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Details

Stereochemistry RACEMIC
Molecular Formula C16H19ClN2.C4H4O4
Molecular Weight 390.861
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CHLORPHENIRAMINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN(C)CCC(C1=CC=C(Cl)C=C1)C2=CC=CC=N2

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 C16H19ClN2
Molecular Weight 274.788
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

1949
72
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7468
 15.2 nM [Kd]
Inhibitor
7468
 203.0 nM [Ki]
Inhibitor
7468
 136.0 µM [IC50]
Antagonist
2491
Hay Fever
 12.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Histamine H1 receptor
Approved
7883
Chlor-Trimeton
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
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
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
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
A comparison of acrivastine versus chlorpheniramine in the treatment of chronic idiopathic urticaria.
1989
[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
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
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
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
[Stevens-Johnson syndrome plus intrahepatic cholestasis caused by clindamycin or chlorpheniramine].
2009 May 15
Continuous quinacrine treatment results in the formation of drug-resistant prions.
2009 Nov
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
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

Patents

JP2001064159A
6
JP2002356430A
6
JP2008127365A
9
JP2008526895A
30
JP2009161467A
9
JP2011195559A
9
JP2011246449A
6
JP2013237711A
14
JPH08225447A
10

Sample Use Guides

In Vivo Use Guide
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 Tue Oct 22 00:41:01 UTC 2019
Edited
by admin
on Tue Oct 22 00:41:01 UTC 2019
Record UNII
V1Q0O9OJ9Z
Record Status Validated (UNII)
Record Version
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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
PYRIDAMAL
Brand 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
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
CHLORPHENAMINE MALEATE [EP]
Common Name English
2-PYRIDINEPROPANAMINE, .GAMMA.-(4-CHLOROPHENYL)-N,N-DIMETHYL-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
CHLORPHENIRAMINE MALEATE [USP]
Common 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 Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
CFR 21 CFR 341.12
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
Code System Code Type Description
EPA CompTox
113-92-8
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
PRIMARY
RXCUI
142429
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL505
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
PRIMARY
MERCK INDEX
M3456
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
CHLORPHENIRAMINE MALEATE
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
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.
EVMPD
SUB01243MIG
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
PRIMARY
CAS
113-92-8
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-037-5
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
PRIMARY
NCI_THESAURUS
C28925
Created by admin on Tue Oct 22 00:41:01 UTC 2019 , Edited by admin on Tue Oct 22 00:41:01 UTC 2019
PRIMARY
Related Record Type Details
Structure of CHLORPHENIRAMINE MALEATE, (-)-
ENANTIOMER -> RACEMATE
Structure of DEXCHLORPHENIRAMINE MALEATE
ENANTIOMER -> RACEMATE
Structure of CHLORPHENIRAMINE MALEATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
Structure of CHLORPHENIRAMINE MALEATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Structure of CHLORPHENIRAMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of 2,2'-DIPYRIDYLAMINE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of MONODESMETHYLCHLORPHENIRAMINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-(4-CHLOROPHENYL)-4-(DIMETHYLAMINO)-2-(PYRIDIN-2-YL)BUTANENITRILE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-(4-CHLOROPHENYL)-4-(DIMETHYLAMINO)-2-(2-(DIMETHYLAMINO)ETHYL)BUTANENITRILE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of CHLORPHENIRAMINE
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