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

Description
Curator's Comment:: 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
0.400000000000000022 µM [IC50]
12 nM [IC50]
2 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

703728000000
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

703728000000
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
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
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
Antihistamines in the treatment of dermatitis.
2003 Nov-Dec
Clinical pharmacology of clemastine in healthy dogs.
2004 Jun
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
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Rituximab treatment in patients with primary Sjögren's syndrome: an open-label phase II study.
2005 Sep
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
Neoadjuvant concurrent chemoradiation with weekly paclitaxel and carboplatin for patients with oesophageal cancer: a phase II study.
2006 May 22
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
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
Stereoselective synthesis of (-)-hydroxyclemastine as a versatile intermediate for the H1 receptor antagonist clemastine.
2007 Dec
Early detection of adverse drug events within population-based health networks: application of sequential testing methods.
2007 Dec
[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
Laparoscopic ileocolic resection versus infliximab treatment of distal ileitis in Crohn's disease: a randomized multicenter trial (LIR!C-trial).
2008 Aug 22
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
Synovial tissue response to rituximab: mechanism of action and identification of biomarkers of response.
2008 Jul
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
Neoadjuvant chemoradiation followed by surgery versus surgery alone for patients with adenocarcinoma or squamous cell carcinoma of the esophagus (CROSS).
2008 Nov 26
Canine African trypanosoma.
2008 Sep
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS).
2008 Sep
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
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
Psychoactive medication and traffic safety.
2009 Mar
Hypersensitivity reactions associated with platinum antineoplastic agents: a systematic review.
2010
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
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
[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
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
Treatment of locally advanced carcinomas of head and neck with intensity-modulated radiation therapy (IMRT) in combination with cetuximab and chemotherapy: the REACH protocol.
2010 Nov 26
[Progress of study on antitumor effects of antibody dependent cell mediated cytotoxicity--review].
2010 Oct
A Phase Ib dose-escalation study to evaluate safety and tolerability of the addition of the aminopeptidase inhibitor tosedostat (CHR-2797) to paclitaxel in patients with advanced solid tumours.
2010 Oct 26
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Allergic Rhinitis
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 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