Identification
- Summary
Mepyramine is an antihistamine agent used for the symptomatic treatment of allergy, hypersensitivity reactions, and pruritic skin disorders.
- Brand Names
- Midol Complete, Midol Cramps & Bodyaches, Pamprin Multi-symptom, Premsyn Pms, Vanacof-8
- Generic Name
- Mepyramine
- DrugBank Accession Number
- DB06691
- Background
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.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Mepyramine (DB06691)
- Weight
- Average: 285.384
Monoisotopic: 285.184112373 - Chemical Formula
- C17H23N3O
- 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
Pharmacology
- Indication
Indicated for the treatment of allergic conditions, symptomatic relief of hypersensitivity reaction, and treatment of pruritic skin disorders.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Allergic rhinitis ••• ••• Symptomatic treatment of Allergies ••• ••• Used in combination to treat Atopic dermatitis (ad) Combination Product in combination with: Hydrocortisone acetate (DB14539) •••••••••••• ••••• Symptomatic treatment of Common cold ••• ••• Symptomatic treatment of Hay fever ••• ••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - 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
- Adverse Effects
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The signs and symptoms that are produced after the acute overdosage of Mepyramine include Convulsions, Coma, Ataxia, Hyperpyrexia, Tremor, Extrapyramidal effects, Excitement.
- Pathways
Pathway Category Mepyramine H1-Antihistamine Action Drug 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Mepyramine is combined with 1,2-Benzodiazepine. Acebutolol The metabolism of Acebutolol can be decreased when combined with Mepyramine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Mepyramine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Mepyramine. Acrivastine The risk or severity of QTc prolongation can be increased when Mepyramine is combined with Acrivastine. - Food Interactions
- Avoid alcohol.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Mepyramine maleate R35D29L3ZA 59-33-6 JXYWFNAQESKDNC-BTJKTKAUSA-N Mepyramine tannate A9310LW34B 183969-60-0 FPPPOGQYQQBHQR-HBNMXAOGSA-N - Product Images
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Childrens PediaClear 8 Liquid 12.5 mg/15mL Oral GM Pharmaceuticals, INC 2019-08-19 Not applicable US 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acetaminophen 500mg Caffeine 60mg Pyrilamine maleate 15mg Mepyramine maleate (15 mg/1) + Acetaminophen (500 mg/1) + Caffeine (60 mg/1) Tablet Oral Opmx Llc 2020-04-01 Not applicable US Acetaminophen 500mg Caffeine 60mg Pyrilamine maleate 15mg Mepyramine maleate (15 mg/1) + Acetaminophen (500 mg/1) + Caffeine (60 mg/1) Tablet Oral Walgreens Co. 2019-07-05 Not applicable US Acetaminophen 500mg Caffeine 60mg Pyrilamine maleate 15mg Mepyramine maleate (15 mg/1) + Acetaminophen (500 mg/1) + Caffeine (60 mg/1) Tablet Oral Opmx Llc 2020-04-01 Not applicable US Acetaminophen 500mg Caffeine 60mg Pyrilamine maleate 15mg Mepyramine maleate (15 mg/1) + Acetaminophen (500 mg/1) + Caffeine (60 mg/1) Tablet Oral Opmx Llc 2020-04-01 Not applicable US Acetaminophen,Caffeine and Pyrilamine Maleate Mepyramine maleate (15 mg/1) + Acetaminophen (500 mg/1) + Caffeine (60 mg/1) Tablet Oral Apnar Pharma Lp 2022-07-05 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image A-Tan 12X Suspension Mepyramine tannate (30 mg/5mL) + Guaifenesin (100 mg/5mL) + Phenylephrine tannate (5 mg/5mL) Suspension Oral Amneal Pharmaceuticals 2006-01-06 2008-12-05 US Atrohist Pediatric Mepyramine tannate (12.5 mg/5mL) + Chlorpheniramine tannate (2 mg/5mL) + Phenylephrine tannate (5 mg/5mL) Suspension Oral Physicians Total Care, Inc. 1994-09-23 2008-12-05 US C-Tanna 12D Suspension Mepyramine tannate (30 mg/5mL) + Pentoxyverine tannate (30 mg/5mL) + Phenylephrine tannate (5 mg/5mL) Suspension Oral Prasco, Laboratories 2006-01-01 2008-10-31 US Capron DMT Mepyramine maleate (30 mg/1) + Dextromethorphan hydrobromide monohydrate (30 mg/1) Tablet Oral Capital Pharma 2017-01-26 Not applicable US Chlor-Tan A 12 Suspension Mepyramine tannate (12.5 mg/5mL) + Chlorpheniramine tannate (2 mg/5mL) + Phenylephrine tannate (5 mg/5mL) Suspension Oral Amneal Pharmaceuticals 2006-01-06 2008-12-05 US
Categories
- ATC Codes
- D04AA02 — Mepyramine
- D04AA — Antihistamines for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- Drug Categories
- Amines
- Aminopyridines
- Anti-Allergic Agents
- Antihistamines for Systemic Use
- Antihistamines for Topical Use
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Hypnotics and Sedatives
- Neurotransmitter Agents
- Potential QTc-Prolonging Agents
- Pyridines
- QTc Prolonging Agents
- Sleep Aids, Pharmaceutical
- Substituted Ethylene Diamines
- Chemical TaxonomyProvided by Classyfire
- 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 / Alkyl aryl ether / Amine / Aminopyridine / Anisole / Aromatic heteromonocyclic compound / Azacycle / Dialkylarylamine / Ether / Heteroaromatic compound show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- aromatic ether, ethylenediamine derivative (CHEBI:6762)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- HPE317O9TL
- CAS number
- 91-84-9
- 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
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
- 9009
- ChEBI
- 6762
- ChEMBL
- CHEMBL511
- ZINC
- ZINC000019144216
- PharmGKB
- PA165817939
- PDBe Ligand
- Y5E
- Wikipedia
- Mepyramine
- PDB Entries
- 8x63
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Suspended Not Available Labor, First Stage 1 3 Completed Treatment Nasal Congestion 1 2, 3 Completed Treatment Cervicobrachial Neuralgia 1 Not Available Not Yet Recruiting Basic Science Peripheral neuropathy 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Oral 12.5 mg/15mL Tablet, chewable Oral Liquid Oral Gel Topical Capsule Oral Powder Oral Capsule, liquid filled Oral Tablet, film coated Oral Tablet, coated Oral Solution Oral Liquid Ophthalmic Suspension Oral Powder Not applicable 25 kg/25kg Tablet Oral Tablet, extended release Oral Syrup Oral Cream - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 3.27 HANSCH,C ET AL. (1995) pKa 8.85 (at 20 °C) PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 0.781 mg/mL ALOGPS logP 2.89 ALOGPS logP 3.04 Chemaxon logS -2.6 ALOGPS pKa (Strongest Basic) 8.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 28.6 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 87.74 m3·mol-1 Chemaxon Polarizability 32.89 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9662 Blood Brain Barrier + 0.9382 Caco-2 permeable + 0.6226 P-glycoprotein substrate Substrate 0.822 P-glycoprotein inhibitor I Non-inhibitor 0.8781 P-glycoprotein inhibitor II Non-inhibitor 0.8079 Renal organic cation transporter Inhibitor 0.7157 CYP450 2C9 substrate Non-substrate 0.7894 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6168 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.8722 CYP450 3A4 inhibitor Non-inhibitor 0.937 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6972 Ames test Non AMES toxic 0.928 Carcinogenicity Non-carcinogens 0.8897 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4469 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5722 hERG inhibition (predictor II) Inhibitor 0.7313
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.3150798 predictedDarkChem Lite v0.1.0 [M-H]- 169.80714 predictedDeepCCS 1.0 (2019) [M+H]+ 185.6504798 predictedDarkChem Lite v0.1.0 [M+H]+ 172.16516 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.0653798 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.2583 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Parsons ME, Ganellin CR: Histamine and its receptors. Br J Pharmacol. 2006 Jan;147 Suppl 1:S127-35. [Article]
- Snowman AM, Snyder SH: Cetirizine: actions on neurotransmitter receptors. J Allergy Clin Immunol. 1990 Dec;86(6 Pt 2):1025-8. [Article]
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
- 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. [Article]
- 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. [Article]
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
- 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. [Article]
- 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
- 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. [Article]
Drug created at January 13, 2009 17:35 / Updated at February 02, 2024 22:54