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 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 |
---|---|---|
Evaluation of several solid phase extraction liquid chromatography/tandem mass spectrometry on-line configurations for high-throughput analysis of acidic and basic drugs in rat plasma. | 2001 |
|
Inhibitory effect of olopatadine hydrochloride on the sneezing response induced by intranasal capsaicin challenge in guinea pigs. | 2001 Jun |
|
Dose reduction of steroid premedication for paclitaxel: no increase of hypersensitivity reactions. | 2001 Jun |
|
[Comparative antihistamine and anti-allergic effects of various antihistamine preparations]. | 2002 |
|
[Severe adverse event following iv administration of 10 ml 6% Dextran60 (0.6 g) in a healthy volunteer]. | 2002 Oct |
|
Hypersensitivity vasculitis induced by cefoperazone/sulbactam. | 2003 Jan 3 |
|
Identification of some new clemastine metabolites in dog, horse, and human urine with liquid chromatography/tandem mass spectrometry. | 2004 |
|
Interstitial granulomatous dermatitis with arthritis. | 2004 Jul |
|
Itch and skin rash from chocolate during fluoxetine and sertraline treatment: case report. | 2004 Nov 2 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
[Tolerance to coxibs in patients with intolerance to non-steroidal anti-inflammatory drugs (NSAIDs)]. | 2005 Oct 7 |
|
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 |
|
Neoadjuvant concurrent chemoradiation with weekly paclitaxel and carboplatin for patients with oesophageal cancer: a phase II study. | 2006 May 22 |
|
Early detection of adverse drug events within population-based health networks: application of sequential testing methods. | 2007 Dec |
|
Intraoperative anaphylaxis after intravenous atropine. | 2007 Mar |
|
Laparoscopic ileocolic resection versus infliximab treatment of distal ileitis in Crohn's disease: a randomized multicenter trial (LIR!C-trial). | 2008 Aug 22 |
|
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 |
|
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 |
|
Evaluation of efficacy and sedative profiles of H(1) antihistamines by large-scale surveillance using the visual analogue scale (VAS). | 2008 Sep |
|
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines. | 2009 Aug 31 |
|
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 |
|
Anaphylaxis to mefenamic acid in a patient with new onset of systemic lupus erythematosus. | 2010 Jul-Aug |
|
Chloroquine-induced Pruritus. | 2010 May |
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
Fri Dec 16 16:46:33 UTC 2022
by
admin
on
Fri Dec 16 16:46:33 UTC 2022
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Record UNII |
95QN29S1ID
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QD04AA14
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WHO-VATC |
QR06AA04
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LIVERTOX |
NBK548709
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WHO-ATC |
R06AA54
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WHO-VATC |
QR06AA54
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WHO-ATC |
D04AA14
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NCI_THESAURUS |
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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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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3738
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95QN29S1ID
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95QN29S1ID
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ACTIVE MOIETY |