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
Thumb
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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
USodium-dependent serotonin transporter
inhibitor
Humans
USodium-dependent noradrenaline transporter
inhibitor
Humans
USodium-dependent dopamine transporter
inhibitor
Humans
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
PathwayCategory
Chlorphenamine 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
AbametapirThe serum concentration of Chlorpheniramine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Chlorpheniramine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Chlorpheniramine can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Chlorpheniramine can be decreased when combined with Acalabrutinib.
AcebutololThe risk or severity of QTc prolongation can be increased when Chlorpheniramine is combined with Acebutolol.
AcenocoumarolThe risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Chlorpheniramine.
AcetophenazineThe risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Acetophenazine.
AcetylcholineThe risk or severity of adverse effects can be increased when Chlorpheniramine is combined with Acetylcholine.
AclidiniumChlorpheniramine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
Additional Data Available
  • Extended Description
    Extended Description

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

    Learn more
  • 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

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol.
  • Take with food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Chlorpheniramine gluconate79YPK3BAIT25387-68-2OCMSTKFGYJZBIY-IFWQJVLJSA-N
Chlorpheniramine hydrochloride5S6VUP419V56343-98-7NOXNCSQBTYNMHD-UHFFFAOYSA-N
Chlorpheniramine maleateV1Q0O9OJ9Z113-92-8DBAKFASWICGISY-BTJKTKAUSA-N
Chlorpheniramine tannate72JT935YTT1405-56-7KOOFUFFGNZKXFG-HBNMXAOGSA-N
Product Images
International/Other Brands
Chlo-Amine / Chlor-Trimeton (Schering-Plough) / Haynon / Piriton (GlaxoSmithKline)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Chlorpheniramine Maleate Injection USPLiquidIntramuscular; Intravenous; SubcutaneousOmega Laboratories LtdNot applicableNot applicableCanada flag
Chlortripolon Inj 10mg/mlLiquidIntramuscular; Intravenous; SubcutaneousSchering Plough1953-12-311999-08-04Canada flag
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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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
4 Hour Allergy ReliefTablet4 mg/1OralBetter Living Brands, LLC1992-12-192022-07-22US flag
Aller-ChlorSyrup2 mg/5mLOralRugby Laboratories, Inc.2003-01-172018-07-29US flag
Aller-chlorTablet4 mg/1OralRUGBY LABORATORIES1992-12-19Not applicableUS flag
Aller-chlorTablet4 mg/1OralA-S Medication Solutions1992-12-192018-03-31US flag
Aller-chlorTablet4 mg/1OralLake Erie Medical DBA Quality Care Products LLC1992-12-192017-06-01US flag
Aller-chlorSyrup2 mg/5mLOralRUGBY LABORATORIES2014-03-202020-09-30US flag
AllergyTablet4 mg/1OralStrategic Sourcing Services, LLC (Sunmark)1992-12-19Not applicableUS flag
AllergyTablet4 mg/1OralCardinal Health1992-12-192020-02-07US flag
AllergyTablet4 mg/1OralREMEDYREPACK INC.2009-02-262017-10-19US flag
AllergyTablet4 mg/1OralKroger1987-07-152015-12-01US flag
Additional Data Available
  • Application Number
    Application Number

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

    Learn more
  • 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 EndRegionImage
999 Cold RemedyChlorpheniramine maleate (2 mg/6000mg) + Acetaminophen (100 mg/6000mg)CapsuleOralChina Resources Sanjiu Medical & Pharmaceutical Co., Ltd.2003-07-03Not applicableUS flag
999 Cold Remedy GranularChlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g)GranuleOralChina Resources Sanjiu Medical & Pharmaceutical Co., Ltd.2003-07-03Not applicableUS flag
999 Cold Remedy GranularChlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g)CapsuleOralChina Resources Sanjiu Medical & Pharmaceutical Co Ltd2003-07-032013-09-21US flag
999 GANMAOLING ColdChlorpheniramine maleate (2 mg/1) + Acetaminophen (100 mg/1) + Caffeine (2 mg/1)CapsuleOralKingsway2012-07-30Not applicableUS flag
AccuHistChlorpheniramine maleate (1 mg/1mL) + Phenylephrine hydrochloride (2.5 mg/1mL)SolutionOralTiber Laboratories, LLC2010-01-252013-04-30US flag
AccuHist PDXChlorpheniramine maleate (1 mg/1mL) + Dextromethorphan hydrobromide monohydrate (2.5 mg/1mL) + Phenylephrine hydrochloride (2.5 mg/1mL)SolutionOralTiber Laboratories, LLC2010-01-252013-04-30US flag
Acetaminophen, Ascorbic acid, Chlorpheniramine MaleateChlorpheniramine maleate (1 mg/12000mg) + Acetaminophen (160 mg/12000mg) + Ascorbic acid (50 mg/12000mg)Powder, for solutionOralContract Pharmacal Corp.2015-01-19Not applicableUS flag
Acetaminophen, Chlorpheniramine Maleate, Dextromethorphan Hydrobromide, Phenylephrine HydrochlorideChlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-282012-12-29US flag
Acetaminophen, Chlorpheniramine Maleate, Dextromethorphan Hydrobromide, Phenylephrine HydrochlorideChlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-282012-12-29US flag
Acetaminophen, Chlorpheniramine Maleate, Phenylephrine HydrochlorideChlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-08-02Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Allergy DN IIChlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitOralBreckenridge Pharmaceutical, Inc.2008-11-012010-03-31US flag
Allergy DN IIChlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitOralBreckenridge Pharmaceutical, Inc.2008-11-012010-03-31US flag
Allergy DN PEChlorpheniramine 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)KitOralBreckenridge Pharmaceutical, Inc.2008-11-012010-03-31US flag
AlleRx Dose PackChlorpheniramine 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)KitOralCornerstone Therapeutics Inc.2008-02-012012-10-31US flag
AlleRx Dose Pack DFChlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitOralCornerstone Therapeutics Inc.2006-08-012012-10-31US flag
AlleRx Dose Pack DFChlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitOralCornerstone Therapeutics Inc.2006-08-012012-10-31US flag
AlleRx Dose Pack PEChlorpheniramine 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)KitOralCornerstone Therapeutics Inc.2006-09-012012-10-31US flag
Atrohist PediatricChlorpheniramine tannate (2 mg/5mL) + Mepyramine tannate (12.5 mg/5mL) + Phenylephrine tannate (5 mg/5mL)SuspensionOralPhysicians Total Care, Inc.1994-09-232008-12-05US flag
Atuss DS Tannate SuspensionChlorpheniramine maleate (4 mg/5mL) + Dextromethorphan hydrobromide monohydrate (30 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-21Not applicableUS flag
Atuss HS TannateChlorpheniramine maleate (4 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-212009-08-03US flag

Categories

ATC Codes
R06AB54 — Chlorphenamine, combinationsR06AB04 — Chlorphenamine
Drug Categories
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
  1. MSDS [Link]
  2. Berko Ilac: Iburamin (ibuprofen/chlorpheniramine) cold syrup [Link]
  3. ilacaBak: Pulmotus (levodropropizine/chlorpheniramine maleate) oral syrup [Link]
Human Metabolome Database
HMDB0001944
KEGG Drug
D07398
KEGG Compound
C06905
PubChem Compound
2725
PubChem Substance
46508253
ChemSpider
2624
BindingDB
35938
RxNav
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
Chlorphenamine
AHFS Codes
  • 04:04.20 — Propylamine Derivatives
MSDS
Download (72.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionStreptococcal Infections1
4CompletedTreatmentAtopic Dermatitis (AD) / Effects of Immunotherapy1
4RecruitingPreventionProtamine Adverse Reaction1
3CompletedTreatmentRhinitis, Allergic, Seasonal1
3CompletedTreatmentSeasonal Allergic Rhinitis (SAR)1
3RecruitingTreatmentMulti-food Allergy / Peanut Allergies1
3TerminatedTreatmentAllergic Rhinitis Due to Dust Mite1
3Unknown StatusTreatmentAcute Rhinitis / Influenza-like illness or flu-like symptoms1
3Unknown StatusTreatmentAllergic Rhinitis (AR)1
3Unknown StatusTreatmentHepatocellular Carcinoma1

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
FormRouteStrength
CapsuleOral
SyrupOral160 mg/5mL
CapsuleOral300 mg
Tablet, coatedOral650 mg
Syrup100 mg/4mL
SolutionOral
Tablet1 mg
Capsule, liquid filledOral1 mg
Capsule, liquid filledOral4 mg
TabletOral650 mg
Capsule, liquid filledNot applicable
Granule, effervescentOral
Powder, for solutionOral
Capsule2 mg
SyrupOral2 mg/5mL
Capsule, gelatin coatedOral
Tablet, coatedOral
Tablet
Liquid; tabletIntramuscular; Oral; Subcutaneous
Liquid; tabletOral; Parenteral
Tablet, coatedOral2 mg
Syrup20 mg/5mL
Tablet, coatedOral4 mg
Tablet2 mg
SyrupOral120 mg/5ml
Capsule25 mg
SuspensionOral
Syrup90 mg/5mL
Syrup110 mg/5mL
Syrup1.5 mg/5mL
Syrup1 mg/15mL
SyrupOral10 mg/5ml
Tablet4 mg
SyrupOral100 mg/5ml
Granule, for solutionOral
SyrupOral30 mg/5ml
Syrup500 mcg/5mL
LiquidTopical
Capsule4 mg
Tablet650 mg
Capsule
Tablet, extended releaseOral12 mg/1
Tablet, extended releaseOral
Kit; tablet; tablet, extended releaseOral
Syrup
Solution / dropsOral1 mg/1mL
Tablet, coatedOral100 mg
Solution / dropsOral
Injection, solution20 mg/2mL
Injection, solution10 mg/1mL
PowderNot applicable1 kg/1kg
SyrupOral
TabletOral4 mg/1
Tablet, film coated, extended releaseOral12 mg/1
Injection
LiquidIntramuscular; Intravenous; Subcutaneous
Cream1 g/100g
SyrupOral0.04 g
TabletOral4 mg
SyrupOral0.05 g
Tablet750 mcg
SyrupOral40 mg
Syrup4 mg/5mL
Kit; tabletOral
CapsuleOral325 mg
CapsuleOral200 mg
Tablet, coatedOral200 mg
Capsule15 mg
Solution / dropsOral50 mg/5mL
Syrup6 mg/15mL
Capsule, coated pelletsOral
Capsule1 mg
Capsule5 mg
SyrupOral5 mg/5ml
Solution / dropsOral2 mg/5mL
Tablet, sugar coatedOral
Syrup750 mcg/5mL
Solution / dropsOral125 mg/5mL
Solution / dropsNasal
LozengeOral2 mg/1
Kit; powder, for solutionOral
Capsule, liquid filledOral500 mg
Capsule, liquid filledOral250 mg
Solution / dropsOral1 mg/15mL
TabletOral300 mg
Syrup15 mg/15ml
Tablet, film coatedOral
Syrup10 mg/5ml
Tablet325 mg
Syrup100 mg/5ml
Syrup2 mg/5ml
LiquidOral2 mg/1mL
LiquidOral2 mg/5mL
Tablet, coatedOral4 mg/1
Tablet, effervescentOral
Syrup150 mg/5ml
Kit; powderOral
Syrup125 mg/5mL
TabletOral250 mg
GranuleOral
Powder, for solutionOral500 mg
TabletOral325 mg
SyrupOral160 mg
PowderOral250 mg
PowderOral10 mg
PowderOral11 mg
Tablet, film coatedOral650 mg
CapsuleOral1.25 mg/1
SyrupOral100 mg
TabletOral200 mg
SuspensionOral200 mg
TabletOral500 mg
Solution / dropsOphthalmic0.05 %
Solution / dropsOral1 mg/5mL
SyrupOral120 mg
CapsuleOral250 mg
Capsule, delayed release pelletsOral
PowderOral500 mg
Syrup4 mg/15mL
SuspensionOral100 mg/5mL
Syrup44 mg/5mL
Syrup50 mg/5mL
Tablet, film coatedOral4 mg/1
Syrup2 mg/15mL
Syrup1 mg/5mL
Tablet, multilayerOral
SolutionNasal35 mg
GranuleOral500 mg
Powder, for solutionOral325 mg
Granule, effervescentOral500 mg
SolutionOral1 mg/5mL
PowderOral
Syrup45 mg/5mL
TabletOral
SyrupOral
LiquidOral
Tablet, multilayer, extended releaseOral
Solution / dropsNasal50 mg
SyrupOral3 g
Injection, solution1 g/10mL
Tablet, chewableOral
Syrup75 mg/5mL
TabletOral
TabletOral10 mg
SuspensionOral1 mg/5mL
Tablet, extended releaseOral
Capsule, extended releaseOral
Suspension, extended releaseOral
SyrupOral15 mg/5ml
Tablet500 mg
Tablet200 mg
Powder, for solution400 mg
SuspensionOral1000 mg/1
Syrup25 mg/5mL
KitOral
SyrupOral20 mg/5mL
Tablet, coatedOral250 mg
Capsule, liquid filledOral
Syrup12.5 mg/5mL
Prices
Unit descriptionCostUnit
Ahist 12 mg tablet1.1USD tablet
Myci chlor-tan 8 mg caplet0.75USD caplet
Chlorpheniramine powder0.67USD g
Chlor-trimeton allergy0.31USD each
Chlor-trimeton 8 mg repetab0.24USD tablet
Aller-chlor 4 mg tablet0.06USD tablet
Pediacare allergy solution0.05USD ml
Allergy 4 mg tablet0.04USD tablet
Chlorpheniramine 4 mg tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7863287No2011-01-042027-02-28US flag
US8062667No2011-11-222029-03-29US flag
US8790700No2014-07-292027-03-15US flag
US9066942No2015-06-302032-01-03US flag
US6383471No2002-05-072019-04-06US flag
US6248363No2001-06-192019-11-23US flag
US9107921No2015-08-182032-01-03US flag
US10238640No2019-03-262024-05-25US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Liquid
Experimental Properties
PropertyValueSource
boiling point (°C)142 °CNot Available
water solubility5500 mg/L (at 37 °C)BEILSTEIN
logP3.38HANSCH,C ET AL. (1995)
pKa9.13 (at 25 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility0.0519 mg/mLALOGPS
logP3.74ALOGPS
logP3.58ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.85 m3·mol-1ChemAxon
Polarizability30.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9754
Blood Brain Barrier+0.962
Caco-2 permeable+0.8749
P-glycoprotein substrateSubstrate0.6136
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.9376
Renal organic cation transporterInhibitor0.7916
CYP450 2C9 substrateNon-substrate0.8026
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.6472
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9096
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9023
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7501
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9183
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.3361 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8702
hERG inhibition (predictor II)Inhibitor0.7145
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
GC-MS Spectrum - EI-BGC-MSsplash10-0zfr-6290000000-2ca3230cde716588805e
Mass Spectrum (Electron Ionization)MSsplash10-0zfr-6490000000-8e58cd1c686f23a7dac6
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-01b9-3900000000-ea4ccfd2afe05f49fc7a
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-004i-0090000000-9e46eb080de95d4f8f8e
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-014i-1920000000-d2d2acf559d9070a1d47
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-0zfr-6190000000-2ca3230cde716588805e
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-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0290000000-03651b7b90a1745fdf23
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0uy0-0960000000-1f750af75fe542c6c06f
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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
  1. 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
  1. 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
  1. 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 October 27, 2020 11:12

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