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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
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
Salts
Name/CASStructureProperties
Diphenylpyraline Hydrochloride
Thumb
  • InChI Key: LPRLDRXGWKXRMQ-UHFFFAOYSA-N
  • Monoisotopic Mass: 317.154642102
  • Average Mass: 317.853
DBSALT000807
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Benzylether
  • Piperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.9896
Blood Brain Barrier+0.9912
Caco-2 permeable+0.8103
P-glycoprotein substrateSubstrate0.7232
P-glycoprotein inhibitor IInhibitor0.6457
P-glycoprotein inhibitor IINon-inhibitor0.96
Renal organic cation transporterInhibitor0.8556
CYP450 2C9 substrateNon-substrate0.7922
CYP450 2D6 substrateSubstrate0.5316
CYP450 3A4 substrateSubstrate0.5729
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateInhibitor0.8931
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-inhibitor0.9492
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9468
Ames testNon AMES toxic0.7893
CarcinogenicityNon-carcinogens0.9481
BiodegradationNot ready biodegradable0.9066
Rat acute toxicity2.3662 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8094
hERG inhibition (predictor II)Inhibitor0.5695
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point206Not Available
logP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0188 mg/mLALOGPS
logP3.82ALOGPS
logP3.66ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.36 m3·mol-1ChemAxon
Polarizability32.97 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesR06AA07
AHFS Codes
  • 92:04.00*
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
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