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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H34O3
Molecular Weight 406.5571
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NANDROLONE PHENPROPIONATE

SMILES

[H][C@@]12CC[C@H](OC(=O)CCC3=CC=CC=C3)[C@@]1(C)CC[C@]4([H])[C@@]5([H])CCC(=O)C=C5CC[C@@]24[H]

InChI

InChIKey=UBWXUGDQUBIEIZ-QNTYDACNSA-N
InChI=1S/C27H34O3/c1-27-16-15-22-21-11-9-20(28)17-19(21)8-10-23(22)24(27)12-13-25(27)30-26(29)14-7-18-5-3-2-4-6-18/h2-6,17,21-25H,7-16H2,1H3/t21-,22+,23+,24-,25-,27-/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).

CNS Activity

Approval Year

1959
138
Targets

Targets

Primary TargetPharmacologyConditionPotency
Androgen receptor
42
Target ID: P10275
Gene ID: 367.0
Gene Symbol: AR
Target Organism: Homo sapiens (Human)
Agonist
2678
Agonist
2678
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

1.28312646E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

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:
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

PubMed

TitleDatePubMed
Detection of nandrolone, testosterone, and their esters in rat and human hair samples.
1999 Oct
Sport nutritional supplements: quality and doping controls.
2001
[The combined effect of retabolile and support loads on the post-traumatic reparation process in suspended rat muscles].
2001
[What is the role of hormonal treatments in acne?].
2001 Apr
The role of nandrolone decanoate in patients with end stage renal disease in the erythropoietin era.
2001 Apr
Body composition and anthropometry in bodybuilders: regional changes due to nandrolone decanoate administration.
2001 Apr
Gas chromatography-combustion-isotope ratio mass spectrometry analysis of 19-norsteroids: application to the detection of a nandrolone metabolite in urine.
2001 Aug 15
Novel amino acid substitutional mutation, tyrosine-739-aspartic acid, in the androgen receptor gene in complete androgen insensitivity syndrome.
2001 Jun
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
Validity of radioimmunological methods for determining free testosterone in serum.
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
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
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
Metabolic effects of nandrolone decanoate and resistance training in men with HIV.
2002 Dec
Physical provocation potentiates aggression in male rats receiving anabolic androgenic steroids.
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
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
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
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
Patents

Patents

JP2002522389A
24
JP2010526091A
24

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 PHENPROPIONATE
JAN   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
17β-Hydroxyestr-4-en-3-one hydrocinnamate
Systematic Name English
NANDROLONE PHENYLPROPIONATE [JAN]
Common Name English
DURABOLIN
Brand Name English
NANDROLONE PHENPROPIONATE [VANDF]
Common Name English
NANDROLONE PHENYLPROPIONATE
MART.  
Common Name English
NSC-23162
Code English
NANDROLONE PHENPROPIONATE [MI]
Common Name English
Nandrolone phenpropionate [WHO-DD]
Common Name English
NANDROLONE PHENPROPIONATE [USP IMPURITY]
Common Name English
NANDROLONE PHENPROPIONATE [ORANGE BOOK]
Common Name English
NANDROLONE PHENYLPROPIONATE [MART.]
Common Name English
NANDROLONE PHENPROPIONATE CIII
USP-RS  
Common Name English
Classification Tree Code System Code
DSLD 4210 (Number of products:3)
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
DEA NO. 4000
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
NCI_THESAURUS C243
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C66218
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200412
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
DRUG BANK
DB00984
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
EVMPD
SUB03385MIG
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
DRUG CENTRAL
1882
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
NSC
23162
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023353
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
CAS
62-90-8
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
FDA UNII
KF7Z9K2T3W
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
CHEBI
7468
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-551-9
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
MESH
C008580
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
MERCK INDEX
m7720
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY Merck Index
RXCUI
31495
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY RxNorm
PUBCHEM
229455
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
SMS_ID
100000085709
Created by admin on Fri Dec 15 19:08:45 UTC 2023 , Edited by admin on Fri Dec 15 19:08:45 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of NANDROLONE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966