Phenindamine

Identification

Generic Name
Phenindamine
DrugBank Accession Number
DB01619
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 261.3609
Monoisotopic: 261.151749613
Chemical Formula
C19H19N
Synonyms
  • Fenindamina
  • Phenindamine
  • Phenindaminum
  • Thephorin
External IDs
  • NU-1504

Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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
Humans
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

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.

Pathways
PathwayCategory
Phenindamine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

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.
DrugInteraction
AmphetamineAmphetamine may decrease the sedative activities of Phenindamine.
BenzphetamineBenzphetamine may decrease the sedative activities of Phenindamine.
Benzylpenicilloyl polylysinePhenindamine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent.
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Phenindamine.
DextroamphetamineDextroamphetamine may decrease the sedative activities of Phenindamine.
Food Interactions
  • Avoid alcohol.
  • Take with food. Food reduces irritation.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Phenindamine tartrate28725X3PV8569-59-5WFXURHIXPXVPGM-UHFFFAOYSA-N
International/Other Brands
Nolahist / Thephorin

Categories

ATC Codes
R06AX04 — Phenindamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Aromatic heteropolycyclic compound / Azacycle / Hydrocarbon derivative / Indene / Monocyclic benzene moiety / Organic nitrogen compound / Organoheterocyclic compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indene (CHEBI:8065)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
772BQ8KSST
CAS number
82-88-2
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

References

General References
Not Available
Human Metabolome Database
HMDB0015556
KEGG Drug
D08353
KEGG Compound
C07790
PubChem Compound
11291
PubChem Substance
46508187
ChemSpider
10817
BindingDB
50089147
RxNav
33283
ChEBI
8065
ChEMBL
CHEMBL278398
Therapeutic Targets Database
DAP001073
PharmGKB
PA164750491
Drugs.com
Drugs.com Drug Page
Wikipedia
Phenindamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)16.62Chemaxon
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-MSsplash10-0f8a-0290000000-547a5e3db2e5cabcc59f
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/MSsplash10-03di-0090000000-286f3213a2cbc0130ca5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-fac102025378fd65fb1d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-d2a60ba7f9432788d233
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-f4c5f79a34bb17b0db16
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-3690000000-b5ba0baf635a05223110
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0690000000-0a15d978dbf755c46f0d
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]-173.0405895
predicted
DarkChem Lite v0.1.0
[M-H]-161.31914
predicted
DeepCCS 1.0 (2019)
[M+H]+173.5434895
predicted
DarkChem Lite v0.1.0
[M+H]+163.67714
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.5852895
predicted
DarkChem Lite v0.1.0
[M+Na]+169.77028
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Regulator
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Martinez-Gomez MA, Carril-Aviles MM, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. J Chromatogr A. 2007 Apr 20;1147(2):261-9. doi: 10.1016/j.chroma.2007.02.054. Epub 2007 Feb 22. [Article]

Drug created at August 29, 2007 20:15 / Updated at June 12, 2020 17:41