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Chlorpheniramine
Identification
- Name
- Chlorpheniramine
- Accession Number
- DB01114
- Description
A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than promethazine.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Chlorpheniramine (DB01114)
- Weight
- Average: 274.788
Monoisotopic: 274.123676325 - Chemical Formula
- C16H19ClN2
- Synonyms
- 1-(p-chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropane
- 1-(p-chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamine
- 2-[p-chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine
- 3-(p-chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine
- Chlorophenylpyridamine
- Chlorphenamin
- Chlorphenamine
- Chlorphenaminum
- Chlorpheniramine
- Chlorpheniramine polistirex
- Chlorpheniraminum
- Clorfenamina
- Clorfeniramina
- γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine
- γ-(4-chlorophenyl)-γ-(2-pyridyl)propyldimethylamine
Pharmacology
- Indication
For the treatment of rhinitis, urticaria, allergy, common cold, asthma and hay fever.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Chlorpheniramine, is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
- Mechanism of action
Chlorpheniramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
Target Actions Organism AHistamine H1 receptor antagonistHumans USodium-dependent serotonin transporter inhibitorHumans USodium-dependent noradrenaline transporter inhibitorHumans USodium-dependent dopamine transporter inhibitorHumans - Absorption
Well absorbed in the gastrointestinal tract.
- Volume of distribution
- Not Available
- Protein binding
72%
- Metabolism
Primarily hepatic via Cytochrome P450 (CYP450) enzymes.
- Route of elimination
- Not Available
- Half-life
21-27 hours
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Oral LD50 (rat): 306 mg/kg; Oral LD50 (mice): 130 mg/kg; Oral LD50 (guinea pig): 198 mg/kg [Registry of Toxic Effects of Chemical Substances. Ed. D. Sweet, US Dept. of Health & Human Services: Cincinatti, 2010.] Also a mild reproductive toxin to women of childbearing age.
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Chlorphenamine 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 Unlock Additional DataAbametapir The serum concentration of Chlorpheniramine can be increased when it is combined with Abametapir. Abatacept The metabolism of Chlorpheniramine can be increased when combined with Abatacept. Abiraterone The metabolism of Chlorpheniramine can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Chlorpheniramine can be decreased when combined with Acalabrutinib. Acebutolol The risk or severity of QTc prolongation can be increased when Chlorpheniramine is combined with Acebutolol. Acenocoumarol The risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Acenocoumarol. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Chlorpheniramine. Acetophenazine The risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Acetophenazine. Acetylcholine The risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Acetylcholine. Aclidinium Chlorpheniramine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid alcohol.
- Take with food.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Chlorpheniramine gluconate 79YPK3BAIT 25387-68-2 OCMSTKFGYJZBIY-IFWQJVLJSA-N Chlorpheniramine hydrochloride 5S6VUP419V 56343-98-7 NOXNCSQBTYNMHD-UHFFFAOYSA-N Chlorpheniramine maleate V1Q0O9OJ9Z 113-92-8 DBAKFASWICGISY-BTJKTKAUSA-N Chlorpheniramine tannate 72JT935YTT 1405-56-7 KOOFUFFGNZKXFG-HBNMXAOGSA-N - Product Images
- International/Other Brands
- Chlo-Amine / Chlor-Trimeton (Schering-Plough) / Haynon / Piriton (GlaxoSmithKline)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataChlorpheniramine Maleate Injection USP Liquid Intramuscular; Intravenous; Subcutaneous Omega Laboratories Ltd Not applicable Not applicable Canada 
Chlortripolon Inj 10mg/ml Liquid Intramuscular; Intravenous; Subcutaneous Schering Plough 1953-12-31 1999-08-04 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional Data4 Hour Allergy Relief Tablet 4 mg/1 Oral Better Living Brands, LLC 1992-12-19 2022-07-22 US 
Aller-chlor Syrup 2 mg/5mL Oral RUGBY LABORATORIES 2014-03-20 2020-09-30 US Aller-chlor Tablet 4 mg/1 Oral RUGBY LABORATORIES 1992-12-19 Not applicable US Aller-chlor Tablet 4 mg/1 Oral A-S Medication Solutions 1992-12-19 2018-03-31 US Aller-Chlor Syrup 2 mg/5mL Oral Rugby Laboratories, Inc. 2003-01-17 2018-07-29 US Aller-chlor Tablet 4 mg/1 Oral Lake Erie Medical DBA Quality Care Products LLC 1992-12-19 2017-06-01 US Allergy Tablet 4 mg/1 Oral A S Medication Solutions 1992-12-19 Not applicable US Allergy Tablet 4 mg/1 Oral A-S Medication Solutions 1992-12-19 2019-06-30 US Allergy Tablet 4 mg/1 Oral REMEDYREPACK INC. 2009-02-26 2017-10-19 US Allergy Tablet 4 mg/1 Oral Cardinal Health 1992-12-19 2020-02-07 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 999 Cold Remedy Chlorpheniramine maleate (2 mg/6000mg) + Acetaminophen (100 mg/6000mg) Capsule Oral China Resources Sanjiu Medical & Pharmaceutical Co., Ltd. 2003-07-03 Not applicable US 999 Cold Remedy Granular Chlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g) Granule Oral China Resources Sanjiu Medical & Pharmaceutical Co., Ltd. 2003-07-03 Not applicable US 999 Cold Remedy Granular Chlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g) Capsule Oral China Resources Sanjiu Medical & Pharmaceutical Co Ltd 2003-07-03 2013-09-21 US 999 GANMAOLING Cold Chlorpheniramine maleate (2 mg/1) + Acetaminophen (100 mg/1) + Caffeine (2 mg/1) Capsule Oral Kingsway 2012-07-30 Not applicable US AccuHist Chlorpheniramine maleate (1 mg/1mL) + Phenylephrine hydrochloride (2.5 mg/1mL) Solution Oral Tiber Laboratories, LLC 2010-01-25 2013-04-30 US AccuHist PDX Chlorpheniramine maleate (1 mg/1mL) + Dextromethorphan hydrobromide monohydrate (2.5 mg/1mL) + Phenylephrine hydrochloride (2.5 mg/1mL) Solution Oral Tiber Laboratories, LLC 2010-01-25 2013-04-30 US Acetaminophen, Ascorbic acid, Chlorpheniramine Maleate Chlorpheniramine maleate (1 mg/12000mg) + Acetaminophen (160 mg/12000mg) + Ascorbic acid (50 mg/12000mg) Powder, for solution Oral Contract Pharmacal Corp. 2015-01-19 Not applicable US Acetaminophen, Chlorpheniramine Maleate, Dextromethorphan Hydrobromide, Phenylephrine Hydrochloride Chlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1) + Phenylephrine hydrochloride (5 mg/1) Tablet, coated Oral AAA Pharmaceutical, Inc. 2012-12-28 2012-12-29 US Acetaminophen, Chlorpheniramine Maleate, Dextromethorphan Hydrobromide, Phenylephrine Hydrochloride Chlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1) + Phenylephrine hydrochloride (5 mg/1) Tablet, coated Oral AAA Pharmaceutical, Inc. 2012-12-28 2012-12-29 US Acetaminophen, Chlorpheniramine Maleate, Phenylephrine Hydrochloride Chlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1) Tablet, coated Oral AAA Pharmaceutical, Inc. 2012-08-02 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Allergy DN II Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) Kit Oral Breckenridge Pharmaceutical, Inc. 2008-11-01 2010-03-31 US Allergy DN II Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) Kit Oral Breckenridge Pharmaceutical, Inc. 2008-11-01 2010-03-31 US Allergy DN PE Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (40 mg/1) + Phenylephrine hydrochloride (10 mg/1) Kit Oral Breckenridge Pharmaceutical, Inc. 2008-11-01 2010-03-31 US AlleRx Dose Pack Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (10 mg/1) + Pseudoephedrine hydrochloride (120 mg/1) Kit Oral Cornerstone Therapeutics Inc. 2008-02-01 2012-10-31 US AlleRx Dose Pack DF Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) Kit Oral Cornerstone Therapeutics Inc. 2006-08-01 2012-10-31 US AlleRx Dose Pack DF Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) Kit Oral Cornerstone Therapeutics Inc. 2006-08-01 2012-10-31 US AlleRx Dose Pack PE Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (40 mg/1) + Phenylephrine hydrochloride (10 mg/1) Kit Oral Cornerstone Therapeutics Inc. 2006-09-01 2012-10-31 US Atrohist Pediatric Chlorpheniramine tannate (2 mg/5mL) + Mepyramine tannate (12.5 mg/5mL) + Phenylephrine tannate (5 mg/5mL) Suspension Oral Physicians Total Care, Inc. 1994-09-23 2008-12-05 US Atuss DS Tannate Suspension Chlorpheniramine maleate (4 mg/5mL) + Dextromethorphan hydrobromide monohydrate (30 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Suspension Oral Atley Pharmaceuticals 2006-11-21 Not applicable US Atuss HS Tannate Chlorpheniramine maleate (4 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL) Suspension Oral Atley Pharmaceuticals 2006-11-21 2009-08-03 US
Categories
- ATC Codes
- R06AB54 — Chlorphenamine, combinations
- R06AB — Substituted alkylamines
- R06A — ANTIHISTAMINES FOR SYSTEMIC USE
- R06 — ANTIHISTAMINES FOR SYSTEMIC USE
- R — RESPIRATORY SYSTEM
- Drug Categories
- Anti-Allergic Agents
- Antidepressive Agents
- Antihistamines for Systemic Use
- Antipruritics
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Moderate Risk QTc-Prolonging Agents
- Neurotransmitter Agents
- OCT1 inhibitors
- OCT2 Inhibitors
- Propylamine Derivatives
- Pyridines
- QTc Prolonging Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- Substituted Alkylamines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pheniramines. These are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Pheniramines
- Direct Parent
- Pheniramines
- Alternative Parents
- Chlorobenzenes / Aralkylamines / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Chlorobenzene / Halobenzene / Heteroaromatic compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary amino compound, pyridines, monochlorobenzenes (CHEBI:52010)
Chemical Identifiers
- UNII
- 3U6IO1965U
- CAS number
- 132-22-9
- InChI Key
- SOYKEARSMXGVTM-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
- IUPAC Name
- [3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
- SMILES
- CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
References
- Synthesis Reference
Anil M. Salpekar, John Johnson, "Acetaminophen compositions containing low doses of chlorpheniramine maleate, method for preparing same and tablets formed therefrom." U.S. Patent US4631284, issued April, 1975.
US4631284- General References
- MSDS [Link]
- External Links
- Human Metabolome Database
- HMDB0001944
- KEGG Drug
- D07398
- KEGG Compound
- C06905
- PubChem Compound
- 2725
- PubChem Substance
- 46508253
- ChemSpider
- 2624
- BindingDB
- 35938
- 2400
- ChEBI
- 52010
- ChEMBL
- CHEMBL505
- Therapeutic Targets Database
- DAP000336
- PharmGKB
- PA448960
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Chlorpheniramine
- AHFS Codes
- 04:04.20 — Propylamine Derivatives
- MSDS
- Download (72.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Streptococcal Infections 1 4 Recruiting Prevention Protamine Adverse Reaction 1 3 Completed Treatment Rhinitis, Allergic, Seasonal 1 3 Unknown Status Treatment Acute Rhinitis / Influenza-like illness or flu-like symptoms 1 3 Withdrawn Treatment Acute Rhinitis 1 2 Completed Treatment Allergic Reactions 1 2 Completed Treatment Geriatric Hip Fracture Pain Management 1 2 Terminated Treatment Allergic Rhinitis (AR) 1 2 Terminated Treatment Hepatitis B Chronic Infection 1 2 Terminated Treatment Sunburn 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amend
- Anip Acquisition Co.
- A-S Medication Solutions LLC
- Breckenridge Pharmaceuticals
- C.O. Truxton Inc.
- Cardinal Health
- Consolidated Midland Corp.
- Contract Pharm
- Cypress Pharmaceutical Inc.
- Deltex Pharmaceuticals Inc.
- Direct Dispensing Inc.
- Dispensing Solutions
- Edwards Pharmaceuticals
- Hi Tech Pharmacal Co. Inc.
- Iopharm Laboratories Inc.
- Ivax Pharmaceuticals
- Kowa Pharmaceuticals America Inc.
- Kraft Pharmaceutical Co. Inc.
- Larken Laboratories Inc.
- Liberty Pharmaceuticals
- Magna Pharmaceuticals
- Major Pharmaceuticals
- Mallinckrodt Inc.
- McNeil Laboratories
- Meda AB
- Misemer Pharmaceuticals Inc.
- Mismer Pharmace
- Nucare Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Pecos Pharmaceutical Inc.
- Perrigo Co.
- Physicians Total Care Inc.
- Prepackage Specialists
- Provident Pharmaceuticals LLC
- Qualitest
- Rico Pharmacal
- River's Edge Pharmaceuticals
- Rugby Laboratories
- S&P Healthcare
- Schering-Plough Inc.
- Time-Cap Labs
- Tya Pharmaceuticals
- Watson Pharmaceuticals
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Capsule Oral Solution Oral Capsule, liquid filled Not applicable Granule, effervescent Oral Powder, for solution Oral Syrup Oral 2 mg/5mL Capsule, gelatin coated Oral Tablet, coated Oral Liquid; tablet Intramuscular; Oral; Subcutaneous Liquid; tablet Oral; Parenteral Suspension Oral Granule, for solution Oral Liquid Topical Tablet, extended release Oral 12 mg/1 Tablet, extended release Oral Kit; tablet; tablet, extended release Oral Solution / drops Oral Powder Not applicable 1 kg/1kg Tablet Oral 4 mg/1 Tablet, film coated, extended release Oral 12 mg/1 Liquid Intramuscular; Intravenous; Subcutaneous Syrup Oral Kit; tablet Oral Capsule, coated pellets Oral Tablet, sugar coated Oral Solution / drops Nasal Lozenge Oral 2 mg/1 Kit; powder, for solution Oral Tablet, film coated Oral Liquid Oral 2 mg/1mL Liquid Oral 2 mg/5mL Tablet, coated Oral 4 mg/1 Tablet, effervescent Oral Kit; powder Oral Granule Oral Capsule Oral 1.25 mg/1 Capsule, delayed release pellets Oral Tablet, film coated Oral 4 mg/1 Tablet, multilayer Oral Powder Oral Tablet Oral Syrup Oral Liquid Oral Tablet, multilayer, extended release Oral Tablet, chewable Oral Tablet Oral Tablet, extended release Oral Capsule, extended release Oral Suspension, extended release Oral Suspension Oral 1000 mg/1 Kit Oral Capsule, liquid filled Oral - Prices
Unit description Cost Unit Ahist 12 mg tablet 1.1USD tablet Myci chlor-tan 8 mg caplet 0.75USD caplet Chlorpheniramine powder 0.67USD g Chlor-trimeton allergy 0.31USD each Chlor-trimeton 8 mg repetab 0.24USD tablet Aller-chlor 4 mg tablet 0.06USD tablet Pediacare allergy solution 0.05USD ml Allergy 4 mg tablet 0.04USD tablet Chlorpheniramine 4 mg tablet 0.02USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS7863287 No 2011-01-04 2027-02-28 US US8062667 No 2011-11-22 2029-03-29 US US8790700 No 2014-07-29 2027-03-15 US US9066942 No 2015-06-30 2032-01-03 US US6383471 No 2002-05-07 2019-04-06 US US6248363 No 2001-06-19 2019-11-23 US US9107921 No 2015-08-18 2032-01-03 US US10238640 No 2019-03-26 2024-05-25 US Additional Data Available- Filed On
Properties
- State
- Liquid
- Experimental Properties
Property Value Source boiling point (°C) 142 °C Not Available water solubility 5500 mg/L (at 37 °C) BEILSTEIN logP 3.38 HANSCH,C ET AL. (1995) pKa 9.13 (at 25 °C) PERRIN,DD (1965) - Predicted Properties
Property Value Source Water Solubility 0.0519 mg/mL ALOGPS logP 3.74 ALOGPS logP 3.58 ChemAxon logS -3.7 ALOGPS pKa (Strongest Basic) 9.47 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 16.13 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 80.85 m3·mol-1 ChemAxon Polarizability 30.82 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 + 0.9754 Blood Brain Barrier + 0.962 Caco-2 permeable + 0.8749 P-glycoprotein substrate Substrate 0.6136 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.9376 Renal organic cation transporter Inhibitor 0.7916 CYP450 2C9 substrate Non-substrate 0.8026 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.6472 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9096 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9023 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7501 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9183 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 3.3361 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8702 hERG inhibition (predictor II) Inhibitor 0.7145
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Tagawa M, Kano M, Okamura N, Higuchi M, Matsuda M, Mizuki Y, Arai H, Iwata R, Fujii T, Komemushi S, Ido T, Itoh M, Sasaki H, Watanabe T, Yanai K: Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-chlorpheniramine, a classical antihistamine. Br J Clin Pharmacol. 2001 Nov;52(5):501-9. [PubMed:11736858]
- Salata JJ, Jurkiewicz NK, Wallace AA, Stupienski RF 3rd, Guinosso PJ Jr, Lynch JJ Jr: Cardiac electrophysiological actions of the histamine H1-receptor antagonists astemizole and terfenadine compared with chlorpheniramine and pyrilamine. Circ Res. 1995 Jan;76(1):110-9. [PubMed:8001268]
- Hasenohrl RU, Kuhlen A, Frisch C, Galosi R, Brandao ML, Huston JP: Comparison of intra-accumbens injection of histamine with histamine H1-receptor antagonist chlorpheniramine in effects on reinforcement and memory parameters. Behav Brain Res. 2001 Oct 15;124(2):203-11. [PubMed:11640974]
- Yasuda SU, Wellstein A, Likhari P, Barbey JT, Woosley RL: Chlorpheniramine plasma concentration and histamine H1-receptor occupancy. Clin Pharmacol Ther. 1995 Aug;58(2):210-20. [PubMed:7648771]
- Nicholson AN, Pascoe PA, Turner C, Ganellin CR, Greengrass PM, Casy AF, Mercer AD: Sedation and histamine H1-receptor antagonism: studies in man with the enantiomers of chlorpheniramine and dimethindene. Br J Pharmacol. 1991 Sep;104(1):270-6. [PubMed:1686208]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Serotonin:sodium symporter activity
- Specific Function
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Norepinephrine:sodium symporter activity
- Specific Function
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188]
- Yasuda SU, Wellstein A, Likhari P, Barbey JT, Woosley RL: Chlorpheniramine plasma concentration and histamine H1-receptor occupancy. Clin Pharmacol Ther. 1995 Aug;58(2):210-20. [PubMed:7648771]
- Yasuda SU, Zannikos P, Young AE, Fried KM, Wainer IW, Woosley RL: The roles of CYP2D6 and stereoselectivity in the clinical pharmacokinetics of chlorpheniramine. Br J Clin Pharmacol. 2002 May;53(5):519-25. [PubMed:11994058]
- He N, Zhang WQ, Shockley D, Edeki T: Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. Eur J Clin Pharmacol. 2002 Feb;57(12):847-51. [PubMed:11936702]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Flockhart Table of Drug Interactions [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]
Drug created on June 13, 2005 07:24 / Updated on August 05, 2020 23:35
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