Alfaxalone

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

Identification

Generic Name
Alfaxalone
DrugBank Accession Number
DB11371
Background

Alfaxalone, also known as alphaxalone or alphaxolone, is a neuroactive steroid and general anaesthetic. It is used in veterinary practice under the trade name Alfaxan, and is licensed for use in both dogs and cats. Along with alfadolone, it is also one of the constituents of anesthetic drug mixture althesin.

Type
Small Molecule
Groups
Vet approved
Structure
Weight
Average: 332.484
Monoisotopic: 332.23514489
Chemical Formula
C21H32O3
Synonyms
  • Alfaxalone
External IDs
  • GR 2/234
  • GR-2/234

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

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
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Alfaxalone is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Alfaxalone.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Alfaxalone.
AgomelatineThe risk or severity of CNS depression can be increased when Agomelatine is combined with Alfaxalone.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with Alfaxalone.
Food Interactions
Not Available

Categories

ATC Codes
N01AX05 — Alfaxalone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 3-alpha-hydroxysteroids / 11-oxosteroids / Secondary alcohols / Ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
11-oxosteroid / 20-oxosteroid / 3-alpha-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Hydrocarbon derivative / Hydroxysteroid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
corticosteroid hormone (CHEBI:34531)
Affected organisms
Not Available

Chemical Identifiers

UNII
BD07M97B2A
CAS number
23930-19-0
InChI Key
DUHUCHOQIDJXAT-OLVMNOGESA-N
InChI
InChI=1S/C21H32O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h13-17,19,23H,4-11H2,1-3H3/t13-,14+,15-,16+,17-,19+,20-,21+/m0/s1
IUPAC Name
(1S,2S,5R,7S,10S,11S,14S,15S)-14-acetyl-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C(=O)C[C@]12C)C(C)=O

References

General References
  1. Roan R: Use of alfaxalone in rabbits. Vet Rec. 2009 Feb 7;164(6):188. [Article]
  2. Strachan FA, Mansel JC, Clutton RE: A comparison of microbial growth in alfaxalone, propofol and thiopental. J Small Anim Pract. 2008 Apr;49(4):186-90. doi: 10.1111/j.1748-5827.2007.00473.x. Epub 2008 Jan 11. [Article]
  3. Vettorato E: Prolonged intravenous infusion of alfaxalone in a cat. Vet Anaesth Analg. 2013 Sep;40(5):551-2. doi: 10.1111/vaa.12044. Epub 2013 Apr 24. [Article]
  4. Herbert GL, Murison PJ: Eye position of cats anaesthetised with alfaxalone or propofol. Vet Rec. 2013 Apr 6;172(14):365. doi: 10.1136/vr.101404. Epub 2013 Feb 5. [Article]
  5. Goodwin W, Keates H, Pasloske K, Pearson M, Sauer B, Ranasinghe MG: Plasma pharmacokinetics and pharmacodynamics of alfaxalone in neonatal foals after an intravenous bolus of alfaxalone following premedication with butorphanol tartrate. Vet Anaesth Analg. 2012 Sep;39(5):503-10. doi: 10.1111/j.1467-2995.2012.00734.x. Epub 2012 May 30. [Article]
  6. Bertelsen MF, Sauer CD: Alfaxalone anaesthesia in the green iguana (Iguana iguana). Vet Anaesth Analg. 2011 Sep;38(5):461-6. doi: 10.1111/j.1467-2995.2011.00640.x. [Article]
  7. Jungck E, Kloss T, Blendl M, Hoerster W, Klaucke D: [Experiences with the steroid narcotic alfaxalone/alfadolone (Aurantex) in emergency patients in rescue service]. Anasth Intensivther Notfallmed. 1983 Feb;18(1):8-13. [Article]
  8. Brewster ME, Estes KS, Bodor N: Development of a non-surfactant formulation for alfaxalone through the use of chemically-modified cyclodextrins. J Parenter Sci Technol. 1989 Nov-Dec;43(6):262-5. [Article]
  9. Adami C, d'Ovidio D, Casoni D: Alfaxalone-butorphanol versus alfaxalone-morphine combination for immersion anaesthesia in oriental fire-bellied toads (Bombina orientalis). Lab Anim. 2015 Aug 25. pii: 0023677215601300. [Article]
  10. Tamura J, Ishizuka T, Fukui S, Oyama N, Kawase K, Itami T, Miyoshi K, Sano T, Pasloske K, Yamashita K: Sedative effects of intramuscular alfaxalone administered to cats. J Vet Med Sci. 2015 Aug;77(8):897-904. doi: 10.1292/jvms.14-0200. Epub 2015 Mar 19. [Article]
KEGG Drug
D07282
KEGG Compound
C13803
PubChem Compound
104845
PubChem Substance
347827976
ChemSpider
94637
BindingDB
50164570
RxNav
1544577
ChEBI
34531
ChEMBL
CHEMBL190279
ZINC
ZINC000004081122
PDBe Ligand
EY4
Wikipedia
Alfaxalone
PDB Entries
6cdu

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0242 mg/mLALOGPS
logP3.23ALOGPS
logP3.06Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)18.3Chemaxon
pKa (Strongest Basic)-1.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area54.37 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity93.57 m3·mol-1Chemaxon
Polarizability38.64 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ac1-3930000000-0197081ff727780b04f8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0039000000-4d7fc9157c4850320de7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-7902a8c65893a338db45
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01c1-0796000000-5b18c81705dab0f27f45
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-0009000000-3d9e6dfe6707eebca6f6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uea-0049000000-fe4aaf99c7f65bd153f1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-1910000000-67541086006653468fe3
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]-188.6011187
predicted
DarkChem Lite v0.1.0
[M-H]-170.29575
predicted
DeepCCS 1.0 (2019)
[M+H]+189.6120187
predicted
DarkChem Lite v0.1.0
[M+H]+172.12064
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.82014
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:13 / Updated at February 21, 2021 18:53