NAV

Xylazine

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

Identification

Summary

Xylazine is a non-opioid and clonidine analog with analgesic and muscle relaxant properties used as a tranquilizer used in veterinary medicine.

Generic Name
Xylazine
DrugBank Accession Number
DB11477
Background

Xylazine is a clonidine analog used as a non-opioid tranquilizer in veterinary medicine and as an emetic, especially in cats.3,7,6 It acts as an agonist at α2 adrenoceptors; however, its affinity is lower than the one reported for other α2 adrenergic receptor agonists such as detomidine and medetomidine.5 Xylazine is not approved for human use and requires a veterinary licence for its purchase and use.8 The intentional and unintentional use of xylazine is a cause for concern due to its side effects.4 The use of xylazine can lead to hypotension and bradycardia1,2, and when combined with central nervous system depressants, such as benzodiazepines or alcohol, it can significantly depress vital functions and increase the risk of overdose and death.7 Xylazine is sometimes used as an adulterant and combined with opioids and recreational drugs; however, it has no antidote, and the use of naloxone has no effect on xylazine.7,8

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 220.33
Monoisotopic: 220.103419697
Chemical Formula
C12H16N2S
Synonyms
  • Xilazina
  • Xylazine
  • Xylazinum
External IDs
  • BAY 1470
  • WH 7286
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AAlpha-2 adrenergic receptors
agonist
Humans
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

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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
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Xylazine is combined with 1,2-Benzodiazepine.
AcebutololThe therapeutic efficacy of Xylazine can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Xylazine.
AcemetacinThe risk or severity of hypertension can be increased when Xylazine is combined with Acemetacin.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Xylazine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Xylazine hydrochlorideNGC3S0882S23076-35-9QYEFBJRXKKSABU-UHFFFAOYSA-N
International/Other Brands
Anased / Chanazine / Rompun / Sedazine

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Xylenes
Direct Parent
m-Xylenes
Alternative Parents
Aniline and substituted anilines / 1,3-thiazines / Isothioureas / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Hydrocarbon derivative / Isothiourea / M-xylene / Meta-thiazine / Organic 1,3-dipolar compound / Organic nitrogen compound / Organoheterocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
2KFG9TP5V8
CAS number
7361-61-7
InChI Key
BPICBUSOMSTKRF-UHFFFAOYSA-N
InChI
InChI=1S/C12H16N2S/c1-9-5-3-6-10(2)11(9)14-12-13-7-4-8-15-12/h3,5-6H,4,7-8H2,1-2H3,(H,13,14)
IUPAC Name
N-(2,6-dimethylphenyl)-5,6-dihydro-4H-1,3-thiazin-2-amine
SMILES
CC1=CC=CC(C)=C1NC1=NCCCS1

References

General References
  1. Beasley M: Xylazine. N Z Vet J. 1995 Jun;43(3):125. [Article]
  2. Fyffe JJ: Xylazine. N Z Vet J. 1995 Oct;43(5):204-5. [Article]
  3. Haskins SC, Patz JD, Farver TB: Xylazine and xylazine-ketamine in dogs. Am J Vet Res. 1986 Mar;47(3):636-41. [Article]
  4. Haigh JC: Misuse of xylazine. Can Vet J. 1988 Oct;29(10):782-4. [Article]
  5. Schwartz DD, Clark TP: Affinity of detomidine, medetomidine and xylazine for alpha-2 adrenergic receptor subtypes. J Vet Pharmacol Ther. 1998 Apr;21(2):107-11. [Article]
  6. Colby ED, McCarthy LE, Borison HL: Emetic action of xylazine on the chemoreceptor trigger zone for vomiting in cats. J Vet Pharmacol Ther. 1981 Jun;4(2):93-6. doi: 10.1111/j.1365-2885.1981.tb00716.x. [Article]
  7. CDC: Notes from the Field: Xylazine, a Veterinary Tranquilizer, Identified as an Emerging Novel Substance in Drug Overdose Deaths — Connecticut, 2019–2020 [Link]
  8. Canadian Centre on Substance Use and Addiction: Xylazine Drug Alert [Link]
Human Metabolome Database
HMDB0259938
KEGG Drug
D08683
ChemSpider
5505
BindingDB
50027069
RxNav
1099660
ChEBI
92386
ChEMBL
CHEMBL297362
ZINC
ZINC000000002248
Wikipedia
Xylazine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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 Solubility0.261 mg/mLALOGPS
logP3.23ALOGPS
logP3.63Chemaxon
logS-2.9ALOGPS
pKa (Strongest Basic)6.94Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area24.39 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity68.82 m3·mol-1Chemaxon
Polarizability24.76 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0229-3920000000-b822873abe0cc77b6500
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0229-3920000000-b822873abe0cc77b6500
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-56ce964cb9c5555a3ed4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1090000000-cd3c80ff9ecdf42c4c4d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05fr-0980000000-147c4edd3d7f3e9eff75
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-5900000000-8faa3de1d10661a38526
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-5910000000-f3be60936e030eebc32e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-6225ecf8ba8258cb1941
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]-156.2926705
predicted
DarkChem Lite v0.1.0
[M-H]-147.50743
predicted
DeepCCS 1.0 (2019)
[M+H]+157.2638705
predicted
DarkChem Lite v0.1.0
[M+H]+149.86543
predicted
DeepCCS 1.0 (2019)
[M+Na]+156.4371705
predicted
DarkChem Lite v0.1.0
[M+Na]+156.95755
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Alpha-2 adrenergic receptors (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Components:
NameUniProt ID
Alpha-2A adrenergic receptorP08913
Alpha-2B adrenergic receptorP18089
Alpha-2C adrenergic receptorP18825
References
  1. Schwartz DD, Clark TP: Affinity of detomidine, medetomidine and xylazine for alpha-2 adrenergic receptor subtypes. J Vet Pharmacol Ther. 1998 Apr;21(2):107-11. [Article]

Drug created at February 25, 2016 19:05 / Updated at September 05, 2022 12:50