Basic information
- CAS
442-52-4- Standard SMILES
Clc1ccc(Cn2c(CN3CCCC3)nc3ccccc32)cc1- InChIKey
CJXAEXPPLWQRFR-UHFFFAOYSA-N- Molecular formula
- C19H20ClN3
- Average molar mass
- 325.8 g/mol
- Monoisotopic mass
- 325.1345753
Overview
Clemizole is 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. It has a role as a histamine antagonist. It is a member of benzimidazoles, a member of pyrrolidines and a member of monochlorobenzenes. It is a conjugate base of a clemizole(1+). It derives from a hydride of a 1H-benzimidazole.
Names & identifiers
- Preferred name
- Clemizole
- IUPAC
- 1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole
- English name
- Clemizole
- Molecular formula
- C19H20ClN3
- Molecular weight
- 325.84
Names & synonyms
Clemizole442-52-4HistacurClemizolClemizolumClemizolo1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole1-(p-Chlorobenzyl)-2-pyrrolidylmethylenebenzimidazoleAL-20 FREE BASENSC-46261DTXSID00469391H-Benzimidazole, 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-
Show more names
DepocuralHistakoolNSC 46261LergopeninClemizole USP/EP/BPClemizole (free base)Clemizole, 10 mM in DMSO1-p-Chlorobenzyl-2-pyrrolidino-methylbenzimidazole
T97CB3796LBenzimidazole, 1-(p-chlorobenzyl)-2-(1-pyrrolidinylmethyl)-CHEBI:521401H-Benzimidazole, 1-((4-chlorophenyl)methyl)-2-(1-pyrrolidinylmethyl)-NSC462611-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole1-((4-chlorophenyl)methyl)-2-(pyrrolidin-1-ylmethyl)benzimidazoleRefChem:918812
Database identifiers
- CAS
442-52-4
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 21.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 377
Experimental & physicochemical properties
Human DrugsPharmaceuticals
Collision Cross Section178.06 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 239 · 239-241℃
- Boiling point
- 506.1 · 506.1±40.0 °C(Predicted)
- Density
- 1.25 · 1.25±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 2 O; · insoluble in H2O; ≥16.2 mg/mL in DMSO; ≥95.8 mg/mL in EtOH
- form
- solid
- pka
- 9.08 · 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- 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
Chemistry & industry
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesPyrrolimidazole, 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.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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