Suramin

{{Drugbox
 * Verifiedfields = changed
 * Watchedfields = changed
 * verifiedrevid = 411355479
 * IUPAC_name = 8-[(4-methyl-3-{[3-({[3-({2-methyl-5-
 * image = Suramin.svg
 * image2 = Suramin_sf.gif


 * tradename = Antrypol
 * pregnancy_category =
 * legal_status =
 * routes_of_administration =


 * bioavailability =
 * metabolism =
 * excretion =


 * CASNo_Ref = {{cascite|correct|CAS}}
 * CAS_number = 145-63-1
 * ATC_prefix = P01
 * ATC_suffix = CX02
 * ATC_supplemental = {{ATCvet|P51|AE02}}
 * PubChem = 5361
 * IUPHAR_ligand = 1728
 * DrugBank_Ref = {{drugbankcite|changed|drugbank}}
 * DrugBank = DB04786
 * ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 * ChemSpiderID = 5168
 * UNII_Ref = {{fdacite|correct|FDA}}
 * UNII = 6032D45BEM
 * KEGG_Ref = {{keggcite|changed|kegg}}
 * KEGG = C07974
 * ChEBI_Ref = {{ebicite|changed|EBI}}
 * ChEBI = 45906
 * ChEMBL_Ref = {{ebicite|correct|EBI}}
 * ChEMBL = 265502

| C=51 | H=40 | N=6 | O=23 | S=6 }} Suramin is a drug developed by Oskar Dressel and Richard Kothe of Bayer, Germany in 1916, and is still sold by Bayer under the brand name Germanin.
 * 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 = {{stdinchicite|correct|chemspider}}
 * 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 = {{stdinchicite|correct|chemspider}}
 * StdInChIKey = FIAFUQMPZJWCLV-UHFFFAOYSA-N

According to the National Cancer Institute there are no active clinical trials (as of April 1, 2008). Completed and closed clinical trials are listed here:

In addition to Germanin, the National Cancer Institute also lists the following "Foreign brand names": 309 F or 309 Fourneau, Bayer 205, Moranyl, Naganin, Naganine.

Protozoa
It is used for treatment of human sleeping sickness caused by trypanosomes.

Helminthiasis
It has been used in the treatment of onchocerciasis.

Other
It has been investigated as treatment for prostate cancer.

Chemistry
The molecular formula of suramin is C51H34N6O23S6. It is a symmetric molecule in the center of which lies urea, NH-CO-NH. Suramin contains 8 benzene rings, 4 of which are fused in pairs (naphthalene), 4 amide groups in addition to the one of urea and six sulfonate groups. When given as drug it usually contains six sodium ions that form a salt with the six sulfonate groups.

Dosing
Suramin is administered by a single weekly intravenous injection for six weeks. The dose per injection is 1 g.

Adverse reactions
The most frequent adverse reactions are nausea and vomiting. About 90% of patients will get an urticarial rash (like a nettle or poison ivy-type 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.

Research
Suramin is also used in research as a broad-spectrum antagonist of P2 receptors and agonist of Ryanodine receptors.

Its effect on telomerase has been investigated.