Suramin sodium

Base Information

• Chemical Name: Suramin sodium
• CAS No.: 129-46-4
• Deprecated CAS: 90586-65-5
• Molecular Formula: C51H34N6Na6O23S6
• Molecular Weight: 1429.19
• Hs Code.: 29242998
• European Community (EC) Number: 204-949-3
• UNII: 89521262IH
• DSSTox Substance ID: DTXSID30156024
• Wikidata: Q27270002
• NCI Thesaurus Code: C1848
• Pharos Ligand ID: 8N89YAPB6UR7
• ChEMBL ID: CHEMBL413376
• Mol file: 129-46-4.mol

Synonyms:Germanin;Hexasodium Salt Suramin;Monosodium Salt Suramin;Moranil;Naganin;Naganol;Naphuride;Salt Suramin, Hexasodium;Salt Suramin, Monosodium;Sodium, Suramin;Suramin;Suramin Sodium;Suramin, Hexasodium Salt;Suramin, Monosodium Salt

Chemical Property of Suramin sodium

Chemical Property:

• Appearance/Colour: White crystalline powder
• PSA: 551.01000
• LogP: 11.61040
• Storage Temp.: 0-6°C
• Solubility.: H2O: >10mg/mL
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 23
• Rotatable Bond Count: 10
• Exact Mass: 1427.9385741
• Heavy Atom Count: 92
• Complexity: 2940

Purity/Quality:

99.90% ^*data from raw suppliers

Suramin Hexasodium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)C(=O)NC2=C3C(=CC(=CC3=C(C=C2)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])NC(=O)C4=CC(=CC=C4)NC(=O)NC5=CC=CC(=C5)C(=O)NC6=C(C=CC(=C6)C(=O)NC7=C8C(=CC(=CC8=C(C=C7)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-])C.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
• Recent ClinicalTrials: Study to Evaluate the Tolerance and Pharmacokinetics of Suramin Sodium
• Indications: Suramin is used in the treatment of early-stage infections of Trypanosoma brucei gambiense and Trypanosoma brucei rhodesiense. It is used prior to melarsoprol treatment to clear the blood and lymph of trypanosomes. Pentamidine is generally preferred for the treatment of early-stage Trypanosoma brucei gambiense. Suramin is also the only drug available for effectively eliminating the adult filariae (macrofilariae) in onchocerciasis. It should only be used in individual cases. Suramin (Germanin) is a derivative of a nonmetallic dye whose antiparasitic mechanism of action is not clear. It appears to act on parasite specificα-glycerophosphate oxidase, thymidylate synthetase, dihydrofolate reductase, and protein kinase but not on host enzymes. Suramin is widely used as a macrofilaricide in human onchocerciasis, and its action on microfilariae also is considerable. It also is useful in the treatment of the hemolymphatic stage of African trypanosomiasis. Early treatment of the infection with suramin clears trypanosomes from the blood and lymphatics within 30 minutes and keeps them clear for approximately 3 months. Suramin inhibits a number of filarial enzymes involved with carbohydrate metabolism as well as the production of adenosine triphosphate (ATP). It is 35 times more inhibitory to the dihydrofolate reductase of O. volvulus than to the same enzyme in human tissue. It is a potent inhibitor of reverse transcriptase, the DNA polymerase of retroviruses, and also has some effects on the infective and cytopathic effects of HIV. It is being evaluated as an anticancer drug, reducing pain and delaying progression in hormone-refractory prostate cancer. Its most significant toxicity has been the development of severe polyradiculoneuropathy.
• Description: Introduced into therapy for the treatment of early trypanosomiasis in the 1920s, suramin, a bis-hexasulfonatednaphthylurea, is still considered to be the drug of choice for treatment of non-CNS-associated African trypanosomiasis.
• Uses: antiviral Sodium salt of Suramin, a hepatitis C virus NS3 helicase inhibitor. Also used in the treatment of arthritis due to problematic collagen. Suramin sodium is a compound with a dyelike structure. Suramin is most effective against T. b. rhodesiense, but has also been used against T. b. gambiense infection. The compound causes side effects such as nausea, photophobia, and peripheral neuropathy which disappear shortly after conclusion of administration. Because the drug is unable to pass the bloodbrain barrier, prompt treatment of patients is essential. Suramin in combination with tryparsamide is an alternative that has been investigated.
• Clinical Use: Suramin sodium is a high molecular-weight bisurea derivative containing six sulfonic acid groups as their sodium salts. It was developed in Germany shortly after World War I as a byproduct of research efforts directed toward the development of potential antiparasitic agents from dyestuffs. The drug has been used for more than half a century for the treatment of early cases of trypanosomiasis. Not until several decades later, however, was suramin discovered to be a long-term prophylactic agent whose effectiveness after a single intravenous injection is maintained for up to 3 months. The drug is tightly bound to plasma proteins, causing its excretion in the urine to be almost negligible. Tissue penetration of the drug does not occur, apparently because of its high molecular weight and highly ionic character. Thus, an injected dose remains in the plasma for a very long period. Newer, more effective drugs are now available for short-term treatment and prophylaxis of African sleeping sickness. Suramin is also used for prophylaxis of onchocerciasis. It is available from the CDC. Suramin is used primarily to treat African trypanosomiasis, for which it is the drug of choice. It is effective in treating disease caused by Trypanosoma gambiense and T. rhodesiense but not T. cruzi (Chagas’ disease). It can be used alone prophylactically or during the initial hemolymphatic stages of the disease. Later stages, particularly those involving the CNS, are more commonly treated with a combination of suramin and the arsenical melarsoprol. When CNS involvement occurs, the poor penetration of suramin and pentamidine into the CSF requires alternative forms of chemotherapy, such as melarsoprol in combination with suramin. In treating Onchocerca volvulus infections, suramin kills adult worms and is an alternative to ivermectin. Suramin is used after initial treatment with diethylcarbamazine, which is used to kill the microfilariae. It produces favorable results in pemphigus and prolongs the time to disease progression in hormone-refractory prostate cancer. African sleeping sickness (early stage before CNS involvement) Onchocerciasis

Technology Process of Suramin sodium

There total 8 articles about Suramin sodium 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: 72.31%

8-(3-(3-aminobenzamide)-4-methylbenzamido)-naphthalene-1,3,5-trisulfonic acid trisodium salt + 1,1'-carbonyldiimidazole (530-62-1) → suramin sodium (129-46-4)

Guidance literature:

With Imidazole hydrochloride; In water; acetonitrile; for 19h;

Reference yield:

8-(3-amino-4-methylbenzamido)naphthalene-1,3,5-trisulfonic acid trisodium salt → suramin sodium (129-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 68.8 percent / toluene; H₂O / pH 4

2: 85.3 percent / H₂ / Pd/C / H₂O

3: toluene; H₂O / pH 4

With hydrogen; palladium on activated charcoal; In water; toluene;

DOI:10.1021/jm050301p

Reference yield:

8-(4-methyl-3-nitrobenzamido)naphthalene-1,3,5-trisulfonic acid trisodium salt → suramin sodium (129-46-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95.6 percent / H₂ / Pd/C / H₂O

2: 68.8 percent / toluene; H₂O / pH 4

3: 85.3 percent / H₂ / Pd/C / H₂O

4: toluene; H₂O / pH 4

With hydrogen; palladium on activated charcoal; In water; toluene;

DOI:10.1021/jm050301p

upstream raw materials:

phosgene

4-methyl-3-nitrobenzoyl chloride

1,1'-carbonyldiimidazole

Refernces

• 1、 Ullmann, Heiko,Meis, Sabine,Hongwiset, Darunee,Marzian, Claudia,Wiese, Michael,Nickel, Peter,Communi, Didier,Boeynaems, Jean-Marie,Wolf, Christian,Hausmann, Ralf,Schmalzing, Günther,Kassack, Matthias U.. "Synthesis and structure-activity relationships of suramin-derived P2Y 11 receptor antagonists with nanomolar potency". . p. 7040 - 7048. Retrieved 2007/10/03.