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

Details

Stereochemistry RACEMIC
Molecular Formula C16H19ClN2
Molecular Weight 274.789
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORPHENIRAMINE

SMILES

CN(C)CCC(c1ccc(cc1)Cl)c2ccccn2

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 274.789
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

-611625600000
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
Health Status: healthy
Age Group: 27-40 years
Sex: M+F
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)
Health Status: unhealthy
Age Group: 34 years (range: 13-52 years)
Sex: M+F
Sources:
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
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
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Sources:
Diarrhea 1 patient
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Sources:
Nausea 1 patient
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Sources:
Tryptase increased 1 patient
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
Sources:
Urticaria 2 patients
4 mg single, intravenous
Dose: 4 mg
Route: intravenous
Route: single
Dose: 4 mg
Sources:
unhealthy, 50-54 years
Health Status: unhealthy
Age Group: 50-54 years
Sex: F
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
Toxic epidermal necrolysis associated with pentazocine therapy and severe reversible renal failure.
1973 Mar
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity.
1975 Feb
Oral facial dyskinesia accociated with prolonged use of antihistaminic decongestants.
1975 Sep 4
Skeletal muscle necrosis following membrane-active drugs plus serotonin.
1976 May
Aplastic anaemia after prolonged treatment with chlorpheniramine.
1977 Mar 5
Jaundice during cyproheptadine treatment.
1978 Mar 25
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.
1978 Oct 7
The I antigen as an immune complex receptor in a case of haemolytic anaemia induced by an antihistaminic agent.
1981 Sep
Reaction to phenylpropalamine/chlorpheniramine/belladonna compound in a women with unrecognised autonomic dysfunction.
1982 Jul 31
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
Treatment of lethal pertussis vaccine reaction with histamine H1 antagonists.
1987 Jun
Histamine and hepatic glutathione in the mouse.
1987 May 25
Chronic chlorpheniramine therapy: subsensitivity, drug metabolism, and compliance.
1987 Nov
Antihistaminic-opioid combination: effect on locomotor activity in mice.
1988 Sep-Oct
[Antimycobacterial antihistaminics].
1989 Aug
Drug-induced acute pulmonary edema--sequential changes in CT images.
1991 Nov-Dec
Proconvulsant effect of ketotifen, a histamine H1 antagonist, confirmed by the use of d-chlorpheniramine with monitoring electroencephalography.
1993 Apr
Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema.
1993 Dec
Role of cysteinyl-leukotrienes and histamine in mediating intrinsic tone in isolated human bronchi.
1994 Jan
Benefit/risk ratio of the antihistamines (H1-receptor antagonists) terfenadine and chlorpheniramine in children.
1994 Jun
In vivo and in vitro interaction of the novel selective histamine H1 receptor antagonist mizolastine with H1 receptors in the rodent.
1995 May
Combining event rates from clinical trials: comparison of Bayesian and classical methods.
1996 May
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
The specificity of a chlorphenamine-imprinted polymer and its application.
2001 Aug 3
Repeated pre-treatment with antihistamines suppresses [corrected] transcriptional up-regulations of histamine H(1) receptor and interleukin-4 genes in toluene-2,4-diisocyanate-sensitized rats.
2008 Dec
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats.
2008 Mar
Allergic hemiglossitis as a unique case of food allergy: a case report.
2008 Mar 6
Ultra-fast chromatographic micro-assay for quantification of diphenidol in plasma: application in an oral multi-dose switchability trial.
2008 Oct
Rare case of "red man" syndrome in a female patient treated with oral vancomycin for Clostridium difficile diarrhoea.
2009
Investigation of enantiomeric separation of basic drugs by capillary electrophoresis using clindamycin phosphate as a novel chiral selector.
2009 Aug
Suspected anaphylactic reactions associated with anaesthesia.
2009 Feb
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
Extended weekly dose-dense paclitaxel/carboplatin is feasible and active in heavily pre-treated platinum-resistant recurrent ovarian cancer.
2009 Mar 10
Continuous quinacrine treatment results in the formation of drug-resistant prions.
2009 Nov
Retro-orbital oedema and transient blindness following endoscopic oesophagogastroduodenoscopy: a case report.
2009 Sep 2
Dextromethorphan, chlorphenamine and serotonin toxicity: case report and systematic literature review.
2010 Dec
Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting.
2010 Dec
Differential responding of autonomic function to histamine H₁ antagonism in irritable bowel syndrome.
2010 Dec
Transport of phenylethylamine at intestinal epithelial (Caco-2) cells: mechanism and substrate specificity.
2010 Feb
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
Simultaneous determination of paracetamol, pseudoephedrine, dextrophan and chlorpheniramine in human plasma by liquid chromatography-tandem mass spectrometry.
2010 Mar 1
Evaluation of the enantioseparation capability of the novel chiral selector clindamycin phosphate towards basic drugs by micellar electrokinetic chromatography.
2010 Mar 12
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity.
2011 Apr
The discovery of phthalazinone-based human H1 and H3 single-ligand antagonists suitable for intranasal administration for the treatment of allergic rhinitis.
2011 Apr 14
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.
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 Jun 26 03:13:00 UTC 2021
Edited
by admin
on Sat Jun 26 03:13:00 UTC 2021
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
CHLORPHENIRAMINE [HSDB]
Common Name English
CHLORPHENAMINE [WHO-DD]
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 Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
NDF-RT N0000175587
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
NDF-RT N0000000190
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
WHO-VATC QR06AB04
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
LIVERTOX 195
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 03
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
WHO-ATC R06AB54
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
WHO-VATC QR06AB54
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
Code System Code Type Description
DRUG CENTRAL
616
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
EPA CompTox
132-22-9
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
NCI_THESAURUS
C61672
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
PUBCHEM
2725
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
RXCUI
2400
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
HSDB
3032
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
DRUG BANK
DB01114
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-054-0
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
LACTMED
Chlorpheniramine
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
CAS
132-22-9
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
INN
104
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
WIKIPEDIA
CHLORPHENAMINE
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
EVMPD
SUB06201MIG
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
MESH
D002744
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
MERCK INDEX
M3456
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY Merck Index
IUPHAR
6976
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
FDA UNII
3U6IO1965U
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
ChEMBL
CHEMBL505
Created by admin on Sat Jun 26 03:13:00 UTC 2021 , Edited by admin on Sat Jun 26 03:13:00 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SUB_CONCEPT->SUBSTANCE
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY