Clemizole hydrochloride

Base Information

• Chemical Name: Clemizole hydrochloride
• CAS No.: 1163-36-6
• Molecular Formula: C19H20ClN3^.HCl
• Molecular Weight: 362.302
• European Community (EC) Number: 214-605-4
• NSC Number: 759290
• UNII: 85W6I13D8M
• DSSTox Substance ID: DTXSID9045136
• Wikidata: Q27269676
• NCI Thesaurus Code: C81152
• ChEMBL ID: CHEMBL1256817
• Mol file: 1163-36-6.mol

Synonyms:Clemizole hydrochloride;1163-36-6;Clemizole HCl;Clemizole (hydrochloride);Allercur;Reactrol;Clemizole hydrochloride [JAN];Allercure hydrochloride;UNII-85W6I13D8M;MLS000120342;DTXSID9045136;85W6I13D8M;AL 20;EINECS 214-605-4;1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole;hydrochloride;NSC-759290;P 48;SMR000058430;1-(p-Chlorobenzyl)-2-(1-pyrrolidinylmethyl)benzimidazole hydrochloride;1-[(4-Chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-1H-benzimidazole hydrochloride;Clemizole hydrochloride (JAN);DTXCID7025136;1-(p-Chlorobenzil)-2-pirrolidil-metil-benzimidazolo cloridato;1-p-Chlorobenzyl-pyrrolidyl-methylene-benzimidazole hydrochloride;1-p-Chlorobenzyl-2-(1-pyrrolidinylmethyl)benzimidazole hydrochloride;1-(p-Chlorobenzil)-2-pirrolidil-metil-benzimidazolo cloridato [Italian];hydron;chloride;BENZIMIDAZOLE, 1-(p-CHLOROBENZYL)-2-(1-PYRROLIDINYLMETHYL)-, MONOHYDROCHLORIDE;SR-01000000057;NCGC00015243-02;CAS-1163-36-6;Clemizole.HCl;1H-Benzimidazole, 1-((4-chlorophenyl)methyl)-2-(1-pyrrolidinylmethyl)-, monohydrochloride;1H-Benzimidazole, 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-, monohydrochloride;Allercur (TN);Reactrol (TN);Prestwick_116;Opera_ID_1842;C19H20ClN3.ClH;1-[(4-chlorophenyl)methyl]-2-(pyrrolidin-1-ylmethyl)benzimidazole hydrochloride;MLS000028396;MLS002222168;SCHEMBL210095;CHEMBL1256817;CHEBI:31409;AMY3317;C19-H20-Cl-N3.Cl-H;EPX-100;EX-A346;DNFMJYXRIMLMBZ-UHFFFAOYSA-N;AL-20;HMS1568N15;Pharmakon1600-01505990;BCP11344;CLEMIZOLE HYDROCHLORIDE [MI];Tox21_110108;Tox21_500284;1-p-Chlorobenzyl-2-(1-pyrrolidinyl)methylbenzimidazole hydrochloride;HY-30234A;MFCD00051435;NSC759290;1-(p-chlorobenzyl)-2-(1-pyrrolidinylmethyl)-benzimidazolmonohydrochloride;AKOS024370943;Tox21_110108_1;CCG-213997;CLEMIZOLE HYDROCHLORIDE [MART.];CS-1489;LP00284;NSC 759290;CLEMIZOLE HYDROCHLORIDE [WHO-DD];NCGC00015243-10;NCGC00093738-01;NCGC00093738-02;NCGC00180972-01;NCGC00260969-01;1163-36-6 (HCl);AC-35229;AS-74415;Clemizole hydrochloride, >=98% (HPLC);AL20;C3468;EU-0100284;FT-0607159;C 5040;D01705;A803600;SR-01000000057-2;SR-01000000057-8;Q27269676;SR-01000000057-10;1-p-Chlorobenzyl-2-pyrrolidylmethyl benzimidazole hydrochloride;1-(p-Chlorobenzyl)-2-pyrrolidylmethylenebenzimidazole hydrochloride;1-(4-Chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)benzimidazole Hydrochloride;1-(4-Chlorobenzyl)-2-(pyrrolidinylmethyl)-1 3-benzimidazole hydrochloride;1-(p-Chlorobenzyl)-2-(1-pyrrolidinylmethyl)-benzimidazol monohydrochloride;1-(4-Chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzo[d]imidazole hydrochloride;1-[(4-chlorophenyl)methyl]-2-[(pyrrolidin-1-yl)methyl]-1H-1,3-benzodiazole hydrochloride;1H-bencimidazol, 1-[(4-clorofenil) metil]-2-(1-pirrolidinilmetil)-, monoclorhidrato (9CI);1H-Benzimidazol, 1-[(4-clorofenil)metil]-2-(1-pirrolidinilmetil)-, clorhidrato (1:1);Benzimidazole 1-(p-chlorobenzyl)-2-(1-pyrrolidinylmethyl)-monohydrochloride (8CI);1H-Benzimidazole 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-monohydrochloride (9CI);1H-Benzimidazole, 1-[(4-chlorophenyl)methyl]-2-(1-pyrrolidinylmethyl)-, hydrochloride (1:1)

Chemical Property of Clemizole hydrochloride

Chemical Property:

• Vapor Pressure: 2.29E-10mmHg at 25°C
• Melting Point: 239-241°
• Boiling Point: 506.1 °C at 760 mmHg
• Flash Point: 259.9 °C
• PSA: 21.06000
• Density: 1.25 g/cm3
• LogP: 5.07370
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble2mg/mL, clear (warmed)
• Water Solubility.: 16.84mg/L at 25℃
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 361.1112531
• Heavy Atom Count: 24
• Complexity: 377

Purity/Quality:

99.9% ^*data from raw suppliers

Clemizole hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)CC2=NC3=CC=CC=C3N2CC4=CC=C(C=C4)Cl.Cl
• Recent ClinicalTrials: EPX-100 (Clemizole Hydrochloride) as Add-on Therapy to Control Convulsive Seizures in Patients With Dravet Syndrome
• Recent EU Clinical Trials: A 20-Week Multicenter, Randomized, Double-Blind, Placebo-Controlled Trial of EPX-100 (Clemizole HCl) as Adjunctive Therapy in Patients with Dravet Syndrome (ARGUS trial)
• Uses: Clemizole Hydrochloride inhibits Hepatitis C RNA replication in cell culture through the suppression of the binding between the nonstructural protein 4B and the viral RNA genome with little toxicity for the host cell. Clemizole Hydrochloride is also a potent inhibitor of transient receptor potential channel TRPC5. Clemizole is an antihistamine that antagonizes the histamine 1 receptor at high nanomolar concentrations. It less potently blocks transient receptor potential canonical channel 5 (TRPC5; IC50 = 1.0-1.3 μM), with at least 6-fold selectivity for TRPC5 over other TRP channels. Clemizole also has hepatitis C antiviral action through inhibition of NS4B function, showing synergy with boceprevir , and it inhibits seizures in a zebrafish model of Dravet Syndrome.
• Therapeutic Function: Antihistaminic

Technology Process of Clemizole hydrochloride

There total 1 articles about Clemizole hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

clemizole (442-52-4) → clemizole hydrochloride (1163-36-6)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 0.0833333h;

Reference yield:

cobalt(II) chloride hexahydrate + clemizole hydrochloride (1163-36-6) → dichloro[1-(p-chlorobenzyl)-2-(1-pyrrolidinylmethyl-N)-1,3,-benzimidazole-N(3)]cobalt(II) (294672-98-3)

Guidance literature:

With NH₃; In ethanol; CoCl2*6H2O was added to ethanolic soln. of chemizole hydrochloride in 1:2 molar ratio, pH was adjusted to 8-9 with aq. NH3; soln. was slowly evapd. at room temp.;

DOI:10.1107/S0108270100005710

Reference yield:

clemizole hydrochloride (1163-36-6) → clemizole tetrachlorocobaltate(II)

Guidance literature:

With hydrogenchloride; cobalt(II) chloride; for 0.166667h; Heating;

DOI:10.1107/S0108270196015922

upstream raw materials:

clemizole

Downstream raw materials:

3-[4-(chlorophenyl)methyl]-2-(1-pyrrolidiniomethyl)-1H-benzimidazolium tetrachlorocopper(II)

3-[4-(chlorophenyl)methyl]-2-(1-pyrrolidiniomethyl)-1H-benzimidazolium tetrachlorocobalt(II)

dichloro[1-(p-chlorobenzyl)-2-(1-pyrrolidinylmethyl-N)-1,3,-benzimidazole-N⁽³⁾]cobalt(II)

Refernces