Nandrolone Decanoate

HCID 9677CAS 360-70-3

Basic information

Standard SMILES
CCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C
InChIKey
JKWKMORAXJQQSR-MOPIKTETSA-N
Molecular formula
C28H44O3
Average molar mass
428.6 g/mol
Monoisotopic mass
428.32904527

Overview

Nandrolone decanoate is a steroid ester.

Names & identifiers

Preferred name
Nandrolone Decanoate
IUPAC
[(8R,9S,10R,13S,14S,17S)-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] decanoate
English name
Nandrolone Decanoate
Molecular formula
C28H44O3
Molecular weight
428.65

Names & synonyms

NANDROLONE DECANOATE360-70-3DTXSID7023352Nandrolone decanoate ciii17beta-Hydroxyestr-4-en-3-one 17-decanoateDTXCID203352H45187T098Estr-4-en-3-one, 17-((1-oxodecyl)oxy)-, (17beta)-Decadurobolin(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl decanoate19 Nortestosterone Decanoate(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo(8.7.0.0^(2,7).0^(11,15))heptadec-6-en-14-yl decanoate
Show more names
DECADURABOLINAnabolicumNandrolone DeconateNandrolone Decanoate (DECA)19-NORTESTOSTERONE 17-DECANOATE17-beta-hydroxy-estr-4-en-3-ondecanoateNand DecaCartalax1Decanofort
RefChem:5568917 beta Hydroxyestr 4 en 3 one 17 decanoate17 beta-hydroxyestr-4-en-3-one 17-decanoate19 nor 4 Androstene 17 beta ol 3 one 17 decanoate206-639-3Deca-DurabolinRetabolilNorandrostenolone decanoate

Database identifiers

CAS
360-70-3
PubChem CID
9677
DTXSID
DTXSID7023352
ChEMBL
CHEMBL1200946
ChEBI
CHEBI:7467
UNII
H45187T098
EC Number
206-639-3
Nikkaji
J5.698G

Properties

Computed structural properties

XLogP
7.3
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
10
Heavy atoms
31

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals -> Listed in ZINC15

LogP2.62
Human Drugs · 3 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point · 2 items

32-35

118 °C

Physical DescriptionSolid

Physicochemical properties

Melting point
33 · 33-37°C
Boiling point
483.46 °C · 483.46°C (rough estimate)
alpha
32 · 32 º
Density
1.0406 · 1.0406 (rough estimate)
refractive index
1.47 · 1.4700 (estimate)
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (19.5%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P263, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 87 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationNandrolone decanoate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Estr-4-en-3-one, 17-[(1-oxodecyl)oxy]-, (17.beta.)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (19.5%)

Toxicology

Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

nandrolone decanoate

DILI Positive

Intramuscular

DOI:10.1016/j.drudis.2019.09.022

Safety data

wgk
3
rtecs
KG7967000
hs_code
2937290000
Toxicity
LD50 intraperitoneal in mouse: > 566mg/kg
risk_code
40
Signal word
Danger

Chemistry & industry

Pharmacology

Protein BindingData regarding the percent protein binding of nandrolone decanoate is not readily available. After nandrolone decanoate is hydrolyzed to [nandrolone], it is bound to sex hormone binding globulin.
Pharmacodynamics · 1 item

Nandrolone decanoate is an alkylated anabolic steroid indicated in the management of anemia of renal insufficiency and as an adjunct therapy in the treatment of senile and postmenopausal osteoporosis. It has a long duration of action as it is given every 3-4 weeks, and a wide therapeutic window as acute overdoses are rare. Patients should be counselled regarding the risks of giving this drug to patients with cardiac, renal, or hepatic diseases.

Mechanism of Action · 1 item

Nandrolone decanoate is hydrolyzed to [nandrolone], possibly by PDE7B. Nandrolone is brought into cells by receptor mediated endocytosis, where it interacts with the androgen receptor. After binding to the androgen receptor, a conformational change occurs, the androgen receptor enters the nucleus, dimerizes, and can then bind to segments of DNA to regulate transcription. Androgens can also regulate transcription through activation of ERK, Akt, and MAPK; or binding to and competitively inhibiting transcription factors.

Biological Half-Life · 1 item

Nandrolone decanoate has an absorption half life of 6 days and an elimination half life of 4.3 hours. Alternate studies have shown that nandrolone decanoate has a terminal half life of 7.1, 11.7, and 11.8 hours for doses of 50, 100, and 150 mg respectively.

Metabolism/Metabolites · 1 item

Nandrolone decanoate is hydrolyzed to [nandrolone], possibly by PDE7B. Nandrolone is further metabolized to the urinary metabolites 19-norandrosterone, 19-noretiocholanolone, and 19-norepiandrosterone. 19-norandrosterone is 3-O-glucuronidated by UGT2B7, UGT 1A4, UGT2B4, UGT1A3, and UGT1A1. 19-noretiocholanolone is 3-O-glucuronidated by UGT2B7, UGT2B4, UGT1A4, UGT1A10, UGT1A3, and UGT1A1.

MeSH Pharmacological Classification · 2 items

These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power.

Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS.

Uses & manufacturing

Use ClassificationPharmaceuticals
Applications · 3 items

DescriptionNandrolone decanoate, also known as nandrolone caprinate, is an alkylated anabolic steroid indicated in the management of anemia of renal insufficiency and as an adjunct therapy in the treatment of senile and postmenopausal osteoporosis. The process for creating esters of [nandrolone] was patented in Spain in 1959 and in 1960, it was described as having a long duration of action and strong anabolic effect compared to nandrolone and other esters. Nandrolone decanoate was granted FDA approval on 5 October 1962.

UsesNandrolone Decanoate is an anabolic steroid. Nandrolone decanoate is used in the treatment of osteoporosis in postmenopausal women. Nandrolone Decanoate is also used for some aplastic anemias. Control led Substance.

General DescriptionNandrolone decanoate,17β-hydroxyestr-4-en-3-one 17-decanoate, has been used inthe management of certain anemias, but the availability oferythropoietin has greatly reduced this use.

Upstream & downstream products

Upstream raw materials

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]

Additional notes

DefinitionChEBI: Nandrolone decanoate is a steroid ester.

Related reactions

1 records

Linked notes

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