential effects of nandrolone decanoate in fast and slow rat skeletal muscles.
2001 Mar
[Treatment of endometriosis with dienogest: preliminary report].
2001 May
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.
2001 May
Aggression in male rats receiving anabolic androgenic steroids: effects of social and environmental provocation.
2001 Nov
Effect of nandrolone decanoate on the lipid profile of male peritoneal dialysis patients.
2001 Nov-Dec
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
Melatonin elicits nuclear exclusion of the human androgen receptor and attenuates its activity.
2001 Oct 1
[Urinary nandrolone metabolites in antidoping control].
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
Determination of nandrolone and metabolites in urine samples from sedentary persons and sportsmen.
2001 Sep 25
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
Randomized prospective comparison between erythropoietin and androgens in CAPD patients.
2002 Apr
Aromatase and breast cancer: W39R, an inactive protein.
2002 Apr
Effects of withdrawal from anabolic androgenic steroids on aggression in adult male rats.
2002 Apr 1
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
Metabolic effects of nandrolone decanoate and resistance training in men with HIV.
2002 Dec
Abuse of performance-enhancing drugs in sport.
2002 Feb
Role of IGF-I and IGF-binding proteins within diaphragm muscle in modulating the effects of nandrolone.
2002 Feb
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.
2002 Jan
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
The effects of nandrolone decanoate on nutritional parameters in hemodialysis patients.
2002 Jul
Steroid receptor concentration in aged rat hindlimb muscle: effect of anabolic steroid administration.
2002 Jul
Treatment for HIV wasting withdrawn.
2002 Jun
Anabolic androgenic steroid affects competitive behaviour, behavioural response to ethanol and brain serotonin levels.
2002 Jun 15
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
Successful DNA typing of a urine sample in a doping control case using human mitochondrial DNA analysis.
2002 Sep
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
HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
NORANDROSTENOLONE
Common Name English
NANDROLONE CIII
USP-RS  
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
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
LIVERTOX 667
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
NDF-RT N0000175824
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
NCI_THESAURUS C243
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
DEA NO. 4000
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
WHO-ATC A14AB01
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
NCI_THESAURUS C2360
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
FDA ORPHAN DRUG 712219
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
WHO-ATC S01XA11
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
WHO-VATC QS01XA11
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
Code System Code Type Description
FDA UNII
6PG9VR430D
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
MESH
D009277
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
DRUG CENTRAL
1879
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
HSDB
3368
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
WIKIPEDIA
NANDROLONE
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
RXCUI
7244
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00984
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
CAS
434-22-0
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-101-0
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
NCI_THESAURUS
C29279
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
IUPHAR
6949
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
USP_CATALOG
1454008
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY USP-RS
PUBCHEM
9904
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
INN
295
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
EPA CompTox
434-22-0
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
MERCK INDEX
M7720
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL2104906
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY
EVMPD
SUB09148MIG
Created by admin on Sat Jun 26 07:14:24 UTC 2021 , Edited by admin on Sat Jun 26 07:14:24 UTC 2021
PRIMARY