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Identification
NameTripelennamine
Accession NumberDB00792  (APRD00689)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat asthma; HAY fever; urticaria; and rhinitis; and also in veterinary applications. Tripelennamine is administered by various routes, including topically. [PubChem]

Structure
Thumb
Synonyms
PBZ
PBZ-sr
Tripelennamin
Tripelennamina
Tripélennamine
Tripelennaminum
External Identifiers
  • RP 2750
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bug Bite Balmcream1.00 %topicalMagically Gone IncNot applicableNot applicableCanada
Pyribenzamine Tab 50mgtablet50 mgoralNovartis Consumer Health Canada Inc.1947-12-311999-07-21Canada
Vagin-Xcream2 %topicalAssociated National Brokerage Inc.2001-08-01Not applicableCanada
Vaginex W Tripelennamine Crm 2%cream2 %vaginalJulius Schmid Canada Ltd.1984-12-311997-08-07Canada
Unapproved/Other Products Not Available
International Brands
NameCompany
AzaronChefaro
PyribenzamineNovartis
TripelCorsa Industries
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Tripelennamine citrate
ThumbNot applicableDBSALT001316
Tripelennamine Hydrochloride
Thumb
  • InChI Key: FSSICIQKZGUEAE-UHFFFAOYSA-N
  • Monoisotopic Mass: 291.150225426
  • Average Mass: 291.819
DBSALT000689
Categories
UNII3C5ORO99TY
CAS number91-81-6
WeightAverage: 255.358
Monoisotopic: 255.173547687
Chemical FormulaC16H21N3
InChI KeyInChIKey=UFLGIAIHIAPJJC-UHFFFAOYSA-N
InChI
InChI=1S/C16H21N3/c1-18(2)12-13-19(16-10-6-7-11-17-16)14-15-8-4-3-5-9-15/h3-11H,12-14H2,1-2H3
IUPAC Name
N-benzyl-N-[2-(dimethylamino)ethyl]pyridin-2-amine
SMILES
CN(C)CCN(CC1=CC=CC=C1)C1=CC=CC=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Phenylmethylamine
  • Benzylamine
  • Aminopyridine
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed for the symptomatic relief of hypersensitivity reactions, coughs, and the common cold.
PharmacodynamicsUsed to treat the effects of colds and allergies. Tripelennamine is an antihistamine. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Tripelennamine is a histamine H1 antagonist. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
Mechanism of actionTripelennamine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Related Articles
AbsorptionWell absorbed in the digestive tract.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include clumsiness or unsteadiness, convulsions, drowsiness, dryness of mouth, nose, or throat, feeling faint, flushing or redness of face, hallucinations, muscle spasms (especially of neck and back), restlessness, shortness of breath or troubled breathing, shuffling walk, tic-like movements of head and face, trembling and shaking of hands and trouble in sleeping.
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+0.9325
Blood Brain Barrier+0.9134
Caco-2 permeable+0.7269
P-glycoprotein substrateSubstrate0.7902
P-glycoprotein inhibitor INon-inhibitor0.9577
P-glycoprotein inhibitor IINon-inhibitor0.9639
Renal organic cation transporterInhibitor0.7383
CYP450 2C9 substrateNon-substrate0.8052
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5332
CYP450 1A2 substrateNon-inhibitor0.5861
CYP450 2C9 inhibitorNon-inhibitor0.8713
CYP450 2D6 inhibitorInhibitor0.8663
CYP450 2C19 inhibitorInhibitor0.5878
CYP450 3A4 inhibitorNon-inhibitor0.9792
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8473
Ames testNon AMES toxic0.9483
CarcinogenicityNon-carcinogens0.9032
BiodegradationNot ready biodegradable0.9961
Rat acute toxicity2.3139 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7151
hERG inhibition (predictor II)Inhibitor0.6518
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
  • Anabolic inc
  • Barr laboratories inc
  • Heather drug co inc
  • Impax laboratories inc
  • Lannett co inc
  • Nylos trading co inc
  • Parke davis div warner lambert co
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Creamtopical1.00 %
Tabletoral50 mg
Creamtopical2 %
Creamvaginal2 %
Prices
Unit descriptionCostUnit
Tripelennamine powder9.94USD g
Tripelennamine hcl powder7.35USD g
Dehistine syrup0.03USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility587 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.3Not Available
logS-2.64ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility2.84 mg/mLALOGPS
logP3.05ALOGPS
logP3.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity81.27 m3·mol-1ChemAxon
Polarizability29.86 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesD04AA04R06AC04
AHFS Codes
  • 04:04.08
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular Weight:
55783.61 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Shimizu K, Nakajyo S, Urakawa N: [Drug sensitivity of the isolated stomach and ileal preparation from a vole]. Nihon Heikatsukin Gakkai Zasshi. 1982 May;18(2):93-103. [PubMed:6759742 ]
  3. Chiba S: Blocking effect of tripelennamine on histamine--induced positive chronotropic and inotropic responses of the dog atrium. Tohoku J Exp Med. 1976 Nov;120(3):299-300. [PubMed:996853 ]
  4. Sansone M: Antihistaminic-opioid combination: effect on locomotor activity in mice. Pol J Pharmacol Pharm. 1988 Sep-Oct;40(5):515-23. [PubMed:3253717 ]
  5. Ohta Y, Kobayashi T, Ishiguro I: Role of endogenous serotonin and histamine in the pathogenesis of gastric mucosal lesions in unanaesthetised rats with a single treatment of compound 48/80, a mast cell degranulator. Pharmacol Res. 1999 Apr;39(4):261-7. [PubMed:10208755 ]
  6. Suzuki T, Mori T, Tsuji M, Misawa M, Onodera K: Interactions between H1-antagonists and opioids: a drug discrimination study. Psychopharmacology (Berl). 1997 Jun;131(4):346-53. [PubMed:9226736 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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Drug created on June 13, 2005 07:24 / Updated on November 24, 2015 12:26