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
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
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB00283Curator'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
Sources: http://www.drugbank.ca/drugs/DB00283
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL368 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25033456 |
0.4 µM [IC50] | ||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16288909 |
12.0 nM [IC50] | ||
Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9616188 |
2.0 µM [Ki] | ||
Target ID: CHEMBL231 Sources: http://www.drugbank.ca/drugs/DB00283 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CLEMASTINE Approved UseClemastine 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 Date1992 |
|||
Sources: https://www.drugs.com/pro/clemastine.html |
Primary | CLEMASTINE Approved UseClemastine 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 Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15664345/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15664345/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15664345/ |
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
Dose | Population | Adverse events |
---|---|---|
4 mg single, oral Highest studied dose |
healthy n = 24 |
|
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) Sources: Page: page 58Rash (1 patient) Nausea (1 patient) Pallor (1 patient) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
---|---|---|
The effect of betahistine on vestibular habituation: comparison of rotatory and sway habituation training. | 2001 Jul |
|
Simultaneous screening and quantitation of 18 antihistamine drugs in blood by liquid chromatography ionspray tandem mass spectrometry. | 2001 Sep 15 |
|
Phase II study of bi-weekly administration of paclitaxel and cisplatin in patients with advanced oesophageal cancer. | 2002 Mar 4 |
|
[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 |
|
Interactions of olopatadine and selected antihistamines with model and natural membranes. | 2003 Dec |
|
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 |
|
[Multilocular painful urticarial plaques. Eosinophilic cellulitis (Wells syndrome)]. | 2004 Oct 27 |
|
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 |
|
[Tolerance to coxibs in patients with intolerance to non-steroidal anti-inflammatory drugs (NSAIDs)]. | 2005 Oct 7 |
|
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 |
|
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 |
|
Treatment of non-small cell lung cancer with intensity-modulated radiation therapy in combination with cetuximab: the NEAR protocol (NCT00115518). | 2006 May 8 |
|
[Chikungunya: fever and joint pains after vacation in a tropical area]. | 2008 Feb |
|
Medication with antihistamines impairs allergen-specific immunotherapy in mice. | 2008 Mar |
|
Clinical practice. Diagnosis and treatment of cow's milk allergy. | 2009 Aug |
|
Acute cough: a diagnostic and therapeutic challenge. | 2009 Dec 16 |
|
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 |
|
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 |
|
Hyperimmune anti-HBs plasma as alternative to commercial immunoglobulins for prevention of HBV recurrence after liver transplantation. | 2010 Jul 4 |
|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/clemastine.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16288909
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
Edited
Sat Dec 16 07:32:46 GMT 2023
by
admin
on
Sat Dec 16 07:32:46 GMT 2023
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Record UNII |
19259EGQ3D
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29578
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |