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
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-
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 | ( + / - ) |
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 |
---|---|---|
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 |
|
[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 |
|
[Dexchlorpheniramine-induced acute hepatitis: a case with positive rechallenge]. | 1998 Oct |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
Involvement of histamine H3 receptors in scratching behaviour in mast cell-deficient mice. | 2003 Jul |
|
Aseptic meningitis associated with intravenous administration of dexchlorpheniramine. | 2003 May |
|
2-O-(2-hydroxybutyl)-beta-cyclodextrin as a chiral selector for the capillary electrophoretic separation of chiral drugs. | 2005 Aug |
|
Synergistic action of famotidine and chlorpheniramine on acetic acid-induced chronic gastric ulcer in rats. | 2005 Dec 7 |
|
Excitatory effect of histamine on neuronal activity of rat globus pallidus by activation of H2 receptors in vitro. | 2005 Nov |
|
Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs. | 2006 Mar |
|
Histamine induces MUC5AC expression via a hCLCA1 pathway. | 2007 |
|
Rare case of "red man" syndrome in a female patient treated with oral vancomycin for Clostridium difficile diarrhoea. | 2009 |
|
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 |
|
Differential responding of autonomic function to histamine H₁ antagonism in irritable bowel syndrome. | 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 |
|
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 |
|
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 Jun 25 21:04:24 UTC 2021
by
admin
on
Fri Jun 25 21:04:24 UTC 2021
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Record UNII |
V1Q0O9OJ9Z
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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
Created by
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CFR |
21 CFR 341.12
Created by
admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
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Code System | Code | Type | Description | ||
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113-92-8
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PRIMARY | |||
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142429
Created by
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PRIMARY | RxNorm | ||
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CHEMBL505
Created by
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PRIMARY | |||
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M3456
Created by
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PRIMARY | Merck Index | ||
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V1Q0O9OJ9Z
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PRIMARY | |||
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5281068
Created by
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PRIMARY | |||
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CHLORPHENIRAMINE MALEATE
Created by
admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
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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. | ||
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DBSALT000987
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SUB01243MIG
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113-92-8
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204-037-5
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admin on Fri Jun 25 21:04:24 UTC 2021 , Edited by admin on Fri Jun 25 21:04:24 UTC 2021
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C28925
Created by
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PRIMARY | |||
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1123000
Created by
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PRIMARY | USP-RS |
Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |