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Identification
NameTriprolidine
Accession NumberDB00427  (APRD00306)
TypeSmall Molecule
GroupsApproved
Description

First generation histamine H1 antagonist used in allergic rhinitis; asthma; and urticaria. It is a component of cough and cold medicines. It may cause drowsiness. [PubChem]

Structure
Thumb
Synonyms
Actahist
Actidil
Actifed
Allerfed
Corphed
Histafed
Myfed
Myidyl
Trilitron
Triphed
Tripolidina
Triprolidin
Triprolidine
Triprolidinum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Histexsyrup2.5 mg/5mLoralAllegis Pharmaceuticals, LLC2014-03-04Not applicableUs
Histex Pd Dropssyrup.938 mg/mLoralAllegis Pharmaceuticals, LLC2014-03-06Not applicableUs
Vanahist Pdliquid.625 mg/mLoralGm Pharmaceuticals,Inc2014-03-19Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
AnminAND
VenenSato Seiyaku
Brand mixtures
NameLabellerIngredients
Actifed DM SyrupGlaxo Wellcome Inc.
Actifed DM TabletsGlaxo Wellcome Inc.
Actifed Plus CapletGlaxo Wellcome Inc.
Actifed Plus CapletsMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
Actifed SyrupGlaxo Wellcome Inc.
Actifed TabletsGlaxo Wellcome Inc.
AprodineRebel Distributors Corp
CoactifedGlaxosmithkline Inc
CotrifedTechnilab Pharma Inc.
Covan SyrupPharmascience Inc
Ed-A-hist PseEDWARDS PHARMACEUTICALS, INC.
Histex AcAllegis Pharmaceuticals, LLC
Histex-DMAllegis Pharmaceuticals, LLC
Histex-PEAllegis Pharmaceuticals, LLC
Poly Hist NcPoly Pharmaceuticals, Inc.
Ratio-cotridinTeva Canada Limited
Ratio-cotridin ExpectorantTeva Canada Limited
SilafedSilarx Pharmaceuticals, Inc
Triacin-CSTI Pharma LLC
Triprofed TabIcn Canada Ltd.
Wal-actWALGREEN CO.
Salts
Name/CASStructureProperties
Triprolidine Hydrochloride
Thumb
  • InChI Key: WYUYEJNGHIOFOC-NWBUNABESA-N
  • Monoisotopic Mass: 314.154976453
  • Average Mass: 314.852
DBSALT000623
Categories
UNII2L8T9S52QM
CAS number486-12-4
WeightAverage: 278.3914
Monoisotopic: 278.178298714
Chemical FormulaC19H22N2
InChI KeyInChIKey=CBEQULMOCCWAQT-WOJGMQOQSA-N
InChI
InChI=1S/C19H22N2/c1-16-7-9-17(10-8-16)18(19-6-2-3-12-20-19)11-15-21-13-4-5-14-21/h2-3,6-12H,4-5,13-15H2,1H3/b18-11+
IUPAC Name
2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine
SMILES
CC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropenes. These are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropenes
Direct ParentPhenylpropenes
Alternative Parents
Substituents
  • Phenylpropene
  • Styrene
  • Toluene
  • N-alkylpyrrolidine
  • Pyridine
  • Heteroaromatic compound
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the symptomatic relief of seasonal or perennial allergic rhinitis or nonallergic rhinitis; allergic conjunctivitis; and mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Also used in combination with other agents for the symptomatic relief of symptoms associated with the common cold.
PharmacodynamicsIn allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Triprolidine, is a histamine H1 antagonist that 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. Triprolidine has anticholinergic and sedative effects.
Mechanism of actionTriprolidine 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
AbsorptionRapidly absorbed in the intestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life4 to 6 hours.
ClearanceNot Available
ToxicitySymptoms of overdose include drowsiness, weakness, inco-ordination, difficulty with micturition, respiratory depression, hypotension, agitation, irritability, convulsions, hypertension, palpitation and tachycardia.
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+0.9905
Blood Brain Barrier+0.9664
Caco-2 permeable-0.5814
P-glycoprotein substrateSubstrate0.6644
P-glycoprotein inhibitor IInhibitor0.8311
P-glycoprotein inhibitor IINon-inhibitor0.6624
Renal organic cation transporterInhibitor0.8612
CYP450 2C9 substrateNon-substrate0.8143
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6075
CYP450 1A2 substrateNon-inhibitor0.8613
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8598
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9551
BiodegradationNot ready biodegradable0.9833
Rat acute toxicity2.7123 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7001
hERG inhibition (predictor II)Non-inhibitor0.5557
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
  • Usl pharma inc
  • Alpharma us pharmaceuticals division
  • Halsey drug co inc
  • Pharmaceutical assoc inc div beach products
  • Vitarine pharmaceuticals inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral
Tablet, coatedoral
Syruporal2.5 mg/5mL
Syruporal
Syruporal.938 mg/mL
Liquidoral
Liquidoral.625 mg/mL
Tablet, film coatedoral
Prices
Unit descriptionCostUnit
Triprolidine hcl crystals40.33USD g
Triprolidine 1.25 mg/5 ml liq0.15USD ml
Tripohist 1.25 mg/5 ml liquid0.14USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point60 °CPhysProp
water solubility74.9 mg/LNot Available
logP3.92HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0537 mg/mLALOGPS
logP4.14ALOGPS
logP4.05ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.53 m3·mol-1ChemAxon
Polarizability33.09 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 ReferenceNot Available
General References
  1. Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [PubMed:2568212 ]
  2. Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [PubMed:7913608 ]
  3. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [PubMed:2866055 ]
  4. Telekes A, Holland RL, Withington DA, Peck AW: Effects of triprolidine and dipipanone in the cold induced pain test, and the central nervous system of healthy volunteers. Br J Clin Pharmacol. 1987 Jul;24(1):43-50. [PubMed:3620284 ]
External Links
ATC CodesR06AX07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72.7 KB)
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Triprolidine.
AcetazolamideThe serum concentration of Triprolidine can be increased when it is combined with Acetazolamide.
AclidiniumAclidinium may increase the anticholinergic activities of Triprolidine.
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Triprolidine.
Ammonium chlorideThe serum concentration of Triprolidine can be decreased when it is combined with Ammonium chloride.
AmphetamineAmphetamine may decrease the sedative activities of Triprolidine.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Triprolidine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Triprolidine.
AzelastineTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Triprolidine.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Triprolidine.
Benzylpenicilloyl PolylysineTriprolidine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Triprolidine.
Botulinum Toxin Type ATriprolidine may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BTriprolidine may increase the anticholinergic activities of Botulinum Toxin Type B.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
BuprenorphineTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
CabergolineCabergoline may increase the hypertensive activities of Triprolidine.
Calcium AcetateThe serum concentration of Triprolidine can be increased when it is combined with Calcium Acetate.
CathinoneCathinone may decrease the sedative activities of Triprolidine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Triprolidine.
Cimetropium BromideTriprolidine may increase the anticholinergic activities of Cimetropium Bromide.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Triprolidine.
DiclofenamideThe serum concentration of Triprolidine can be increased when it is combined with Diclofenamide.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Triprolidine.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Triprolidine.
DoxofyllineThe risk or severity of adverse effects can be increased when Triprolidine is combined with Doxofylline.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
EluxadolineTriprolidine may increase the activities of Eluxadoline.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Triprolidine.
EthanolTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
EthoxzolamideThe serum concentration of Triprolidine can be increased when it is combined with Ethoxzolamide.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Triprolidine.
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Triprolidine.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Triprolidine.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Triprolidine is combined with Glucagon recombinant.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Triprolidine.
HydrocodoneTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Triprolidine.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Triprolidine.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Triprolidine.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Triprolidine.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Triprolidine.
LinezolidLinezolid may increase the hypertensive activities of Triprolidine.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Triprolidine.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Triprolidine.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Triprolidine.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Triprolidine.
MethotrimeprazineTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Triprolidine.
MetyrosineTriprolidine may increase the sedative activities of Metyrosine.
MianserinMianserin may increase the anticholinergic activities of Triprolidine.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Triprolidine.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
MirabegronThe risk or severity of adverse effects can be increased when Triprolidine is combined with Mirabegron.
MirtazapineTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
MorphineThe risk or severity of adverse effects can be increased when Triprolidine is combined with Morphine.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Triprolidine.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Triprolidine.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Triprolidine.
OrphenadrineTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Triprolidine.
ParaldehydeTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
ParoxetineThe risk or severity of adverse effects can be increased when Triprolidine is combined with Paroxetine.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
PhenelzinePhenelzine may increase the hypertensive activities of Triprolidine.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Triprolidine.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Triprolidine.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Triprolidine.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Triprolidine.
Potassium ChlorideTriprolidine may increase the ulcerogenic activities of Potassium Chloride.
PramipexoleTriprolidine may increase the sedative activities of Pramipexole.
PramlintidePramlintide may increase the anticholinergic activities of Triprolidine.
PrazosinPrazosin may decrease the vasoconstricting activities of Triprolidine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Triprolidine.
RamosetronTriprolidine may increase the activities of Ramosetron.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Triprolidine.
RopiniroleTriprolidine may increase the sedative activities of Ropinirole.
RotigotineTriprolidine may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Triprolidine.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Triprolidine.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Triprolidine.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Triprolidine.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Triprolidine.
SuvorexantTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TacrineThe therapeutic efficacy of Triprolidine can be decreased when used in combination with Tacrine.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Triprolidine.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Triprolidine.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Triprolidine.
ThalidomideTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
TiotropiumTriprolidine may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Triprolidine is combined with Topiramate.
TranylcypromineTranylcypromine may increase the hypertensive activities of Triprolidine.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Triprolidine.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Triprolidine.
VenlafaxineVenlafaxine may increase the tachycardic activities of Triprolidine.
ZolpidemTriprolidine may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
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. Peroutka SJ, Snyder SH: Two distinct serotonin receptors: regional variations in receptor binding in mammalian brain. Brain Res. 1981 Mar 16;208(2):339-47. [PubMed:7214150 ]
  2. Claro E, Arbones L, Garcia A, Picatoste F: Phosphoinositide hydrolysis mediated by histamine H1-receptors in rat brain cortex. Eur J Pharmacol. 1986 Apr 16;123(2):187-96. [PubMed:3011460 ]
  3. Kuzmin AI, Zaretsky DV, Kalenikova EI, Zaretskaja MV, Medvedev OS, Chazov EI: The effect of histamine receptor antagonists on stress-induced catecholamine secretion: an adrenomedullary microdialysis study in the rat. Eur J Pharmacol. 1999 Aug 13;378(3):311-6. [PubMed:10493107 ]
  4. Ziganshina LE, Ziganshin AU, Hoyle CH, Burnstock G: Acute paw oedema formation induced by ATP: re-evaluation of the mechanisms involved. Inflamm Res. 1996 Feb;45(2):96-102. [PubMed:8907591 ]
  5. Hiroi T, Ohishi N, Imaoka S, Yabusaki Y, Fukui H, Funae Y: Mepyramine, a histamine H1 receptor antagonist, inhibits the metabolic activity of rat and human P450 2D forms. J Pharmacol Exp Ther. 1995 Feb;272(2):939-44. [PubMed:7853212 ]
  6. Estelle F, Simons R: H1-receptor antagonists: safety issues. Ann Allergy Asthma Immunol. 1999 Nov;83(5):481-8. [PubMed:10582735 ]
  7. Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [PubMed:2568212 ]
  8. Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [PubMed:7913608 ]
  9. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [PubMed:2866055 ]
  10. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

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. 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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on January 15, 2016 17:38