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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26ClNO.C4H4O4
Molecular Weight 459.962
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CLEMASTINE FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.CN1CCC[C@@H]1CCO[C@](C)(C2=CC=CC=C2)C3=CC=C(Cl)C=C3

InChI

InChIKey=PMGQWSIVQFOFOQ-YKVZVUFRSA-N
InChI=1S/C21H26ClNO.C4H4O4/c1-21(17-7-4-3-5-8-17,18-10-12-19(22)13-11-18)24-16-14-20-9-6-15-23(20)2;5-3(6)1-2-4(7)8/h3-5,7-8,10-13,20H,6,9,14-16H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t20-,21-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C21H26ClNO
Molecular Weight 343.89
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.sciencedirect.com/topics/page/Clemastine and https://www.drugs.com/pro/clemastine.html

Clemastine is an antihistamine with anticholinergic (drying) and sedative side effects. Clemastine is a selective histamine H1 antagonist and 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. It is used for the relief of symptoms associated with allergic rhinitis such as sneezing, rhinorrhea, pruritus and acrimation. Also for the management of mild, uncomplicated allergic skin manifestations of urticaria and angioedema. Used as self-medication for temporary relief of symptoms associated with the common cold.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.4 µM [IC50]
12.0 nM [IC50]
2.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CLEMASTINE

Approved Use

Clemastine fumarate tablets are indicated for the relief of symptoms associated with allergic rhinitis such as sneezing, rhinorrhea, pruritus, and lacrimation. Clemastine fumarate tablets are also indicated for the relief of mild, uncomplicated allergic skin manifestations of urticaria and angioedema.

Launch Date

1992
Primary
CLEMASTINE

Approved Use

Clemastine fumarate tablets are indicated for the relief of symptoms associated with allergic rhinitis such as sneezing, rhinorrhea, pruritus, and lacrimation. Clemastine fumarate tablets are also indicated for the relief of mild, uncomplicated allergic skin manifestations of urticaria and angioedema.

Launch Date

1992
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.7 ng/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
650 pg/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1010 pg/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.2 ng × h/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
15529 pg × h/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
26230 pg × h/mL
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8 h
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
17.28 h
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
23.94 h
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLEMASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
4 mg single, oral
Highest studied dose
Dose: 4 mg
Route: oral
Route: single
Dose: 4 mg
Sources:
healthy
Health Status: healthy
Sex: M
Sources:
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
healthy
Disc. AE: Itching, Rash...
AEs leading to
discontinuation/dose reduction:
Itching (1 patient)
Rash (1 patient)
Nausea (1 patient)
Pallor (1 patient)
Sources:
1 mg single, oral
healthy
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Itching 1 patient
Disc. AE
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
healthy
Nausea 1 patient
Disc. AE
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
healthy
Pallor 1 patient
Disc. AE
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
healthy
Rash 1 patient
Disc. AE
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
healthy
Vomiting 1 patient
Disc. AE
1 mg single, oral
healthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 2 uM]
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Inhibitory effect of olopatadine hydrochloride on the sneezing response induced by intranasal capsaicin challenge in guinea pigs.
2001 Jun
[Stem cell factor production from cultured nasal epithelial cells--effect on SCF production by drugs].
2002 Feb
Phase II study of bi-weekly administration of paclitaxel and cisplatin in patients with advanced oesophageal cancer.
2002 Mar 4
Interactions of olopatadine and selected antihistamines with model and natural membranes.
2003 Dec
Role of histamine receptors in the regulation of edema and circulation postburn.
2003 Dec
Hypersensitivity vasculitis induced by cefoperazone/sulbactam.
2003 Jan 3
Antihistamines in the treatment of dermatitis.
2003 Nov-Dec
Clinical pharmacology of clemastine in healthy dogs.
2004 Jun
[Multilocular painful urticarial plaques. Eosinophilic cellulitis (Wells syndrome)].
2004 Oct 27
Phase I clinical study of the recombinant antibody toxin scFv(FRP5)-ETA specific for the ErbB2/HER2 receptor in patients with advanced solid malignomas.
2005
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.
2005 Aug
High-performance liquid chromatographic-tandem mass spectrometric method for the determination of clemastine in human plasma.
2005 Feb 25
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
First-line therapy with gemcitabine and paclitaxel in locally, recurrent or metastatic breast cancer: a phase II study.
2005 Nov 29
Rituximab treatment in patients with primary Sjögren's syndrome: an open-label phase II study.
2005 Sep
Clemastine, a conventional antihistamine, is a high potency inhibitor of the HERG K+ channel.
2006 Jan
[Pharmacological analysis of anti-inflammatory effects of low-intensity extremely high-frequency electromagnetic radiation].
2006 Nov-Dec
Neoadjuvant chemoradiation followed by surgery versus surgery alone for patients with adenocarcinoma or squamous cell carcinoma of the esophagus (CROSS).
2008 Nov 26
A similarity search using molecular topological graphs.
2009
Acute cough: a diagnostic and therapeutic challenge.
2009 Dec 16
Psoriasis vulgaris and digestive system disorders: is there a linkage?
2009 Jan
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Use of venlafaxine compared with other antidepressants and the risk of sudden cardiac death or near death: a nested case-control study.
2010 Feb 5
Anaphylaxis to mefenamic acid in a patient with new onset of systemic lupus erythematosus.
2010 Jul-Aug
[Progress of study on antitumor effects of antibody dependent cell mediated cytotoxicity--review].
2010 Oct
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Allergic Rhinitis Initial dose: 1.34 mg orally twice a day. Dosage may be increased as required, but not to exceed 2.68 mg orally 3 times a day.
Route of Administration: Oral
IHERG tails at -40 mV following depolarizing pulses to +20 mV were inhibited by clemastine with an IC50 value of 12 nM in HEK 293 cells
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:41:49 GMT 2025
Edited
by admin
on Mon Mar 31 21:41:49 GMT 2025
Record UNII
19259EGQ3D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLEMASTINE HYDROGEN FUMARATE
MI  
Preferred Name English
CLEMASTINE FUMARATE
EP   HSDB   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
Clemastine fumarate [WHO-DD]
Common Name English
TAVIST
Brand Name English
CLEMASTINE FUMARATE [MART.]
Common Name English
CLEMASTINE FUMARATE [HSDB]
Common Name English
CLEMASTINE FUMARATE [ORANGE BOOK]
Common Name English
CLEMASTINE FUMARATE [USP MONOGRAPH]
Common Name English
CLEMASTINE FUMARATE [VANDF]
Common Name English
CLEMASTINE FUMARATE [EP MONOGRAPH]
Common Name English
CLEMASTINE FUMARATE [JAN]
Common Name English
TAVIST-D COMPONENT CLEMASTINE FUMARATE
Common Name English
PYRROLIDINE, 2-(2-(1-(4-CHLOROPHENYL)-1-PHENYLETHOXY)ETHYL)-1-METHYL-, (R-(R*,R*))-, (E)-2-BUTENEDIOATE (1:1)
Common Name English
CLEMASTINE FUMARATE [USP-RS]
Common Name English
CLEMASTINE HYDROGEN FUMARATE [MI]
Common Name English
(+)-(2R)-2-(2-(((R)-P-CHLORO-.ALPHA.-METHYL-.ALPHA.-PHENYLBENZYL)OXY)ETHYL)-1-METHYLPYRROLIDINE FUMARATE (1:1)
Common Name English
CLEMASTINE FUMARATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
Code System Code Type Description
CAS
14976-57-9
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
DRUG BANK
DBSALT000901
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
ChEMBL
CHEMBL1626
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
SMS_ID
100000087930
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
ECHA (EC/EINECS)
239-055-2
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
EPA CompTox
DTXSID6047785
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
NCI_THESAURUS
C47454
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
MERCK INDEX
m3613
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY Merck Index
PUBCHEM
5281069
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
FDA UNII
19259EGQ3D
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
HSDB
6507
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
EVMPD
SUB01335MIG
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
CHEBI
3739
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
RS_ITEM_NUM
1134506
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
DAILYMED
19259EGQ3D
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY
RXCUI
142430
Created by admin on Mon Mar 31 21:41:49 GMT 2025 , Edited by admin on Mon Mar 31 21:41:49 GMT 2025
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY