CHLORPHENIRAMINE HYDROCHLORIDE

US Approved OTC

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H19ClN2.ClH
Molecular Weight	311.249
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of CHLORPHENIRAMINE HYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=NOXNCSQBTYNMHD-UHFFFAOYSA-N

InChI=1S/C16H19ClN2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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	( + / - )

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) 8 Target ID: CHEMBL612856 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750932	Inhibitor 8297	136.0 µM [IC50]
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2879912 \| https://www.ncbi.nlm.nih.gov/pubmed/18363822	Antagonist 2778	12.0 nM [IC50]
Sodium-dependent serotonin transporter 40 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 8297	15.2 nM [Kd]
Sodium-dependent dopamine transporter 42 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 8297	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 8429	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

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 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MATE1 306 MATE2 263	P-gp 1537

Drug as perpetrator

Target	Modality	Activity
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9616188/	weak [Ki 11 uM]
MATE2 263	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 191.2 uM]
MATE1 308	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19164462/	yes [Ki 87.6 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11284026/ Page: 6.0	no
CYP2D6 1217	substrate 3367 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 1647	inhibitor 1626 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
Reaction to phenylpropalamine/chlorpheniramine/belladonna compound in a women with unrecognised autonomic dysfunction.	1982 Jul 31	6124702
Histamine and hepatic glutathione in the mouse.	1987 May 25	2884542
[Antimycobacterial antihistaminics].	1989 Aug	2513793
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
Central nervous system effects of H1-receptor antagonists in the elderly.	1999 Feb	10071518
Synergistic antiallergic activity of combined histamine H1- and cysteinyl leukotriene1-receptor blockade in human bronchus.	2001 May 11	11432448
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
[Molecular diversity of organic cation transporter (OCT) mediating renal excretion of drugs].	2002 Nov	12440152
[A successfully treated case of intraoperative latex anaphylaxis during abdominal aorta aneurysm resection].	2003 Jan	12632613
Involvement of histamine H3 receptors in scratching behaviour in mast cell-deficient mice.	2003 Jul	12890190
Adrenaline given outside the context of life threatening allergic reactions.	2003 Mar 15	12637407
[Roles of histamine receptors in pain perception: a study using receptors gene knockout mice].	2003 Nov	14569158
Up-regulation of histamine H(1) receptors in an allergic rat nasal mucosa model.	2004 Mar	15054595
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
Cutaneous adverse drug reaction to oral chlorphenamine detected with patch testing.	2005 Jan	15701135
Enhanced antinociception by intracerebroventricularly administered orexin A in histamine H1 or H2 receptor gene knockout mice.	2005 Nov	16202530
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro.	2005 Nov	16143415
Phase II study of gemcitabine, doxorubicin and paclitaxel (GAT) as first-line chemotherapy for metastatic breast cancer: a translational research experience.	2006 Mar 21	16551351
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	19075512
Block of HERG k channel by classic histamine h(1) receptor antagonist chlorpheniramine.	2009 Jun	19885040
Hepatotoxicity induced by methimazole in a previously healthy patient.	2009 Sep	19534646
Dextromethorphan, chlorphenamine and serotonin toxicity: case report and systematic literature review.	2010 Dec	21175434
Transport of phenylethylamine at intestinal epithelial (Caco-2) cells: mechanism and substrate specificity.	2010 Feb	19962438
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
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 Dec 15 15:21:07 GMT 2023` Edited by `admin` on `Fri Dec 15 15:21:07 GMT 2023`
Record UNII	5S6VUP419V
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CHLORPHENIRAMINE HYDROCHLORIDE

Common Name

English

CHLORPHENIRAMINE HCL

Common Name

English

CHLORPHENAMINE HYDROCHLORIDE

Common Name

English

Chlorphenamine hydrochloride [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29578