Identification

Name
Chlorphenamine
Accession Number
DB01114  (APRD00001, DB09440)
Type
Small Molecule
Groups
Approved
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. [PubChem]

Structure
Thumb
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
  • Chlorphenaminum
  • Chlorpheniramine
  • Chlorpheniramine polistirex
  • Chlorpheniraminum
  • Clorfenamina
  • Clorfeniramina
  • γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine
  • γ-(4-chlorophenyl)-γ-(2-pyridyl)propyldimethylamine
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chlorpheniramine Maleate Injection USPLiquid10 mgIntramuscular; Intravenous; SubcutaneousOmega Laboratories LtdNot applicableNot applicableCanada
Chlortripolon Inj 10mg/mlLiquid10 mgIntramuscular; Intravenous; SubcutaneousSchering Plough1953-12-311999-08-04Canada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
4 Hour Allergy ReliefTablet4 mg/1OralBetter Living Brands1992-12-19Not applicableUs
Aller-chlorTablet4 mg/1OralA-S Medication Solutions1992-12-19Not applicableUs
Aller-ChlorSyrup2 mg/5mLOralRugby2003-01-17Not applicableUs
Aller-chlorSyrup2 mg/5mLOralRugby2014-03-20Not applicableUs
Aller-chlorTablet4 mg/1OralLake Erie Medical Dba Quality Care Produts Llc1992-12-192018-04-17Us
Aller-chlorTablet4 mg/1OralRugby1992-12-19Not applicableUs
AllergyTablet4 mg/1OralA-S Medication Solutions1992-12-19Not applicableUs
AllergyTablet4 mg/1OralCardinal Health1992-12-192020-02-07Us
AllergyTablet4 mg/1OralKroger1987-07-152015-12-01Us
AllergyTablet4 mg/1OralRemedy Repack2017-07-072018-10-26Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
999 Cold RemedyChlorpheniramine maleate (2 mg/6000mg) + Acetaminophen (100 mg/6000mg)CapsuleOralChina Resources Sanjiu Medical & Pharmaceutical Co., Ltd.2003-07-03Not applicableUs
999 Cold Remedy GranularChlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g)GranuleOralChina Resources Sanjiu Medical & Pharmaceutical Co., Ltd.2003-07-03Not applicableUs
999 Cold Remedy GranularChlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g)CapsuleOralChina Resources Sanjiu Medical & Pharmaceutical Co Ltd2003-07-032013-09-21Us
999 GANMAOLING ColdChlorpheniramine maleate (2 mg/1) + Acetaminophen (100 mg/1) + Caffeine (2 mg/1)CapsuleOralKingsway2012-07-30Not applicableUs
AccuHistChlorpheniramine maleate (1 mg/1mL) + Phenylephrine hydrochloride (2.5 mg/1mL)SolutionOralTiber Laboratories, LLC2010-01-252013-04-30Us
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
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.2012-12-28Not applicableUs
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.2012-12-28Not applicableUs
Acetaminophen, Chlorpheniramine Maleate, Phenylephrine HydrochlorideChlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-28Not applicableUs
Acetaminophen, Chlorpheniramine Maleate, Phenylephrine HydrochlorideChlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1)Tablet, coatedOralAAA Pharmaceutical, Inc.2012-12-28Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Allergy DN IIChlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitBreckenridge Pharmaceutical, Inc.2008-11-012010-03-31Us
Allergy DN IIChlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)KitBreckenridge Pharmaceutical, Inc.2008-11-012010-03-31Us
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)KitBreckenridge Pharmaceutical, Inc.2008-11-012010-03-31Us
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
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
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
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
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
Atuss DS Tannate SuspensionChlorpheniramine maleate (4 mg/5mL) + Dextromethorphan hydrobromide monohydrate (30 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-21Not applicableUs
Atuss HS TannateChlorpheniramine maleate (4 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)SuspensionOralAtley Pharmaceuticals2006-11-212009-08-03Us
International/Other Brands
Chlo-Amine / Chlor-Trimeton (Schering-Plough) / Clofeniramina / Haynon / Piriton (GlaxoSmithKline)
Categories
UNII
3U6IO1965U
CAS number
132-22-9
Weight
Average: 274.788
Monoisotopic: 274.123676325
Chemical Formula
C16H19ClN2
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

Pharmacology

Indication

For the treatment of rhinitis, urticaria, allergy, common cold, asthma and hay fever.

Associated Conditions
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
Human
USodium-dependent serotonin transporter
inhibitor
Human
USodium-dependent noradrenaline transporter
inhibitor
Human
USodium-dependent dopamine transporter
inhibitor
Human
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
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
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Chlorphenamine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Chlorphenamine is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Chlorphenamine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Chlorphenamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Chlorphenamine is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Chlorphenamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Chlorphenamine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Chlorphenamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Chlorphenamine is combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Chlorphenamine.
Food Interactions
  • Avoid alcohol.
  • Take with food.

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]
External Links
Human Metabolome Database
HMDB0001944
KEGG Drug
D07398
KEGG Compound
C06905
PubChem Compound
2725
PubChem Substance
46508253
ChemSpider
2624
BindingDB
35938
ChEBI
52010
ChEMBL
CHEMBL505
Therapeutic Targets Database
DAP000336
PharmGKB
PA448960
IUPHAR
1213
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Chlorpheniramine
ATC Codes
R06AB54 — Chlorphenamine, combinationsR06AB04 — Chlorphenamine
AHFS Codes
  • 04:04.20 — Propylamine Derivatives
MSDS
Download (72.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers4
1Not Yet RecruitingTreatmentAdenocarcinoma Of Esophagus / Squamous Cell Carcinoma (SCC) / Tumors, Solid1
1Not Yet RecruitingTreatmentBladder Small Cell Neuroendocrine Carcinoma / Castration-Resistant Prostate Carcinoma / Metastatic Bladder Urothelial Carcinoma / Metastatic Urethral Urothelial Carcinoma / Prostate Carcinoma Metastatic in the Bone / Prostate Neuroendocrine Neoplasm / Prostate Small Cell Carcinoma / Stage III Bladder Cancer AJCC v8 / Stage III Prostate Cancer AJCC v8 / Stage III Urethral Cancer AJCC v8 / Stage IV Bladder Cancer AJCC v8 / Stage IV Prostate Cancer AJCC v8 / Stage IV Urethral Cancer AJCC v8 / Stage IVA Bladder Cancer AJCC v8 / Stage IVB Bladder Cancer AJCC v8 / Transitional Cell Carcinoma / Ureter Small Cell Carcinoma1
1, 2RecruitingTreatmentCancer of the Ovary1
2CompletedTreatmentAllergic Reactions1
2Not Yet RecruitingTreatmentCancer, Breast / Estrogen Receptor Positive Tumor / Her2-Positive Breast Cancer1
2Not Yet RecruitingTreatmentEstrogen Receptor Negative / HER2/Neu Negative / Metastatic Breast Cancer (MBC) / Progesterone Receptor Negative / Recurrent Breast Carcinoma / Triple Negative Breast Cancer (TNBC)1
2RecruitingTreatmentNasal Cavity Adenocarcinoma / Nasal Cavity Tumor / Paranasal Sinus Cancer1
2RecruitingTreatmentSunburn1
2TerminatedTreatmentAllergic Rhinitis (AR)1
2Unknown StatusTreatmentRhinitis, Seasonal, Allergic1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
3Not Yet RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
3RecruitingTreatmentCancer of the Ovary / Fallopian Tube Cancer / Primary Peritoneal Cancer1
3RecruitingTreatmentCervical Cancers1
3Unknown StatusTreatmentAcute Rhinitis / Flu-like Syndromes1
3WithdrawnTreatmentAcute Rhinitis1
4CompletedPreventionAcellular Pertussis / Diphtheria / Healthy Volunteers / Tetanus1
4RecruitingPreventionProtamine Adverse Reaction1
4Unknown StatusTreatmentVitiligo1
Not AvailableCompletedBasic ScienceHypovolaemia / Temperature Change, Body1
Not AvailableCompletedTreatmentPeriodontitis1
Not AvailableUnknown StatusPreventionPoisoning1

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
SolutionOral
Granule, effervescentOral
SyrupOral2 mg/5mL
Capsule, gelatin coatedOral
Tablet, coatedOral4 mg/1
Tablet, coatedOral
KitOral
Liquid; tabletIntramuscular; Oral; Subcutaneous
Liquid; tabletOral; Parenteral
SyrupOral
Granule, for solutionOral
LiquidTopical
SuspensionOral
Tablet, extended releaseOral12 mg/1
Tablet, extended releaseOral12 mg
Kit; tablet; tablet, extended releaseOral
TabletOral12 mg
Solution / dropsOral
TabletOral4 mg/1
Tablet, film coated, extended releaseOral12 mg/1
LiquidIntramuscular; Intravenous; Subcutaneous10 mg
SyrupOral2.5 mg
Kit; tabletOral
Tablet, extended releaseOral
Tablet, sugar coatedOral
Solution / dropsNasal
LozengeOral2 mg/1
Kit; powder, for solutionOral
Tablet, film coatedOral
CapsuleOral
LiquidOral2 mL/1mL
LiquidOral2 mg/5mL
Tablet, effervescentOral
Kit; powderOral
Powder, for solutionOral
GranuleOral
CapsuleOral1.25 mg/1
PowderOral
Tablet, chewableOral
Capsule, delayed release pelletsOral
Tablet, film coatedOral4 mg/1
Tablet, multilayerOral
TabletOral4 mg
Capsule, extended releaseOral
Tablet, multilayer, extended releaseOral
TabletOral
Suspension, extended releaseOral
SuspensionOral1000 mg/1
Kit
LiquidOral
Capsule, liquid filledOral
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)
US7863287No2011-01-042027-02-28Us
US8062667No2011-11-222029-03-29Us
US8790700No2014-07-292027-03-15Us
US9066942No2015-06-302032-01-03Us
US6383471No2002-05-072019-04-06Us
US6248363No2001-06-192019-11-23Us
US9107921No2015-08-182032-01-03Us

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

Taxonomy

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
Pheniramine / Chlorobenzene / Halobenzene / Aralkylamine / Aryl chloride / Benzenoid / Monocyclic benzene moiety / Aryl halide / Heteroaromatic compound / Tertiary aliphatic amine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary amino compound, pyridines, monochlorobenzenes (CHEBI:52010)

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Transporters

Kind
Protein
Organism
Human
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
Human
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 December 10, 2018 13:38