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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H30O2
Molecular Weight 302.4518
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORETHANDROLONE

SMILES

CC[C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4([H])[C@@]3([H])CC[C@@]21C)O

InChI

InChIKey=ZDHCJEIGTNNEMY-XGXHKTLJSA-N
InChI=1S/C20H30O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h12,15-18,22H,3-11H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H30O2
Molecular Weight 302.4518
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

NORETHANDROLONE, a nandrolone derivative, is a synthetic hormone with anabolic and androgenic properties and moderate progestational activity. It was used to treat, among others, anorexia nervosa, severe burns and trauma, decubitus ulcers, osteoporosis, gastrointestinal diseases. Its list of prescriptions included preparation for and recovery from surgery, bone fracture healing, severe or prolonged illness, and various forms of malnourishment in adults and children. It was withdrawn for the market in most countries in the 1960s, however, it remains viable on the veterinary drug market in Australia.

Originator

Curator's Comment:: G.D. Searle, LLC is a wholly owned trademark of Pfizer.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nilevar

Approved Use

Nilevar was prescribed for a variety of illnesses that were benefited by a protein sparing anabolic agent, Listed indications included preparation for and recovery from surgery, severe or prolonged illness, anorexia nervosa, severe burns and trauma, decubitus ulcers, osteoporosis, bone fracture healing, gastrointestinal disease, prolonged corticosteroid administration, and various forms of malnourishment in adults and children.
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day steady, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 43 years
n = 1
Health Status: unhealthy
Age Group: 43 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Cholestasis...
AEs leading to
discontinuation/dose reduction:
Cholestasis (grade 5, 1 patient)
Sources:
20 mg 1 times / day steady, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: steady
Dose: 20 mg, 1 times / day
Co-administed with::
Prednisone(5.0 mg. daily)
Sources:
unhealthy, 57 years
n = 1
Health Status: unhealthy
Age Group: 57 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Peliosis hepatis...
AEs leading to
discontinuation/dose reduction:
Peliosis hepatis (grade 5, 1 patient)
Sources:
40 mg 1 times / day steady, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 75 years
n = 1
Health Status: unhealthy
Condition: generalized purpura | weakness
Age Group: 75 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Jaundice...
AEs leading to
discontinuation/dose reduction:
Jaundice (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Cholestasis grade 5, 1 patient
Disc. AE
300 mg 1 times / day steady, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 43 years
n = 1
Health Status: unhealthy
Age Group: 43 years
Sex: M
Population Size: 1
Sources:
Peliosis hepatis grade 5, 1 patient
Disc. AE
20 mg 1 times / day steady, oral
Dose: 20 mg, 1 times / day
Route: oral
Route: steady
Dose: 20 mg, 1 times / day
Co-administed with::
Prednisone(5.0 mg. daily)
Sources:
unhealthy, 57 years
n = 1
Health Status: unhealthy
Age Group: 57 years
Sex: F
Population Size: 1
Sources:
Jaundice 1 patient
Disc. AE
40 mg 1 times / day steady, oral
Dose: 40 mg, 1 times / day
Route: oral
Route: steady
Dose: 40 mg, 1 times / day
Sources:
unhealthy, 75 years
n = 1
Health Status: unhealthy
Condition: generalized purpura | weakness
Age Group: 75 years
Sex: F
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Heterogenous changes in neuropeptide Y, norepinephrine and epinephrine concentrations in the hearts of diabetic rats.
2005 Aug 31
Factors and markers of growth hormone secretion and gonadal function in Fanconi anemia.
2007 Apr
Wound healing in patients with cancer.
2008 Jan 11
Heart lesions associated with anabolic steroid abuse: comparison of post-mortem findings in athletes and norethandrolone-induced lesions in rabbits.
2009 Jul
Impact of acute psychosocial stress on peripheral blood gene expression pathways in healthy men.
2009 Oct
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:57:58 UTC 2021
Edited
by admin
on Fri Jun 25 22:57:58 UTC 2021
Record UNII
P7W01638W6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORETHANDROLONE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
NORETHANDROLONE [INN]
Common Name English
17.ALPHA.-ETHYL-17.BETA.-HYDROXYESTR-4-EN-3-ONE
Systematic Name English
NORETHANDROLONE [MART.]
Common Name English
NILEVAR
Brand Name English
NSC-70581
Code English
SOLEVAR
Brand Name English
NORETHANDROLONE [WHO-DD]
Common Name English
PRONABOL
Brand Name English
NORETHANDROLONE [MI]
Common Name English
Classification Tree Code System Code
LIVERTOX NORETHANDROLONE
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
DEA NO. 4000
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
WHO-ATC A14AA09
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
NCI_THESAURUS C243
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
WHO-VATC QA14AA09
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C80802
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
EPA CompTox
52-78-8
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
EVMPD
SUB09361MIG
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-153-5
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
MERCK INDEX
M8055
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY Merck Index
RXCUI
7513
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY RxNorm
INN
664
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
DRUG CENTRAL
1961
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
WIKIPEDIA
NORETHANDROLONE
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL1697845
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
DRUG BANK
DB12787
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
FDA UNII
P7W01638W6
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
MESH
D009639
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
PUBCHEM
5858
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
CAS
52-78-8
Created by admin on Fri Jun 25 22:57:58 UTC 2021 , Edited by admin on Fri Jun 25 22:57:58 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY