Amitraz

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

Identification

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Name
Amitraz
Accession Number
DB11373
Type
Small Molecule
Groups
Experimental, Vet approved
Description

Amitraz is a non-systemic acaricide and insecticide. It was generated in 1969 by the Boots Co. in England. Amitraz presents insect repellent effects and hence, it can be used as an insecticide and pesticide. Its insecticide effect is due to its agonistic activity in the alpha-adrenergic system, its interaction with the octopamine receptors in the central nervous system and its driven inhibition of the synthesis of monoamine oxidases and prostaglandins. All the abovementioned effects are translated into the overexcitation, paralysis, and death in insects.

Amitraz presents a lower effect in mammals and thus, it is widely used in the treatment of mite- or tick-infestation of dogs.

Structure
Thumb
Synonyms
  • 1,5-di(2,4-dimethylphenyl)-3-methyl-1,3,5-triazapenta-1,4-diene
  • Amitraz
  • Amitraze
  • Amitrazum
  • N,N'-(methyliminodimethylidyne)bis-2,4-xylidine
External IDs
U-36-059 / U-36,059 / U-36059
International/Other Brands
Mitac
Categories
UNII
33IAH5017S
CAS number
33089-61-1
Weight
Average: 293.406
Monoisotopic: 293.189197751
Chemical Formula
C19H23N3
InChI Key
QXAITBQSYVNQDR-ZIOPAAQOSA-N
InChI
InChI=1S/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+
IUPAC Name
(E)-N'-(2,4-dimethylphenyl)-N-[(E)-[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide
SMILES
CN(\C=N\C1=C(C)C=C(C)C=C1)\C=N\C1=C(C)C=C(C)C=C1

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
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypertension can be increased when 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid is combined with Amitraz.
1-benzylimidazoleThe risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Amitraz.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of hypertension can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Amitraz.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of hypertension can be increased when Amitraz is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Amitraz.
4-MethoxyamphetamineThe risk or severity of hypertension can be increased when 4-Methoxyamphetamine is combined with Amitraz.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of hypertension can be increased when Amitraz is combined with 5-methoxy-N,N-dimethyltryptamine.
AbediterolThe risk or severity of hypertension can be increased when Amitraz is combined with Abediterol.
AcebutololThe therapeutic efficacy of Amitraz can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Amitraz.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

References

General References
  1. Lee S, Kim TH, Shin YW, Jeon Y, Kim J: Amitraz. Acta Crystallogr Sect E Struct Rep Online. 2013 Jul 24;69(Pt 8):o1300. doi: 10.1107/S1600536813019764. eCollection 2013. [PubMed:24109378]
  2. Varma PV, Bhatt S, Bhat RY: Amitraz poisoning. Indian J Pediatr. 2013 Apr;80(4):349-50. doi: 10.1007/s12098-012-0772-2. Epub 2012 May 11. [PubMed:22576295]
  3. Caprotta CG, Martinez M, Tiszler M, Guerra V: [Amitraz poisoning]. Arch Argent Pediatr. 2009 Oct;107(5):456-8. doi: 10.1590/S0325-00752009000500015. [PubMed:19809769]
  4. Gursoy S, Kunt N, Kaygusuz K, Kafali H: Intravenous amitraz poisoning. Clin Toxicol (Phila). 2005;43(2):113-6. [PubMed:15822764]
  5. Aydin K, Per H, Kurtoglu S, Poyrazoglu MH, Narin N, Aslan D: Amitraz poisoning in children. Eur J Pediatr. 2002 Jun;161(6):349-50. Epub 2002 Apr 16. [PubMed:12029457]
  6. Yaramis A, Soker M, Bilici M: Amitraz poisoning in children. Hum Exp Toxicol. 2000 Aug;19(8):431-3. [PubMed:11125712]
  7. Saha T, Chatterjee S, Saha K, Chowdhury A, Somchoudhury AK, Bhattacharyya A: Residues of amitraz, a new acaricide, on tea. Bull Environ Contam Toxicol. 2000 Aug;65(2):215-21. [PubMed:10885999]
  8. Godara R, Parveen S, Katoch R, Yadav A, Verma PK, Katoch M, Kaur D, Ganai A, Raghuvanshi P, Singh NK: Acaricidal activity of extract of Artemisia absinthium against Rhipicephalus sanguineus of dogs. Parasitol Res. 2014 Feb;113(2):747-54. doi: 10.1007/s00436-013-3704-9. Epub 2013 Nov 28. [PubMed:24288053]
  9. Hepperle J, Mack D, Sigalov I, Schuler S, Anastassiades M: Analysis of "Amitraz (sum)" in pears with incurred residues - Comparison of the approach covering the individual metabolites via LC-MS/MS with the approach involving cleavage to 2,4-dimethylaniline. Food Chem. 2015 Jan 1;166:240-7. doi: 10.1016/j.foodchem.2014.06.003. Epub 2014 Jun 11. [PubMed:25053051]
  10. Leung VK, Chan TY, Yeung VT: Amitraz poisoning in humans. J Toxicol Clin Toxicol. 1999;37(4):513-4. [PubMed:10465251]
  11. Duncan KL: Treatment of amitraz toxicosis. J Am Vet Med Assoc. 1993 Oct 15;203(8):1115-6. [PubMed:8244851]
External Links
KEGG Drug
D02380
KEGG Compound
C10995
ChemSpider
33405
ChEBI
2665
ChEMBL
CHEMBL1365675
Wikipedia
Amitraz

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 Solubility0.000647 mg/mLALOGPS
logP4.42ALOGPS
logP5.41ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)8.83ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.96 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98 m3·mol-1ChemAxon
Polarizability35.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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

Taxonomy

Classification
Not classified

Drug created on February 25, 2016 11:14 / Updated on June 04, 2019 07:20