Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H32O3 |
Molecular Weight | 332.477 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC(=O)[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@H](O)CC[C@]34C
InChI
InChIKey=DUHUCHOQIDJXAT-OLVMNOGESA-N
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
Molecular Formula | C21H32O3 |
Molecular Weight | 332.477 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.alfaxan.co.uk/what-is-alfaxanCurator's Comment: description was created based on several sources, including:
http://www.vasg.org/pdfs/alfaxalone_vasg_05_11.pdf | https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM326904.pdf
Sources: http://www.alfaxan.co.uk/what-is-alfaxan
Curator's Comment: description was created based on several sources, including:
http://www.vasg.org/pdfs/alfaxalone_vasg_05_11.pdf | https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM326904.pdf
Alfaxalone is a rapidly acting hydrophobic synthetic neurosteroid. It is indicated for the induction and maintenance of anesthesia and for induction of anesthesia followed by maintenance with an inhalant anesthetic, in cats and dogs. Alfaxalone induces anaesthesia through activity at the gamma amino butyric acid sub-type A receptor (GABAA) present on cells in the Central Nervous System (CNS). Alfaxalone enhances the effects of GABA at the GABAA receptors resulting in opening of channels into the cells and an influx of chloride ions. This causes hyperpolarisation of the cells and inhibition of neural impulse transmission. Alfaxalone can be safely combined with premedicants (xylazine, (dex)medetomidine, acepromazine, midazolam), opioids (morphine, methadone, hydromorphone, butorphanol, nalbuphine, buprenorphine, fentanyl), and NSAIDs. Alfaxalone’s adverse reactions are: hypotension, tachycardia, apnea, hypertension, bradypnea and others.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4187 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22538831 |
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Target ID: CHEMBL2072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22538831 |
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Target ID: GABAA receptor (Bovine) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3032320 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Alfaxan Approved UseALFAXAN is indicated for the induction and maintenance of anesthesia and for induction of anesthesia followed by maintenance with an inhalant anesthetic, in cats and dogs. Launch Date1.3468032E12 |
PubMed
Title | Date | PubMed |
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GABAA receptor subtypes: ligand binding heterogeneity demonstrated by photoaffinity labeling and autoradiography. | 1993 Oct |
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Selective cyclodextrin inhibition of alfaxolone-induced ataxia. | 1996 May |
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Identification of a human nuclear receptor defines a new signaling pathway for CYP3A induction. | 1998 Oct 13 |
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Influence of membrane cholesterol on modulation of the GABA(A) receptor by neuroactive steroids and other potentiators. | 2001 Nov |
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Mutation of the GABAA receptor M1 transmembrane proline increases GABA affinity and reduces barbiturate enhancement. | 2002 Mar |
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Pharmacological characterization of the homomeric and heteromeric UNC-49 GABA receptors in C. elegans. | 2003 Mar |
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A single M1 residue in the beta2 subunit alters channel gating of GABAA receptor in anesthetic modulation and direct activation. | 2003 Oct 31 |
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Quantification of collagen and proteoglycan deposition in a murine model of airway remodelling. | 2005 Apr 8 |
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Plasma pharmacokinetics of alfaxalone in dogs after an intravenous bolus of Alfaxan-CD RTU. | 2006 Jul |
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In silico prediction of pregnane X receptor activators by machine learning approaches. | 2007 Jan |
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Changes in relative potency among positive GABA(A) receptor modulators upon discontinuation of chronic benzodiazepine treatment in rhesus monkeys. | 2007 May |
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A comparison of microbial growth in alfaxalone, propofol and thiopental. | 2008 Apr |
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The pharmacokinetics and pharmacodynamics of alfaxalone in cats after single and multiple intravenous administration of Alfaxan at clinical and supraclinical doses. | 2008 Dec |
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Anaesthesia for the geriatric dog and cat. | 2008 Jun 1 |
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Cardiorespiratory and anesthetic effects of clinical and supraclinical doses of alfaxalone in dogs. | 2008 Nov |
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Clinical evaluation of alfaxalone in cyclodextrin for the induction of anaesthesia in rabbits. | 2008 Sep 27 |
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Use of alfaxalone in rabbits. | 2009 Feb 7 |
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The cardiorespiratory and anesthetic effects of clinical and supraclinical doses of alfaxalone in cats. | 2009 Jan |
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Induction of anaesthesia in wild rabbits using a new alfaxalone formulation. | 2009 Jan 24 |
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Plasma pharmacokinetics of alfaxalone in both premedicated and unpremedicated Greyhound dogs after single, intravenous administration of Alfaxan at a clinical dose. | 2009 Oct |
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Effects of gamma-aminobutyric acid (GABA) agonists and a GABA uptake inhibitor on pharmacoresistant seizure like events in organotypic hippocampal slice cultures. | 2009 Oct |
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Role of neurosteroids in regulating cell death and proliferation in the late gestation fetal brain. | 2009 Oct 20 |
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Alfaxalone in cyclodextrin for induction and maintenance of anaesthesia in ponies undergoing field castration. | 2009 Sep |
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Retinal afferents synapse with relay cells targeting the middle temporal area in the pulvinar and lateral geniculate nuclei. | 2010 |
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Systemic central venous oxygen saturation is associated with clot strength during traumatic hemorrhagic shock: A preclinical observational model. | 2010 Dec 7 |
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Alfaxalone induction dose following administration of medetomidine and butorphanol in the dog. | 2010 Jan |
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Induction of anaesthesia with alfaxalone or propofol before isoflurane maintenance in cats. | 2010 Jul 17 |
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Effect of propofol and alfaxalone on pain after ovariohysterectomy in cats. | 2010 Mar 13 |
Patents
Sample Use Guides
Induction of general anesthesia in cats: range 2.2 - 9.7 mg/kg for cats that did not receive a preanesthetic and 1.0 - 10.8 mg/kg for cats that received a preanesthetic.
Induction of general anesthesia in dogs: range 1.5 - 4.5 mg/kg for dogs that did not receive a preanesthetic and between 0.2 - 3.5 mg/kg for dogs that received a preanesthetic.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19535226
Alfaxalone at a concentration of 50 uM reversibly blocked ongoing Seizure like events (SLEs) in organotypic hippocampal slice cultures. At a concentration of 20 uM it did not block ongoing SLEs but significantly reduced strength and duration of SLEs.
Substance Class |
Chemical
Created
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BD07M97B2A
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Validated (UNII)
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NCI_THESAURUS |
C245
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WHO-VATC |
QN01AX05
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WHO-ATC |
N01AX05
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CFR |
21 CFR 522.52
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DEA NO. |
2731
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SUB05316MIG
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m1498
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1544577
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BD07M97B2A
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ALFAXALONE
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ACTIVE MOIETY |