Oxabolone cipionate

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Oxabolone cipionate
Accession Number
DB13185
Type
Small Molecule
Groups
Experimental
Description

Oxabolone cipionate is the C17β cypionate ester and a prodrug of Oxabolone. A synthetic anabolic-androgenic (AAS) steroid, it is a derivative of 19-nortestosterone (nandrolone). It is considered as a performance enhancing drug thus is prohibited from use in sports.

Structure
Thumb
Synonyms
  • 4-hydroxy-19-nortestosterone 17β-cypionate
  • Cipionate d'oxabolone
  • Cipionato de oxabolona
  • Oxabolone 17-cyclopentanepropionate
  • Oxabolone cypionate
  • Oxaboloni cipionas
External IDs
FI 5852 / FI-5852
Categories
UNII
5RXY50Q01N
CAS number
1254-35-9
Weight
Average: 414.586
Monoisotopic: 414.277009704
Chemical Formula
C26H38O4
InChI Key
KHKDIUPVDIEHAH-KXLSUQFWSA-N
InChI
InChI=1S/C26H38O4/c1-26-15-14-18-17-9-11-22(27)25(29)20(17)8-7-19(18)21(26)10-12-23(26)30-24(28)13-6-16-4-2-3-5-16/h16-19,21,23,29H,2-15H2,1H3/t17-,18-,19-,21+,23+,26+/m1/s1
IUPAC Name
(1S,2R,10R,11S,14S,15S)-6-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl 3-cyclopentylpropanoate
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=C(O)C(=O)CC[C@]4([H])[C@@]3([H])CC[C@]12C)OC(=O)CCC1CCCC1

Pharmacology

Indication

Used as a performance enhancing drug illicitly in athletes.

Pharmacodynamics

Androgenic effects include enhanced secondary sexual characteristics.

Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

The prodrug oxabolone cipionate is converted to oxabolone. Oxabolone is then metabolized into 4-Hydroxyestr-4-en-3,17-dione (M2) which is the most abundant metabolite via oxidation of the 17-hydroxyl group. 4-Hydroxyestran-3,17-dione (M1) is formed by reduction of the A ring double bond along with the oxidation of the 17-hydroxyl group. Three isomeric compounds exist as another metabolite, as the 3α,4-dihydroxy-5α-estran-17-one, 3α,4-dihydroxy-5β-estran-17-one, and 3β,4-dihydroxy-5α-estran-17-one [2].

Route of elimination

The metabolites and unchanged form of oxabolone can be detected in the urine [2].

Half life
Not Available
Clearance

The elimination on the first day following intravenous injection of oxabolone cipionate is slow and reaches a rapid excretion phase with the maximum urinary level in the fifth day of administration [2].

Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
AcrivastineAcrivastine may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
AdefovirAdefovir may decrease the excretion rate of Oxabolone cipionate which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Kicman AT: Pharmacology of anabolic steroids. Br J Pharmacol. 2008 Jun;154(3):502-21. doi: 10.1038/bjp.2008.165. [PubMed:18500378]
  2. Barbarulo MV, Buiarelli F, Ciardi M, Giarrusso A, Rosati F, Cartoni GP: Capillary GC-MS investigation of the metabolism and excretion of oxabolone in man Journal of Separation Science. 1995 Nov 1;18(11):705–708.
  3. Hartgens F, Kuipers H: Effects of androgenic-anabolic steroids in athletes. Sports Med. 2004;34(8):513-54. [PubMed:15248788]
  4. Hartgens F, Rietjens G, Keizer HA, Kuipers H, Wolffenbuttel BH: Effects of androgenic-anabolic steroids on apolipoproteins and lipoprotein (a). Br J Sports Med. 2004 Jun;38(3):253-9. [PubMed:15155420]
External Links
PubChem Compound
68952
PubChem Substance
347829285
ChemSpider
62175
ChEBI
31940
ChEMBL
CHEMBL2105318
Wikipedia
Oxabolone_cipionate
ATC Codes
A14AB03 — Oxabolone cipionate

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00377 mg/mLALOGPS
logP4.43ALOGPS
logP5.29ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)9.23ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity116.85 m3·mol-1ChemAxon
Polarizability48.9 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Estrogens and derivatives / Hydroxysteroids / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Enols / Organic oxides / Hydrocarbon derivatives
Substituents
Steroid ester / Estrogen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / Estrane-skeleton / 4-hydroxysteroid / Hydroxysteroid / Oxosteroid / Delta-4-steroid / Cyclohexenone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Drug created on June 15, 2017 16:50 / Updated on November 02, 2018 07:35