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Identification
NameDiphenylpyraline
Accession NumberDB01146  (APRD00719)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
1-Methyl-4-hydroxypiperidine benzhydryl etherNot AvailableNot Available
1-Methyl-4-piperidyl benzhydryl etherNot AvailableNot Available
4-(Benzhydryloxy)-1-methylpiperidineNot AvailableNot Available
4-(Benzhydryloxy)-N-methylpiperidineNot AvailableNot Available
DifenilpiralinaNot AvailableNot Available
DiphenylpyralamineNot AvailableNot Available
DiphenylpyralinumNot AvailableNot Available
Salts
Name/CAS Structure Properties
Diphenylpyraline Hydrochloride
Thumb
  • InChI Key: LPRLDRXGWKXRMQ-UHFFFAOYSA-N
  • Monoisotopic Mass: 317.154642102
  • Average Mass: 317.853
DBSALT000807
Brand names
NameCompany
AllergenNot Available
ArbidNot Available
BelfeneNot Available
DiafenRiker
HisprilNopco
HistynNot Available
LergobineNot Available
LyssipollLyssia
MepibenNot Available
NeargalNot Available
Brand mixtures
Brand NameIngredients
Biohisdex Dm DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Biohisdine Dm DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Chemhisdex Dm DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
Chemhisdine Dm DecongestantDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
CodalinCodeine Phosphate + Diphenylpyraline Hydrochloride + Phenylephrine Hydrochloride
CorytabAcetaminophen + Caffeine + Diphenylpyraline Hydrochloride
Creo-Rectal AdulteCamphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate
Creo-Rectal EnfantCamphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate
Creo-Rectal NourrissonCamphor + Diphenylpyraline Hydrochloride + Guaiacol Carbonate
Emercidin D TabAcetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Emercreme No4 Ont EfaBacitracin + Benzocaine + Cetylpyridinium Chloride + Diphenylpyraline Hydrochloride + Tyrothricin
MetrateDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Potassium Iodide + Sodium Citrate
Nezger TabAcetylsalicylic Acid + Diphenylpyraline Hydrochloride + Guaifenesin + Phenylephrine Hydrochloride
Oradrine 2 TabAcetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Oradrine TabletsAcetaminophen + Caffeine + Codeine Phosphate + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Oradrine-2 TabAcetaminophen + Caffeine + Diphenylpyraline Hydrochloride + Phenylpropanolamine Hydrochloride
Protectosil Plus EfaDiphenylpyraline Hydrochloride + Silicone
Sinugex 38Acetaminophen + Caffeine + Diphenylpyraline Hydrochloride
Solucodan-HDiphenylpyraline Hydrochloride + Hydrocodone Bitartrate + Menthol + Potassium Guaiacol Sulphonate + Sodium Citrate
Vito Bronches SiropDextromethorphan Hydrobromide + Diphenylpyraline Hydrochloride + Potassium Iodide + Sodium Citrate
Categories
CAS number147-20-6
WeightAverage: 281.392
Monoisotopic: 281.177964363
Chemical FormulaC19H23NO
InChI KeyOWQUZNMMYNAXSL-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
IUPAC Name
4-(diphenylmethoxy)-1-methylpiperidine
SMILES
CN1CCC(CC1)OC(C1=CC=CC=C1)C1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassDiphenylmethanes
Direct parentDiphenylmethanes
Alternative parentsBenzylethers; Piperidines; Tertiary Amines; Dialkyl Ethers; Polyamines
Substituentsbenzylether; piperidine; tertiary amine; ether; polyamine; dialkyl ether; organonitrogen compound; amine
Classification descriptionThis compound belongs to the diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Pharmacology
IndicationFor use in the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
PharmacodynamicsDiphenylpyraline 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 actionAntihistamines 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.
AbsorptionWell absorbed after oral administration.
Volume of distributionNot Available
Protein binding> 99% in human serum albumin
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9896
Blood Brain Barrier + 0.9912
Caco-2 permeable + 0.8103
P-glycoprotein substrate Substrate 0.7232
P-glycoprotein inhibitor I Inhibitor 0.6457
P-glycoprotein inhibitor II Non-inhibitor 0.96
Renal organic cation transporter Inhibitor 0.8556
CYP450 2C9 substrate Non-substrate 0.7922
CYP450 2D6 substrate Substrate 0.5316
CYP450 3A4 substrate Substrate 0.5729
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8931
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.9492
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9468
Ames test Non AMES toxic 0.7893
Carcinogenicity Non-carcinogens 0.9481
Biodegradation Not ready biodegradable 0.9066
Rat acute toxicity 2.3662 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.8094
hERG inhibition (predictor II) Inhibitor 0.5695
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
PackagersNot Available
Dosage forms
FormRouteStrength
LiquidIntradermal
LiquidSubcutaneous
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point206Not Available
logP3.7Not Available
Predicted Properties
PropertyValueSource
water solubility1.88e-02 g/lALOGPS
logP3.82ALOGPS
logP3.66ChemAxon
logS-4.2ALOGPS
pKa (strongest basic)8.87ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area12.47ChemAxon
rotatable bond count4ChemAxon
refractivity87.36ChemAxon
polarizability32.97ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Knox, L.H. and Kapp, R.; U.S. Patent 2,479,843; August 23, 1949; assigned to Nopco
Chemical Company.

US2479843
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
ResourceLink
KEGG DrugD01172
PubChem Compound3103
PubChem Substance46504936
ChemSpider2992
BindingDB50241333
ChEBI59788
ChEMBL
Therapeutic Targets DatabaseDAP001071
PharmGKBPA164746377
Drug Product Database777285
WikipediaDiphenylpyraline
ATC CodesR06AA07V01AA02V01AA20
AHFS Codes
  • 92:04.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
Food InteractionsNot Available

Targets

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

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

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Drug created on June 13, 2005 07:24 / Updated on April 15, 2014 11:55