Alfaxalone

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

Identification

Name
Alfaxalone
Accession Number
DB11371
Type
Small Molecule
Groups
Vet approved
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
GR 2/234 / GR-2/234
Categories
UNII
BD07M97B2A
CAS number
23930-19-0
Weight
Average: 332.484
Monoisotopic: 332.23514489
Chemical Formula
C21H32O3
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

Pharmacology

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

Interactions

Drug Interactions
DrugInteraction
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Alfaxalone.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Alfaxalone.
AceprometazineThe risk or severity of adverse effects can be increased when Aceprometazine is combined with Alfaxalone.
AdipiplonThe risk or severity of adverse effects can be increased when Adipiplon is combined with Alfaxalone.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Alfaxalone.
AlaproclateThe risk or severity of adverse effects can be increased when Alfaxalone is combined with Alaproclate.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Alfaxalone.
AlimemazineThe risk or severity of adverse effects can be increased when Alfaxalone is combined with Alimemazine.
AllopregnanoloneThe risk or severity of adverse effects can be increased when Alfaxalone is combined with Allopregnanolone.
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Alfaxalone.
Food Interactions
Not Available

References

General References
  1. Roan R: Use of alfaxalone in rabbits. Vet Rec. 2009 Feb 7;164(6):188. [PubMed:19202182]
  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. [PubMed:18194193]
  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. [PubMed:23611452]
  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. [PubMed:23385007]
  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. [PubMed:22642499]
  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. [PubMed:21831051]
  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. [PubMed:6846760]
  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. [PubMed:2600731]
  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. [PubMed:26306614]
  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. [PubMed:25786416]
External Links
KEGG Drug
D07282
KEGG Compound
C13803
PubChem Compound
104845
PubChem Substance
347827976
ChemSpider
94637
BindingDB
50164570
ChEBI
34531
ChEMBL
CHEMBL190279
HET
EY4
Wikipedia
Alfaxalone
ATC Codes
N01AX05 — Alfaxalone
PDB Entries
6cdu

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
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
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ac1-3930000000-0197081ff727780b04f8

Taxonomy

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
Progestogin-skeleton / 20-oxosteroid / 3-hydroxysteroid / 3-alpha-hydroxysteroid / Hydroxysteroid / Oxosteroid / 11-oxosteroid / Cyclic alcohol / Secondary alcohol / Ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
corticosteroid hormone (CHEBI:34531)

Drug created on February 25, 2016 11:13 / Updated on August 02, 2018 06:23