You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameIsothipendyl
Accession NumberDB08802
TypeSmall Molecule
GroupsApproved
DescriptionIsothipendyl is an antihistamine and anticholinergic used as an antipruritic.
Structure
Thumb
Synonyms
Actapront
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ActaprontPurissimus
Alergis JaleaDeutsche Pharma
AndantolDeutsche Pharma
ApaisylMerck
CalmogelSanofi
NilergexI.C.I.
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Isothipendyl hydrochloride
ThumbNot applicableDBSALT000907
Categories
UNIIWVZ7K9P0JY
CAS number482-15-5
WeightAverage: 285.407
Monoisotopic: 285.129968313
Chemical FormulaC16H19N3S
InChI KeyInChIKey=OQJBSDFFQWMKBQ-UHFFFAOYSA-N
InChI
InChI=1S/C16H19N3S/c1-12(18(2)3)11-19-13-7-4-5-8-14(13)20-15-9-6-10-17-16(15)19/h4-10,12H,11H2,1-3H3
IUPAC Name
dimethyl(1-{9-thia-2,4-diazatricyclo[8.4.0.0³,⁸]tetradeca-1(14),3(8),4,6,10,12-hexaen-2-yl}propan-2-yl)amine
SMILES
CC(CN1C2=CC=CC=C2SC2=C1N=CC=C2)N(C)C
Taxonomy
ClassificationNot classified
Pharmacology
IndicationFor the topical treatment of itching associated with allergic reactions.
PharmacodynamicsIsothipendyl, an azaphenothiazine derivative, competitively binds to histamine (H1) receptors, resulting in inhibition of the pharmacological effects of histamines. It also has some sedative, anticholinergic and antiserotoninergic effects.
Mechanism of actionIsothipendyl is a selective histamine H1 antagonist and binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9928
Blood Brain Barrier+0.9804
Caco-2 permeable+0.808
P-glycoprotein substrateSubstrate0.7871
P-glycoprotein inhibitor IInhibitor0.6515
P-glycoprotein inhibitor IINon-inhibitor0.655
Renal organic cation transporterInhibitor0.5198
CYP450 2C9 substrateNon-substrate0.7399
CYP450 2D6 substrateSubstrate0.7027
CYP450 3A4 substrateSubstrate0.5135
CYP450 1A2 substrateInhibitor0.9167
CYP450 2C9 inhibitorNon-inhibitor0.88
CYP450 2D6 inhibitorInhibitor0.7844
CYP450 2C19 inhibitorNon-inhibitor0.8657
CYP450 3A4 inhibitorNon-inhibitor0.8468
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5185
Ames testNon AMES toxic0.8079
CarcinogenicityNon-carcinogens0.9305
BiodegradationNot ready biodegradable0.993
Rat acute toxicity2.5794 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9751
hERG inhibition (predictor II)Inhibitor0.7695
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point213-216U.S. Patent 2,974,139.
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
logP3.45ALOGPS
logP3.66ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity86.66 m3·mol-1ChemAxon
Polarizability31.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

U.S. Patent 2,974,139.

General References
  1. Moreau A, Dompmartin A, Dubreuil A, Leroy D: Phototoxic and photoprotective effects of topical isothipendyl. Photodermatol Photoimmunol Photomed. 1995 Apr;11(2):50-4. [PubMed:8546983 ]
External Links
ATC CodesD04AA22R06AD09
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Isothipendyl.
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Isothipendyl.
AmphetamineAmphetamine may decrease the sedative activities of Isothipendyl.
BenzphetamineBenzphetamine may decrease the sedative activities of Isothipendyl.
Benzylpenicilloyl PolylysineIsothipendyl may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Isothipendyl.
ChlorphentermineChlorphentermine may decrease the sedative activities of Isothipendyl.
DextroamphetamineDextroamphetamine may decrease the sedative activities of Isothipendyl.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Isothipendyl.
Hydroxyamphetamine hydrobromideHydroxyamphetamine hydrobromide may decrease the sedative activities of Isothipendyl.
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Isothipendyl.
MephentermineMephentermine may decrease the sedative activities of Isothipendyl.
MethamphetamineMethamphetamine may decrease the sedative activities of Isothipendyl.
PhenterminePhentermine may decrease the sedative activities of Isothipendyl.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Histamine receptor activity
Specific Function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular Weight:
55783.61 Da
References
  1. Moreau A, Dompmartin A, Dubreuil A, Leroy D: Phototoxic and photoprotective effects of topical isothipendyl. Photodermatol Photoimmunol Photomed. 1995 Apr;11(2):50-4. [PubMed:8546983 ]
Comments
comments powered by Disqus
Drug created on October 15, 2010 10:26 / Updated on August 17, 2016 12:24