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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

ClC1=CC=C(CN2C(CN3CCCC3)=NC4=CC=CC=C24)C=C1.[H][C@]56SC(C)(C)[C@@H](N5C(=O)[C@H]6NC(=O)CC7=CC=CC=C7)C(O)=O

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 C16H18N2O4S
Molecular Weight 334.39
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C19H20ClN3
Molecular Weight 325.835
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment: clemizole is able to pass the blood-brain barrier

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CLEMIZOLE

Approved Use

Allergic disease
Primary
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.4 h
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

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes
yes
yes
yes
yes
likely (co-administration study)
Comment: When coadministered with ritonavir (CYP3A4 inhibitor), decreased the amount of the human-predominant clemizole metabolites (M1 and M6)
Page: 4,5
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[Antimycobacterial antihistaminics].
1989 Aug
Application of capillary electrophoresis to the determination of various benzylpenicillin salts.
2004 Apr 2
[Current syphilis therapies and serological control. Commentary on the article by M. Hartmann in Hautarzt, Volume 2 (2004)].
2004 Nov
Discovery of a hepatitis C target and its pharmacological inhibitors by microfluidic affinity analysis.
2008 Sep
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
The hepatitis C virus (HCV) NS4B RNA binding inhibitor clemizole is highly synergistic with HCV protease inhibitors.
2010 Jul 1
The Future of HCV Therapy: NS4B as an Antiviral Target.
2010 Nov
Green tea catechin, epigallocatechin gallate, suppresses signaling by the dsRNA innate immune receptor RIG-I.
2010 Sep 22
Chemical genetics-based discovery of indole derivatives as HCV NS5B polymerase inhibitors.
2014 Mar 21
Patents

Patents

Sample Use Guides

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
Created
by admin
on Fri Dec 15 16:12:38 GMT 2023
Edited
by admin
on Fri Dec 15 16:12:38 GMT 2023
Record UNII
5UL276H6TF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLEMIZOLE PENICILLIN
INN   MART.   WHO-DD  
INN  
Official Name English
BENZYLPENICILLIN COMBINED WITH 1-P-CHLOROBENZYL-2-(1-PYRROLIDINYLMETHYL)BENZIMIDAZOLE
Common Name English
CLEMIZOLE PENICILLIN [MART.]
Common Name English
CLEMIZOLPENICILLIN
Common Name English
PENICILLIN G MIXTURE WITH CLEMIZOLE [MI]
Common Name English
Clemizole penicillin [WHO-DD]
Common Name English
clemizole penicillin [INN]
Common Name English
CLEMIZOL-PENICILLIN GRUNENTHAL
Brand Name English
PENICILLIN G MIXTURE WITH CLEMIZOLE
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
Code System Code Type Description
PUBCHEM
94316
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
SMS_ID
100000085810
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
CAS
6011-39-8
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
MESH
C030906
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
FDA UNII
5UL276H6TF
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
RXCUI
21226
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID10975533
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
CHEBI
52139
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
INN
827
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
EVMPD
SUB13390MIG
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
MERCK INDEX
m8473
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C80594
Created by admin on Fri Dec 15 16:12:39 GMT 2023 , Edited by admin on Fri Dec 15 16:12:39 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY