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Cythioate

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

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Identification

Generic Name
Cythioate
DrugBank Accession Number
DB11392
Background

Cythioate is a member of the organothiophosphate compounds that is used as an insecticide and anthelmintic. It is mainly used in veterinary as a treatment for fleas.

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 297.28
Monoisotopic: 296.989451836
Chemical Formula
C8H12NO5PS2
Synonyms
Not Available
External IDs
  • AC 26,691
  • CL 26691
  • ENT 25,640
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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
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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Interactions

Drug Interactions
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.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Proban

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic thiophosphoric acids and derivatives
Sub Class
Thiophosphoric acid esters
Direct Parent
Phenyl thiophosphates
Alternative Parents
Benzenesulfonamides / Benzenesulfonyl compounds / Thiophosphate triesters / Phenoxy compounds / Organosulfonamides / Aminosulfonyl compounds / Organooxygen compounds / Organic oxides / Organic nitrogen compounds / Hydrocarbon derivatives
Substituents
Aminosulfonyl compound / Aromatic homomonocyclic compound / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
3OOH7Q4333
CAS number
115-93-5
InChI Key
BSBSDQUZDZXGFN-UHFFFAOYSA-N
InChI
InChI=1S/C8H12NO5PS2/c1-12-15(16,13-2)14-7-3-5-8(6-4-7)17(9,10)11/h3-6H,1-2H3,(H2,9,10,11)
IUPAC Name
O,O-dimethyl O-4-sulfamoylphenyl phosphorothioate
SMILES
COP(=S)(OC)OC1=CC=C(C=C1)S(N)(=O)=O

References

General References
  1. Bowen PM, Caldwell NJ: Use of cythioate to control external parasites on cats and dogs. Vet Med Small Anim Clin. 1982 Jan;77(1):79-80. [Article]
  2. Dryden MW: Differential activity of cythioate against female and male Ctenocephalides felis on cats. Am J Vet Res. 1992 May;53(5):801-2. [Article]
  3. Manson ER, Malynicz GL: The use of cythioate in the treatment of demodectic mange in the dog. Aust Vet J. 1969 Nov;45(11):533-4. [Article]
  4. Yarborough JH, Yarborough JH 3rd: A clinical evaluation of cythioate, a new oral systemic parasiticide for dogs. Vet Med Small Anim Clin. 1968 Jun;63(6):584-6. [Article]
  5. Doval CP, Gupta I: Effect of cythioate on cholinesterase activity in erythrocytes and plasma and transaminase activity in serum of sheep and dogs. Indian J Exp Biol. 1976 Mar;14(2):193-4. [Article]
  6. Schenker R, Tinembart O, Humbert-Droz E, Cavaliero T, Yerly B: Comparative speed of kill between nitenpyram, fipronil, imidacloprid, selamectin and cythioate against adult Ctenocephalides felis (Bouche) on cats and dogs. Vet Parasitol. 2003 Mar 10;112(3):249-54. [Article]
  7. Crystal MM, DeMilo AB: Susceptibility of laboratory-reared northern fowl mites, Ornithonyssus sylviarum (Acari: Macronyssidae), to selected acaricides. Exp Appl Acarol. 1988 Jul;4(4):353-8. [Article]
  8. Hazelwood JC, Stefan GE, Bowen JM: Motor unit irritability in Beagles Before and after exposure to cholinesterase inhibitors. Am J Vet Res. 1979 Jun;40(6):852-6. [Article]
  9. Smith HG Jr, Goulding RL: Toxicological aspects of three organophosphorus compounds (Cythioate, Famphur, and Fenthion) in the host-ectoparasite system. J Econ Entomol. 1970 Oct;63(5):1640-6. [Article]
  10. Lammler G, Gruner D: Chemotherapeutic studies on Litomosoides carinii infection of Mastomys natalensis. 6. The filaricidal activity of organophosphorus compounds. Tropenmed Parasitol. 1975 Sep;26(3):359-69. [Article]
KEGG Drug
D07768
ChemSpider
7992
ChEMBL
CHEMBL2104588
ZINC
ZINC000001569224
Wikipedia
Cythioate

Clinical Trials

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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 Solubility0.488 mg/mLALOGPS
logP1.92ALOGPS
logP1.27Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.27Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area87.85 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity68.03 m3·mol-1Chemaxon
Polarizability26.09 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
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/MSsplash10-0002-0090000000-2346cc9a71e337452a01
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-a3c2e79ce9c29cc6e769
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0159-0290000000-4da28b1b4790e9171350
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-846ecafe2ae1ece4a1ed
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0229-9800000000-cee06553720541e3546a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-2900000000-a4259ac5f1595e03d67a
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]-171.5971694
predicted
DarkChem Lite v0.1.0
[M-H]-154.29164
predicted
DeepCCS 1.0 (2019)
[M+H]+156.64966
predicted
DeepCCS 1.0 (2019)
[M+Na]+162.74292
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:22 / Updated at June 12, 2020 16:53