Chlorpheniramine

Identification

Summary

Chlorpheniramine is a histamine-H1 receptor antagonist indicated for the management of symptoms associated with upper respiratory allergies.

Brand Names
Aller-chlor, Allerest PE, Children's Nyquil Cold and Cough, Codar Ar, Coricidin Hbp Cold & Flu, Coricidin Hbp Cough and Cold, Dimetapp Long Acting Cough Plus Cold, Robitussin Pediatric Cough & Cold LA, Scot-tussin Sugar Free DM, Sudogest, Tussicaps, Tussionex, Tuxarin, Tuzistra, Wal-finate, Wal-finate-D
Generic Name
Chlorpheniramine
DrugBank Accession Number
DB01114
Background

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.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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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.

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
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Chlorpheniramine is combined with 1,2-Benzodiazepine.
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 metabolism of Acebutolol can be decreased when combined with Chlorpheniramine.
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.
Interactions
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Food Interactions
  • Avoid alcohol.
  • Take with food.

Products

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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 USPLiquid10 mg / mLIntramuscular; Intravenous; SubcutaneousOmega Laboratories LtdNot applicableNot applicableCanada flag
Chlortripolon Inj 10mg/mlLiquid10 mg / mLIntramuscular; Intravenous; SubcutaneousSchering Plough1953-12-311999-08-04Canada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
4 Hour Allergy ReliefTablet4 mg/1OralBetter Living Brands, LLC1992-12-192022-07-22US flag
Aller-chlorTablet4 mg/1OralA-S Medication Solutions1992-12-19Not applicableUS flag
Aller-chlorTablet4 mg/1OralLake Erie Medical DBA Quality Care Products LLC1992-12-192017-06-01US flag
Aller-chlorTablet4 mg/1OralRUGBY LABORATORIES1992-12-19Not applicableUS flag
Aller-ChlorSyrup2 mg/5mLOralRugby Laboratories, Inc.2003-01-172018-07-29US flag
Aller-chlorSyrup2 mg/5mLOralRUGBY LABORATORIES2014-03-202020-09-30US flag
AllergyTablet4 mg/1OralPreferred Pharmaceuticals Inc.2017-04-24Not applicableUS flag
AllergyTablet4 mg/1OralAidarex Pharmaceuticals LLC1992-12-19Not applicableUS flag
AllergyTablet4 mg/1OralAllegiant Health2014-12-15Not applicableUS flag
AllergyTablet4 mg/1OralKroger1987-07-152015-12-01US flag
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
A-FERİN 1 MG +160 MG/5 ML PEDİYATRİK ŞURUP, 100 MLChlorpheniramine maleate (1 mg/5mL) + Acetaminophen (160 mg/5mL)SyrupOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2020-08-14Not applicableTurkey flag
A-FERİN 300 MG/2 MG/10 MG KAPSÜL, 1000 ADETChlorpheniramine maleate (2 mg) + Acetaminophen (300 mg) + Codeine phosphate (10 mg)CapsuleOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2020-08-14Not applicableTurkey flag
A-FERİN 300 MG/2 MG/10 MG KAPSÜL, 20 ADETChlorpheniramine maleate (2 mg) + Acetaminophen (300 mg) + Codeine phosphate (10 mg)CapsuleOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2020-08-14Not applicableTurkey flag
A-FERİN 300 MG/2 MG/10 MG KAPSÜL, 30 ADETChlorpheniramine maleate (2 mg) + Acetaminophen (300 mg) + Codeine phosphate (10 mg)CapsuleOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2020-08-14Not applicableTurkey flag
A-FERİN 300 MG/2 MG/10 MG KAPSÜL, 500 ADETChlorpheniramine maleate (2 mg) + Acetaminophen (300 mg) + Codeine phosphate (10 mg)CapsuleOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2020-08-14Not applicableTurkey flag
A-FERIN FORTE 650 MG/4 MG FİLM KAPLI TABLET, 15 ADETChlorpheniramine maleate (4 mg) + Acetaminophen (650 mg)Tablet, coatedOralHÜSNÜ ARSAN İLAÇLARI A.Ş.2020-08-14Not applicableTurkey 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)
Affected organisms
  • Humans and other mammals

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
MSDS
Download (72.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionProtamine Adverse Reaction1
4CompletedPreventionStreptococcal Infections1
4CompletedTreatmentDermatitis, Dermatitis Atopic / Effects of Immunotherapy1
3CompletedTreatmentSeasonal Allergic Rhinitis2
3RecruitingTreatmentMulti-food Allergy / Peanut Allergies1
3TerminatedBasic ScienceImmunologic Desensitization1
3TerminatedTreatmentAllergic Rhinitis Due to Dust Mite1
3Unknown StatusTreatmentAllergic Rhinitis (Disorder)1
3Unknown StatusTreatmentCommon Cold / Influenza-like illness or flu-like symptoms1
3WithdrawnTreatmentCommon Cold1

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
CapsuleOral4 mg
CapsuleOral
SolutionOral
Capsule
Capsule, liquid filledNot applicable
Granule, effervescentOral
Powder, for solutionOral
SyrupOral2 mg/5mL
Capsule, gelatin coatedOral
Tablet, coatedOral
Tablet4 mg
Liquid; tabletIntramuscular; Oral; Subcutaneous
Liquid; tabletOral; Parenteral
SuspensionOral
Granule, for solutionOral
LiquidTopical
CapsuleOral
Tablet, extended releaseOral12 mg/1
Tablet, extended releaseOral12 mg
Kit; tablet; tablet, extended releaseOral
TabletOral12 mg / tab
Solution / dropsOral
SyrupOral
PowderNot applicable1 kg/1kg
TabletOral
TabletOral4 mg/1
Tablet, film coated, extended releaseOral12 mg/1
InjectionIntramuscular; Intravenous; Subcutaneous
LiquidIntramuscular; Intravenous; Subcutaneous10 mg / mL
SyrupOral2.5 mg / 5 mL
SyrupOral0.04 g
SyrupOral40 mg
SyrupOral50 mg
Tablet, coatedOral8 mg
Tablet, coatedOral12 mg
SolutionParenteral10 mg
Kit; tabletOral
Capsule, coated pelletsOral
Tablet, sugar coatedOral
Solution / dropsNasal
LozengeOral2 mg/1
Kit; powder, for solutionOral
TabletOral15 mg
Syrup
Tablet, film coatedOral
LiquidOral2 mg/1mL
LiquidOral2 mg/5mL
Tablet, coatedOral4 mg/1
Tablet, effervescentOral
Tablet
Kit; powderOral
GranuleOral
CapsuleOral1.25 mg/1
TabletOral4 mg / tab
SyrupOral0.05 g
Capsule, delayed release pelletsOral
Tablet, film coatedOral4 mg/1
Tablet, multilayerOral
SolutionNasal
PowderOral
GranuleOral500 mg
TabletOral
Suspension
LiquidOral
SyrupOral
LiquidOral
Tablet, multilayer, extended releaseOral
SprayNasal
Capsule, coatedOral
Tablet, chewableOral
ElixirOral
Tablet, delayed releaseOral
Injection, solution
Tablet, coatedOral
Tablet, extended releaseOral
Capsule, extended releaseOral
Suspension, extended releaseOral
SuspensionOral1000 mg/1
KitOral
Solution / dropsOphthalmic
Capsule, liquid filledOral
Elixir
Tablet, coatedOral4 mg
SolutionParenteral10 mg/1ml
Tablet, sugar coatedOral4 mg
Tablet, film coatedOral4 mg
Solution
TabletOral4 mg
TabletOral2 mg
Elixir
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

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

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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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
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. [Article]
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. [Article]

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]

Drug created on June 13, 2005 13:24 / Updated on September 19, 2021 19:53