NAV

Oxabolone cipionate

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

Identification

Generic Name
Oxabolone cipionate
DrugBank Accession Number
DB13185
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 414.586
Monoisotopic: 414.277009704
Chemical Formula
C26H38O4
Synonyms
  • 4-hydroxy-19-nortestosterone 17β-cypionate
  • Cipionate d'oxabolone
  • Cipionato de oxabolona
  • Oxabolone 17-cyclopentanepropionate
  • Oxabolone cipionate
  • Oxabolone cypionate
  • Oxaboloni cipionas
External IDs
  • FI 5852
  • FI-5852
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Pharmacology

Indication

Used as a performance enhancing drug illicitly in athletes.

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Contraindications & Blackbox Warnings
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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.

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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.

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAbacavir 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.
AcetazolamideAcetazolamide may increase the excretion rate of Oxabolone cipionate which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
Not Available

Categories

ATC Codes
A14AB03 — Oxabolone cipionate
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
3-oxo-delta-4-steroid / 3-oxosteroid / 4-hydroxysteroid / Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone / Delta-4-steroid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
5RXY50Q01N
CAS number
1254-35-9
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

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. [Article]
  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. [Article]
  3. Hartgens F, Kuipers H: Effects of androgenic-anabolic steroids in athletes. Sports Med. 2004;34(8):513-54. [Article]
  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. [Article]
PubChem Compound
68952
PubChem Substance
347829285
ChemSpider
62175
ChEBI
31940
ChEMBL
CHEMBL2105318
ZINC
ZINC000026892649
Wikipedia
Oxabolone_cipionate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0100900000-3b6d2dea50976712ccbe
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-0090500000-73fbc744714a63b95003
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1433900000-6cc2a514d7b0b447fb14
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-3593800000-fbedabda6a9dc3352e1b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-7518900000-6a7e14eb4cc2b455048b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1791100000-29af4da0b8d027e56c7e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-220.9254653
predicted
DarkChem Lite v0.1.0
[M-H]-203.58447
predicted
DeepCCS 1.0 (2019)
[M+H]+222.0242653
predicted
DarkChem Lite v0.1.0
[M+H]+205.47989
predicted
DeepCCS 1.0 (2019)
[M+Na]+221.4524653
predicted
DarkChem Lite v0.1.0
[M+Na]+211.52594
predicted
DeepCCS 1.0 (2019)

Drug created at June 15, 2017 22:50 / Updated at February 21, 2021 18:54