N-(4-CHLOROPHENYL)-N'-(ISOPROPYL)-IMIDODICARBONIMIDIC DIAMIDE

Base Information

• Chemical Name: N-(4-CHLOROPHENYL)-N'-(ISOPROPYL)-IMIDODICARBONIMIDIC DIAMIDE
• CAS No.: 500-92-5
• Deprecated CAS: 46920-30-3
• Molecular Formula: C11H16 Cl N5
• Molecular Weight: 253.735
• European Community (EC) Number: 207-915-6
• UNII: S61K3P7B2V
• DSSTox Substance ID: DTXSID3022794
• Wikipedia: Proguanil
• NCI Thesaurus Code: C61907
• RXCUI: 2382
• Metabolomics Workbench ID: 53385
• ChEMBL ID: CHEMBL1377
• Mol file: 500-92-5.mol

Synonyms:Biguanide,1-(p-chlorophenyl)-5-isopropyl- (8CI); 1-(p-Chlorophenyl)-5-isopropylbiguanide;1-Isopropyl-5-(4-chlorophenyl)biguanide; Bigumal; Chlorguanid; Chlorguanide;Chloroguanide; N1-p-Chlorophenyl-N5-isopropylbiguanide; Paludrin; Proguanil

Chemical Property of N-(4-CHLOROPHENYL)-N'-(ISOPROPYL)-IMIDODICARBONIMIDIC DIAMIDE

Chemical Property:

• Melting Point: 129°
• Refractive Index: 1.6110 (estimate)
• Boiling Point: 402.7°Cat760mmHg
• PKA: 11.15±0.10(Predicted)
• Flash Point: 197.4°C
• PSA: 83.79000
• Density: 1.29g/cm³
• LogP: 3.26330
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 253.1094232
• Heavy Atom Count: 17
• Complexity: 292

Purity/Quality:

99% ^*data from raw suppliers

Proguanil >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antimalarial Agents
• Canonical SMILES: CC(C)N=C(N)N=C(N)NC1=CC=C(C=C1)Cl
• Isomeric SMILES: CC(C)N=C(N)/N=C(\N)/NC1=CC=C(C=C1)Cl
• Recent ClinicalTrials: Enhancing Preventive Therapy of Malaria In Children With Sickle Cell Anemia in East Africa (EPiTOMISE)
• Recent EU Clinical Trials: Pharmacokinetic Interactions between Ciprofloxacin and Chloroquine / Proguanil Prophylaxis
• Recent NIPH Clinical Trials: Comparative study of drug interaction with CYP2C19 substrate by Vonoprazan and Esomeprazole in healthy adults
• Indications: Proguanil is used in combination with chloroquine as chemoprophylaxis against falciparum malaria in areas with a low frequency of resistance, i.e. tropical Africa. Chloroguanide hydrochloride (Paludrine) is activated to a triazine metabolite, cycloguanil, which also interferes with parasite folic acid synthesis. It is a dihydrofolate reductase inhibitor that is used for the prophylaxis of malaria caused by all susceptible strains of plasmodia. Chloroguanide is rapidly absorbed from the gastrointestinal tract. Peak plasma levels occur 2 to 4 hours after oral administration, and the drug is excreted in the urine with an elimination half-life of 12 to 21 hours. Its side effects and spectrum of antimalarial activity are quite similar to those of pyrimethamine.The conversion of chloroguanide to the active metabolite is decreased in pregnancy and also as a result of genetic polymorphism in 3% of whites and Africans and 20% of Asians.
• Description: Chloroguanide is active with respect to exoerythrocyte and erythrocyte forms of plasmodia. It is most beneficial for suppressive therapy. It is used for preventing malaria, and it should be started 2 weeks before entering a malarial zone and should be taken for 8 weeks. Synonyms of this drug are biguanide, bigunal, paludrine, proguanil, and others.
• Uses: Proguanil is medicaments; used in preparation of pyrrolecarboxamide derivatives as anti-malarial agents.
• Clinical Use: Antimalarial prophylaxis (usually in combination with chloroquine) Treatment and prophylaxis for drug-resistant falciparum malaria (in combination with atovaquone)

Technology Process of N-(4-CHLOROPHENYL)-N'-(ISOPROPYL)-IMIDODICARBONIMIDIC DIAMIDE

There total 28 articles about N-(4-CHLOROPHENYL)-N'-(ISOPROPYL)-IMIDODICARBONIMIDIC DIAMIDE 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:

1-(4-chlorophenyl)-3-cyanoguanidine (1482-62-8) + isopropylamine (75-31-0) → proguanil (500-92-5)

Guidance literature:

With ethanol; copper(II) sulfate;

DOI:10.1039/jr9460000729

Reference yield:

isopropylamine (75-31-0) → proguanil (500-92-5)

Guidance literature:

With water; at 130 ℃;

Reference yield:

3-cyano-1-isopropylguanidine (44830-55-9) + p-chloroaniline hydrochloride (20265-96-7) → proguanil (500-92-5)

Guidance literature:

With water;

upstream raw materials:

ethanol

1-(4-chlorophenyl)guanidine

1-isopropylthiourea

3-cyano-1-isopropylguanidine

Downstream raw materials:

{Rh(paludrine)2Cl₂}{Rh(paludrine)Cl₄}

Refernces

• 1、 -. "PROGUANIL TO TREAT SKIN/MUCOSAL DISEASES". . . Retrieved 2009/12/04.
• 2、 BAMI. "On the preparation of paludrine (proguanil).". . p. 77 - 77. Retrieved 2007/11/02.