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Showing drug card for Diphenylpyraline (DB01146)

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Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:48:17
Primary Accession Number DB01146
Secondary Accession Number
  • APRD00719
Name Diphenylpyraline
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms
  1. Diphenylpyralamine
  2. Diphenylpyraline Hydrochloride
  3. Diphenylpyrilene
Brand Names
  1. Allergen
  2. Belfene
  3. Dafen
  4. Dayfen
  5. Diafen
  6. Hispril
  7. Histryl
  8. Histyn
  9. Hystryl
  10. Lyssipoll
  11. Mepiben
  12. Neargal
Brand Mixtures
  1. Biohisdex Dm Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  2. Biohisdine Dm Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  3. Chemhisdex Dm Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  4. Chemhisdine Dm Decongestant (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  5. Codalin (Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride)
  6. Corytab (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride)
  7. Creo-Rectal Adulte (Camphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate)
  8. Creo-Rectal Enfant (Camphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate)
  9. Creo-Rectal Nourrisson (Camphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate)
  10. Emercidin D Tab (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride)
  11. Emercreme No4 Ont Efa (Bacitracin + Benzocaine + Cetylpyridinium Chloride + Diphenylpyraline Hydrochloride + Tyrothricin)
  12. Metrate (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Potassium Iodide + Sodium Citrate)
  13. Nezger Tab (Acetylsalicylic Acid + Diphenylpyraline Hydrochloride + Guaifenesin + Phenylephrine Hydrochloride)
  14. Oradrine 2 Tab (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride)
  15. Oradrine Tablets (Acetaminophen + Caffeine + Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride)
  16. Oradrine-2 Tab (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride)
  17. Protectosil Plus Efa (Diphenylpyraline Hydrochloride + Silicone)
  18. Sinugex 38 (Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride)
  19. Solucodan-H (Diphenylpyraline Hydrochloride + Hydrocodone Bitartrate + Menthol + Potassium Guaiacol Sulphonate + Sodium Citrate)
  20. Vito Bronches Sirop (Dextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Potassium Iodide + Sodium Citrate)
Chemical IUPAC Name 4-[di(phenyl)methoxy]-1-methylpiperidine
Chemical Formula C19H23NO
Chemical Structure Structure
CAS Registry Number 147-20-6
InChI Identifier InChI=1/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
InChI Key OWQUZNMMYNAXSL-UHFFFAOYAE
KEGG Drug D01172 Link Image
KEGG Compound Not Available
PubChem Compound 3103 Link Image
PubChem Substance 615228 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00777285 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Diphenylpyraline Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 281.3920
Monoisotopic Molecular Weight 281.1780
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.88e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 3.7 Source: PhysProp
Predicted LogP 3.82 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.18 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1
Canonical SMILES CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1
Drug Category
  • Antihistamines
ATC Codes
AHFS Codes
  • 92:04.00*
Indication For use in the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
Pharmacology 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.
Toxicity Not Available
Protein Binding > 99% in human serum albumin
Biotransformation Hepatic
Half Life Not Available
Dosage Forms
Form Route
Liquid Intradermal
Liquid Subcutaneous
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. 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 Link Image]
  2. 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 Link Image]
  3. 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 Link Image]
  4. Drugs.com Link Image
  5. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Histamine H1 receptor
Drug Target 1 [top]
Target 1 ID 492
Target 1 Name Histamine H1 receptor
Target 1 Synonyms Not Available
Target 1 Gene Name HRH1
Target 1 Protein Sequence >Histamine H1 receptor 
MSLPNSSCLLEDKMCEGNKTTMASPQLMPLVVVLSTICLVTVGLNLLVLYAVRSERKLHT
VGNLYIVSLSVADLIVGAVVMPMNILYLLMSKWSLGRPLCLFWLSMDYVASTASIFSVFI
LCIDRYRSVQQPLRYLKYRTKTRASATILGAWFLSFLWVIPILGWNHFMQQTSVRREDKC
ETDFYDVTWFKVMTAIINFYLPTLLMLWFYAKIYKAVRQHCQHRELINRSLPSFSEIKLR
PENPKGDAKKPGKESPWEVLKRKPKDAGGGSVLKSPSQTPKEMKSPVVFSQEDDREVDKL
YCFPLDIVHMQAAAEGSSRDYVAVNRSHGQLKTDEQGLNTHGASEISEDQMLGDSQSFSR
TDSDTTTETAPGKGKLRSGSNTGLDYIKFTWKRLRSHSRQYVSGLHMNRERKAAKQLGFI
MAAFILCWIPYFIFFMVIAFCKNCCNEHLHMFTIWLGYINSTLNPLIYPLCNENFKKTFK
RILHIRS
Target 1 Number of Residues 495
Target 1 Molecular Weight 55785
Target 1 Theoretical pI 9.58
Target 1 GO Classification
Function
amine receptor activity
histamine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in rhodopsin-like receptor activity
Target 1 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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 30-49
  • 64-83
  • 102-123
  • 146-165
  • 190-210
  • 419-438
  • 451-470
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 510296 Link Image
Target 1 UniProtKB/Swiss-Prot ID P35367 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name HRH1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1464 bp 
ATGAGCCTCCCCAATTCCTCCTGCCTCTTAGAAGACAAGATGTGTGAGGGCAACAAGACC
ACTATGGCCAGCCCCCAGCTGATGCCCCTGGTGGTGGTCCTGAGCACTATCTGCTTGGTC
ACAGTAGGGCTCAACCTGCTGGTGCTGTATGCCGTACGGAGTGAGCGGAAGCTCCACACT
GTGGGGAACCTGTACATCGTCAGCCTCTCGGTGGCGGACTTGATCGTGGGTGCCGTCGTC
ATGCCTATGAACATCCTCTACCTGCTCATGTCCAAGTGGTCACTGGGCCGTCCTCTCTGC
CTCTTTTGGCTTTCCATGGACTATGTGGCCAGCACAGCGTCCATTTTCAGTGTCTTCATC
CTGTGCATTGATCGCTACCGCTCTGTCCAGCAGCCCCTCAGGTACCTTAAGTATCGTACC
AAGACCCGAGCCTCGGCCACCATTCTGGGGGCCTGGTTTCTCTCTTTTCTGTGGGTTATT
CCCATTCTAGGCTGGAATCACTTCATGCAGCAGACCTCGGTGCGCCGAGAGGACAAGTGT
GAGACAGACTTCTATGATGTCACCTGGTTCAAGGTCATGACTGCCATCATCAACTTCTAC
CTGCCCACCTTGCTCATGCTCTGGTTCTATGCCAAGATCTACAAGGCCGTACGACAACAC
TGCCAGCACCGGGAGCTCATCAATAGGTCCCTCCCTTCCTTCTCAGAAATTAAGCTGAGG
CCAGAGAACCCCAAGGGGGATGCCAAGAAACCAGGGAAGGAGTCTCCCTGGGAGGTTCTG
AAAAGGAAGCCAAAAGATGCTGGTGGTGGATCTGTCTTGAAGTCACCATCCCAAACCCCC
AAGGAGATGAAATCCCCAGTTGTCTTCAGCCAAGAGGATGATAGAGAAGTAGACAAACTC
TACTGCTTTCCACTTGATATTGTGCACATGCAGGCTGCGGCAGAGGGGAGTAGCAGGGAC
TATGTAGCCGTCAACCGGAGCCATGGCCAGCTCAAGACAGATGAGCAGGGCCTGAACACA
CATGGGGCCAGCGAGATATCAGAGGATCAGATGTTAGGTGATAGCCAATCCTTCTCTCGA
ACGGACTCAGATACCACCACAGAGACAGCACCAGGCAAAGGCAAATTGAGGAGTGGGTCT
AACACAGGCCTGGATTACATCAAGTTTACTTGGAAGAGGCTCCGCTCGCATTCAAGACAG
TATGTATCTGGGTTGCACATGAACCGCGAAAGGAAGGCCGCCAAACAGTTGGGTTTTATC
ATGGCAGCCTTCATCCTCTGCTGGATCCCTTATTTCATCTTCTTCATGGTCATTGCCTTC
TGCAAGAACTGTTGCAATGAACATTTGCACATGTTCACCATCTGGCTGGGCTACATCAAC
TCCACACTGAACCCCCTCATCTACCCCTTGTGCAATGAGAACTTCAAGAAGACATTCAAG
AGAATTCTGCATATTCGCTCCTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID HRH1 Link Image
Target 1 GenAtlas ID HRH1 Link Image
Target 1 HGNC ID HGNC:5182 Link Image
Target 1 Chromosome Location 3
Target 1 Locus 3p25
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Fukui H, Fujimoto K, Mizuguchi H, Sakamoto K, Horio Y, Takai S, Yamada K, Ito S: Molecular cloning of the human histamine H1 receptor gene. Biochem Biophys Res Commun. 1994 Jun 15;201(2):894-901. [PubMed Link Image]
  2. De Backer MD, Gommeren W, Moereels H, Nobels G, Van Gompel P, Leysen JE, Luyten WH: Genomic cloning, heterologous expression and pharmacological characterization of a human histamine H1 receptor. Biochem Biophys Res Commun. 1993 Dec 30;197(3):1601-8. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  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 Link Image]
  3. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  4. 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 Link Image]

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.