Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H19ClN2 |
Molecular Weight | 274.788 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC(C1=CC=C(Cl)C=C1)C2=CC=CC=N2
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
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 | ( + / - ) |
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL612856 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16750932 |
136.0 µM [IC50] | ||
Target ID: CHEMBL231 |
12.0 nM [IC50] | ||
Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) |
15.2 nM [Kd] | ||
Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) |
203.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Chlor-Trimeton Approved UseUses
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 Date1950 |
Cmax
Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
Value | Dose | Co-administered | 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 |
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) Sources: Urticaria (2 patients) Abdominal cramp (1 patient) Nausea (1 patient) Diarrhea (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
weak [Ki 11 uM] | ||||
yes [Ki 191.2 uM] | ||||
yes [Ki 87.6 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/11284026/ Page: 6.0 |
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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity. | 1975 Feb |
|
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants. | 1975 Sep 4 |
|
Skeletal muscle necrosis following membrane-active drugs plus serotonin. | 1976 May |
|
The I antigen as an immune complex receptor in a case of haemolytic anaemia induced by an antihistaminic agent. | 1981 Sep |
|
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 |
|
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 |
|
[Antimycobacterial antihistaminics]. | 1989 Aug |
|
Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema. | 1993 Dec |
|
Benefit/risk ratio of the antihistamines (H1-receptor antagonists) terfenadine and chlorpheniramine in children. | 1994 Jun |
|
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 |
|
Mechanism responsible for epileptogenic activity by first-generation H1-antagonists in rats. | 2000 Dec 22 |
|
A new model of allergic rhinitis in rats by topical sensitization and evaluation of H(1)-receptor antagonists. | 2000 Jun |
|
Synergistic antiallergic activity of combined histamine H1- and cysteinyl leukotriene1-receptor blockade in human bronchus. | 2001 May 11 |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
[An exceptional case of hypersensitivity to actinomycin D. Case report and review of the literature]. | 2001 Sep-Oct |
|
Ketoconazole potentiates terfenadine-induced apoptosis in human Hep G2 cells through inhibition of cytochrome p450 3A4 activity. | 2002 |
|
Enhanced antinociception by intrathecally-administered morphine in histamine H1 receptor gene knockout mice. | 2002 Jun |
|
Single-patient drug trial methodology for allergic rhinitis. | 2002 Sep |
|
Involvement of histamine H3 receptors in scratching behaviour in mast cell-deficient mice. | 2003 Jul |
|
Adrenaline given outside the context of life threatening allergic reactions. | 2003 Mar 15 |
|
Up-regulation of histamine H(1) receptors in an allergic rat nasal mucosa model. | 2004 Mar |
|
2-O-(2-hydroxybutyl)-beta-cyclodextrin as a chiral selector for the capillary electrophoretic separation of chiral drugs. | 2005 Aug |
|
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro. | 2005 Nov |
|
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish. | 2007 Apr |
|
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats. | 2008 Mar |
|
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 |
|
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 |
|
Identification of human Ether-à-go-go related gene modulators by three screening platforms in an academic drug-discovery setting. | 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 |
|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/chlorpheniramine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1673158
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
Edited
Sat Dec 16 17:09:18 GMT 2023
by
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on
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Record UNII |
3U6IO1965U
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
R06AB04
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N0000175587
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N0000000190
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QR06AB04
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LIVERTOX |
195
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WHO-ESSENTIAL MEDICINES LIST |
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R06AB54
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NCI_THESAURUS |
C29578
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WHO-VATC |
QR06AB54
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C61672
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205-054-0
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Chlorpheniramine
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CHLORPHENAMINE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR | |||
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SUB_CONCEPT->SUBSTANCE | |||
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TRANSPORTER -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |