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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
Structure of ALFAXALONE

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

HIDE SMILES / InChI

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Alfaxan

Approved Use

ALFAXAN 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 Date

1.3468032E12
PubMed

PubMed

TitleDatePubMed
GABAA receptor subtypes: ligand binding heterogeneity demonstrated by photoaffinity labeling and autoradiography.
1993 Oct
Selective cyclodextrin inhibition of alfaxolone-induced ataxia.
1996 May
Identification of a human nuclear receptor defines a new signaling pathway for CYP3A induction.
1998 Oct 13
Influence of membrane cholesterol on modulation of the GABA(A) receptor by neuroactive steroids and other potentiators.
2001 Nov
Mutation of the GABAA receptor M1 transmembrane proline increases GABA affinity and reduces barbiturate enhancement.
2002 Mar
Pharmacological characterization of the homomeric and heteromeric UNC-49 GABA receptors in C. elegans.
2003 Mar
A single M1 residue in the beta2 subunit alters channel gating of GABAA receptor in anesthetic modulation and direct activation.
2003 Oct 31
Quantification of collagen and proteoglycan deposition in a murine model of airway remodelling.
2005 Apr 8
Plasma pharmacokinetics of alfaxalone in dogs after an intravenous bolus of Alfaxan-CD RTU.
2006 Jul
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Changes in relative potency among positive GABA(A) receptor modulators upon discontinuation of chronic benzodiazepine treatment in rhesus monkeys.
2007 May
A comparison of microbial growth in alfaxalone, propofol and thiopental.
2008 Apr
The pharmacokinetics and pharmacodynamics of alfaxalone in cats after single and multiple intravenous administration of Alfaxan at clinical and supraclinical doses.
2008 Dec
Anaesthesia for the geriatric dog and cat.
2008 Jun 1
Cardiorespiratory and anesthetic effects of clinical and supraclinical doses of alfaxalone in dogs.
2008 Nov
Clinical evaluation of alfaxalone in cyclodextrin for the induction of anaesthesia in rabbits.
2008 Sep 27
Use of alfaxalone in rabbits.
2009 Feb 7
The cardiorespiratory and anesthetic effects of clinical and supraclinical doses of alfaxalone in cats.
2009 Jan
Induction of anaesthesia in wild rabbits using a new alfaxalone formulation.
2009 Jan 24
Plasma pharmacokinetics of alfaxalone in both premedicated and unpremedicated Greyhound dogs after single, intravenous administration of Alfaxan at a clinical dose.
2009 Oct
Effects of gamma-aminobutyric acid (GABA) agonists and a GABA uptake inhibitor on pharmacoresistant seizure like events in organotypic hippocampal slice cultures.
2009 Oct
Role of neurosteroids in regulating cell death and proliferation in the late gestation fetal brain.
2009 Oct 20
Alfaxalone in cyclodextrin for induction and maintenance of anaesthesia in ponies undergoing field castration.
2009 Sep
Retinal afferents synapse with relay cells targeting the middle temporal area in the pulvinar and lateral geniculate nuclei.
2010
Systemic central venous oxygen saturation is associated with clot strength during traumatic hemorrhagic shock: A preclinical observational model.
2010 Dec 7
Alfaxalone induction dose following administration of medetomidine and butorphanol in the dog.
2010 Jan
Induction of anaesthesia with alfaxalone or propofol before isoflurane maintenance in cats.
2010 Jul 17
Effect of propofol and alfaxalone on pain after ovariohysterectomy in cats.
2010 Mar 13
Patents

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
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.
Name Type Language
ALFAXALONE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
PHAXAN
Brand Name English
ALFAXALONE [GREEN BOOK]
Common Name English
GR 2/234
Code English
ALFAXALONE [JAN]
Common Name English
GR-2/234
Code English
ALPHAXALONE
Common Name English
ALFAXALONE [MI]
Common Name English
alfaxalone [INN]
Common Name English
ALFAXALONE [MART.]
Common Name English
Alfaxalone [WHO-DD]
Common Name English
3.ALPHA.-HYDROXY-5.ALPHA.-PREGNANE-11,20-DIONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
WHO-VATC QN01AX05
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
WHO-ATC N01AX05
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
CFR 21 CFR 522.52
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
DEA NO. 2731
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
Code System Code Type Description
EVMPD
SUB05316MIG
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
MERCK INDEX
m1498
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PRIMARY Merck Index
INN
3218
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PRIMARY
RXCUI
1544577
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PRIMARY RxNorm
DAILYMED
BD07M97B2A
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
NCI_THESAURUS
C72161
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL190279
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PRIMARY
EPA CompTox
DTXSID9022576
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PRIMARY
FDA UNII
BD07M97B2A
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
SMS_ID
100000087893
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
DRUG BANK
DB11371
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
MESH
C006477
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
WIKIPEDIA
ALFAXALONE
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
DRUG CENTRAL
133
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
CAS
23930-19-0
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY
PUBCHEM
104845
Created by admin on Fri Dec 15 15:28:07 UTC 2023 , Edited by admin on Fri Dec 15 15:28:07 UTC 2023
PRIMARY