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.

Structure

Similar Structures

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

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Chlorpheniramine gluconate	79YPK3BAIT	25387-68-2	OCMSTKFGYJZBIY-IFWQJVLJSA-N
Chlorpheniramine hydrochloride	5S6VUP419V	56343-98-7	NOXNCSQBTYNMHD-UHFFFAOYSA-N
Chlorpheniramine maleate	V1Q0O9OJ9Z	113-92-8	DBAKFASWICGISY-BTJKTKAUSA-N
Chlorpheniramine tannate	72JT935YTT	1405-56-7	KOOFUFFGNZKXFG-HBNMXAOGSA-N

Product Images

Prescription Products

Name	Dosage	Route	Labeller	Marketing Start	Marketing End
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Chlorpheniramine Maleate Injection USP	Liquid	Intramuscular; Intravenous; Subcutaneous	Omega Laboratories Ltd	Not applicable	Not applicable
Chlortripolon Inj 10mg/ml	Liquid	Intramuscular; Intravenous; Subcutaneous	Schering Plough	1953-12-31	1999-08-04

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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

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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4 Hour Allergy Relief	Tablet	4 mg/1	Oral	Better Living Brands, LLC	1992-12-19	2022-07-22
Aller-chlor	Tablet	4 mg/1	Oral	RUGBY LABORATORIES	1992-12-19	Not applicable
Aller-chlor	Tablet	4 mg/1	Oral	A-S Medication Solutions	1992-12-19	Not applicable
Aller-Chlor	Syrup	2 mg/5mL	Oral	Rugby	2003-01-17	Not applicable
Aller-chlor	Syrup	2 mg/5mL	Oral	RUGBY LABORATORIES	2014-03-20	2020-09-30
Aller-chlor	Tablet	4 mg/1	Oral	Lake Erie Medical Dba Quality Care Produts Llc	1992-12-19	2018-04-17
Allergy	Tablet	4 mg/1	Oral	Allegiant Health	2014-12-15	Not applicable
Allergy	Tablet	4 mg/1	Oral	Kroger	1987-07-15	2015-12-01
Allergy	Tablet	4 mg/1	Oral	A-S Medication Solutions	1992-12-19	Not applicable
Allergy	Tablet	4 mg/1	Oral	SUPERVALU INC.	1992-12-19	Not applicable

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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

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
999 Cold Remedy	Chlorpheniramine maleate (2 mg/6000mg) + Acetaminophen (100 mg/6000mg)	Capsule	Oral	China Resources Sanjiu Medical & Pharmaceutical Co., Ltd.	2003-07-03	Not applicable
999 Cold Remedy Granular	Chlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g)	Granule	Oral	China Resources Sanjiu Medical & Pharmaceutical Co., Ltd.	2003-07-03	Not applicable
999 Cold Remedy Granular	Chlorpheniramine maleate (4 mg/90g) + Acetaminophen (200 mg/90g)	Capsule	Oral	China Resources Sanjiu Medical & Pharmaceutical Co Ltd	2003-07-03	2013-09-21
999 GANMAOLING Cold	Chlorpheniramine maleate (2 mg/1) + Acetaminophen (100 mg/1) + Caffeine (2 mg/1)	Capsule	Oral	Kingsway	2012-07-30	Not applicable
AccuHist	Chlorpheniramine maleate (1 mg/1mL) + Phenylephrine hydrochloride (2.5 mg/1mL)	Solution	Oral	Tiber Laboratories, LLC	2010-01-25	2013-04-30
AccuHist PDX	Chlorpheniramine maleate (1 mg/1mL) + Dextromethorphan hydrobromide monohydrate (2.5 mg/1mL) + Phenylephrine hydrochloride (2.5 mg/1mL)	Solution	Oral	Tiber Laboratories, LLC	2010-01-25	2013-04-30
Acetaminophen, Chlorpheniramine Maleate, Dextromethorphan Hydrobromide, Phenylephrine Hydrochloride	Chlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1) + Phenylephrine hydrochloride (5 mg/1)	Tablet, coated	Oral	AAA Pharmaceutical, Inc.	2012-12-28	Not applicable
Acetaminophen, Chlorpheniramine Maleate, Dextromethorphan Hydrobromide, Phenylephrine Hydrochloride	Chlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1) + Phenylephrine hydrochloride (5 mg/1)	Tablet, coated	Oral	AAA Pharmaceutical, Inc.	2012-12-28	Not applicable
Acetaminophen, Chlorpheniramine Maleate, Phenylephrine Hydrochloride	Chlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1)	Tablet, coated	Oral	AAA Pharmaceutical, Inc.	2012-12-28	Not applicable
Acetaminophen, Chlorpheniramine Maleate, Phenylephrine Hydrochloride	Chlorpheniramine maleate (2 mg/1) + Acetaminophen (325 mg/1) + Phenylephrine hydrochloride (5 mg/1)	Tablet, coated	Oral	AAA Pharmaceutical, Inc.	2012-08-02	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Allergy DN II	Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)	Kit	Oral	Breckenridge Pharmaceutical, Inc.	2008-11-01	2010-03-31
Allergy DN II	Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)	Kit	Oral	Breckenridge Pharmaceutical, Inc.	2008-11-01	2010-03-31
Allergy DN PE	Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (40 mg/1) + Phenylephrine hydrochloride (10 mg/1)	Kit	Oral	Breckenridge Pharmaceutical, Inc.	2008-11-01	2010-03-31
AlleRx Dose Pack	Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (10 mg/1) + Pseudoephedrine hydrochloride (120 mg/1)	Kit	Oral	Cornerstone Therapeutics Inc.	2008-02-01	2012-10-31
AlleRx Dose Pack DF	Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)	Kit	Oral	Cornerstone Therapeutics Inc.	2006-08-01	2012-10-31
AlleRx Dose Pack DF	Chlorpheniramine maleate (4 mg/1) + Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1)	Kit	Oral	Cornerstone Therapeutics Inc.	2006-08-01	2012-10-31
AlleRx Dose Pack PE	Chlorpheniramine maleate (8 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Methscopolamine nitrate (2.5 mg/1) + Phenylephrine hydrochloride (40 mg/1) + Phenylephrine hydrochloride (10 mg/1)	Kit	Oral	Cornerstone Therapeutics Inc.	2006-09-01	2012-10-31
Atrohist Pediatric	Chlorpheniramine tannate (2 mg/5mL) + Mepyramine tannate (12.5 mg/5mL) + Phenylephrine tannate (5 mg/5mL)	Suspension	Oral	Physicians Total Care, Inc.	1994-09-23	2008-12-05
Atuss DS Tannate Suspension	Chlorpheniramine maleate (4 mg/5mL) + Dextromethorphan hydrobromide monohydrate (30 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)	Suspension	Oral	Atley Pharmaceuticals	2006-11-21	Not applicable
Atuss HS Tannate	Chlorpheniramine maleate (4 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)	Suspension	Oral	Atley Pharmaceuticals	2006-11-21	2009-08-03

International/Other Brands

Chlo-Amine / Chlor-Trimeton (Schering-Plough) / 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.

Target	Actions	Organism
AHistamine H1 receptor	antagonist	Humans
USodium-dependent serotonin transporter	inhibitor	Humans
USodium-dependent noradrenaline transporter	inhibitor	Humans
USodium-dependent dopamine transporter	inhibitor	Humans

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Adverse Effects

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

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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

Pathway	Category
Chlorphenamine H1-Antihistamine Action	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Chlorpheniramine.
(S)-Warfarin	The metabolism of (S)-Warfarin can be decreased when combined with Chlorpheniramine.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine	The metabolism of Chlorpheniramine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Chlorpheniramine.
2,5-Dimethoxy-4-ethylthioamphetamine	2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Chlorpheniramine.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Chlorpheniramine.
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Chlorpheniramine.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be decreased when combined with Chlorpheniramine.
4-Methoxyamphetamine	The metabolism of 4-Methoxyamphetamine can be decreased when combined with Chlorpheniramine.
5-androstenedione	The metabolism of 5-androstenedione can be decreased when combined with Chlorpheniramine.

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Extended Description

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

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Severity

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Evidence Level

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Action

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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

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
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Chlorpheniramine

ATC Codes

R06AB54 — Chlorphenamine, combinations

R06AB04 — Chlorphenamine

AHFS Codes

04:04.20 — Propylamine Derivatives

MSDS

Download (72.8 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Healthy Volunteers	2
1	Completed	Other	Acetaminophen Toxicity	1
1	Completed	Other	Healthy Volunteers	1
2	Completed	Treatment	Allergic Reactions	1
2	Completed	Treatment	Geriatric Hip Fracture Pain Management	1
2	Terminated	Treatment	Allergic Rhinitis (AR)	1
2	Terminated	Treatment	Hepatitis B Chronic Infection	1
2	Terminated	Treatment	Sunburn	1
2	Unknown Status	Treatment	Rhinitis, Seasonal, Allergic	1
2, 3	Not Yet Recruiting	Treatment	Anterior Cruciate Ligament Rupture / Muscle Weakness	1
3	Completed	Treatment	Rhinitis, Allergic, Seasonal	1
3	Unknown Status	Treatment	Acute Rhinitis / Flu-like Syndromes	1
3	Withdrawn	Treatment	Acute Rhinitis	1
4	Completed	Prevention	Streptococcal Infections	1
4	Recruiting	Prevention	Protamine Adverse Reaction	1
Not Available	Completed	Treatment	Anal Condyloma / Fissure in Ano / Hemorrhoids / Rectal Fistulas	1
Not Available	Completed	Treatment	Pneumonia	1
Not Available	Not Yet Recruiting	Supportive Care	Pain NOS	1
Not Available	Recruiting	Prevention	Endoscopy	1
Not Available	Unknown Status	Prevention	Poisoning	1
Not Available	Withdrawn	Not Available	Osteoarthritis (OA)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Amend
Anip Acquisition Co.
A-S Medication Solutions LLC
Breckenridge Pharmaceuticals
C.O. Truxton Inc.
Cardinal Health
Consolidated Midland Corp.
Contract Pharm
Cypress Pharmaceutical Inc.
Deltex Pharmaceuticals Inc.
Direct Dispensing Inc.
Dispensing Solutions
Edwards Pharmaceuticals
Hi Tech Pharmacal Co. Inc.
Iopharm Laboratories Inc.
Ivax Pharmaceuticals
Kowa Pharmaceuticals America Inc.
Kraft Pharmaceutical Co. Inc.
Larken Laboratories Inc.
Liberty Pharmaceuticals
Magna Pharmaceuticals
Major Pharmaceuticals
Mallinckrodt Inc.
McNeil Laboratories
Meda AB
Misemer Pharmaceuticals Inc.
Mismer Pharmace
Nucare Pharmaceuticals Inc.
PD-Rx Pharmaceuticals Inc.
Pecos Pharmaceutical Inc.
Perrigo Co.
Physicians Total Care Inc.
Prepackage Specialists
Provident Pharmaceuticals LLC
Qualitest
Rico Pharmacal
River's Edge Pharmaceuticals
Rugby Laboratories
S&P Healthcare
Schering-Plough Inc.
Time-Cap Labs
Tya Pharmaceuticals
Watson Pharmaceuticals
Wockhardt Ltd.

Dosage forms

Form	Route	Strength
Capsule	Oral
Solution	Oral
Capsule, liquid filled	Not applicable
Granule, effervescent	Oral
Powder, for solution	Oral
Syrup	Oral	2 mg/5mL
Capsule, gelatin coated	Oral
Tablet, coated	Oral
Liquid; tablet	Intramuscular; Oral; Subcutaneous
Liquid; tablet	Oral; Parenteral
Suspension	Oral
Granule, for solution	Oral
Liquid	Topical
Tablet, extended release	Oral	12 mg/1
Tablet, extended release	Oral
Kit; tablet; tablet, extended release	Oral
Solution / drops	Oral
Powder	Not applicable	1 kg/1kg
Tablet	Oral	4 mg/1
Tablet, film coated, extended release	Oral	12 mg/1
Tablet, coated	Oral	4 mg/1
Liquid	Intramuscular; Intravenous; Subcutaneous
Syrup	Oral
Kit; tablet	Oral
Capsule, coated pellets	Oral
Tablet, sugar coated	Oral
Solution / drops	Nasal
Lozenge	Oral	2 mg/1
Kit; powder, for solution	Oral
Tablet, film coated	Oral
Liquid	Oral	2 mL/1mL
Liquid	Oral	2 mg/5mL
Tablet, effervescent	Oral
Kit; powder	Oral
Granule	Oral
Capsule	Oral	1.25 mg/1
Capsule, delayed release pellets	Oral
Tablet, film coated	Oral	4 mg/1
Tablet, multilayer	Oral
Powder	Oral
Tablet	Oral
Syrup	Oral
Liquid	Oral
Tablet, multilayer, extended release	Oral
Tablet, chewable	Oral
Tablet	Oral
Tablet, extended release	Oral
Capsule, extended release	Oral
Suspension, extended release	Oral
Suspension	Oral	1000 mg/1
Kit	Oral
Capsule, liquid filled	Oral

Prices

Unit description	Cost	Unit
Ahist 12 mg tablet	1.1USD	tablet
Myci chlor-tan 8 mg caplet	0.75USD	caplet
Chlorpheniramine powder	0.67USD	g
Chlor-trimeton allergy	0.31USD	each
Chlor-trimeton 8 mg repetab	0.24USD	tablet
Aller-chlor 4 mg tablet	0.06USD	tablet
Pediacare allergy solution	0.05USD	ml
Allergy 4 mg tablet	0.04USD	tablet
Chlorpheniramine 4 mg tablet	0.02USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
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US7863287	No	2011-01-04	2027-02-28
US8062667	No	2011-11-22	2029-03-29
US8790700	No	2014-07-29	2027-03-15
US9066942	No	2015-06-30	2032-01-03
US6383471	No	2002-05-07	2019-04-06
US6248363	No	2001-06-19	2019-11-23
US9107921	No	2015-08-18	2032-01-03
US10238640	No	2004-05-25	2024-05-25

Additional Data Available

Filed On

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

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Properties

State

Liquid

Experimental Properties

Property	Value	Source
boiling point (°C)	142 °C	Not Available
water solubility	5500 mg/L (at 37 °C)	BEILSTEIN
logP	3.38	HANSCH,C ET AL. (1995)
pKa	9.13 (at 25 °C)	PERRIN,DD (1965)

Predicted Properties

Property	Value	Source
Water Solubility	0.0519 mg/mL	ALOGPS
logP	3.74	ALOGPS
logP	3.58	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.85 m³·mol^-1	ChemAxon
Polarizability	30.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9754
Blood Brain Barrier	+	0.962
Caco-2 permeable	+	0.8749
P-glycoprotein substrate	Substrate	0.6136
P-glycoprotein inhibitor I	Non-inhibitor	0.8782
P-glycoprotein inhibitor II	Non-inhibitor	0.9376
Renal organic cation transporter	Inhibitor	0.7916
CYP450 2C9 substrate	Non-substrate	0.8026
CYP450 2D6 substrate	Substrate	0.8919
CYP450 3A4 substrate	Substrate	0.6472
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9096
CYP450 2D6 inhibitor	Inhibitor	0.8932
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.9023
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7501
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.9183
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	3.3361 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8702
hERG inhibition (predictor II)	Inhibitor	0.7145

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-0zfr-6290000000-2ca3230cde716588805e
Mass Spectrum (Electron Ionization)	MS	splash10-0zfr-6490000000-8e58cd1c686f23a7dac6
MS/MS Spectrum - Quattro_QQQ 10V, N/A	LC-MS/MS	splash10-01b9-3900000000-ea4ccfd2afe05f49fc7a
MS/MS Spectrum - Quattro_QQQ 25V, N/A	LC-MS/MS	splash10-004i-0090000000-9e46eb080de95d4f8f8e
MS/MS Spectrum - Quattro_QQQ 40V, N/A	LC-MS/MS	splash10-014i-1920000000-d2d2acf559d9070a1d47
MS/MS Spectrum - EI-B (Unknown) , Positive	LC-MS/MS	splash10-0zfr-6190000000-2ca3230cde716588805e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001i-0290000000-03651b7b90a1745fdf23
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0uy0-0960000000-1f750af75fe542c6c06f
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not 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

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	66	N/A	N/A	17846138
IC 50 (nM)	8.8	N/A	N/A	1673158
Ki (nM)	15	N/A	N/A	6149136
Ki (nM)	2.51	N/A	N/A	7925364 / 8903934
Ki (nM)	2.67	N/A	N/A	12065734
Ki (nM)	30	N/A	N/A	6146381
Ki (nM)	4.81	N/A	N/A	12065734
Ki (nM)	7	N/A	N/A	21381763

Details1. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Tagawa M, Kano M, Okamura N, Higuchi M, Matsuda M, Mizuki Y, Arai H, Iwata R, Fujii T, Komemushi S, Ido T, Itoh M, Sasaki H, Watanabe T, Yanai K: Neuroimaging of histamine H1-receptor occupancy in human brain by positron emission tomography (PET): a comparative study of ebastine, a second-generation antihistamine, and (+)-chlorpheniramine, a classical antihistamine. Br J Clin Pharmacol. 2001 Nov;52(5):501-9. [PubMed:11736858]
Salata JJ, Jurkiewicz NK, Wallace AA, Stupienski RF 3rd, Guinosso PJ Jr, Lynch JJ Jr: Cardiac electrophysiological actions of the histamine H1-receptor antagonists astemizole and terfenadine compared with chlorpheniramine and pyrilamine. Circ Res. 1995 Jan;76(1):110-9. [PubMed:8001268]
Hasenohrl RU, Kuhlen A, Frisch C, Galosi R, Brandao ML, Huston JP: Comparison of intra-accumbens injection of histamine with histamine H1-receptor antagonist chlorpheniramine in effects on reinforcement and memory parameters. Behav Brain Res. 2001 Oct 15;124(2):203-11. [PubMed:11640974]
Yasuda SU, Wellstein A, Likhari P, Barbey JT, Woosley RL: Chlorpheniramine plasma concentration and histamine H1-receptor occupancy. Clin Pharmacol Ther. 1995 Aug;58(2):210-20. [PubMed:7648771]
Nicholson AN, Pascoe PA, Turner C, Ganellin CR, Greengrass PM, Casy AF, Mercer AD: Sedation and histamine H1-receptor antagonism: studies in man with the enantiomers of chlorpheniramine and dimethindene. Br J Pharmacol. 1991 Sep;104(1):270-6. [PubMed:1686208]

Details2. Sodium-dependent serotonin transporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Serotonin:sodium symporter activity
Specific Function: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name: SLC6A4
Uniprot ID: P31645
Uniprot Name: Sodium-dependent serotonin transporter
Molecular Weight: 70324.165 Da

References

Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]

Details3. Sodium-dependent noradrenaline transporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Norepinephrine:sodium symporter activity
Specific Function: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name: SLC6A2
Uniprot ID: P23975
Uniprot Name: Sodium-dependent noradrenaline transporter
Molecular Weight: 69331.42 Da

References

Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]

Details4. Sodium-dependent dopamine transporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Monoamine transmembrane transporter activity
Specific Function: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name: SLC6A3
Uniprot ID: Q01959
Uniprot Name: Sodium-dependent dopamine transporter
Molecular Weight: 68494.255 Da

References

Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821]

Enzymes

Details1. Cytochrome P450 3A7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A7
Uniprot ID: P24462
Uniprot Name: Cytochrome P450 3A7
Molecular Weight: 57525.03 Da

References

Flockhart Table of Drug Interactions [Link]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Flockhart Table of Drug Interactions [Link]

Details3. Cytochrome P450 2D6

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

Hamelin BA, Bouayad A, Drolet B, Gravel A, Turgeon J: In vitro characterization of cytochrome P450 2D6 inhibition by classic histamine H1 receptor antagonists. Drug Metab Dispos. 1998 Jun;26(6):536-9. [PubMed:9616188]
Yasuda SU, Wellstein A, Likhari P, Barbey JT, Woosley RL: Chlorpheniramine plasma concentration and histamine H1-receptor occupancy. Clin Pharmacol Ther. 1995 Aug;58(2):210-20. [PubMed:7648771]
Yasuda SU, Zannikos P, Young AE, Fried KM, Wainer IW, Woosley RL: The roles of CYP2D6 and stereoselectivity in the clinical pharmacokinetics of chlorpheniramine. Br J Clin Pharmacol. 2002 May;53(5):519-25. [PubMed:11994058]
He N, Zhang WQ, Shockley D, Edeki T: Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. Eur J Clin Pharmacol. 2002 Feb;57(12):847-51. [PubMed:11936702]
Flockhart Table of Drug Interactions [Link]

Details4. Cytochrome P450 3A5

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP3A5
Uniprot ID: P20815
Uniprot Name: Cytochrome P450 3A5
Molecular Weight: 57108.065 Da

References

Flockhart Table of Drug Interactions [Link]

Transporters

Details1. Solute carrier family 22 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Quaternary ammonium group transmembrane transporter activity
Specific Function: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name: SLC22A2
Uniprot ID: O15244
Uniprot Name: Solute carrier family 22 member 2
Molecular Weight: 62579.99 Da

References

Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]

Details2. Solute carrier family 22 member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Secondary active organic cation transmembrane transporter activity
Specific Function: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name: SLC22A1
Uniprot ID: O15245
Uniprot Name: Solute carrier family 22 member 1
Molecular Weight: 61153.345 Da

References

Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]

Drug created on June 13, 2005 07:24 / Updated on October 17, 2019 21:27

Chlorpheniramine

Identification

Structure for Chlorpheniramine (DB01114)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References

References

Enzymes

References

References

References

References

Transporters

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References