Suramin

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Suramin
Suramin.svg
Suramin sf.gif
Systematic (IUPAC) name
8,8'-{Carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]}di(1,3,5-naphthalenetrisulfonic acid)
Clinical data
Trade names Antrypol, 309 F or 309 Fourneau, Bayer 205, Moranyl, Naganin, Naganine
Legal status
Routes of
administration		 injection
Identifiers
CAS Number 145-63-1 YesY
ATC code P01CX02 (WHO) QP51AE02 (WHO)
PubChem CID: 5361
IUPHAR/BPS 1728
DrugBank DB04786 N
ChemSpider 5168 YesY
UNII 6032D45BEM YesY
KEGG C07974 N
ChEBI CHEBI:45906 N
ChEMBL CHEMBL265502 YesY
Chemical data
Formula C51H40N6O23S6
Molecular mass 1297.29
  • 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=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) YesY
  • Key:FIAFUQMPZJWCLV-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Suramin is an antiparasitic 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]:378-379[2]

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.[3]

Medical uses

Protozoa

It is used for treatment of human sleeping sickness caused by trypanosomes.[4]

Helminthiasis

It has been used in the treatment of onchocerciasis.[5]

Adverse reactions

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.[6]

Chemistry

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

Suramin was studied as a possible treatment for prostate cancer in a clinical trial.[7]

It has been studied in a mouse model of autism[8][9][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

  1. ↑ Walter Sneader. Drug Discovery: A History. John Wiley & Sons, 2005 ISBN 9780471899792
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ http://medicalxpress.com/news/2013-03-drug-treatment-autism-symptoms-mouse.html
  9. ↑ http://news.sciencemag.org/biology/2014/06/century-old-drug-reverses-signs-autism-mice
  10. ↑ http://www.nature.com/tp/journal/v4/n6/full/tp201433a.html
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Mastrangelo E, Pezzullo M, Tarantino D, Petazzi R, Germani F, Kramer D, Robel I, Rohayem J, Bolognesi M, Milani M (2012) Structure-based inhibition of norovirus RNA-dependent RNA-polymerases. J Mol Biol
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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