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 IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Pyrilamine maleateR35D29L3ZA 59-33-6JXYWFNAQESKDNC-BTJKTKAUSA-NDetails
Product Images
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.
Ara Menstrual CompleteAra Avanti Rx Analytics Inc
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
Capron DmtCapital Pharma
Centracol DM - SyrPrometic Pharma Inc.
Codituss DMQualitest
Comfort-timeTime Cap Laboratories
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
Hycomine-SBristol Myers Squibb
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
Kroger Allergy ReliefKroger
Leader PremenstrualCardinal Health
Lemon TimeNovartis
Maximum Strength Menstrual CompleteRite Aid
Menstrual CompleteKroger
Menstrual Complete Maximum StrengthH.E.B.
Menstrual Midol CompleteBayer Inc Consumer Care
Menstrual Pain ReliefDolgencorp
Menstrual Pain Relief Maximum StrengthRite Aid
Menstrual Pain Relief Maximum Strength / Multi SymptomDolgencorp
Menstrual Pain Relief Maximum Strength, Multi-symptomChain Drug Marketing Association
Menstrual ReliefWalgreen
Menstrual Relief Extra StrengthBetter Living Brands
Menstrual Relief Maximum StrengthTarget Corporation.
Menstrual Relief Maximum Strength Multi SymptomCardinal Health
Menstrual Relief Multi-symptomTarget Corporation.
MidolNavajo Manuracturing Company
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
Ninjacof-ACenturion Labs
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, Inc.
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 StrengthCvs Health
Poly Hist DhcPoly Pharmaceuticals
Poly Hist PdPoly Pharmaceuticals
Pre Menstrual Relief Maximum StrengthAmerisource Bergen (Good Neighbor Pharmacy) 46122
Prefrin A LiqAllergan
Premsyn Pms Premenstrual Syndrome ReliefChattem, Inc.
Pro-chloPro Pharma, Llc
Pro-clear AcPro Pharma, Llc
Pyrilamine Maleate and Phenylephrine HydrochlorideXspire Pharma
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
Texaclear Kids AllergyGm Pharmaceuticals
Trendar Pms CapletWhitehall Robins Inc.
Trendar Pms TabletsWhitehall Robins Inc.
Triaminic Expectorant Dh SyrupNovartis
Triaminic Time Release TabNovartis
Triaminicin Colds & Flu CapletsNovartis
Trisulfaminic SusShepherd Pharmaceuticals Inc.
Trisulfaminic TabShepherd Pharmaceuticals Inc.
Tussaminic C Forte SyrupNovartis
Tussaminic C Pediatric SyrupNovartis
Tussaminic Dh Forte SyrupNovartis
Tussaminic Dh Pediatric SyrupNovartis
Vanacof AcGm Pharmaceuticals
Vanacof-8Gm Pharmaceuticals
Vanatab AcGm Pharmaceuticals
Zotex-CVertical Pharmaceuticals, Inc.
Categories
UNIIHPE317O9TL
CAS number91-84-9
WeightAverage: 285.384
Monoisotopic: 285.184112373
Chemical FormulaC17H23N3O
InChI KeyYECBIJXISLIIDS-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
Pharmacology
Indication

Mepyramine is a first generation antihistamine used in treating allergies, ymptomatic relief of hypersensitivity reaction, and in pruritic skin disorders.

Structured Indications
PharmacodynamicsNot Available
Mechanism of action

Mepyramine 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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Histamine H1 receptorProteinyes
antagonist
HumanP35367 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

The 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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Mepyramine.Experimental, Illicit
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Mepyramine.Experimental, Illicit
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mepyramine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Mepyramine.Experimental, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Mepyramine.Approved, Illicit
BenzphetamineBenzphetamine may decrease the sedative activities of Mepyramine.Approved, Illicit
Benzylpenicilloyl PolylysineMepyramine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Mepyramine.Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Mepyramine.Illicit, Withdrawn
DextroamphetamineDextroamphetamine may decrease the sedative activities of Mepyramine.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Mepyramine.Approved, Illicit
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Mepyramine.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Mepyramine.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine hydrobromide may decrease the sedative activities of Mepyramine.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Mepyramine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Mepyramine.Investigational
MephentermineMephentermine may decrease the sedative activities of Mepyramine.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Mepyramine.Approved, Illicit
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Mepyramine.Approved, Investigational
MMDAMMDA may decrease the sedative activities of Mepyramine.Experimental, Illicit
PhenterminePhentermine may decrease the sedative activities of Mepyramine.Approved, Illicit
PseudoephedrinePseudoephedrine may decrease the sedative activities of Mepyramine.Approved
RitobegronRitobegron may decrease the sedative activities of Mepyramine.Investigational
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Mepyramine.Withdrawn
Food Interactions
  • Avoid alcohol
  • Take with food
References
Synthesis ReferenceUS2502151
General ReferencesNot Available
External Links
ATC CodesR06AC01 — MepyramineD04AA02 — Mepyramine
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
CapsuleOral
PowderOral
Capsule, liquid filledOral
Tablet, film coatedOral
TabletOral
Tablet, coatedOral
SyrupOral
SolutionOral
LiquidOphthalmic
LiquidOral
Tablet, extended releaseOral
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 RuleNoChemAxon
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 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0076-0290000000-f68a382a2e28b5f2b1fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0930000000-a4aabde6bd23d5631e8dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-0461973c5b6a31124ad2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-5803a397af45d47e559fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-1900000000-005c71fce551a8ce71a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-2900000000-fbd3ea6b25f6238e4903View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-7580edc933e367e03bd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0920000000-116fdb01e72f6eed832cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-d384a4904e9cf89d30a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-1900000000-760bc84c56f7512a6a55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00fr-7900000000-8873262b3e31b11b3cccView in MoNA
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
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 2-benzylaminopyridines. These are aromatic compounds containing pyridine ring substituted at the 2-position by a benzylamine group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct Parent2-benzylaminopyridines
Alternative ParentsPhenoxy compounds / Methoxybenzenes / Dialkylarylamines / Anisoles / Aminopyridines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds
Substituents2-benzylaminopyridine / Phenoxy compound / Anisole / Methoxybenzene / Dialkylarylamine / Phenol ether / Alkyl aryl ether / Aminopyridine / Imidolactam / Pyridine
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorsaromatic ether, ethylenediamine derivative (CHEBI:6762 )

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
Uniprot Name:
Histamine H1 receptor
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
Uniprot Name:
Cytochrome P450 2D6
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
Uniprot Name:
Solute carrier family 22 member 4
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
Uniprot Name:
Solute carrier family 22 member 5
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 ]
Drug created on January 13, 2009 10:35 / Updated on June 11, 2017 16:44