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

Details

Stereochemistry RACEMIC
Molecular Formula C16H19ClN2.C4H4O4
Molecular Weight 390.8613
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CHLORPHENIRAMINE MALEATE

SMILES

CN(C)CCC(c1ccc(cc1)Cl)c2ccccn2.C(\[H])(=C(\[H])/C(=O)O)/C(=O)O

InChI

InChIKey=DBAKFASWICGISY-BTJKTKAUSA-N
InChI=1S/C16H19ClN2.C4H4O4/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13;5-3(6)1-2-4(7)8/h3-9,11,15H,10,12H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0723
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

-6.116256E11
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
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
[Antimycobacterial antihistaminics].
1989 Aug
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
[Dexchlorpheniramine-induced acute hepatitis: a case with positive rechallenge].
1998 Oct
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Involvement of histamine H3 receptors in scratching behaviour in mast cell-deficient mice.
2003 Jul
Aseptic meningitis associated with intravenous administration of dexchlorpheniramine.
2003 May
2-O-(2-hydroxybutyl)-beta-cyclodextrin as a chiral selector for the capillary electrophoretic separation of chiral drugs.
2005 Aug
Synergistic action of famotidine and chlorpheniramine on acetic acid-induced chronic gastric ulcer in rats.
2005 Dec 7
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.
2005 Nov
Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs.
2006 Mar
Histamine induces MUC5AC expression via a hCLCA1 pathway.
2007
Rare case of "red man" syndrome in a female patient treated with oral vancomycin for Clostridium difficile diarrhoea.
2009
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
Differential responding of autonomic function to histamine H₁ antagonism in irritable bowel syndrome.
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
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
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 Fri Jun 25 21:04:24 UTC 2021
Edited
by admin
on Fri Jun 25 21:04:24 UTC 2021
Record UNII
V1Q0O9OJ9Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLORPHENIRAMINE MALEATE
MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
2-(P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)BENZYL)PYRIDINE MALEATE (1:1)
Common Name English
ISOCLOR COMPONENT CHLORPHENIRAMINE MALEATE
Common Name English
ORNADE COMPONENT CHLORPHENIRAMINE MALEATE
Common Name English
TELDRIN
Brand Name English
CHLORPHENAMINE MALEATE [MART.]
Common Name English
CHLORPHENIRAMINE MALEATE COMPONENT OF ADVIL ALLERGY SINUS
Common Name English
TRIAMINIC COMPONENT CHLORPHENIRAMINE MALEATE
Common Name English
CHLORPHENIRAMINE MALEATE [USP MONOGRAPH]
Common Name English
PYRIDAMAL
Brand Name English
CHLORPHENAMINE MALEATE [EP MONOGRAPH]
Common Name English
CHLORPHENAMINE HYDROGEN MALEATE [WHO-IP]
Common Name English
CHLORPROPHENPYRIDAMINE MALEATE
Common Name English
CHLORPHENIRAMINE MALEATE COMPONENT OF CODIMAL-L.A. 12
Common Name English
CHLORPHENIRAMINE MALEATE COMPONENT OF TRIAMINIC
Common Name English
CHLORPHENAMINI HYDROGENOMALEAS [WHO-IP LATIN]
Common Name English
CHLORPHENIRAMINE MALEATE COMPONENT OF CONTAC
Common Name English
HISTASPAN
Common Name English
NEORESTAMIN
Common Name English
NSC-756684
Code English
DRIZE COMPONENT CHLORPHENIRAMINE MALEATE
Common Name English
ADVIL ALLERGY SINUS COMPONENT CHLORPHENIRAMINE MALEATE
Common Name English
CODIMAL-L.A. 12 COMPONENT CHLORPHENIRAMINE MALEATE
Common Name English
CHLORPHENAMINE MALEATE
EP   MART.   WHO-DD  
Common Name English
2-PYRIDINEPROPANAMINE, .GAMMA.-(4-CHLOROPHENYL)-N,N-DIMETHYL-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
CHLORPHENIRAMINE MALEATE [VANDF]
Common Name English
CHLORPHENIRAMINE MALEATE [JAN]
Common Name English
SYNISTAMIN
Common Name English
CHLORPHENIRAMINE MALEATE COMPONENT OF DRIZE
Common Name English
CHLORPHENIRAMINE MALEATE [ORANGE BOOK]
Common Name English
CHLORPHENIRAMINE MALEATE COMPONENT OF ISOCLOR
Common Name English
CHLORPHENAMINE MALEATE [WHO-DD]
Common Name English
CHLORPHENIRAMINE MALEATE [MI]
Common Name English
DEMAZIN COMPONENT CHLORPHENIRAMINE MALEATE
Common Name English
PHENETRON
Brand Name English
CONTAC COMPONENT CHLORPHENIRAMINE MALEATE
Common Name English
EFIDAC
Brand Name English
CHLOR-TRIMETON
Brand Name English
CHLORPHENIRAMINE MALEATE [USP-RS]
Common Name English
CHLORPHENIRAMINE MALEATE COMPONENT OF ORNADE
Common Name English
KLOROMIN
Brand Name English
ANTAGONATE
Brand Name English
CHLORPHENIRAMINE MALEATE COMPONENT OF DEMAZIN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
CFR 21 CFR 341.12
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
Code System Code Type Description
EPA CompTox
113-92-8
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
RXCUI
142429
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL505
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
MERCK INDEX
M3456
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY Merck Index
FDA UNII
V1Q0O9OJ9Z
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
PUBCHEM
5281068
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CHLORPHENIRAMINE MALEATE
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY Description: A white, crystalline powder; odourless.Solubility: Soluble in 4 parts of water; soluble in ethanol (~750 g/l) TS; slightly soluble in ether R.Category: Antihistaminic.Storage: Chlorphenamine hydrogen maleate should be kept in a tightly closed container, protected from light.
DRUG BANK
DBSALT000987
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
EVMPD
SUB01243MIG
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
CAS
113-92-8
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-037-5
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
NCI_THESAURUS
C28925
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY
USP_CATALOG
1123000
Created by admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
PRIMARY USP-RS
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY