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
Show more names
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
- Formal charge
- 0
- Complexity
- 680
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Melting Point
32-35
118 °C
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
- solubility
- 45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.8 mg/mL
- form
- powder
- color
- white to light yellow
- Water Solubility
- 664 ug/L · 664ug/L(37 ºC)
- InChIKey
- JKWKMORAXJQQSR-MOPIKTETSA-N
- SMILES
- [C@@]12([H])CC[C@H](OC(=O)CCCCCCCCC)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H] |&1:0,4,17,21,23,33,r|
- CAS DataBase Reference
- 360 · 360-70-3
- FDA UNII
- 45187 T098 · H45187T098
- NCI Drug Dictionary
- nandrolone decanoate
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 351 · H351-H360FD
- Precautionary statements
- 201 · P201-P202-P280-P308+P313-P405-P501
- Hazard Codes
- Xn
- Risk Statements
- 40 · 40
- Safety Statements
- 22 · 22-36
- WGK Germany
- 3 · 3
- RTECS
- 7967000 · KG7967000
- HS Code
- 2937290000 · 2937290000
- Toxicity
- 50 intraperitoneal · LD50 intraperitoneal in mouse: > 566mg/kg
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Drug Induced Liver Injury
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
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 22-36
- Hazard statements
- H351-H360FD
- Precautionary statements
- P201-P202-P280-P308+P313-P405-P501
Chemistry & industry
Pharmacology
Pharmacodynamics
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
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
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
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
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.
Absorption, Distribution and Excretion
A 50 mg intramuscular dose of nandrolone decanoate reaches a mean Cmax 2.14 ng/mL, with a mean Tmax of 30 hours, and a mean AUC of 400 h\*ng/mL. A 100 mg intramuscular dose of nandrolone decanoate reaches a mean Cmax 4.26 ng/mL, with a mean Tmax of 30 hours, and a mean AUC of 862 h\*ng/mL. A 150 mg intramuscular dose of nandrolone decanoate reaches a mean Cmax 5.16 ng/mL, with a mean Tmax of 72 hours, and a mean AUC of 1261 h\*ng/mL.
Nandrolone decanoate is eliminated as urinary metabolites, however data regarding elimination in the feces are not readily available. Data in cattle shows that [nandrolone] is 30% eliminated in the feces.
50 mg, 100 mg, and 150 mg doses of nadrolone decanoate had mean apparent clearances of 80.0 L/h, 74.3 L/h, and 76.2 L/h respectively.
Uses & manufacturing
Applications
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
Additional notes
DefinitionChEBI: Nandrolone decanoate is a steroid ester.
Related reactions
Linked notes
Loading…