Identification

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Name
Mepyramine
Accession Number
DB06691
Type
Small Molecule
Groups
Approved, Vet approved
Description

Mepyramine, or pyrilamine, targets the H1 receptor. It is a first generation antihistamine. However, it rapidly permeates the brain and so often causes drowsiness as a side effect. It has been found in over-the-counter combination products for colds and menstrual symptoms, but is considered to be an unapproved prescription medication used for cough, cold, or allergic conditions.

Structure
Thumb
Synonyms
  • Mepiramina
  • Mepyramine
  • N-(p-methoxybenzyl)-N',N'-dimethyl-N-(α-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
Mepyramine maleateR35D29L3ZA59-33-6JXYWFNAQESKDNC-BTJKTKAUSA-N
Mepyramine tannateA9310LW34B183969-60-0FPPPOGQYQQBHQR-HBNMXAOGSA-N
Product Images
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Childrens PediaClear 8Liquid12.5 mg/1mLOralGM Pharmaceuticals, INC2019-06-25Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Aldex DMepyramine maleate (16 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)SuspensionOralPernix Therapeutics2010-06-012014-12-31Us
Antitussive Decong Antihistamine SyrMepyramine 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 CompleteMepyramine maleate (15 mg) + Acetaminophen (500 mg) + Caffeine (60 mg)TabletOralAra Avanti Rx Analytics Inc2018-04-06Not applicableCanada
Babys Own Cough SyrMepyramine maleate (160 mg) + Ammonium chloride (910 mg) + Guaifenesin (1 g)LiquidOralG.T. Fulford Pharmaceuticals1977-12-311998-06-25Canada
Bronchodex Fort-DM SyrMepyramine maleate (10 mg) + Ammonium chloride (129.6 mg) + Dextromethorphan hydrobromide (15 mg) + Levomenthol (.405 mg) + Sodium citrate (64.8 mg)SyrupOralTherapex Division De E Z Em Canada Inc1980-12-311997-07-22Canada
Bronchosirum Pour EnfantsMepyramine 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
BuscapinaMepyramine maleate (15 mg/1) + Acetaminophen (500 mg/1) + Caffeine (60 mg/1)Tablet, coatedOralOpmx Llc2018-01-05Not applicableUs
Caldomine Dh AdulteMepyramine 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 EnfantMepyramine 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 DMMepyramine maleate (7.5 mg/5mL) + Dextromethorphan hydrobromide monohydrate (7.5 mg/5mL)LiquidOralCapital Pharmaceutical2013-06-20Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
A-Tan 12X SuspensionMepyramine tannate (30 mg/5mL) + Guaifenesin (100 mg/5mL) + Phenylephrine tannate (5 mg/5mL)SuspensionOralAmneal Pharmaceuticals2006-01-062008-12-05Us
Atrohist PediatricMepyramine tannate (12.5 mg/5mL) + Chlorpheniramine tannate (2 mg/5mL) + Phenylephrine tannate (5 mg/5mL)SuspensionOralPhysicians Total Care, Inc.1994-09-232008-12-05Us
C-Tanna 12D SuspensionMepyramine tannate (30 mg/5mL) + Pentoxyverine tannate (30 mg/5mL) + Phenylephrine tannate (5 mg/5mL)SuspensionOralPrasco, Laboratories2006-01-012008-10-31Us
Chlor-Tan A 12 SuspensionMepyramine tannate (12.5 mg/5mL) + Chlorpheniramine tannate (2 mg/5mL) + Phenylephrine tannate (5 mg/5mL)SuspensionOralAmneal Pharmaceuticals2006-01-062008-12-05Us
Corzall PlusMepyramine maleate (7.5 mg/5mL) + Pentoxyverine citrate (20 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralHawthorn Pharmaceuticals, Inc.2009-08-282011-08-26Us
Deconsal CTMepyramine maleate (16 mg/1) + Phenylephrine hydrochloride (10 mg/1)Tablet, chewableOralCornerstone Therapeutics Inc.2006-10-012009-07-01Us
Deconsal DMMepyramine maleate (16 mg/1) + Dextromethorphan hydrobromide monohydrate (15 mg/1) + Phenylephrine hydrochloride (10 mg/1)Tablet, chewableOralCornerstone Therapeutics Inc.2006-10-012009-08-01Us
Dextro Phenyl PyrilMepyramine (15.5 mg/5mL) + Dextromethorphan (25 mg/5mL) + Phenylephrine (15.5 mg/5mL)LiquidOralRiver's Edge Pharmaceuticals, LLC2008-08-012010-07-31Us
Poly Hist DhcMepyramine maleate (7.5 mg/5mL) + Dihydrocodeine bitartrate (7.5 mg/5mL) + Phenylephrine hydrochloride (5 mg/5mL)LiquidOralPoly Pharmaceuticals2009-11-122012-01-31Us
Poly Hist PdMepyramine maleate (12.5 mg/5mL) + Chlorpheniramine maleate (2 mg/5mL) + Phenylephrine hydrochloride (7.5 mg/5mL)LiquidOralPoly Pharmaceuticals2004-08-052011-08-31Us
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

Indicated for the treatment of allergic conditions, symptomatic relief of hypersensitivity reaction, and treatment of pruritic skin disorders.

Associated Conditions
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
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Mepyramine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Mepyramine.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Mepyramine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Mepyramine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Mepyramine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Mepyramine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when Mepyramine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbexinostatThe risk or severity of QTc prolongation can be increased when Mepyramine is combined with Abexinostat.
AcebutololThe metabolism of Acebutolol can be decreased when combined with Mepyramine.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Mepyramine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
  • Avoid alcohol
  • Take with food

References

Synthesis Reference
US2502151
General References
Not Available
External Links
Human Metabolome Database
HMDB0015639
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
D04AA02 — MepyramineR06AC01 — Mepyramine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3CompletedTreatmentCervicobrachial Neuralgia1
3CompletedTreatmentNasal Congestion / Rhinitis1
4SuspendedNot AvailableLabor, First Stage1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidOral12.5 mg/1mL
Tablet, chewableOral
LiquidOral
CapsuleOral
PowderOral
Capsule, liquid filledOral
Tablet, film coatedOral
Tablet, coatedOral
SolutionOral
LiquidOphthalmic
SuspensionOral
PowderNot applicable25 kg/25kg
TabletOral
Tablet, extended releaseOral
SyrupOral
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
Humans
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
Humans
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. 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]
  2. Kortunay S, Bozkurt A, Basci NE, Brosen K, Kayaalp SO: Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers. Pharmacol Toxicol. 2001 Dec;89(6):331-4. [PubMed:11903961]

Transporters

Kind
Protein
Organism
Humans
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
Humans
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 02, 2019 04:42