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
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 Date7.0372799E11 |
|||
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 Date7.0372799E11 |
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 |
---|---|---|
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 |
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
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C29578
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D002974
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SUB06648MIG
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6063
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DB00283
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DTXSID2022832
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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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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)