NORETHANDROLONE

First approved in 1956

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H30O2
Molecular Weight	302.451
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@](O)(CC)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

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	302.451
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://anabolic.org/nilevar-norethandrolone/ | https://www.ncbi.nlm.nih.gov/mesh/68009639

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 It was withdrawn for the market in most countries in the 1960s, however, it remains viable on the veterinary drug market in Australia.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

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
anorexia nervosa 1 Sources: https://anabolic.org/nilevar-norethandrolone/	Primary		Approved 8429	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/13851171	unhealthy, 43 years n = 1 Health Status: unhealthy Age Group: 43 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13851171	Disc. AE: Cholestasis... AEs leading to discontinuation/dose reduction: Cholestasis (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/13851171
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: https://pubmed.ncbi.nlm.nih.gov/13851171	unhealthy, 57 years n = 1 Health Status: unhealthy Age Group: 57 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13851171	Disc. AE: Peliosis hepatis... AEs leading to discontinuation/dose reduction: Peliosis hepatis (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/13851171
40 mg 1 times / day steady, oral Dose: 40 mg, 1 times / day Route: oral Route: steady Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13851177	unhealthy, 75 years n = 1 Health Status: unhealthy Condition: generalized purpura \| weakness Age Group: 75 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13851177	Disc. AE: Jaundice... AEs leading to discontinuation/dose reduction: Jaundice (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/13851177

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/13851171	unhealthy, 43 years n = 1 Health Status: unhealthy Age Group: 43 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13851171
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: https://pubmed.ncbi.nlm.nih.gov/13851171	unhealthy, 57 years n = 1 Health Status: unhealthy Age Group: 57 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13851171
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: https://pubmed.ncbi.nlm.nih.gov/13851177	unhealthy, 75 years n = 1 Health Status: unhealthy Condition: generalized purpura \| weakness Age Group: 75 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13851177

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L1LAH
AHH Chemical co.,ltd	MT-57194	http://www.ahhchemical.com/product/MT-57194.html
AN PharmaTech	AN-41633
Aurora Fine Chemicals LLC	A17.921.621	http://online.aurorafinechemicals.com/info?ID=A17.921.621
BioSynth	W-105795	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/W-105795.html
ChemMol	49425869	http://www.chemmol.com/chemmol/49425869.html
ChemMol	99097792	http://www.chemmol.com/chemmol/99097792.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0619614
Compound Cloud	5858
LGC Standards	DRE-C15644900	https://www.lgcstandards.com/US/en/p/DRE-C15644900
LGC Standards	LGCAMP1199.00-11	https://www.lgcstandards.com/US/en/p/LGCAMP1199.00-11
LGC Standards	LGCFOR1199.00	https://www.lgcstandards.com/US/en/p/LGCFOR1199.00
Lab Network	LN01287267	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01287267
NovoSeek	5858
OChem	2882	http://www.ocheminc.com/index.php?act=psearch&pid=198N409
Race Chemical	RV022507422
Sigma Aldrich	N-914
Sigma Aldrich	N-914\|CERILLIAN
Sigma-Aldrich	N-914_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/n914?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Tetrahedron	TS74808
Toronto Research Chemicals	KIT6610
Toronto Research Chemicals	N675000
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-1081M
ZINC	ZINC000003875356	http://zinc15.docking.org/substances/ZINC000003875356

PubMed

Title	Date	PubMed
The metabolism of norethandrolone in the horse: characterization of 16-, 20- and 21-oxygenated metabolites by gas chromatography/mass spectrometry.	2001 Feb	11288196
Heterogenous changes in neuropeptide Y, norepinephrine and epinephrine concentrations in the hearts of diabetic rats.	2005 Aug 31	15955747
Altered serotonin synthesis, turnover and dynamic regulation in multiple brain regions of mice lacking the serotonin transporter.	2005 Nov	16183083
Rapid test by liquid chromatography/tandem mass spectrometry to evaluate equine urine reactivity towards 17beta-OH steroids.	2006	16862626
[Nosologic discussion between Fanconi disease and congenital dyskeratosis: 1 case of congenital bone marrow aplasia].	2006 Sep	16854573
Factors and markers of growth hormone secretion and gonadal function in Fanconi anemia.	2007 Apr	17336561
Determination of anabolic steroids in muscle tissue by liquid chromatography-tandem mass spectrometry.	2007 Oct 17	17887801
Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry.	2008	18085508
Wound healing in patients with cancer.	2008 Jan 11	18264518
Catecholamine reuptake inhibition causes weight loss by increasing locomotor activity and thermogenesis.	2008 May	17687262
Oxandrolone Improves Height Velocity and BMI in Patients with Cystic Fibrosis.	2009	20145725
Heart lesions associated with anabolic steroid abuse: comparison of post-mortem findings in athletes and norethandrolone-induced lesions in rabbits.	2009 Jul	19027274
Impact of acute psychosocial stress on peripheral blood gene expression pathways in healthy men.	2009 Oct	19577611
Restoring arterial pressure with norepinephrine improves muscle tissue oxygenation assessed by near-infrared spectroscopy in severely hypotensive septic patients.	2010 Nov	20689910

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:35 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:35 GMT 2023`
Record UNII	P7W01638W6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORETHANDROLONE

Official Name

English

norethandrolone [INN]

Common Name

English

Norethandrolone [WHO-DD]

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

PRONABOL

Brand Name

English

NORETHANDROLONE [MI]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NORETHANDROLONE