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
- Molecular Weight:
- 325.84
- MDL Number:
- MFCD00051434
- MOL File:
- 442-52-4.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| FDA UNII | T97CB3796L |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H315-H319-H335 |
| Precautionary statements | P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501 |
Clemizole price More Price(29)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| ChemScene | CS-1481 | Clemizole 98.42% | 442-52-4 | 5mg | $43 | 2026-06-04 | Buy |
| Biosynth | AAA44252 | Clemizole | 442-52-4 | 50mg | $400 | 2026-06-04 | Buy |
| ChemScene | CS-1481 | Clemizole 98.42% | 442-52-4 | 10mg | $65 | 2026-06-04 | Buy |
| Biosynth | AAA44252 | Clemizole | 442-52-4 | 0.5g | $1262.5 | 2026-06-04 | Buy |
| ApexBio Technology | A3315 | Clemizole | 442-52-4 | 5mg | $55 | 2026-05-06 | Buy |
Clemizole Chemical Properties,Uses,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.
Clemizole Preparation Products And Raw materials
Raw materials
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Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Jingmo (Xiamen) Biotechnology Co., Ltd | 13621943973; 13621943973 | sales@jamxmpharmatech.com | China | 1191 | 58 |
| Shanghai Topbiochem Technology Co., Ltd | 021-58170097 | info@topbiochem.com | China | 9513 | 58 |
| Shanghai T&W Pharmaceutical Co., Ltd. | +86 21 61551611 | China | 9874 | 58 | |
| Shanghai Aladdin Bio-Chem Technology Co.,LTD | 400-6206333 13167063860 | anhua.mao@aladdin-e.com | China | 29985 | 65 |
| MedChemexpress LLC | 021-58955995 | sales@medchemexpress.cn | United States | 4853 | 58 |
| AdooQ BioScience, LLC | +1 (866) 930-6790 | info@adooq.com | United States | 2774 | 58 |
| Bide Pharmatech Ltd. | 400-164-7117 18317119277 | product02@bidepharm.com | China | 40000 | 60 |
| Shanghai Worldyang Chemical Co.,Ltd. | 021-56795766 | sales@worldyachem.com | China | 9475 | 58 |
| Quality Control Solutions Ltd. | 0755-66853366 13670046396 | orders@qcsrm.com | China | 18188 | 56 |
| Shanghai Macklin Biochemical Co.,Ltd. | 15221275939 15221275939 | shenlinxing@macklin.cn | China | 15775 | 55 |
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