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Identification
Name Diphenylpyraline
Accession Number DB01146 (APRD00719)
Type small molecule
Groups approved
Description

Diphenylpyraline is an antihistamine. Antihistamines used in the treatment of allergy act by competing with histamine for H 1-receptor sites on effector cells. Antihistamines prevent, but do not reverse, responses mediated by histamine alone. Antihistamines antagonize, in varying degrees, most of the pharmacological effects of histamine, including urticaria and pruritus.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Diphenylpyralamine
  • Diphenylpyraline Hydrochloride
  • Diphenylpyrilene
Brand names
  • Allergen
  • Belfene
  • Dafen
  • Dayfen
  • Diafen
  • Hispril
  • Histryl
  • Histyn
  • Hystryl
  • Lyssipoll
  • Mepiben
  • Neargal
Brand name mixtures
  • Biohisdex Dm Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  • Biohisdine Dm Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  • Chemhisdex Dm Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  • Chemhisdine Dm Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  • Codalin (Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  • Corytab (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride)
  • Creo-Rectal Adulte (Camphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate)
  • Creo-Rectal Enfant (Camphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate)
  • Creo-Rectal Nourrisson (Camphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate)
  • Emercidin D Tab (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride)
  • Emercreme No4 Ont Efa (Bacitracin + Benzocaine + Cetylpyridinium Chloride + Diphenylpyraline Hydrochloride + Tyrothricin)
  • Metrate (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Potassium Iodide + Sodium Citrate)
  • Nezger Tab (Acetylsalicylic Acid + Diphenylpyraline Hydrochloride + Guaifenesin + Phenylephrine Hydrochloride)
  • Oradrine 2 Tab (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride)
  • Oradrine Tablets (Acetaminophen + Caffeine + Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride)
  • Oradrine-2 Tab (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride)
  • Protectosil Plus Efa (Diphenylpyraline Hydrochloride + Silicone)
  • Sinugex 38 (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride)
  • Solucodan-H (Diphenylpyraline Hydrochloride + Hydrocodone Bitartrate + Menthol + Potassium Guaiacol Sulphonate + Sodium Citrate)
  • Vito Bronches Sirop (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Potassium Iodide + Sodium Citrate)
Categories
  • Antihistamines
CAS number 147-20-6
Weight Average: 281.392
Monoisotopic: 281.177964363
Chemical Formula C19H23NO
InChI Key InChIKey=OWQUZNMMYNAXSL-UHFFFAOYSA-N
InChI
InChI=1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3
Plain Text
IUPAC Name
4-(diphenylmethoxy)-1-methylpiperidine
SMILES
CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenhydramines
Substructures
  • Diphenhydramines
  • Benzyl Alcohols and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Diphenylmethanes
  • Heterocyclic compounds
  • Aromatic compounds
  • Piperidines
Pharmacology
Indication For use in the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
Pharmacodynamics Diphenylpyraline is an antihistamine that prevents, but does not reverse, responses mediated by histamine alone. Diphenylpyraline antagonizes most of the pharmacological effects of histamine, including urticaria and pruritus. Also, diphenylpyraline may exhibit anticholinergic actions (as do most of the antihistamines) and may thus provide a drying effect on the nasal mucosa.
Mechanism of action Antihistamines such as diphenylpyraline used in the treatment of allergy act by competing with histamine for H1-receptor sites on effector cells. This reduces the effects of histamine, leading to a temporary reduction of allergy symptoms.
Absorption Well absorbed after oral administration.
Volume of distribution Not Available
Protein binding > 99% in human serum albumin
Metabolism

Hepatic
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
Packagers Not Available
Dosage forms
Form Route Strength
Liquid Intradermal
Liquid Subcutaneous
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 3.7 PhysProp
Predicted Properties
Property Value Source
water solubility 1.88e-02 g/l ALOGPS
logP 3.82 ALOGPS
logP 3.66 ChemAxon Molconvert
logS -4.18 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 12.47 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 87.36 ChemAxon Molconvert
polarizability 32.97 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. Pubmed
  2. Ohno T, Kobayashi S, Hayashi M, Sakurai M, Kanazawa I: Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients. J Neurol Sci. 2001 Jan 1;182(2):95-7. Pubmed
  3. Puhakka H, Rantanen T, Virolainen E: Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis. J Int Med Res. 1977;5(1):37-41. Pubmed
External Links
Resource Link
KEGG Drug D01172 Link_out
PubChem Compound 3103 Link_out
PubChem Substance 46504936 Link_out
ChemSpider 2992 Link_out
BindingDB 50241333 Link_out
ChEBI 59788 Link_out
ChEMBL 59788 Link_out
Therapeutic Targets Database DAP001071 Link_out
Drug Product Database 777285 Link_out
Wikipedia http://en.wikipedia.org/wiki/Diphenylpyraline Link_out
ATC Codes
  • R06AA07
  • V01AA02
  • V01AA20
AHFS Codes
  • 92:04.00*
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Nakai T, Kitamura N, Hashimoto T, Kajimoto Y, Nishino N, Mita T, Tanaka C: Decreased histamine H1 receptors in the frontal cortex of brains from patients with chronic schizophrenia. Biol Psychiatry. 1991 Aug 15;30(4):349-56. Pubmed
  4. Taniguchi K, Masuda Y, Takanaka K: Inhibitory effects of histamine H1 receptor blocking drugs on metabolic activations of neutrophils. J Pharmacobiodyn. 1991 Feb;14(2):87-93. Pubmed
  5. Weis R, Schweiger K, Faist J, Rajkovic E, Kungl AJ, Fabian WM, Schunack W, Seebacher W: Antimycobacterial and H1-antihistaminic activity of 2-substituted piperidine derivatives. Bioorg Med Chem. 2008 Dec 15;16(24):10326-31. Epub 2008 Oct 22. Pubmed
  6. Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. Pubmed
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Sodium-dependent dopamine transporter

Pharmacological action: unknown
Actions: inhibitor

Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: Q01959 Link_out
Gene: SLC6A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Lapa GB, Mathews TA, Harp J, Budygin EA, Jones SR: Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties. Eur J Pharmacol. 2005 Jan 4;506(3):237-40. Epub 2004 Dec 8. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:08

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.