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
Sport nutritional supplements: quality and doping controls.
2001
Advances in male hormonal contraception.
2001 Dec
Climodien (estradiol valerate 2 mg plus dienogest 2 mg) is safe and effective in the treatment of postmenopausal complaints.
2001 Dec
Effect of nandrolone decanoate on the lipid profile of male peritoneal dialysis patients.
2001 Nov-Dec
[Urinary nandrolone metabolites in antidoping control].
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
Estradiol valerate/dienogest.
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
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
The popliteal-artery entrapment syndrome in a patient using anabolic steroids.
2002 Apr 18
In situ detection and quantification of bursa of fabricius cellular proliferation or apoptosis in normal or steroid-treated neonatal chicks.
2002 Aug
Molecular imprinted polymer coated QCM for the detection of nandrolone.
2002 Aug
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
Treatment of menstruation-associated recurrence of hereditary pancreatitis with pharmacologic ovarian suppression.
2002 Aug 1
The F-box protein SKP2 mediates androgen control of p27 stability in LNCaP human prostate cancer cells.
2002 Aug 20
Lack of stimulatory effect of dienogest on the expression of intercellular adhesion molecule-1 and vascular cell adhesion molecule-1 by endothelial cell as compared with other synthetic progestins.
2002 Aug 30
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
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
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
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
Endogenous nandrolone metabolites in human urine. Two-year monitoring of male professional soccer players.
2002 Jan-Feb
The effects of nandrolone decanoate on nutritional parameters in hemodialysis patients.
2002 Jul
Nandrolone decanoate treatment induces changes in contractile responses of rat untrained fast-twitch skeletal muscle.
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
Nandrolone (Deca Durabolin) disappears in U.S., generic may return in July.
2002 Jun 28
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
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
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

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