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

Stereochemistry ABSOLUTE
Molecular Formula C21H26ClNO
Molecular Weight 343.89
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLEMASTINE

SMILES

CN1CCC[C@@H]1CCO[C@](C)(C2=CC=CC=C2)C3=CC=C(Cl)C=C3

InChI

InChIKey=YNNUSGIPVFPVBX-NHCUHLMSSA-N
InChI=1S/C21H26ClNO/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/h3-5,7-8,10-13,20H,6,9,14-16H2,1-2H3/t20-,21-/m1/s1

HIDE SMILES / InChI

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
Atrial T (Ta) loop in dogs with or without atrial injury.
1976 May
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
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations].
2002
[Stem cell factor production from cultured nasal epithelial cells--effect on SCF production by drugs].
2002 Feb
[Severe adverse event following iv administration of 10 ml 6% Dextran60 (0.6 g) in a healthy volunteer].
2002 Oct
Antihistamines in the management of canine atopic dermatitis: a retrospective study of 171 dogs (1992-1998).
2002 Spring
Pharmacokinetics and pharmacodynamics of clemastine in healthy horses.
2003 Apr
Role of histamine receptors in the regulation of edema and circulation postburn.
2003 Dec
IgA pemphigus occurring in a 1-month-old infant.
2003 Feb
Efficacy and safety of clemastine-pseudoephedrine-acetaminophen versus pseudoephedrine-acetaminophen in the treatment of seasonal allergic rhinitis in a 1-day, placebo-controlled park study.
2003 Jan
Why aren't lower, effective, OTC doses available earlier by prescription?
2003 Jan
Hypersensitivity vasculitis induced by cefoperazone/sulbactam.
2003 Jan 3
[Tolerance induction in anaphylaxis to carboplatin].
2003 Jul 25
Serious allergic reaction to administration of epirubicin.
2003 Jun
Fatal outcome of a hypersensitivity reaction to paclitaxel: a critical review of premedication regimens.
2004 Jan 26
[Appearance diagnosis. Facial shingles].
2004 Jul 22
Itch and skin rash from chocolate during fluoxetine and sertraline treatment: case report.
2004 Nov 2
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Simultaneous determination of ten antihistamine drugs in human plasma using pipette tip solid-phase extraction and gas chromatography/mass spectrometry.
2006
Epitheliotropic cutaneous lymphoma (mycosis fungoides) in a dog.
2006 Mar
Concurrent chemotherapy (carboplatin, paclitaxel, etoposide) and involved-field radiotherapy in limited stage small cell lung cancer: a Dutch multicenter phase II study.
2006 Mar 13
Laparoscopic ileocolic resection versus infliximab treatment of distal ileitis in Crohn's disease: a randomized multicenter trial (LIR!C-trial).
2008 Aug 22
Major determinants and long-term outcomes of successful balloon dilatation for the pediatric patients with isolated native valvular pulmonary stenosis: a 10-year institutional experience.
2008 Jun 30
Medication with antihistamines impairs allergen-specific immunotherapy in mice.
2008 Mar
Neoadjuvant chemoradiation followed by surgery versus surgery alone for patients with adenocarcinoma or squamous cell carcinoma of the esophagus (CROSS).
2008 Nov 26
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS).
2008 Sep
[Documentation for acute treatment with clemastine (Tavegyl) is missing].
2009 Jul 22-Aug 4
Psychoactive medication and traffic safety.
2009 Mar
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
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
Name Type Language
HS-592
Preferred Name English
CLEMASTINE
INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
CLEMASTIN
Common Name English
clemastine [INN]
Common Name English
Clemastine [WHO-DD]
Common Name English
CLEMASTINE [MI]
Common Name English
PYRROLIDINE, 2-(2-(1-(4-CHLOROPHENYL)-1-PHENYLETHOXY)ETHYL)-1-METHYL-, (R-(R*,R*))
Common Name English
CLEMASTINE [USAN]
Common Name English
CLEMASTINE [VANDF]
Common Name English
(+)-(2R)-2-(-(((R)-P-CHLORO-.ALPHA.-METHYL-.ALPHA.-PHENYLBENZYL)OXY)ETHYL)-1-METHYLPYRROLIDINE
Common Name English
NSC-756685
Code English
Classification Tree Code System Code
WHO-VATC QD04AA14
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
WHO-VATC QR06AA04
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
LIVERTOX NBK548709
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
WHO-ATC R06AA54
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
WHO-VATC QR06AA54
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
WHO-ATC D04AA14
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
WHO-ATC R06AA04
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
Code System Code Type Description
MESH
D002974
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
PRIMARY
EVMPD
SUB06648MIG
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
PRIMARY
RXCUI
2578
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PRIMARY RxNorm
IUPHAR
6063
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PRIMARY
DRUG BANK
DB00283
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PRIMARY
EPA CompTox
DTXSID2022832
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PRIMARY
PUBCHEM
26987
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PRIMARY
NCI_THESAURUS
C61682
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PRIMARY
INN
2231
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PRIMARY
WIKIPEDIA
CLEMASTINE
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PRIMARY
MERCK INDEX
m3613
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PRIMARY Merck Index
DRUG CENTRAL
671
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PRIMARY
ChEMBL
CHEMBL1626
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PRIMARY
NSC
756685
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
PRIMARY
LACTMED
Clemastine
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
PRIMARY
CAS
15686-51-8
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
PRIMARY
SMS_ID
100000080172
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PRIMARY
CHEBI
3738
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PRIMARY
FDA UNII
95QN29S1ID
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PRIMARY
DAILYMED
95QN29S1ID
Created by admin on Mon Mar 31 17:53:45 GMT 2025 , Edited by admin on Mon Mar 31 17:53:45 GMT 2025
PRIMARY