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Identification
NamePhenindamine
Accession NumberDB01619
TypeSmall Molecule
GroupsApproved
Description

Phenindamine is an antihistamine. Phenindamine blocks the effects of the naturally occurring chemical histamine in your body. Antihistamines such as phenindamine appear to compete with histamine for histamine H1- receptor sites on effector cells. The antihistamines antagonize those pharmacological effects of histamine which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release. It is used to treat sneezing, runny nose, itching, watery eyes, hives, rashes, itching, and other symptoms of allergies and the common cold.
Symptoms of a phenindamine overdose include extreme sleepiness, confusion, weakness, ringing in the ears, blurred vision, large pupils, dry mouth, flushing, fever, shaking, insomnia, hallucinations, and possibly seizures.

Structure
Thumb
Synonyms
Fenindamina
Nolahist
Phenindamine
Phenindaminum
Phenindiamine
Thephorin
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
ThephorinNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII772BQ8KSST
CAS number82-88-2
WeightAverage: 261.3609
Monoisotopic: 261.151749613
Chemical FormulaC19H19N
InChI KeyInChIKey=ISFHAYSTHMVOJR-UHFFFAOYSA-N
InChI
InChI=1S/C19H19N/c1-20-12-11-16-15-9-5-6-10-17(15)19(18(16)13-20)14-7-3-2-4-8-14/h2-10,19H,11-13H2,1H3
IUPAC Name
2-methyl-9-phenyl-1H,2H,3H,4H,9H-indeno[2,1-c]pyridine
SMILES
CN1CCC2=C(C1)C(C1=CC=CC=C21)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indenes and isoindenes. These are compounds containing an indene moiety(which consists of a cyclopentadiene fused to a benzene ring), or a isoindene moiety (which consists of a cyclopentadiene fused to cyclohexadiene ring).
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndenes and isoindenes
Sub ClassNot Available
Direct ParentIndenes and isoindenes
Alternative Parents
Substituents
  • Indene
  • Tetrahydropyridine
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed to treat sneezing, runny nose, itching, watery eyes, hives, rashes, itching, and other symptoms of allergies and the common cold.
PharmacodynamicsPhenindamine is an antihistamine. Phenindamine blocks the effects of the naturally occurring chemical histamine in your body. Allergies are caused by an excessive type 1 hypersensitivity response of the body to allergens, mediated by inappropriate histamine signalling. By inhibiting the binding of histamine, antihistamines decrease the normal histamine response from cells, consequently decreasing allergic symptoms.
Mechanism of actionAntihistamines such as phenindamine appear to compete with histamine for histamine H1- receptor sites on effector cells. The antihistamines antagonize those pharmacological effects of histamine which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of a phenindamine overdose include extreme sleepiness, confusion, weakness, ringing in the ears, blurred vision, large pupils, dry mouth, flushing, fever, shaking, insomnia, hallucinations, and possibly seizures.
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+1.0
Blood Brain Barrier+0.9918
Caco-2 permeable+0.7539
P-glycoprotein substrateSubstrate0.8112
P-glycoprotein inhibitor IInhibitor0.6928
P-glycoprotein inhibitor IINon-inhibitor0.668
Renal organic cation transporterInhibitor0.8317
CYP450 2C9 substrateNon-substrate0.8439
CYP450 2D6 substrateNon-substrate0.6852
CYP450 3A4 substrateSubstrate0.5943
CYP450 1A2 substrateNon-inhibitor0.7655
CYP450 2C9 inhibitorNon-inhibitor0.8485
CYP450 2D6 inhibitorInhibitor0.8215
CYP450 2C19 inhibitorNon-inhibitor0.7967
CYP450 3A4 inhibitorNon-inhibitor0.8636
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5834
Ames testNon AMES toxic0.7746
CarcinogenicityNon-carcinogens0.9499
BiodegradationNot ready biodegradable0.7503
Rat acute toxicity2.8173 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5391
hERG inhibition (predictor II)Inhibitor0.6006
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 point91 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0277 mg/mLALOGPS
logP4.04ALOGPS
logP3.62ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.01ChemAxon
pKa (Strongest Basic)9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.03 m3·mol-1ChemAxon
Polarizability31.13 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-03di-4490000000-4842a14b86b472cf0ceeView in MoNA
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesR06AX04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
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. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  2. ter Laak AM, Venhorst J, Donne-Op den Kelder GM, Timmerman H: The histamine H1-receptor antagonist binding site. A stereoselective pharmacophoric model based upon (semi-)rigid H1-antagonists and including a known interaction site on the receptor. J Med Chem. 1995 Aug 18;38(17):3351-60. [PubMed:7650688 ]
  3. Witek TJ Jr, Canestrari DA, Miller RD, Yang JY, Riker DK: The effects of phenindamine tartrate on sleepiness and psychomotor performance. J Allergy Clin Immunol. 1992 Dec;90(6 Pt 1):953-61. [PubMed:1360991 ]
  4. van Drooge MJ, Donne-op den Kelder GM, Timmerman H: The histamine H1-receptor antagonist binding site. Part I: Active conformation of cyproheptadine. J Comput Aided Mol Des. 1991 Aug;5(4):357-70. [PubMed:1686618 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on August 29, 2007 14:15 / Updated on September 16, 2013 17:15