Identification

Name
Phenindamine
Accession Number
DB01619
Type
Small Molecule
Groups
Approved
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
  • Phenindamine
  • Phenindaminum
  • Phenindiamine
  • Thephorin
International/Other Brands
Nolahist / Thephorin
Categories
UNII
772BQ8KSST
CAS number
82-88-2
Weight
Average: 261.3609
Monoisotopic: 261.151749613
Chemical Formula
C19H19N
InChI Key
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

Pharmacology

Indication

Used to treat sneezing, runny nose, itching, watery eyes, hives, rashes, itching, and other symptoms of allergies and the common cold.

Pharmacodynamics

Phenindamine 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 action

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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
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

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.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Phenindamine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Phenindamine.Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative activities of Phenindamine.Experimental
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Phenindamine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Phenindamine.Experimental, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Phenindamine.Approved, Illicit, Investigational
BenzphetamineBenzphetamine may decrease the sedative activities of Phenindamine.Approved, Illicit
Benzylpenicilloyl PolylysinePhenindamine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Phenindamine.Approved, Investigational
ChlorphentermineChlorphentermine may decrease the sedative activities of Phenindamine.Illicit, Withdrawn
DextroamphetamineDextroamphetamine may decrease the sedative activities of Phenindamine.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Phenindamine.Approved, Illicit
GepefrineGepefrine may decrease the sedative activities of Phenindamine.Experimental
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Phenindamine.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Phenindamine.Approved
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Phenindamine.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Phenindamine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Phenindamine.Investigational
MephentermineMephentermine may decrease the sedative activities of Phenindamine.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Phenindamine.Approved, Illicit
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Phenindamine.Experimental
MidomafetamineMidomafetamine may decrease the sedative activities of Phenindamine.Experimental, Illicit, Investigational
MMDAMMDA may decrease the sedative activities of Phenindamine.Experimental, Illicit
PhenterminePhentermine may decrease the sedative activities of Phenindamine.Approved, Illicit
PseudoephedrinePseudoephedrine may decrease the sedative activities of Phenindamine.Approved
RitobegronRitobegron may decrease the sedative activities of Phenindamine.Investigational
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015556
KEGG Compound
C07790
PubChem Compound
11291
PubChem Substance
46508187
ChemSpider
10817
BindingDB
50089147
ChEBI
8065
ChEMBL
CHEMBL278398
Therapeutic Targets Database
DAP001073
PharmGKB
PA164750491
Drugs.com
Drugs.com Drug Page
Wikipedia
Phenindamine
ATC Codes
R06AX04 — Phenindamine

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
Solid
Experimental Properties
PropertyValueSource
melting point (°C)91 °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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03di-3390000000-7cea42f060f24de790da
Mass Spectrum (Electron Ionization)MSsplash10-03di-4490000000-4842a14b86b472cf0cee
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

Description
This 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).
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Indenes and isoindenes
Sub Class
Not Available
Direct Parent
Indenes and isoindenes
Alternative Parents
Benzene and substituted derivatives / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Indene / Monocyclic benzene moiety / Tertiary aliphatic amine / Tertiary amine / Azacycle / Organoheterocyclic compound / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indene (CHEBI:8065)

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 catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
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]

Drug created on August 29, 2007 14:15 / Updated on June 02, 2018 06:51