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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26ClNO
Molecular Weight 343.891
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLEMASTINE

SMILES

C[C@@](c1ccccc1)(c2ccc(cc2)Cl)OCC[C@@]3([H])CCCN3C

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

Molecular Formula C21H26ClNO
Molecular Weight 343.891
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

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
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
First-line therapy with gemcitabine and paclitaxel in locally, recurrent or metastatic breast cancer: a phase II study.
2005 Nov 29
[Tolerance to coxibs in patients with intolerance to non-steroidal anti-inflammatory drugs (NSAIDs)].
2005 Oct 7
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
Simultaneous determination of ten antihistamine drugs in human plasma using pipette tip solid-phase extraction and gas chromatography/mass spectrometry.
2006
Dermatopathic lymphadenopathy: a differential diagnosis of enlarged lymph nodes in uremic pruritus.
2006 Dec
Impact of CYP2D6*10 on H1-antihistamine-induced hypersomnia.
2006 Dec
Clemastine, a conventional antihistamine, is a high potency inhibitor of the HERG K+ channel.
2006 Jan
[Diagnostic image (283). A man with a swollen tongue].
2006 Jul 22
Long-term complete responses after 131I-tositumomab therapy for relapsed or refractory indolent non-Hodgkin's lymphoma.
2006 Jun 19
Epitheliotropic cutaneous lymphoma (mycosis fungoides) in a dog.
2006 Mar
[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
Pharmacological prevention of serious anaphylactic reactions due to iodinated contrast media: systematic review.
2006 Sep 30
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
Early detection of adverse drug events within population-based health networks: application of sequential testing methods.
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
Intraoperative anaphylaxis after intravenous atropine.
2007 Mar
[Angioneurotic orolingual edema associated with the use of rt-PA following a stroke].
2007 Oct
Anti-inflammatory effects of low-intensity extremely high-frequency electromagnetic radiation: frequency and power dependence.
2008 Apr
Histamine upregulates keratinocyte MMP-9 production via the histamine H1 receptor.
2008 Dec
[Chikungunya: fever and joint pains after vacation in a tropical area].
2008 Feb
A highly active and tolerable neoadjuvant regimen combining paclitaxel, carboplatin, 5-FU, and radiation therapy in patients with stage II and III esophageal cancer.
2008 Jan
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
NEOadjuvant therapy monitoring with PET and CT in Esophageal Cancer (NEOPEC-trial).
2008 Jul 31
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
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
A similarity search using molecular topological graphs.
2009
Clinical practice. Diagnosis and treatment of cow's milk allergy.
2009 Aug
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
Acute cough: a diagnostic and therapeutic challenge.
2009 Dec 16
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
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Diagnostic approach identifying hydroxyethyl starch (HES) triggering a severe anaphylactic reaction during anesthesia in a 15-year-old boy.
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
[Discriminant function analysis in the assessment of laboratory test data in the correction of traditional therapy for mild icteric form of viral hepatitis B in children with food allergy].
2010 Jun
Chloroquine-induced Pruritus.
2010 May
Synthesis of (-)-(S,S)-clemastine by invertive N --> C aryl migration in a lithiated carbamate.
2010 May 21
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
Therapeutic efficacy of icatibant in angioedema induced by angiotensin-converting enzyme inhibitors: a case series.
2010 Sep
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 Fri Jun 25 22:00:23 UTC 2021
Edited
by admin
on Fri Jun 25 22:00:23 UTC 2021
Record UNII
95QN29S1ID
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
WHO-VATC QR06AA04
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
LIVERTOX 216
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
WHO-ATC R06AA54
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
WHO-VATC QR06AA54
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
WHO-ATC D04AA14
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
NCI_THESAURUS C29578
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
WHO-ATC R06AA04
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
Code System Code Type Description
MESH
D002974
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
EVMPD
SUB06648MIG
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
RXCUI
2578
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY RxNorm
IUPHAR
6063
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
DRUG BANK
DB00283
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
EPA CompTox
15686-51-8
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
PUBCHEM
26987
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
NCI_THESAURUS
C61682
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
INN
2231
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
WIKIPEDIA
CLEMASTINE
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
MERCK INDEX
M3613
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
671
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL1626
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
LACTMED
Clemastine
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
CAS
15686-51-8
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
FDA UNII
95QN29S1ID
Created by admin on Fri Jun 25 22:00:23 UTC 2021 , Edited by admin on Fri Jun 25 22:00:23 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
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