You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameMepyramine
Accession NumberDB06691
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

Mepyramine (also known as pyrilamine) is a first generation antihistamine, targeting the H1 receptor. However, it rapidly permeates the brain and so often causes drowsiness as a side effect.
It is used in over-the-counter combination products for colds and menstrual symptoms.

Structure
Thumb
Synonyms
Mepyramine
N-(P-Methoxybenzyl)-n',n'-dimethyl-N-(alpha-pyridyl)ethylenediamine
N-[(4-Methoxyphenyl)methyl]-n',n'-dimethyl-N-2-pyridinyl-1,2-ethanediamine
N',n'-dimethyl-N-(P-methoxybenzyl)-N-(2-pyridyl)ethylenediamine
Pyranisamine
pyrilamine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Antitussive Decong Antihistamine SyrProdemdis Enr.
Babys Own Cough SyrG.T. Fulford Pharmaceuticals
Bronchodex Fort-DM SyrTherapex Division De E Z Em Canada Inc
Bronchosirum Pour EnfantsBronchosirum Inc.
Caldomine Dh AdulteTechnilab Pharma Inc.
Caldomine Dh EnfantTechnilab Pharma Inc.
Capron DMCapital Pharmaceutical, Llc
Centracol DM - SyrPrometic Pharma Inc.
Codituss DMQualitest Pharmaceuticals
Comfort-timeTime Cap Labs, Inc
Complete Menstrual ReliefGood Sense (Geiss, Destin & Dunn, Inc.)
Extra Strength Menstrual CompleteVita Health Products Inc
Extra Strength Multi-symptom Pms ReliefVita Health Products Inc
Extra Strength Tylenol Menstrual CapletsMcneil Consumer Healthcare Division Of Johnson & Johnson Inc
Glen PEGlendale Inc
HistaflexAllegis Pharmaceuticals, LLC
HycomineBristol Myers Squibb Canada
Hycomine-SBristol Myers Squibb Canada
I D M Expectorant TabRougier Pharma Division Of Ratiopharm Inc
I.D.M. SolutionRougier Pharma Division Of Ratiopharm Inc
Idm TabRougier Pharma Division Of Ratiopharm Inc
Jack & Jill Cough SyrupThe Buckley's Company
Leader PremenstrualCardinal Health
Lemon TimeNovartis Consumer Health Canada Inc.
Maximum Strength Menstrual CompleteRite Aid
Menstrual CompleteThe Kroger Co.
Menstrual Complete Maximum StrengthRite Aid
Menstrual Midol CompleteBayer Inc Consumer Care
Menstrual Pain ReliefDolgencorp, LLC
Menstrual Pain Relief Maximum StrengthRite Aid
Menstrual Pain Relief Maximum Strength / Multi SymptomDolgencorp, LLC
Menstrual Pain Relief Maximum Strength, Multi-symptomChain Drug Marketing Association Inc
Menstrual ReliefWALGREEN CO.
Menstrual Relief Extra StrengthBetter Living Brands, Llc
Menstrual Relief Maximum StrengthWALGREEN CO.
Menstrual Relief Multi-symptomTarget Corporation
Midol CompleteBayer Health Care Llc, Consumer Care
Midol Complete GelcapsBayer Health Care Llc, Consumer Care
Midol Extra Strength GelcapsBayer Inc Consumer Care
Midol Extra Strength MenstrualBayer Inc Consumer Care
Midol Extra Strength PmsBayer Inc Consumer Care
Midol Multi-symptom Caplets Extra StrengthSterling Winthrop Inc.
Midol Multi-symptom Gelcap Extra StrengthBayer Inc Consumer Care
Midol OneBayer Inc Consumer Care
Midol PmsBayer Inc Consumer Care
Midol Pms Extra Strength TabSterling Winthrop Inc.
Multi-symptom Menstrual Pain ReliefFamily Dollar
Multi-symptom Pms ReliefPendopharm Division Of De Pharmascience Inc
Multi-symptom Pms Relief CapletsJamp Pharma Corporation
Neo AcLaser Pharmaceuticals Llc
NinjacofCenturion Labs, Llc
Ninjacof-ACenturion Labs, Llc
Pamprin Extra Strength CapletsSanofi Consumer Health Inc Sanofi Sante Grand Public Inc
Pamprin Multisymptom Menstrual Pain ReliefChattem, Inc.
Pamprin Pms CapletsSanofi Consumer Health Inc Sanofi Sante Grand Public Inc
Pamprin TabChattem Canada
Pharmacol DM SyrTherapex Division De E Z Em Canada Inc
Pharminicol DM SyrupTherapex Division De E Z Em Canada Inc
PMS Formula Maximum StrengthWOONSOCKET PRESCRIPTION CENTER,INCORPORATED
PMS Midol CompleteBayer Inc Consumer Care
PMS Relief Extra StrengthTanta Pharmaceuticals Inc
PMS Relief Maximum StrengthWOONSOCKET PRESCRIPTION CENTER,INCORPORATED
Poly Hist DhcPoly Pharmaceuticals, Inc.
Poly Hist PdPoly Pharmaceuticals, Inc.
Pre Menstrual Relief Maximum StrengthAmerisource Bergen
Prefrin A LiqAllergan Inc
Premsyn Pms Premenstrual Syndrome ReliefChattem, Inc.
Pro-chloPro Pharma, Llc
Pro-clear AcPro Pharma Llc
Pyrilamine Maleate and Phenylephrine HydrochlorideXspire Pharma Llc
Pyrilamine-phenylephrineAcella Pharmaceuticals, LLC
Ratio-theo-broncRatiopharm Inc Division Of Teva Canada Limited
Relievol Pms Extra Strength CapletsTanta Pharmaceuticals Inc
Relievol Pms Regular Strength TabletsTanta Pharmaceuticals Inc
Ru-hist PlusCarwin Associates, Inc
Ru-hist-DCarwin Associates, Inc
SyncolMarcas Usa Llc
Tantacol DM SyrTanta Pharmaceuticals Inc
Teen Midol CompleteBayer Inc Consumer Care
Teen Pms Relief Complete CapletsTanta Pharmaceuticals Inc
TexaclearGm Pharmaceuticals
Texaclear Fast Acting Allergy ReliefGm Pharmaceuticals, Inc.
Trendar Pms CapletWhitehall Robins Inc.
Trendar Pms TabletsWhitehall Robins Inc.
Triaminic Expectorant Dh SyrupNovartis Consumer Health Canada Inc.
Triaminic Time Release TabNovartis Consumer Health Canada Inc.
Triaminicin Colds & Flu CapletsNovartis Consumer Health Canada Inc.
Trisulfaminic SusShepherd Pharmaceuticals Inc.
Trisulfaminic TabShepherd Pharmaceuticals Inc.
Tussaminic C Forte SyrupNovartis Consumer Health Canada Inc.
Tussaminic C Pediatric SyrupNovartis Consumer Health Canada Inc.
Tussaminic Dh Forte SyrupNovartis Consumer Health Canada Inc.
Tussaminic Dh Pediatric SyrupNovartis Consumer Health Canada Inc.
Vanacof-8Gm Pharmaceuticals,Inc
Zotex-CVertical Pharmaceuticals, Inc.
Salts
Name/CASStructureProperties
Pyrilamine maleate
ThumbNot applicableDBSALT001405
Categories
UNIIHPE317O9TL
CAS number91-84-9
WeightAverage: 285.384
Monoisotopic: 285.184112373
Chemical FormulaC17H23N3O
InChI KeyInChIKey=YECBIJXISLIIDS-UHFFFAOYSA-N
InChI
InChI=1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3
IUPAC Name
N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
SMILES
COC1=CC=C(CN(CCN(C)C)C2=NC=CC=C2)C=C1
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
  • Methoxybenzene
  • Dialkylarylamine
  • Phenylmethylamine
  • Phenol ether
  • Benzylamine
  • Anisole
  • Aminopyridine
  • Alkyl aryl ether
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationMepyramine is a first generation antihistamine used in treating allergies, ymptomatic relief of hypersensitivity reaction, and in pruritic skin disorders.
PharmacodynamicsNot Available
Mechanism of actionMepyramine is a histamine H1 receptor inverse agonist. It binds to a G protein-coupled form of the receptor and promotes a G protein-coupled inactive state of the H1 receptor that interferes with the Gq/11-mediated signaling. Mepyramine competes with histamine for binding at H1-receptor sites on the effector cell surface, resulting in suppression of histaminic edema, flare, and pruritus. The sedative properties of Mepyramine occur at the subcortical level of the CNS.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityThe signs and symptoms that are produced after the acute overdosage of Mepyramine include Convulsions, Coma, Ataxia, Hyperpyrexia, Tremor, Extrapyramidal effects, Excitement.
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9662
Blood Brain Barrier+0.9382
Caco-2 permeable+0.6226
P-glycoprotein substrateSubstrate0.822
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.8079
Renal organic cation transporterInhibitor0.7157
CYP450 2C9 substrateNon-substrate0.7894
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6168
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8722
CYP450 3A4 inhibitorNon-inhibitor0.937
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6972
Ames testNon AMES toxic0.928
CarcinogenicityNon-carcinogens0.8897
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4469 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5722
hERG inhibition (predictor II)Inhibitor0.7313
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Liquid
Syruporal
Capsuleoral
Powderoral
Capsule, liquid filledoral
Tablet, film coatedoral
Tabletoral
Tablet, coatedoral
Solutionoral
Liquidophthalmic
Liquidoral
Tablet (extended-release)oral
Suspensionoral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP3.27HANSCH,C ET AL. (1995)
pKa8.85 (at 20 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility0.781 mg/mLALOGPS
logP2.89ALOGPS
logP3.04ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area28.6 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.74 m3·mol-1ChemAxon
Polarizability32.89 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

DrugSyn.org

US2502151
General ReferencesNot Available
External Links
ATC CodesR06AC01D04AA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
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. Moriyama K, Liu J, Jang Y, Chae YJ, Wang Y, Mitchell J, Grond S, Han X, Xing Y, Xie GX, Pierce Palmer P: Receptor mediation and nociceptin inhibition of bradykinin-induced plasma extravasation in the knee joint of the rat. Inflamm Res. 2009 Dec;58(12):873-80. doi: 10.1007/s00011-009-0058-y. Epub 2009 Jun 21. [PubMed:19544046 ]
  2. Chhabria MT, Patel VT, Rajan KS, Brahmkshatriya PS: Design, synthesis and histamine H1-receptor antagonistic activity of some novel 4-amino-2-(substituted)-5-(substituted) aryl-6-[(substituted aryl) amino] pyrimidines. Arzneimittelforschung. 2009;59(5):243-7. [PubMed:19537525 ]
  3. Mojtahedin A, Tamaddonfard E, Zanboori A: Antinociception induced by central administration of histamine in the formalin test in rats. Indian J Physiol Pharmacol. 2008 Jul-Sep;52(3):249-54. [PubMed:19552055 ]
  4. Parsons ME, Ganellin CR: Histamine and its receptors. Br J Pharmacol. 2006 Jan;147 Suppl 1:S127-35. [PubMed:16402096 ]
  5. Snowman AM, Snyder SH: Cetirizine: actions on neurotransmitter receptors. J Allergy Clin Immunol. 1990 Dec;86(6 Pt 2):1025-8. [PubMed:1979798 ]

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 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular Weight:
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3.
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular Weight:
62751.08 Da
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]
Comments
comments powered by Disqus
Drug created on January 13, 2009 10:35 / Updated on August 17, 2016 12:24