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
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
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 |
|
0.5 mg single, oral Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: |
healthy Health Status: healthy Sex: M+F Sources: |
Disc. AE: Itching, Rash... AEs leading to discontinuation/dose reduction: Itching (1 patient) Sources: Rash (1 patient) Nausea (1 patient) Pallor (1 patient) |
1 mg single, oral Dose: 1 mg Route: oral Route: single Dose: 1 mg Sources: |
healthy Health Status: healthy Sex: M Sources: |
Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (1 patient) Sources: |
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: |
healthy Health Status: healthy Sex: M+F Sources: |
Nausea | 1 patient Disc. AE |
0.5 mg single, oral Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: |
healthy Health Status: healthy Sex: M+F Sources: |
Pallor | 1 patient Disc. AE |
0.5 mg single, oral Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: |
healthy Health Status: healthy Sex: M+F Sources: |
Rash | 1 patient Disc. AE |
0.5 mg single, oral Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: |
healthy Health Status: healthy Sex: M+F Sources: |
Vomiting | 1 patient Disc. AE |
1 mg single, oral Dose: 1 mg Route: oral Route: single Dose: 1 mg Sources: |
healthy Health Status: healthy Sex: M Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Interactions of olopatadine and selected antihistamines with model and natural membranes. | 2003 Dec |
|
Role of histamine receptors in the regulation of edema and circulation postburn. | 2003 Dec |
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Serious allergic reaction to administration of epirubicin. | 2003 Jun |
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Antihistamines in the treatment of dermatitis. | 2003 Nov-Dec |
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Identification of some new clemastine metabolites in dog, horse, and human urine with liquid chromatography/tandem mass spectrometry. | 2004 |
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Fatal outcome of a hypersensitivity reaction to paclitaxel: a critical review of premedication regimens. | 2004 Jan 26 |
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Interstitial granulomatous dermatitis with arthritis. | 2004 Jul |
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[Appearance diagnosis. Facial shingles]. | 2004 Jul 22 |
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Clinical pharmacology of clemastine in healthy dogs. | 2004 Jun |
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Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic. | 2004 Mar |
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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 |
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Itch and skin rash from chocolate during fluoxetine and sertraline treatment: case report. | 2004 Nov 2 |
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[Multilocular painful urticarial plaques. Eosinophilic cellulitis (Wells syndrome)]. | 2004 Oct 27 |
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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 |
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Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine. | 2005 Aug |
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High-performance liquid chromatographic-tandem mass spectrometric method for the determination of clemastine in human plasma. | 2005 Feb 25 |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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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 |
|
The prevention of anaphylactoid reactions to iodinated radiological contrast media: a systematic review. | 2006 Apr 27 |
|
Clemastine, a conventional antihistamine, is a high potency inhibitor of the HERG K+ channel. | 2006 Jan |
|
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 |
|
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 |
|
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 |
|
A novel self-microemulsifying formulation of paclitaxel for oral administration to patients with advanced cancer. | 2006 Sep 18 |
|
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 |
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Stereoselective synthesis of (-)-hydroxyclemastine as a versatile intermediate for the H1 receptor antagonist clemastine. | 2007 Dec |
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Early detection of adverse drug events within population-based health networks: application of sequential testing methods. | 2007 Dec |
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Psoriasis following growth hormone therapy in a child. | 2007 Jan |
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Influence of immunomodulatory drugs on the cytotoxicity induced by monoclonal antibody 17-1A and interleukin-2. | 2007 Mar |
|
[Angioneurotic orolingual edema associated with the use of rt-PA following a stroke]. | 2007 Oct |
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Anti-inflammatory effects of low-intensity extremely high-frequency electromagnetic radiation: frequency and power dependence. | 2008 Apr |
|
[Chikungunya: fever and joint pains after vacation in a tropical area]. | 2008 Feb |
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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 |
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Synovial tissue response to rituximab: mechanism of action and identification of biomarkers of response. | 2008 Jul |
|
Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells. | 2008 Jun 6 |
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Medication with antihistamines impairs allergen-specific immunotherapy in mice. | 2008 Mar |
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Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines. | 2009 Aug 31 |
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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 |
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Anaphylaxis to mefenamic acid in a patient with new onset of systemic lupus erythematosus. | 2010 Jul-Aug |
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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 |
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
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Record UNII |
95QN29S1ID
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Validated (UNII)
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D04AA14
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C29578
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WHO-ATC |
R06AA04
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D002974
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SUB06648MIG
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2578
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6063
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DB00283
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DTXSID2022832
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26987
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C61682
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2231
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CLEMASTINE
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m3613
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671
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CHEMBL1626
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756685
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Clemastine
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15686-51-8
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100000080172
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3738
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95QN29S1ID
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ACTIVE MOIETY |