U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H19ClN2
Molecular Weight 274.788
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORPHENIRAMINE

SMILES

CN(C)CCC(C1=CC=C(Cl)C=C1)C2=CC=CC=N2

InChI

InChIKey=SOYKEARSMXGVTM-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H19ClN2
Molecular Weight 274.788
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Chlorpheniramine is an antihistamine. 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. Chlorpheniramine is used for relieving symptoms of sinus congestion, sinus pressure, runny nose, watery eyes, itching of the nose and throat, and sneezing due to upper respiratory infections (eg, colds), allergies, and hay fever. In addition to being a histamine H1 receptor (HRH1) antagonist, chlorphenamine has been shown to work as a serotonin-norepinephrine reuptake inhibitor or SNRI.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Chlor-Trimeton

Approved Use

Uses temporarily relieves the following symptoms due to hay fever or other upper respiratory allergies: sneezing runny nose itchy, watery eyes itching of the nose or throat

Launch Date

1950
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
30.6 ng/mL
8 mg 2 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
32.5 ng/mL
4 mg 4 times / day steady-state, oral
dose: 4 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
25.9 ng/mL
8 mg 2 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
13.5 ng/mL
0.12 mg/kg bw single, oral
dose: 0.12 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1075.7 ng × h/mL
8 mg 2 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1202.1 ng × h/mL
4 mg 4 times / day steady-state, oral
dose: 4 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
961 ng × h/mL
8 mg 2 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
246.16 ng × h/mL
0.12 mg/kg bw single, oral
dose: 0.12 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
24.5 h
8 mg 2 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
25.1 h
4 mg 4 times / day steady-state, oral
dose: 4 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
25.4 h
8 mg 2 times / day steady-state, oral
dose: 8 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
13.1 h
0.12 mg/kg bw single, oral
dose: 0.12 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
CHLORPHENIRAMINE serum
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: UNKNOWN
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
5 mg single, intravenous
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources:
healthy, 27-40 years
n = 2
Health Status: healthy
Age Group: 27-40 years
Sex: M+F
Population Size: 2
Sources:
48 mg 1 times / day multiple, oral
Studied dose
Dose: 48 mg, 1 times / day
Route: oral
Route: multiple
Dose: 48 mg, 1 times / day
Sources:
unhealthy, 34 years (range: 13-52 years)
n = 10
Health Status: unhealthy
Age Group: 34 years (range: 13-52 years)
Sex: M+F
Population Size: 10
Sources:
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
n = 2
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Population Size: 2
Sources:
Other AEs: Tryptase increased, Urticaria...
Other AEs:
Tryptase increased (1 patient)
Urticaria (2 patients)
Abdominal cramp (1 patient)
Nausea (1 patient)
Diarrhea (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Abdominal cramp 1 patient
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
n = 2
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Population Size: 2
Sources:
Diarrhea 1 patient
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
n = 2
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Population Size: 2
Sources:
Nausea 1 patient
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
n = 2
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Population Size: 2
Sources:
Tryptase increased 1 patient
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
n = 2
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Population Size: 2
Sources:
Urticaria 2 patients
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
n = 2
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Population Size: 2
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
weak [Ki 11 uM]
yes [Ki 191.2 uM]
yes [Ki 87.6 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes
likely (co-administration study)
Comment: The two poor metabolizers with respect to CYP2D6 were included as controls in the present study, as quinidine would not be expected to produce any further inhibition of CYP2D6 in those subjects. However, a slight decrease in AUC(0,∞) and a slight increase in CLoral was observed for both the (R)-(−)- and the (S)-(+)-enantiomers following administration of quinidine, although it is not possible to draw a firm conclusion from such a small number of subjects
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity.
1975 Feb
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants.
1975 Sep 4
Skeletal muscle necrosis following membrane-active drugs plus serotonin.
1976 May
The I antigen as an immune complex receptor in a case of haemolytic anaemia induced by an antihistaminic agent.
1981 Sep
Enhancement of morphine-induced hyperactivity by antihistaminic drugs in mice.
1986 Dec
Antagonism of drug-induced yawning and penile erections in rats.
1986 Mar 18
Antihistaminics enhance morphine-, but not amphetamine- and scopolamine-induced hyperactivity in mice.
1987
Chronic chlorpheniramine therapy: subsensitivity, drug metabolism, and compliance.
1987 Nov
Multicenter, double-blind, multiple-dose, parallel-groups efficacy and safety trial of azelastine, chlorpheniramine, and placebo in the treatment of spring allergic rhinitis.
1988 Nov
Antihistaminic-opioid combination: effect on locomotor activity in mice.
1988 Sep-Oct
[Antimycobacterial antihistaminics].
1989 Aug
Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema.
1993 Dec
Benefit/risk ratio of the antihistamines (H1-receptor antagonists) terfenadine and chlorpheniramine in children.
1994 Jun
The role of histaminergic-noradrenergic axis in naloxone-induced withdrawal symptoms in mice.
1996 Sep
[Dexchlorpheniramine-induced acute hepatitis: a case with positive rechallenge].
1998 Oct
Mechanism responsible for epileptogenic activity by first-generation H1-antagonists in rats.
2000 Dec 22
A new model of allergic rhinitis in rats by topical sensitization and evaluation of H(1)-receptor antagonists.
2000 Jun
Synergistic antiallergic activity of combined histamine H1- and cysteinyl leukotriene1-receptor blockade in human bronchus.
2001 May 11
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
[An exceptional case of hypersensitivity to actinomycin D. Case report and review of the literature].
2001 Sep-Oct
Ketoconazole potentiates terfenadine-induced apoptosis in human Hep G2 cells through inhibition of cytochrome p450 3A4 activity.
2002
Enhanced antinociception by intrathecally-administered morphine in histamine H1 receptor gene knockout mice.
2002 Jun
Single-patient drug trial methodology for allergic rhinitis.
2002 Sep
Involvement of histamine H3 receptors in scratching behaviour in mast cell-deficient mice.
2003 Jul
Adrenaline given outside the context of life threatening allergic reactions.
2003 Mar 15
Up-regulation of histamine H(1) receptors in an allergic rat nasal mucosa model.
2004 Mar
2-O-(2-hydroxybutyl)-beta-cyclodextrin as a chiral selector for the capillary electrophoretic separation of chiral drugs.
2005 Aug
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.
2005 Nov
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.
2007 Apr
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats.
2008 Mar
Toxicity associated with combination oxaliplatin plus fluoropyrimidine with or without cetuximab in the MRC COIN trial experience.
2009 Jan 27
A computational approach to studying monomer selectivity towards the template in an imprinted polymer.
2009 Jul
Block of HERG k channel by classic histamine h(1) receptor antagonist chlorpheniramine.
2009 Jun
Hepatotoxicity induced by methimazole in a previously healthy patient.
2009 Sep
Retro-orbital oedema and transient blindness following endoscopic oesophagogastroduodenoscopy: a case report.
2009 Sep 2
Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting.
2010 Dec
Association of nutritional status and serum albumin levels with development of toxicity in patients with advanced non-small cell lung cancer treated with paclitaxel-cisplatin chemotherapy: a prospective study.
2010 Feb 21
Randomised controlled double-blind non-inferiority trial of two antivenoms for saw-scaled or carpet viper (Echis ocellatus) envenoming in Nigeria.
2010 Jul 27
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity.
2011 Apr
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

Tablets or syrup: 4 mg orally every 4 to 6 hours. Sustained-release: 8 to 16 mg orally every 8 to 12 hours as needed or 16 mg orally once a day as needed. Maximum dose 32 mg/day.
Route of Administration: Oral
In Vitro Use Guide
Chlorpheniramine inhibits the [3H]mepyramine binding to the histamine H1 receptor in guinea pig cortex with IC50 of 8.8 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:09:18 GMT 2023
Edited
by admin
on Sat Dec 16 17:09:18 GMT 2023
Record UNII
3U6IO1965U
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
CHLORPHENIRAMINE
HSDB   MI   VANDF  
Common Name English
CHLORPHENIRAMINE [VANDF]
Common Name English
CHLORPHENIRAMINE [MI]
Common Name English
CHLORPHENIRAMINE COMPONENT OF TUZISTRA
Brand Name English
chlorphenamine [INN]
Common Name English
Chlorphenamine [WHO-DD]
Common Name English
CHLORPHENIRAMINE [HSDB]
Common Name English
CLOFENIRAMINA
Brand Name English
783AHI015X
Common Name English
2-(P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)BENZYL)PYRIDINE
Common Name English
CHLORPHENAMINE
INN   WHO-DD  
INN  
Official Name English
TUZISTRA COMPONENET OF CHLORPHENIRAMINE
Brand Name English
Classification Tree Code System Code
WHO-ATC R06AB04
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
NDF-RT N0000175587
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
NDF-RT N0000000190
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
WHO-VATC QR06AB04
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
LIVERTOX 195
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 03
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
WHO-ATC R06AB54
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
NCI_THESAURUS C29578
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
WHO-VATC QR06AB54
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
Code System Code Type Description
DRUG CENTRAL
616
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID0022804
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
NCI_THESAURUS
C61672
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
PUBCHEM
2725
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
RXCUI
2400
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
HSDB
3032
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
DRUG BANK
DB01114
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-054-0
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
LACTMED
Chlorpheniramine
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
CAS
132-22-9
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
DAILYMED
3U6IO1965U
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
INN
104
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
WIKIPEDIA
CHLORPHENAMINE
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
EVMPD
SUB06201MIG
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
MESH
D002744
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
SMS_ID
100000090540
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
MERCK INDEX
m3456
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY Merck Index
IUPHAR
6976
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
FDA UNII
3U6IO1965U
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL505
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
CHEBI
52010
Created by admin on Sat Dec 16 17:09:20 GMT 2023 , Edited by admin on Sat Dec 16 17:09:20 GMT 2023
PRIMARY
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SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
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BINDING
TRANSPORTER -> INHIBITOR
SUB_CONCEPT->SUBSTANCE
TRANSPORTER -> INHIBITOR
ENANTIOMER -> RACEMATE
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