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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H20ClN3.C16H18N2O4S
Molecular Weight 660.225
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLEMIZOLE PENICILLIN

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)CC3=CC=CC=C3)C(=O)N2[C@H]1C(O)=O.ClC4=CC=C(CN5C(CN6CCCC6)=NC7=C5C=CC=C7)C=C4

InChI

InChIKey=GKPMEGXMKPQRTN-CBDIPHIASA-N
InChI=1S/C19H20ClN3.C16H18N2O4S/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;1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h1-2,5-10H,3-4,11-14H2;3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t;11-,12+,14-/m.1/s1

HIDE SMILES / InChI
Molecular Formula C19H20ClN3
Molecular Weight 325.835
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C16H18N2O4S
Molecular Weight 334.39
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

CNS Active
3,984

Originator

Kaken Pharmaceutical
11

Approval Year

1960
105

Targets

Primary TargetPharmacologyConditionPotency
Transient receptor potential cation channel subfamily M member 5
6
Inhibitor
8,456
 1.0 µM [IC50]
Histamine H1 receptor
316
Antagonist
2,840
Hepatitis C virus
23
Inhibitor
8,456
 8.0 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Allergic disease
6
 Primary
Approved
8,548
CLEMIZOLE
Hepatitis C
42
 Primary
Phase I
435
Unknown

T1/2

ValueDoseCo-administeredAnalytePopulation
3.4 h
100 mg single, oral
 CLEMIZOLE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1,929
substrate
1,180
substrate
1,378
inhibitor
2,195

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
1,111

CYP1A2
1,186

Drug as victim

Tox targets

PubMed

Patents

JP2010539241A
5

Sample Use Guides

In Vivo Use Guide
100 mg Clemizole Hydrochloride Administered Orally Twice a Day for 28 Days
Route of Administration: Oral
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
5UL276H6TF
Record Status Validated (UNII)
Record Version
NIH
NCATS
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