CHLORPHENIRAMINE MALEATE

US Approved OTC

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 Search

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6383755 | https://www.drugs.com/cdi/chlorpheniramine.html | https://www.ncbi.nlm.nih.gov/pubmed/16413139

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

Targets

Primary Target	Pharmacology	Potency
Plasmodium falciparum (isolate K1 / Thailand) 9 Target ID: CHEMBL612856 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750932	Inhibitor 7709	136.0 µM [IC50]
Histamine H1 receptor 298 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2879912 \| https://www.ncbi.nlm.nih.gov/pubmed/18363822	Antagonist 2577	12.0 nM [IC50]
Sodium-dependent serotonin transporter 41 Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16413139 \| https://www.ncbi.nlm.nih.gov/pubmed/4390069 \| https://www.drugbank.ca/drugs/DB01114 \| https://www.ncbi.nlm.nih.gov/pubmed/18363822	Inhibitor 7709	15.2 nM [Kd]
Sodium-dependent dopamine transporter 41 Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/18363822 \| https://www.drugbank.ca/drugs/DB01114	Inhibitor 7709	203.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100 Sources: http://www.rxlist.com/chlor-trimeton-side-effects-drug-center.htm	Primary		Approved 8003	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

C_max

Value	Dose	Analyte	Population
30.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7069073/	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

Value	Dose	Analyte	Population
1075.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7069073/	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

T_1/2

Value	Dose	Analyte	Population
24.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7104467/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7069073/	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

Dose	Population	Adverse events
5 mg single, intravenous Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7106172	healthy, 27-40 years n = 2 Health Status: healthy Age Group: 27-40 years Sex: M+F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/7106172	Sources: https://pubmed.ncbi.nlm.nih.gov/7106172
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: https://pubmed.ncbi.nlm.nih.gov/4008807/	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: https://pubmed.ncbi.nlm.nih.gov/4008807/	Sources: https://pubmed.ncbi.nlm.nih.gov/4008807/
4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31852144	unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/31852144	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: https://pubmed.ncbi.nlm.nih.gov/31852144

AEs

AE	Significance	Dose	Population
Abdominal cramp	1 patient	4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31852144	unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/31852144
Diarrhea	1 patient	4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31852144	unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/31852144
Nausea	1 patient	4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31852144	unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/31852144
Tryptase increased	1 patient	4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31852144	unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/31852144
Urticaria	2 patients	4 mg single, intravenous Dose: 4 mg Route: intravenous Route: single Dose: 4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/31852144	unhealthy, 50-54 years n = 2 Health Status: unhealthy Age Group: 50-54 years Sex: F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/31852144

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1116 inhibitor 1701	inhibitor 1480

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 296 MATE2 257	P-gp 1399

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1735	inhibitor 3041 Sources: https://pubmed.ncbi.nlm.nih.gov/9616188/	weak [Ki 11 uM]
MATE2 257	inhibitor 3041 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 191.2 uM]
MATE1 298	inhibitor 3041 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 87.6 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1399	substrate 3107 Sources: https://pubmed.ncbi.nlm.nih.gov/11284026/ Page: 6.0	no
CYP2D6 1116	substrate 3107 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1874352/	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 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1874352/

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1512	inhibitor 1494 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2766741/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY544662	https://www.001chemical.com/chem/25523-97-1
Alfa Chemistry	1185054-60-7	https://www.alfa-chemistry.com/cas_1185054-60-7.htm
Aurum Pharmatech LLC	T7375	http://www.Aurumpharmatech.com/Product/ProductDetails/T7375
BLD Pharm	BD01108280	http://www.bldpharm.com/products/132-22-9.html
BOC Sciences	132-22-9	https://www.bocsci.com/chlorpheniramine-cas-132-22-9-item-332358.html
BioSynth	W-108317	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-108317.html
Chemspace	CSSB00025765201	https://chem-space.com/CSSB00025765201
Clearsynth	CS-T-51081	https://www.clearsynth.com/en/CST51081.html
Finetech	FT-0665002	http://www.finetechnology-ind.com/prod/detail/pub/1185054-60-7.html
Finetech	FT-0772034	http://www.finetechnology-ind.com/prod/detail/pub/25523-97-1.html
MolPort	MolPort-002-507-837	https://www.molport.com/shop/molecule-link/MolPort-002-507-837
Molcore	MC544662	https://www.molcore.com/product/25523-97-1
Parchem	28520	http://www.parchem.com/chemical-supplier-distributor/Chlorpheniramine-Maleate-B-P--018520.aspx
Smolecule	S525766	http://www.smolecule.com/products/s525766
Smolecule	S793296	https://www.smolecule.com/products/s793296
Synblock Inc	SB19135	http://www.synblock.com/product/132-22-9.html
THE BioTek	bt-267099	https://www.thebiotek.com/product/inhibitors/bt-267099
iChemical	EBD3323802	http://www.ichemical.com/products/132-22-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-2363896855	https://mcule.com/MCULE-2363896855/

PubMed

Title	Date	PubMed
Skeletal muscle necrosis following membrane-active drugs plus serotonin.	1976 May	6632
Aplastic anaemia after prolonged treatment with chlorpheniramine.	1977 Mar 5	65643
Jaundice during cyproheptadine treatment.	1978 Mar 25	630329
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.	1978 Oct 7	709472
The I antigen as an immune complex receptor in a case of haemolytic anaemia induced by an antihistaminic agent.	1981 Sep	6115667
Reaction to phenylpropalamine/chlorpheniramine/belladonna compound in a women with unrecognised autonomic dysfunction.	1982 Jul 31	6124702
[Antimycobacterial antihistaminics].	1989 Aug	2513793
Proconvulsant effect of ketotifen, a histamine H1 antagonist, confirmed by the use of d-chlorpheniramine with monitoring electroencephalography.	1993 Apr	8101246
Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema.	1993 Dec	7508328
Role of cysteinyl-leukotrienes and histamine in mediating intrinsic tone in isolated human bronchi.	1994 Jan	8111568
Benefit/risk ratio of the antihistamines (H1-receptor antagonists) terfenadine and chlorpheniramine in children.	1994 Jun	8201490
In vivo and in vitro interaction of the novel selective histamine H1 receptor antagonist mizolastine with H1 receptors in the rodent.	1995 May	7612054
Combining event rates from clinical trials: comparison of Bayesian and classical methods.	1996 May	8740323
[Dexchlorpheniramine-induced acute hepatitis: a case with positive rechallenge].	1998 Oct	9854210
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Involvement of histamine H3 receptors in scratching behaviour in mast cell-deficient mice.	2003 Jul	12890190
Aseptic meningitis associated with intravenous administration of dexchlorpheniramine.	2003 May	12910046
2-O-(2-hydroxybutyl)-beta-cyclodextrin as a chiral selector for the capillary electrophoretic separation of chiral drugs.	2005 Aug	16122168
Synergistic action of famotidine and chlorpheniramine on acetic acid-induced chronic gastric ulcer in rats.	2005 Dec 7	16437673
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.	2005 Nov	16143415
Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs.	2006 Mar	16278312
Histamine induces MUC5AC expression via a hCLCA1 pathway.	2007	17622767
Rare case of "red man" syndrome in a female patient treated with oral vancomycin for Clostridium difficile diarrhoea.	2009	21886654
Retro-orbital oedema and transient blindness following endoscopic oesophagogastroduodenoscopy: a case report.	2009 Sep 2	19918358
Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting.	2010 Dec	21158687
Differential responding of autonomic function to histamine H₁ antagonism in irritable bowel syndrome.	2010 Dec	20667004
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	20170547
Randomised controlled double-blind non-inferiority trial of two antivenoms for saw-scaled or carpet viper (Echis ocellatus) envenoming in Nigeria.	2010 Jul 27	20668549
Evaluation of the enantioseparation capability of the novel chiral selector clindamycin phosphate towards basic drugs by micellar electrokinetic chromatography.	2010 Mar 12	20132938
Two cases of h(2)-receptor antagonist hypersensitivity and cross-reactivity.	2011 Apr	21461253
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

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 `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

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

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