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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
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Synonyms
  • Fenindamina [inn-spanish]
  • Phenindaminum [inn-latin]
  • Phenindiamine
Synonyms
Fenindamina [inn-spanish]
Phenindaminum [inn-latin]
Phenindiamine
Salts Not Available
Brand names
Name Company
Thephorin
Brand mixtures
Brand Name Ingredients
Amilon
Categories
  • Histamine H1 Antagonists
  • Antihistamines
CAS number 82-88-2
Weight Average: 261.3609
Monoisotopic: 261.151749613
Chemical Formula C19H19N
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenylpropenes
  • Phenylpropylamines
  • Indenes and Derivatives
Substructures
  • Alkanes and Alkenes
  • Phenylpropenes
  • Benzene and Derivatives
  • Cyclopentadienes
  • Aliphatic and Aryl Amines
  • Isoprenes
  • Heterocyclic compounds
  • Aromatic compounds
  • Phenylpropylamines
  • Indenes and Derivatives
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.
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 Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 91 oC
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 2.77e-02 g/l ALOGPS
logP 4.04 ALOGPS
logP 3.62 ChemAxon Molconvert
logS -4 ALOGPS
pKa 0 ChemAxon Molconvert
hydrogen acceptor count 1 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 3.24 ChemAxon Molconvert
rotatable bond count 1 ChemAxon Molconvert
refractivity 85.03 ChemAxon Molconvert
polarizability 31.13 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07790 Link_out
PubChem Compound 11291 Link_out
PubChem Substance 46508187 Link_out
ChemSpider 10817 Link_out
BindingDB 50089147 Link_out
Therapeutic Targets Database DAP001073 Link_out
PharmGKB PA450905 Link_out
Drugs.com http://www.drugs.com/mtm/phenindamine.html Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Phenindamine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Trimethobenzamide Trimethobenzamide and Phenindamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Phenindamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
Trospium Trospium and Phenindamine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Avoid alcohol.
  • Take with food to reduce irritation.
Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P35367 Link_out
Gene: HRH1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on August 29, 2007 14:15 / Updated on February 14, 2012 11:48