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
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
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 | ( + / - ) |
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 Date-6.116256E11 |
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 |
---|---|---|
Oral facial dyskinesia associated with prolonged use of antihistaminic decongestants. | 1975 Sep 4 |
|
Skeletal muscle necrosis following membrane-active drugs plus serotonin. | 1976 May |
|
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule. | 1978 Oct 7 |
|
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 |
|
Histamine and hepatic glutathione in the mouse. | 1987 May 25 |
|
A comparison of acrivastine versus chlorpheniramine in the treatment of chronic idiopathic urticaria. | 1989 |
|
Drug-induced acute pulmonary edema--sequential changes in CT images. | 1991 Nov-Dec |
|
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 |
|
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 |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
Ketoconazole potentiates terfenadine-induced apoptosis in human Hep G2 cells through inhibition of cytochrome p450 3A4 activity. | 2002 |
|
Chlorphenamine. | 2005 Aug 9-15 |
|
Carrier mediated transport of chlorpheniramine and chlorcyclizine across bovine olfactory mucosa: implications on nose-to-brain transport. | 2005 Mar |
|
Enhanced antinociception by intracerebroventricularly administered orexin A in histamine H1 or H2 receptor gene knockout mice. | 2005 Nov |
|
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro. | 2005 Nov |
|
Phase II study of gemcitabine, doxorubicin and paclitaxel (GAT) as first-line chemotherapy for metastatic breast cancer: a translational research experience. | 2006 Mar 21 |
|
Histamine induces MUC5AC expression via a hCLCA1 pathway. | 2007 |
|
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish. | 2007 Apr |
|
Allergic hemiglossitis as a unique case of food allergy: a case report. | 2008 Mar 6 |
|
Toxicity associated with combination oxaliplatin plus fluoropyrimidine with or without cetuximab in the MRC COIN trial experience. | 2009 Jan 27 |
|
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 |
|
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 |
|
Simultaneous determination of paracetamol, pseudoephedrine, dextrophan and chlorpheniramine in human plasma by liquid chromatography-tandem mass spectrometry. | 2010 Mar 1 |
|
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
Fri Dec 15 15:21:07 UTC 2023
by
admin
on
Fri Dec 15 15:21:07 UTC 2023
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Record UNII |
5S6VUP419V
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
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