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

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
n = 24
Health Status: healthy
Sex: M
Population Size: 24
Sources:
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources: Page: page 58
healthy
n = 32
Health Status: healthy
Sex: M+F
Population Size: 32
Sources: Page: page 58
Disc. AE: Itching, Rash...
AEs leading to
discontinuation/dose reduction:
Itching (1 patient)
Rash (1 patient)
Nausea (1 patient)
Pallor (1 patient)
Sources: Page: page 58
1 mg single, oral
Dose: 1 mg
Route: oral
Route: single
Dose: 1 mg
Sources: Page: page 58
healthy
n = 32
Health Status: healthy
Sex: M
Population Size: 32
Sources: Page: page 58
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (1 patient)
Sources: Page: page 58
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: Page: page 58
healthy
n = 32
Health Status: healthy
Sex: M+F
Population Size: 32
Sources: Page: page 58
Nausea 1 patient
Disc. AE
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources: Page: page 58
healthy
n = 32
Health Status: healthy
Sex: M+F
Population Size: 32
Sources: Page: page 58
Pallor 1 patient
Disc. AE
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources: Page: page 58
healthy
n = 32
Health Status: healthy
Sex: M+F
Population Size: 32
Sources: Page: page 58
Rash 1 patient
Disc. AE
0.5 mg single, oral
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources: Page: page 58
healthy
n = 32
Health Status: healthy
Sex: M+F
Population Size: 32
Sources: Page: page 58
Vomiting 1 patient
Disc. AE
1 mg single, oral
Dose: 1 mg
Route: oral
Route: single
Dose: 1 mg
Sources: Page: page 58
healthy
n = 32
Health Status: healthy
Sex: M
Population Size: 32
Sources: Page: page 58
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
Atrial T (Ta) loop in dogs with or without atrial injury.
1976 May
Evaluation of several solid phase extraction liquid chromatography/tandem mass spectrometry on-line configurations for high-throughput analysis of acidic and basic drugs in rat plasma.
2001
Dose reduction of steroid premedication for paclitaxel: no increase of hypersensitivity reactions.
2001 Jun
Simultaneous screening and quantitation of 18 antihistamine drugs in blood by liquid chromatography ionspray tandem mass spectrometry.
2001 Sep 15
Randomized trial of single agent paclitaxel given weekly versus every three weeks and with peroral versus intravenous steroid premedication to patients with ovarian cancer previously treated with platinum.
2002
Fatal outcome of a hypersensitivity reaction to paclitaxel: a critical review of premedication regimens.
2004 Jan 26
Interstitial granulomatous dermatitis with arthritis.
2004 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Evaluation of the rabbit Purkinje fibre assay as an in vitro tool for assessing the risk of drug-induced torsades de pointes in humans.
2006
Simultaneous determination of ten antihistamine drugs in human plasma using pipette tip solid-phase extraction and gas chromatography/mass spectrometry.
2006
Inhibition of mast cell degranulation-induced drop of blood pressure with clemastine, cromolyn and compound 48/80 pretreatment.
2006 Apr
Dermatopathic lymphadenopathy: a differential diagnosis of enlarged lymph nodes in uremic pruritus.
2006 Dec
Treatment of non-small cell lung cancer with intensity-modulated radiation therapy in combination with cetuximab: the NEAR protocol (NCT00115518).
2006 May 8
[Pharmacological analysis of anti-inflammatory effects of low-intensity extremely high-frequency electromagnetic radiation].
2006 Nov-Dec
Development and full validation of a sensitive quantitative assay for the determination of clemastine in human plasma by liquid chromatography-tandem mass spectrometry.
2007 Aug 15
[Emergency checklist: angioedema].
2007 Aug 2
Stereoselective synthesis of (-)-hydroxyclemastine as a versatile intermediate for the H1 receptor antagonist clemastine.
2007 Dec
Psoriasis following growth hormone therapy in a child.
2007 Jan
Influence of immunomodulatory drugs on the cytotoxicity induced by monoclonal antibody 17-1A and interleukin-2.
2007 Mar
Anti-inflammatory effects of low-intensity extremely high-frequency electromagnetic radiation: frequency and power dependence.
2008 Apr
Spectrophotometric determination of some histamine H1-antagonists drugs in their pharmaceutical preparations.
2008 Jan
Synovial tissue response to rituximab: mechanism of action and identification of biomarkers of response.
2008 Jul
Practical recommendations on the use of lenalidomide in the management of myelodysplastic syndromes.
2008 May
Clinical practice. Diagnosis and treatment of cow's milk allergy.
2009 Aug
Application of prolonged microdialysis sampling in carboplatin-treated cancer patients.
2009 Aug
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Hyperimmune anti-HBs plasma as alternative to commercial immunoglobulins for prevention of HBV recurrence after liver transplantation.
2010 Jul 4
Anaphylaxis to mefenamic acid in a patient with new onset of systemic lupus erythematosus.
2010 Jul-Aug
Chloroquine-induced Pruritus.
2010 May
[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 Sat Dec 16 07:32:46 GMT 2023
Edited
by admin
on Sat Dec 16 07:32:46 GMT 2023
Record UNII
19259EGQ3D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
CLEMASTINE FUMARATE COMPONENT OF TAVIST-D
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
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 Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
Code System Code Type Description
CAS
14976-57-9
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
DRUG BANK
DBSALT000901
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL1626
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
SMS_ID
100000087930
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
239-055-2
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID6047785
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
NCI_THESAURUS
C47454
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
MERCK INDEX
m3613
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY Merck Index
PUBCHEM
5281069
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
FDA UNII
19259EGQ3D
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
HSDB
6507
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
EVMPD
SUB01335MIG
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
CHEBI
3739
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
RS_ITEM_NUM
1134506
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
DAILYMED
19259EGQ3D
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY
RXCUI
142430
Created by admin on Sat Dec 16 07:32:46 GMT 2023 , Edited by admin on Sat Dec 16 07:32:46 GMT 2023
PRIMARY RxNorm
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ACTIVE MOIETY