Suramin

{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 411355479 | IUPAC_name = 8,8'-{Carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]}di(1,3,5-naphthalenetrisulfonic acid) | image = Suramin.png | image2 = Suramin_sf.gif

| tradename = Antrypol, 309 F or 309 Fourneau, Bayer 205, Moranyl, Naganin, Naganine | pregnancy_category = | legal_status = not approved by the US FDA | routes_of_administration = injection

| bioavailability = | metabolism = | excretion =

| CASNo_Ref =  ^Y | CAS_number_Ref =  ^Y | CAS_number = 145-63-1 | ATC_prefix = P01 | ATC_suffix = CX02 | ATC_supplemental = Template:ATCvet | PubChem = 5361 | IUPHAR_ligand = 1728 | DrugBank_Ref =  ^N | DrugBank = DB04786 | ChemSpiderID_Ref =  ^Y | ChemSpiderID = 5168 | UNII_Ref =  ^Y | UNII = 6032D45BEM | KEGG_Ref =  ^N | KEGG = C07974 | ChEBI_Ref =  ^N | ChEBI = 45906 | ChEMBL_Ref =  ^Y | ChEMBL = 265502

| C=51 | H=40 | N=6 | O=23 | S=6 

| molecular_weight = 1297.29 | smiles = O=C(Nc1cc(ccc1C)C(=O)Nc3c2c(cc(cc2c(cc3)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)c8cccc(NC(=O)Nc7cc(C(=O)Nc6cc(C(=O)Nc5c4c(cc(cc4c(cc5)S(=O)(=O)O)S(=O)(=O)O)S(=O)(=O)O)ccc6C)ccc7)c8 | InChI = 1/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80) | InChIKey = FIAFUQMPZJWCLV-UHFFFAOYAG | StdInChI_Ref =  ^Y | StdInChI = 1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80) | StdInChIKey_Ref =  ^Y | StdInChIKey = FIAFUQMPZJWCLV-UHFFFAOYSA-N }}

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [2]

Overview[edit | edit source]

Suramin is an antimicrobial drug developed by Oskar Dressel and Richard Kothe of Bayer, Germany in 1916, and is still sold by Bayer under the brand name Germanin. The formula of suramin was kept secret by Bayer for commercial reasons, however, it was elucidated and published in 1924 by Ernest Fourneau and his team of the Pasteur Institute.^[1]

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[2]

Medical uses[edit | edit source]

Protozoa[edit | edit source]

It is used for treatment of human sleeping sickness caused by trypanosomes.^[3]

Helminthiasis[edit | edit source]

It has been used in the treatment of onchocerciasis.^[4]

Other[edit | edit source]

It has been investigated as treatment for prostate cancer.^[5]

Also, suramin as treatment for autism is being evaluated^[6] and there are promising results in adult mice.^[7][8]

Adverse reactions[edit | edit source]

The most frequent adverse reactions are nausea and vomiting. About 90% of patients will get an urticarial rash that disappears in a few days without needing to stop treatment. There is a greater than 50% chance of adrenal cortical damage, but only a smaller proportion will require lifelong corticosteroid replacement. It is common for patients to get a tingling or crawling sensation of the skin with suramin. Suramin will cause clouding of the urine which is harmless: patients should be warned of this to avoid them becoming alarmed.

Kidney damage and exfoliative dermatitis occur less commonly.

Suramin has been applied clinically to HIV/AIDS patients resulting in a significant number of fatal occurrences and as a result the application of this molecule was abandoned for this condition.^[9]

Chemistry[edit | edit source]

The molecular formula of suramin is C₅₁H₄₀N₆O₂₃S₆. It is a symmetric molecule in the center of which lies a urea (NH–CO–NH) functional group. Suramin contains eight benzene rings, four of which are fused in pairs (naphthalene), four amide groups (in addition to the urea) and six sulfonic acid groups. When given as drug, it is usually as the sodium sulfonate, with six sodium ions on the sulfonate groups rather than hydrogens.

Research[edit | edit source]

According to the National Cancer Institute there are no active clinical trials.^[10]

Suramin is also used in research as a broad-spectrum antagonist of P2 receptors^[11][12] and agonist of Ryanodine receptors.^[13]

Its effect on telomerase has been investigated.^[14]

It may have some activity against RNA viruses.^[15]

In addition to antagonism of P2 receptors, Suramin inhibits the activation of heterotrimeric G proteins in a variety of other GPCRs with varying potency. It prevents the association of heteromeric G proteins and therefore the receptors guanine exchange functionality (GEF). With this blockade the GDP will not release from the Gα subunit so it can not be replaced by a GTP and become activated. This has the effect of blocking downstream G protein mediated signaling of various GPCR proteins including rhodopsin, the A1 adenosine receptor, and the D2 dopamine receptor.^[16]

References[edit | edit source]

External links[edit | edit source]

• Suramin bound to proteins in the PDB
• Drug information
• Suramin, drug information by JBC Online
• Suramin in treating patients with recurrent bladder cancer
• National Cancer Institute

Template:Anthelmintics