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
Structure for Phenindamine (DB01619)
- 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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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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
Pathway Category Phenindamine H1-Antihistamine Action Drug 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmphetamine Amphetamine may decrease the sedative and stimulatory activities of Phenindamine. Benzphetamine Benzphetamine may decrease the sedative and stimulatory activities of Phenindamine. Benzylpenicilloyl polylysine Phenindamine may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent. Betahistine The therapeutic efficacy of Betahistine can be decreased when used in combination with Phenindamine. Dextroamphetamine Dextroamphetamine may decrease the sedative and stimulatory activities of Phenindamine. Diethylpropion Diethylpropion may decrease the sedative and stimulatory activities of Phenindamine. Droxidopa The therapeutic efficacy of Droxidopa can be increased when used in combination with Phenindamine. Ephedrine The therapeutic efficacy of Ephedrine can be increased when used in combination with Phenindamine. Epinephrine The therapeutic efficacy of Epinephrine can be increased when used in combination with Phenindamine. Hyaluronidase The therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Phenindamine. 
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- Avoid alcohol.
- Take with food. Food reduces irritation.
Products
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Ingredient UNII CAS InChI Key Phenindamine tartrate 28725X3PV8 569-59-5 WFXURHIXPXVPGM-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
- External Links
- Human Metabolome Database
- HMDB0015556
- KEGG Drug
- D08353
- KEGG Compound
- C07790
- PubChem Compound
- 11291
- PubChem Substance
- 46508187
- ChemSpider
- 10817
- BindingDB
- 50089147
- 33283
- ChEBI
- 8065
- ChEMBL
- CHEMBL278398
- Therapeutic Targets Database
- DAP001073
- PharmGKB
- PA164750491
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Phenindamine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 91 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0277 mg/mL ALOGPS logP 4.04 ALOGPS logP 3.62 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 16.62 Chemaxon pKa (Strongest Basic) 9 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 3.24 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 85.03 m3·mol-1 Chemaxon Polarizability 31.13 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9918 Caco-2 permeable + 0.7539 P-glycoprotein substrate Substrate 0.8112 P-glycoprotein inhibitor I Inhibitor 0.6928 P-glycoprotein inhibitor II Non-inhibitor 0.668 Renal organic cation transporter Inhibitor 0.8317 CYP450 2C9 substrate Non-substrate 0.8439 CYP450 2D6 substrate Non-substrate 0.6852 CYP450 3A4 substrate Substrate 0.5943 CYP450 1A2 substrate Non-inhibitor 0.7655 CYP450 2C9 inhibitor Non-inhibitor 0.8485 CYP450 2D6 inhibitor Inhibitor 0.8215 CYP450 2C19 inhibitor Non-inhibitor 0.7967 CYP450 3A4 inhibitor Non-inhibitor 0.8636 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5834 Ames test Non AMES toxic 0.7746 Carcinogenicity Non-carcinogens 0.9499 Biodegradation Not ready biodegradable 0.7503 Rat acute toxicity 2.8173 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5391 hERG inhibition (predictor II) Inhibitor 0.6006
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-03di-3390000000-7cea42f060f24de790da Mass Spectrum (Electron Ionization) MS splash10-03di-4490000000-4842a14b86b472cf0cee Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
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
- 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]
- 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]
- 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]
- 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]
- 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
- BinderRegulator
- 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
- 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