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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H26O2
Molecular Weight 274.3978
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NANDROLONE

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@H]2O

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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NANDROLONE DECANOATE
PubMed

PubMed

TitleDatePubMed
The effect of anabolic steroid on the distribution of muscle fiber in rat hind limb.
2001
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
[What is the role of hormonal treatments in acne?].
2001 Apr
Human cell lines as an in vitro/in vivo model for prostate carcinogenesis and progression.
2001 Apr
Effects of nandrolone treatment on recovery in horses after strenuous physical exercise.
2001 Aug
Gas chromatography-combustion-isotope ratio mass spectrometry analysis of 19-norsteroids: application to the detection of a nandrolone metabolite in urine.
2001 Aug 15
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
Detection and determination of anabolic steroids in nutritional supplements.
2001 Jul
Novel amino acid substitutional mutation, tyrosine-739-aspartic acid, in the androgen receptor gene in complete androgen insensitivity syndrome.
2001 Jun
Comparison of the efficiences of enzymatic and chemical hydrolysis of (nortestosterone and diethylstilboestrol) glucuronides in bovine urine.
2001 Jun 15
Recombinant expression and purification of human androgen receptor in a baculovirus system.
2001 Jun 15
Differential effects of nandrolone decanoate in fast and slow rat skeletal muscles.
2001 Mar
Doping control for nandrolone using hair analysis.
2001 Mar
Aggression in male rats receiving anabolic androgenic steroids: effects of social and environmental provocation.
2001 Nov
Detection of nandrolone metabolites in urine after a football game in professional and amateur players: a Bayesian comparison.
2001 Nov 1
[New gestagens--advantages and disadvantages].
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
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
Dienogest is as effective as triptorelin in the treatment of endometriosis after laparoscopic surgery: results of a prospective, multicenter, randomized study.
2002 Apr
Aromatase and breast cancer: W39R, an inactive protein.
2002 Apr
The popliteal-artery entrapment syndrome in a patient using anabolic steroids.
2002 Apr 18
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
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
Endogenous nandrolone metabolites in human urine: preliminary results to discriminate between endogenous and exogenous origin.
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
The effects of nandrolone decanoate on nutritional parameters in hemodialysis patients.
2002 Jul
Treatment for HIV wasting withdrawn.
2002 Jun
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
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
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 Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
LIVERTOX 667
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
NDF-RT N0000175824
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
NCI_THESAURUS C243
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
DEA NO. 4000
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
WHO-ATC A14AB01
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
NCI_THESAURUS C2360
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
WHO-ATC S01XA11
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
WHO-VATC QS01XA11
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
Code System Code Type Description
MESH
D009277
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
HSDB
434-22-0
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
WIKIPEDIA
NANDROLONE
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
RXCUI
7244
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB00984
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
CAS
434-22-0
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
ECHA (EC/EINECS)
207-101-0
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
NCI_THESAURUS
C29279
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
IUPHAR
6949
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
PUBCHEM
9904
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
INN
295
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
EPA CompTox
434-22-0
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
MERCK INDEX
M7720
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL2104906
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY
EVMPD
SUB09148MIG
Created by admin on Tue Oct 22 00:47:18 UTC 2019 , Edited by admin on Tue Oct 22 00:47:18 UTC 2019
PRIMARY