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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

2012
PubMed

PubMed

TitleDatePubMed
Selective cyclodextrin inhibition of alfaxolone-induced ataxia.
1996 May
Use of alfaxalone in rabbits.
2009 Feb 7
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
Induction of anaesthesia with alfaxalone or propofol before isoflurane maintenance in cats.
2010 Jul 17
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 GMT 2023 , Edited by admin on Fri Dec 15 15:28:07 GMT 2023
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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Code System Code Type Description
EVMPD
SUB05316MIG
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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
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PRIMARY
NCI_THESAURUS
C72161
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PRIMARY
ChEMBL
CHEMBL190279
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EPA CompTox
DTXSID9022576
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PRIMARY
FDA UNII
BD07M97B2A
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PRIMARY
SMS_ID
100000087893
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PRIMARY
DRUG BANK
DB11371
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PRIMARY
MESH
C006477
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PRIMARY
WIKIPEDIA
ALFAXALONE
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PRIMARY
DRUG CENTRAL
133
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PRIMARY
CAS
23930-19-0
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PRIMARY
PUBCHEM
104845
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PRIMARY