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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

[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

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
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
Hair analysis and detectability of single dose administration of androgenic steroid esters.
2000 Jan 10
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
[Treatment of acute purulent mediastinitis].
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
Non-protein bound dienogest in serum and salivary dienogest in women taking the oral contraceptives Certostat and Valette.
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
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
Anabolic steroids increase exercise tolerance.
2001 Jun
[New gestagens--advantages and disadvantages].
2001 Sep
Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women.
2001 Sep
Determination of nandrolone and metabolites in urine samples from sedentary persons and sportsmen.
2001 Sep 25
Dienogest is as effective as triptorelin in the treatment of endometriosis after laparoscopic surgery: results of a prospective, multicenter, randomized study.
2002 Apr
In situ detection and quantification of bursa of fabricius cellular proliferation or apoptosis in normal or steroid-treated neonatal chicks.
2002 Aug
Nandrolone: generic now in stock.
2002 Aug 9
Endogenous nandrolone metabolites in human urine. Two-year monitoring of male professional soccer players.
2002 Jan-Feb
Characterization of bone mineral composition in the proximal tibia of cynomolgus monkeys: effect of ovariectomy and nandrolone decanoate treatment.
2002 Mar
Synthesis of nitrile derivatives of estrogens.
2002 Oct 21
Nandrolone excretion is not increased by exhaustive exercise in trained athletes.
2002 Sep
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
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
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
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
LIVERTOX 667
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
NDF-RT N0000175824
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NCI_THESAURUS C243
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
WIKIPEDIA Designer-drugs-Nandrolone
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
DEA NO. 4000
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
WHO-ATC A14AB01
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
NCI_THESAURUS C2360
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
FDA ORPHAN DRUG 712219
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
FDA ORPHAN DRUG 855521
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
WHO-ATC S01XA11
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WHO-VATC QS01XA11
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Code System Code Type Description
FDA UNII
6PG9VR430D
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PRIMARY
MESH
D009277
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PRIMARY
RS_ITEM_NUM
1454008
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PRIMARY
DRUG CENTRAL
1879
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PRIMARY
HSDB
3368
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PRIMARY
NSC
3351
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
WIKIPEDIA
NANDROLONE
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
SMS_ID
100000084445
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
RXCUI
7244
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB00984
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PRIMARY
DAILYMED
6PG9VR430D
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
CAS
434-22-0
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-101-0
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
NCI_THESAURUS
C29279
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
IUPHAR
6949
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
PUBCHEM
9904
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
INN
295
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID7023350
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
MERCK INDEX
m7720
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2104906
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
EVMPD
SUB09148MIG
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
CHEBI
7466
Created by admin on Fri Dec 15 15:09:59 UTC 2023 , Edited by admin on Fri Dec 15 15:09:59 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of NANDROLONE
METABOLITE (PARENT)
Structure of 19-NORANDROSTERONE
METABOLITE LESS ACTIVE (PARENT)
Structure of 5.ALPHA.-DIHYDRONANDROLONE
NIH
NCATS
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