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

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

7.0372799E11
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

7.0372799E11
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
Inhibitory effect of olopatadine hydrochloride on the sneezing response induced by intranasal capsaicin challenge in guinea pigs.
2001 Jun
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
Phase II study of bi-weekly administration of paclitaxel and cisplatin in patients with advanced oesophageal cancer.
2002 Mar 4
Antihistamines in the treatment of dermatitis.
2003 Nov-Dec
Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic.
2004 Mar
Pegylated liposomal doxorubicin in combination with mitomycin C, infusional 5-fluorouracil and sodium folinic acid. A phase-I-study in patients with upper gastrointestinal cancer.
2004 May 17
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
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
Inhibition of mast cell degranulation-induced drop of blood pressure with clemastine, cromolyn and compound 48/80 pretreatment.
2006 Apr
Impact of CYP2D6*10 on H1-antihistamine-induced hypersomnia.
2006 Dec
[Pharmacological analysis of anti-inflammatory effects of low-intensity extremely high-frequency electromagnetic radiation].
2006 Nov-Dec
Phase II and pharmacological study of oral paclitaxel (Paxoral) plus ciclosporin in anthracycline-pretreated metastatic breast cancer.
2006 Oct 9
A novel self-microemulsifying formulation of paclitaxel for oral administration to patients with advanced cancer.
2006 Sep 18
Stereoselective synthesis of (-)-hydroxyclemastine as a versatile intermediate for the H1 receptor antagonist clemastine.
2007 Dec
Intraoperative anaphylaxis after intravenous atropine.
2007 Mar
[Angioneurotic orolingual edema associated with the use of rt-PA following a stroke].
2007 Oct
Histamine upregulates keratinocyte MMP-9 production via the histamine H1 receptor.
2008 Dec
Spectrophotometric determination of some histamine H1-antagonists drugs in their pharmaceutical preparations.
2008 Jan
Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells.
2008 Jun 6
Medication with antihistamines impairs allergen-specific immunotherapy in mice.
2008 Mar
Practical recommendations on the use of lenalidomide in the management of myelodysplastic syndromes.
2008 May
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
Psoriasis vulgaris and digestive system disorders: is there a linkage?
2009 Jan
[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
Hyperimmune anti-HBs plasma as alternative to commercial immunoglobulins for prevention of HBV recurrence after liver transplantation.
2010 Jul 4
Structural elucidation of N-oxidized clemastine metabolites by liquid chromatography/tandem mass spectrometry and the use of Cunninghamella elegans to facilitate drug metabolite identification.
2010 May 30
[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
Name Type Language
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
HS-592
Code 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 Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
WHO-VATC QR06AA04
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
LIVERTOX NBK548709
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
WHO-ATC R06AA54
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
WHO-VATC QR06AA54
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
WHO-ATC D04AA14
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
NCI_THESAURUS C29578
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
WHO-ATC R06AA04
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
Code System Code Type Description
MESH
D002974
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
EVMPD
SUB06648MIG
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
RXCUI
2578
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY RxNorm
IUPHAR
6063
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
DRUG BANK
DB00283
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
EPA CompTox
DTXSID2022832
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
PUBCHEM
26987
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
NCI_THESAURUS
C61682
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
INN
2231
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
WIKIPEDIA
CLEMASTINE
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
MERCK INDEX
M3613
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
671
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
ChEMBL
CHEMBL1626
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
NSC
756685
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
LACTMED
Clemastine
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
CAS
15686-51-8
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
SMS_ID
100000080172
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
CHEBI
3738
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
FDA UNII
95QN29S1ID
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY
DAILYMED
95QN29S1ID
Created by admin on Wed Jul 05 22:49:47 UTC 2023 , Edited by admin on Wed Jul 05 22:49:47 UTC 2023
PRIMARY