Uses
ChemicalBook > CAS DataBase List > Clemizole

Clemizole

Uses
Product Name
Clemizole
CAS No.
442-52-4
Chemical Name
Clemizole
Synonyms
Histacur;Depocural;Histakool;NSC 46261;Lergopenin;Clemizole USP/EP/BP;Clemizole (free base);Clemizole, 10 mM in DMSO;1-p-Chlorobenzyl-2-pyrrolidino-methylbenzimidazole;1-(p-Chlorobenzyl)-2-pyrrolidylmethylenebenzimidazole
CBNumber
CB3875322
Molecular Formula
C19H20ClN3
Formula Weight
325.84
MOL File
442-52-4.mol
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Clemizole Property

Melting point:
239-241℃
Boiling point:
506.1±40.0 °C(Predicted)
Density 
1.25±0.1 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
insoluble in H2O; ≥16.2 mg/mL in DMSO; ≥95.8 mg/mL in EtOH
form 
solid
pka
9.08±0.20(Predicted)
color 
White to off-white
InChI
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
InChIKey
CJXAEXPPLWQRFR-UHFFFAOYSA-N
SMILES
C1(CN2CCCC2)N(CC2=CC=C(Cl)C=C2)C2=CC=CC=C2N=1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

ApexBio Technology
Product number
A3315
Product name
Clemizole
Packaging
10mg
Price
$80
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0025972
Product name
CLEMIZOLE
Purity
95.00%
Packaging
10MG
Price
$216.3
Updated
2021/12/16
ApexBio Technology
Product number
A3315
Product name
Clemizole
Packaging
5mg
Price
$50
Updated
2021/12/16
ApexBio Technology
Product number
A3315
Product name
Clemizole
Packaging
10mM(in 1mL DMSO)
Price
$50
Updated
2021/12/16
ApexBio Technology
Product number
A3315
Product name
Clemizole
Packaging
50mg
Price
$300
Updated
2021/12/16
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Clemizole Chemical Properties,Usage,Production

Uses

Pyrrolimidazole, also known as 1-[(4-chlorophenyl)methyl]-2-(pyrrolidone-1-ylmethyl)benzimidazole or crimetazole, has antihistamine activity, moderate sedative effect, and significant antipruritic effect. Recent studies have shown that it has anti-hepatitis C virus activity. This product can prolong the effective refractory period of atrial myocardium and has been reported to treat atrial flutter.

Originator

Allercur,Roerig,US,1960

Definition

ChEBI: A member of the class of benzimidazoles that is 1H-benzimidazole substituted by a pyrrolidin-1-ylmethyl and a 4-chlorobenzyl groups at positions 2 and 1 respectively.

Manufacturing Process

From 13.1 g of N-p-chlorobenzyl-2-nitroaniline (MP 110°C, obtained in the form of orange-red needles, from o-nitrochlorobenzene and pchlorobenzylamine by reaction for 3 hours at 150°C) by reduction with Raneynickel and hydrogen, in which reaction the substance may be suspended in methanol or dissolved in methanol-ethyl acetate at normal pressure and at about 40°C with combination of the theoretical quantity of hydrogen, 12.2 g are obtained of o-amino-N-p-chlorobenzylaniline, which after recrystallization from aqueous methanol has a MP of 90°C.
8 g of o-amino-N-p-chlorobenzylaniline and 2.8 g of pyridine are dissolved in dry ether and reacted with an ethereal solution of 3.9 g of chloracetyl chloride with cooling in a mixture of ice and common salt. 8 g of N-p-chlorobenzyl-N'- chloracetyl-o-phenylene diamine are obtained which can be worked up in the form of the crude product and, in the slightly colored form, has a MP of 130°C.
7.6 g of this compound are boiled with 3.9 g of pyrrolidine in 70 cc of toluene for some hours under reflux. After extraction by shaking with water and treatment with hydrochloric acid the hydrochloride is produced of N-pchlorobenzyl-N'-pyrrolidylacetyl-o-phenylene diamine together with some 1-pchlorobenzyl-2-N-pyrrolidylmethyl-benzimidazole. The former, after recrystallization from butanol, melts with foaming at 205°C, the latter, after recrystallization from butanol melts at 239°C to 241°C, and is in the form of white microscopic rods. Boiling in nitrobenzene converts the former compound into the latter.

Therapeutic Function

Antihistaminic

Biological Activity

the ns4b protein is a key player in hcv replication. disrupting ns4b function thus represents an attractive new anti-hcv strategy. combining clemizole with other anti-hcv agents could increase the antiviral effect achieved with 1 active drug alone and decrease emergence of viral resistance.

in vitro

although significant, clemizole’s antiviral effect was moderate (50% effective concentration of 8 mm against a hcv genotype 2a clone). clemizole’s antiviral effect was highly synergistic with the hcv protease inhibitors vx950 and sch503034, without toxicity. in contrast, clemizole combinations with either interferon, ribavirin, or the nucleoside (nm283) and nonnucleoside (hcv796) hcv polymerase inhibitors were additive [1].

in vivo

clemizole had an unexpectedly short plasma half-life; it was very rapidly biotransformed into a glucuronide (m14) and a dealkylated metabolite (m12) and into a variety of lesser metabolites in c57bl/6j mice [2].

References

[1] einav s, sobol hd, gehrig e, glenn js. the hepatitis c virus (hcv) ns4b rna binding inhibitor clemizole is highly synergistic with hcv protease inhibitors. j infect dis. 2010;202(1):65-74.
[2] nishimura t, hu y, wu m, pham e, suemizu h, elazar m, liu m, idilman r, yurdaydin c, angus p, stedman c, murphy b, glenn j, nakamura m, nomura t, chen y, zheng m, fitch wl, peltz g. using chimeric mice with humanized livers to predict human drug metabolism and a drug-drug interaction. j pharmacol exp ther. 2013;344(2):388-96. doi: 10.1124/jpet.112.198697. epub 2012 nov 8.

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Clemizole Suppliers

Jingmo (Xiamen) Biotechnology Co., Ltd
Tel
13621943973; 13621943973
Email
sales@jamxmpharmatech.com
Country
China
ProdList
1169
Advantage
58
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
12952
Advantage
65
Shanghai Topbiochem Technology Co., Ltd
Tel
021-58170097
Email
info@topbiochem.com
Country
China
ProdList
9514
Advantage
58
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9891
Advantage
58
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 13167063860
Fax
021-50323701
Email
anhua.mao@aladdin-e.com
Country
China
ProdList
25002
Advantage
65
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
AdooQ BioScience, LLC
Tel
+1 (866) 930-6790
Fax
+1 (866) 333-9607
Email
info@adooq.com
Country
United States
ProdList
2782
Advantage
58
Shanghai Worldyang Chemical Co.,Ltd.
Tel
021-021-56795766
Fax
+86-21-56795266
Email
sales@worldyachem.com
Country
China
ProdList
9476
Advantage
58
ChemStrong Scientific Co.,Ltd
Tel
0755-66853366 13670046396
Fax
0755-28363542
Email
sales@chem-strong.com
Country
China
ProdList
18367
Advantage
56
Shanghai Macklin Biochemical Co.,Ltd.
Tel
15221275939
Fax
021-50706099
Email
shenlinxing@macklin.cn
Country
China
ProdList
15872
Advantage
55
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View Lastest Price from Clemizole manufacturers

Career Henan Chemical Co
Product
Clemizole 442-52-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
200kg
Release date
2020-01-02

442-52-4, ClemizoleRelated Search:


  • Clemizole (free base)
  • 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-1H-benzimidazole (Clemizole)
  • 1-(4-Chlorobenzyl)-2-(pyrrolizinomethyl)-1H-benzimidazole
  • 1-(p-Chlorobenzyl)-2-(1-pyrrolidinylmethyl)-1H-benzimidazole
  • Histacur
  • 1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)benzimidazole
  • 1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole
  • 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-1H-benzimidazole
  • 1-(4-CHLOROBENZYL)-2-(PYRROLIDIN-1-YLMETHYL)-1H-BENZO[D]IMIDAZOLE HYDROCHLORIDE
  • 1-p-Chlorobenzyl-2-pyrrolidino-methylbenzimidazole
  • Depocural
  • Histakool
  • Lergopenin
  • NSC 46261
  • 1-p-Chlorobenzyl-2-[1-pyrrolidinylmethyl] benzimidazole
  • 1-(p-Chlorobenzyl)-2-pyrrolidylmethylenebenzimidazole
  • 1H-Benzimidazole,1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-
  • 1-(4-Chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzo[d]imidazole
  • Clemizole USP/EP/BP
  • Clemizole,Histamine Receptor,TRP Channel,inhibit,Hepatitis C virus,Transient receptor potential channels,HCV,Inhibitor,HCV Protease
  • Clemizole, 10 mM in DMSO
  • 442-52-4
  • C19H20ClN3
  • Inhibitors
  • API intermediates