Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H20ClN3 |
Molecular Weight | 325.835 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC=C(CN2C(CN3CCCC3)=NC4=CC=CC=C24)C=C1
InChI
InChIKey=CJXAEXPPLWQRFR-UHFFFAOYSA-N
InChI=1S/C19H20ClN3/c20-16-9-7-15(8-10-16)13-23-18-6-2-1-5-17(18)21-19(23)14-22-11-3-4-12-22/h1-2,5-10H,3-4,11-14H2
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/23143674Curator's Comment: Description was created based on several sources, including
http://adisinsight.springer.com/drugs/800030702
https://www.ncbi.nlm.nih.gov/pubmed/25140002
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23143674
Curator's Comment: Description was created based on several sources, including
http://adisinsight.springer.com/drugs/800030702
https://www.ncbi.nlm.nih.gov/pubmed/25140002
Clemizole is a drug in clinical development for the treatment of hepatitis C virus (HCV) infection. Clemizole is a novel inhibitor of TRPC5 channels. Clemizole is an H1 antagonist. Clemizole, an antihistamine drug that was once widely used for treatment of allergic disease, was recently discovered to be a potent inhibitor (IC50, 24 nM) of the interaction between an HCV protein (NS4B) and HCV RNA. Although clemizole was widely used during the 1950s and 1960s, this was before contemporary regulatory requirements were established for new drug development, and there is very minimal information about its pharmacokinetics and metabolism.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25140002
Curator's Comment: clemizole is able to pass the blood-brain barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1628468 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25140002 |
1.0 µM [IC50] | ||
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1358393 |
|||
Target ID: CHEMBL379 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20486856 |
8.0 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CLEMIZOLE Approved UseAllergic disease |
|||
Primary | Unknown Approved UseUnknown |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/23143674 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
CLEMIZOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://jpet.aspetjournals.org/content/344/2/388 Page: 4.0 |
yes | |||
Sources: https://jpet.aspetjournals.org/content/344/2/388 Page: 4.0 |
yes | |||
Sources: https://jpet.aspetjournals.org/content/344/2/388 Page: 4.0 |
yes | |||
Sources: https://jpet.aspetjournals.org/content/344/2/388 Page: 4.0 |
yes | |||
Sources: https://jpet.aspetjournals.org/content/344/2/388 Page: 4.0 |
yes | |||
Sources: https://jpet.aspetjournals.org/content/344/2/388 Page: 4.0 |
yes | |||
Sources: https://jpet.aspetjournals.org/content/344/2/388 Page: 4,5 |
yes | likely (co-administration study) Comment: When coadministered with ritonavir (CYP3A4 inhibitor), decreased the amount of the human-predominant clemizole metabolites (M1 and M6) Sources: https://jpet.aspetjournals.org/content/344/2/388 Page: 4,5 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Antimycobacterial antihistaminics]. | 1989 Aug |
|
Application of capillary electrophoresis to the determination of various benzylpenicillin salts. | 2004 Apr 2 |
|
New strategies for the treatment of hepatitis C virus infection and implications of resistance to new direct-acting antiviral agents. | 2010 |
|
Antiviral therapy for hepatitis C virus: beyond the standard of care. | 2010 Apr |
|
Chemical genetics-based discovery of indole derivatives as HCV NS5B polymerase inhibitors. | 2014 Mar 21 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00945880
100 mg Clemizole Hydrochloride Administered Orally Twice a Day for 28 Days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1358393
The contractile response to histamine was antagonized by the histamine H1-receptor antagonist, clemizole (0.1 uM), in human isolated myometrial strips. Clemizole (0.1 nM to 10 nM) competitively antagonized the contractile effect of 2-pyridylethylamine.
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
566116
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NCI_THESAURUS |
C29578
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FDA ORPHAN DRUG |
841821
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100000080193
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672
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2782
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SUB06650MIG
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m3614
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C084582
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442-52-4
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DTXSID0046939
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T97CB3796L
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Clemizole
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C81139
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207-133-5
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826
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CHEMBL1407943
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46261
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52140
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)