U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CHLORPHENIRAMINE TANNATE

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

HIDE SMILES / InChI

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

-6.116256E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
30.6 ng/mL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1075.7 ng × h/mL
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
24.5 h
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
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
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
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

Doses

DosePopulationAdverse events​
5 mg single, intravenous
Dose: 5 mg
Route: intravenous
Route: single
Dose: 5 mg
Sources:
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)
Urticaria (2 patients)
Abdominal cramp (1 patient)
Nausea (1 patient)
Diarrhea (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
weak [Ki 11 uM]
yes [Ki 191.2 uM]
yes [Ki 87.6 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

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 Sat Dec 16 03:27:56 UTC 2023
Edited
by admin
on Sat Dec 16 03:27:56 UTC 2023
Record UNII
72JT935YTT
Record Status Validated (UNII)
Record Version
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Name Type Language
CHLORPHENIRAMINE TANNATE
VANDF  
Common Name English
CHLORPHENAMINE TANNATE
WHO-DD  
Common Name English
CHLORPHENAMINE TANNATE [WHO-DD]
Common Name English
CHLORPHENIRAMINE TANNATE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
Code System Code Type Description
RXCUI
221075
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
215-782-0
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
PUBCHEM
71586779
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
SMS_ID
100000084736
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
CAS
1405-56-7
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID90161417
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
NCI_THESAURUS
C97692
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
FDA UNII
72JT935YTT
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
EVMPD
SUB01244MIG
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
DRUG BANK
DBSALT001556
Created by admin on Sat Dec 16 03:27:56 UTC 2023 , Edited by admin on Sat Dec 16 03:27:56 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY