Identification

Name
Mepyramine
Accession Number
DB06691
Type
Small Molecule
Groups
Approved, 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
Product Ingredients
IngredientUNIICASInChI Key
Pyrilamine maleateR35D29L3ZA59-33-6JXYWFNAQESKDNC-BTJKTKAUSA-N
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antitussive Decong Antihistamine SyrPyrilamine maleate (6.5 mg) + Dextromethorphan hydrobromide (15 mg) + Pheniramine maleate (6.5 mg) + Phenylpropanolamine hydrochloride (13 mg)SyrupOralProdemdis Enr.1992-12-312001-04-26Canada
Ara Menstrual CompletePyrilamine maleate (15 mg) + Acetaminophen (500 mg) + Caffeine (60 mg)TabletOralAra Avanti Rx Analytics IncNot applicableNot applicableCanada
Babys Own Cough SyrPyrilamine maleate (160 mg) + Ammonium chloride (910 mg) + Guaifenesin (1 g)LiquidOralG.T. Fulford Pharmaceuticals1977-12-311998-06-25Canada
Bronchodex Fort-DM SyrPyrilamine maleate (10 mg) + Ammonium chloride (129.6 mg) + Dextromethorphan hydrobromide (15 mg) + Menthol (.405 mg) + Sodium Citrate (64.8 mg)SyrupOralTherapex Division De E Z Em Canada Inc1980-12-311997-07-22Canada
Bronchosirum Pour EnfantsPyrilamine maleate (6.25 mg) + Dextromethorphan hydrobromide (15 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg)SyrupOralBronchosirum Inc.1987-12-311997-08-05Canada
Caldomine Dh AdultePyrilamine maleate (12.5 mg) + Hydrocodone bitartrate (5 mg) + Pheniramine maleate (12.5 mg) + Phenylpropanolamine hydrochloride (25 mg)LiquidOralTechnilab Pharma Inc.1981-12-312001-04-04Canada
Caldomine Dh EnfantPyrilamine maleate (6.25 mg) + Hydrocodone bitartrate (1.667 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg)LiquidOralTechnilab Pharma Inc.1982-12-312001-04-04Canada
Capron DMPyrilamine maleate (7.5 mg/5mL) + Dextromethorphan hydrobromide (7.5 mg/5mL)LiquidOralCapital Pharmaceutical2013-06-20Not applicableUs
Capron DMTPyrilamine maleate (30 mg/1) + Dextromethorphan hydrobromide (30 mg/1)TabletOralCapital Pharma2017-01-26Not applicableUs
Centracol DM - SyrPyrilamine maleate (6.25 mg) + Dextromethorphan hydrobromide (15 mg) + Pheniramine maleate (6.25 mg) + Phenylpropanolamine hydrochloride (12.5 mg)SyrupOralPrometic Pharma Inc.1994-12-311999-08-12Canada
Categories
UNII
HPE317O9TL
CAS number
91-84-9
Weight
Average: 285.384
Monoisotopic: 285.184112373
Chemical Formula
C17H23N3O
InChI Key
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

Pharmacology

Indication

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

Structured Indications
Pharmacodynamics
Not 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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not 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 organisms
Not Available
Pathways
PathwayCategory
Mepyramine H1-Antihistamine ActionDrug action
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
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
GepefrineGepefrine may decrease the sedative activities of Mepyramine.Experimental
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Mepyramine.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Mepyramine.Approved
Iofetamine I-123Iofetamine I-123 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
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Mepyramine.Experimental
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Mepyramine.Approved, Investigational
Midomafetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mepyramine.Experimental, Illicit, 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.Approved, Withdrawn
Food Interactions
  • Avoid alcohol
  • Take with food

References

Synthesis Reference
US2502151
General References
Not Available
External Links
Human Metabolome Database
HMDB15639
KEGG Drug
D08183
KEGG Compound
C11798
PubChem Compound
4992
PubChem Substance
175427084
ChemSpider
4818
BindingDB
22567
ChEBI
6762
ChEMBL
CHEMBL511
PharmGKB
PA165817939
Wikipedia
Mepyramine
ATC Codes
R06AC01 — MepyramineD04AA02 — Mepyramine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral
PowderOral
Tablet, coatedOral
Capsule, liquid filledOral
TabletOral
Tablet, film coatedOral
SyrupOral
SolutionOral
LiquidOphthalmic
PillOral
LiquidOral
Tablet, extended releaseOral
SuspensionOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0076-0290000000-f68a382a2e28b5f2b1fb
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0930000000-a4aabde6bd23d5631e8d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0900000000-0461973c5b6a31124ad2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0900000000-5803a397af45d47e559f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-1900000000-005c71fce551a8ce71a9
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-2900000000-fbd3ea6b25f6238e4903
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0090000000-7580edc933e367e03bd4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0920000000-116fdb01e72f6eed832c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-d384a4904e9cf89d30a8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-1900000000-760bc84c56f7512a6a55
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00fr-7900000000-8873262b3e31b11b3ccc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-1900000000-c9b1c86211e3b0d8e024
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-5900000000-30296f89ac06c75ba738
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0076-0390000000-3af09900aa13a2ca6791
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0930000000-b947fc17f6a8ca5aa2c2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0900000000-debdce4be33f8a51cd66

Taxonomy

Description
This compound belongs to the class of organic compounds known as 2-benzylaminopyridines. These are aromatic compounds containing pyridine ring substituted at the 2-position by a benzylamine group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzylamines
Direct Parent
2-benzylaminopyridines
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Dialkylarylamines / Anisoles / Aminopyridines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds
show 2 more
Substituents
2-benzylaminopyridine / Phenoxy compound / Anisole / Methoxybenzene / Dialkylarylamine / Phenol ether / Alkyl aryl ether / Aminopyridine / Imidolactam / Pyridine
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether, ethylenediamine derivative (CHEBI:6762)

Targets

Details
1. Histamine H1 receptor
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 catecholamin...
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...
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...
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 cat...
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 November 09, 2017 03:54