Details
Stereochemistry | EPIMERIC |
Molecular Formula | C76H52O46.C16H19ClN2 |
Molecular Weight | 1975.987 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC(C1=CC=C(Cl)C=C1)C2=CC=CC=N2.OC3=CC(=CC(O)=C3O)C(=O)OC4=CC(=CC(O)=C4O)C(=O)OC[C@H]5O[C@@H](OC(=O)C6=CC(O)=C(O)C(OC(=O)C7=CC(O)=C(O)C(O)=C7)=C6)[C@H](OC(=O)C8=CC(O)=C(O)C(OC(=O)C9=CC(O)=C(O)C(O)=C9)=C8)[C@@H](OC(=O)C%10=CC(O)=C(O)C(OC(=O)C%11=CC(O)=C(O)C(O)=C%11)=C%10)[C@@H]5OC(=O)C%12=CC(O)=C(O)C(OC(=O)C%13=CC(O)=C(O)C(O)=C%13)=C%12
InChI
InChIKey=KOOFUFFGNZKXFG-HBNMXAOGSA-N
InChI=1S/C76H52O46.C16H19ClN2/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h1-20,52,63-65,76-101H,21H2;3-9,11,15H,10,12H2,1-2H3/t52-,63-,64+,65-,76+;/m1./s1
Molecular Formula | C76H52O46 |
Molecular Weight | 1701.1985 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|
Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity. | 1975 Feb |
|
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 |
|
Antagonism of drug-induced yawning and penile erections in rats. | 1986 Mar 18 |
|
Chronic chlorpheniramine therapy: subsensitivity, drug metabolism, and compliance. | 1987 Nov |
|
A comparison of acrivastine versus chlorpheniramine in the treatment of chronic idiopathic urticaria. | 1989 |
|
[Antimycobacterial antihistaminics]. | 1989 Aug |
|
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 |
|
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 |
|
The specificity of a chlorphenamine-imprinted polymer and its application. | 2001 Aug 3 |
|
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 |
|
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 |
|
Ultra-fast chromatographic micro-assay for quantification of diphenidol in plasma: application in an oral multi-dose switchability trial. | 2008 Oct |
|
Suspected anaphylactic reactions associated with anaesthesia. | 2009 Feb |
|
Toxicity associated with combination oxaliplatin plus fluoropyrimidine with or without cetuximab in the MRC COIN trial experience. | 2009 Jan 27 |
|
[Stevens-Johnson syndrome plus intrahepatic cholestasis caused by clindamycin or chlorpheniramine]. | 2009 May 15 |
|
Continuous quinacrine treatment results in the formation of drug-resistant prions. | 2009 Nov |
|
Dextromethorphan, chlorphenamine and serotonin toxicity: case report and systematic literature review. | 2010 Dec |
|
Transport of phenylethylamine at intestinal epithelial (Caco-2) cells: mechanism and substrate specificity. | 2010 Feb |
|
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 |
|
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 03:27:56 UTC 2023
by
admin
on
Sat Dec 16 03:27:56 UTC 2023
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Record UNII |
72JT935YTT
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
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221075
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215-782-0
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71586779
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100000084736
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1405-56-7
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DTXSID90161417
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C97692
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72JT935YTT
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SUB01244MIG
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DBSALT001556
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