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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:29:01 UTC
HMDB IDHMDB14571
Secondary Accession NumbersNone
Metabolite Identification
Common NameTriprolidine
DescriptionTriprolidine is only found in individuals that have used or taken this drug. It is the 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]Triprolidine 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.
Structure
Thumb
Synonyms
ValueSource
(e)-2-[3-(1-Pyrrolidinyl)-1-P-toluenepropenyl]pyridineChEBI
trans-1-(2-Pyridyl)-3-pyrrolidino-1-P-tolylprop-1-eneChEBI
trans-1-(4-Methylphenyl)-1-(2-pyridyl)-3-pyrrolidinoprop-1-eneChEBI
trans-2-(3-(1-Pyrrolidinyl)-1-P-tolylpropenyl)pyridineChEBI
TripolidinaChEBI
TriprolidinumChEBI
Chemical FormulaC19H22N2
Average Molecular Weight278.3914
Monoisotopic Molecular Weight278.178298714
IUPAC Name2-[(1E)-1-(4-methylphenyl)-3-(pyrrolidin-1-yl)prop-1-en-1-yl]pyridine
Traditional Nametriprolidine
CAS Registry Number486-12-4
SMILES
CC1=CC=C(C=C1)C(=C/CN1CCCC1)\C1=CC=CC=N1
InChI Identifier
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+
InChI KeyInChIKey=CBEQULMOCCWAQT-WOJGMQOQSA-N
Chemical 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
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Allergic Agents
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Histamine H1 Antagonists
  • Membrane integrity/stability
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point60 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.37e-02 g/LNot Available
LogP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.054 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
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00427
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00427
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00427
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445597
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTriprolidine
NuGOwiki LinkHMDB14571
Metagene LinkHMDB14571
METLIN IDNot Available
PubChem Compound5282443
PDB IDNot Available
ChEBI ID165539
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [2568212 ]
  2. Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [7913608 ]
  3. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [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. [3620284 ]

Enzymes

General function:
Involved in monooxygenase 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
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. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
55783.6
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. [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. [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. [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. [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. [7853212 ]
  6. Estelle F, Simons R: H1-receptor antagonists: safety issues. Ann Allergy Asthma Immunol. 1999 Nov;83(5):481-8. [10582735 ]
  7. Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [2568212 ]
  8. Simons FE: H1-receptor antagonists. Comparative tolerability and safety. Drug Saf. 1994 May;10(5):350-80. [7913608 ]
  9. Paton DM, Webster DR: Clinical pharmacokinetics of H1-receptor antagonists (the antihistamines). Clin Pharmacokinet. 1985 Nov-Dec;10(6):477-97. [2866055 ]
  10. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]