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 | C21H26ClNO |
Molecular Weight | 343.89 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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 |
---|---|---|
Identification of some new clemastine metabolites in dog, horse, and human urine with liquid chromatography/tandem mass spectrometry. | 2004 |
|
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 |
|
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 |
|
The prevention of anaphylactoid reactions to iodinated radiological contrast media: a systematic review. | 2006 Apr 27 |
|
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 |
|
[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 |
|
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 |
|
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 |
|
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 |
|
Psoriasis following growth hormone therapy in a child. | 2007 Jan |
|
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 |
|
Anti-inflammatory effects of low-intensity extremely high-frequency electromagnetic radiation: frequency and power dependence. | 2008 Apr |
|
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 |
|
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 |
|
NEOadjuvant therapy monitoring with PET and CT in Esophageal Cancer (NEOPEC-trial). | 2008 Jul 31 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Therapeutic efficacy of icatibant in angioedema induced by angiotensin-converting enzyme inhibitors: a case series. | 2010 Sep |
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
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admin
on
Edited
Thu Jul 06 12:59:56 UTC 2023
by
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Thu Jul 06 12:59:56 UTC 2023
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Record UNII |
19259EGQ3D
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C29578
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DBSALT000901
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CHEMBL1626
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |