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{{Drugbox|
{{Drugbox
|IUPAC_name =  
| Verifiedfields = changed
| image = Suramin.svg
| Watchedfields = changed
| CAS_number=
| verifiedrevid = 411355479
| ATC_prefix=P01
| IUPAC_name = 8,8'-{Carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]}di(1,3,5-naphthalenetrisulfonic acid)
| ATC_suffix=CX02  
| image = Suramin.png
| ATC_supplemental=
| image2 = Suramin_sf.gif
| PubChem=5361
 
| DrugBank=
<!--Clinical data-->
|  | C=51 | H=40 | N=6 | O=23 | S=6
| 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
 
<!--Pharmacokinetic data-->
| bioavailability = 
| metabolism = 
| excretion =
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| 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
 
<!--Chemical data-->
  | C=51 | H=40 | N=6 | O=23 | S=6  
| molecular_weight = 1297.29
| molecular_weight = 1297.29
| bioavailability=  
| 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
| metabolism =  
| 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)
| elimination_half-life=
| InChIKey = FIAFUQMPZJWCLV-UHFFFAOYAG
| excretion =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_category =  
| 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)
| legal_status =  
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| routes_of_administration=  
| StdInChIKey = FIAFUQMPZJWCLV-UHFFFAOYSA-N
}}
}}
'''Suramin''' is a medicinal [[medication|drug]] developed by [[Oskar Dressel]] and [[Richard Kothe]] of [[Bayer]], [[Germany]] in [[1916]]. It is used for treatment of human [[sleeping sickness]], [[onchocerciasis]] and other diseases caused by [[trypanosome]]s and [[worm]]s.  It is under investigation as treatment for [[prostate cancer]].
                    __NOTOC__
{{SI}}
{{CMG}}


==Chemistry==
==Overview==
The molecular formula of suramin is '''C<sub>51</sub>H<sub>34</sub>N<sub>6</sub>O<sub>23</sub>S<sub>6</sub>'''. It is a [[symmetry|symmetric]] [[molecule]] in the center of which lies [[urea]], '''NH-CO-NH'''. Suramin contains 8 [[benzene ring]]s, 4 of which are fused in paires ([[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.  
'''Suramin''' is an antimicrobial [[medication|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]].<ref>E. Fourneau, [[Jacques Tréfouël|J. and Th. Tréfouël]] and J. Vallée (1924). "Sur une nouvelle série de médicaments trypanocides", ''C. R. Séances Acad. Sci.'' '''178''': 675.)</ref>
 
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]].<ref>{{cite web|title=WHO Model List of EssentialMedicines|url=http://apps.who.int/iris/bitstream/10665/93142/1/EML_18_eng.pdf?ua=1|work=World Health Organization|accessdate=22 April 2014|date=October 2013}}</ref>
 
==Medical uses==
 
===Protozoa===
It is used for treatment of human [[African trypanosomiasis|sleeping sickness]] caused by [[Trypanosoma|trypanosome]]s.<ref name="pmid14728611">{{cite journal |author=Darsaud A, Chevrier C, Bourdon L, Dumas M, Buguet A, Bouteille B |title=Megazol combined with suramin improves a new diagnosis index of the early meningo-encephalitic phase of experimental African trypanosomiasis |journal=Trop. Med. Int. Health |volume=9 |issue=1 |pages=83–91 |date=January 2004 |pmid=14728611 |doi= 10.1046/j.1365-3156.2003.01154.x|url=http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1360-2276&date=2004&volume=9&issue=1&spage=83}}</ref>
 
===Helminthiasis===
It has been used in the treatment of [[onchocerciasis]].<ref name="pmid678497">{{cite journal |author=Anderson J, Fuglsang H |title=Further studies on the treatment of ocular onchocerciasis with diethylcarbamazine and suramin |journal=Br J Ophthalmol |volume=62 |issue=7 |pages=450–7 |date=July 1978 |pmid=678497 |pmc=1043255 |doi= 10.1136/bjo.62.7.450|url=http://bjo.bmj.com/cgi/pmidlookup?view=long&pmid=678497}}</ref>
 
===Other===
It has been investigated as treatment for [[prostate cancer]].<ref name="pmid15484217">{{cite journal |author=Ahles TA, Herndon JE, Small EJ, ''et al.'' |title=Quality of life impact of three different doses of suramin in patients with metastatic hormone-refractory prostate carcinoma: results of Intergroup O159/Cancer and Leukemia Group B 9480 |journal=Cancer |volume=101 |issue=10 |pages=2202–8 |date=November 2004 |pmid=15484217 |doi=10.1002/cncr.20655}}</ref>


==Dosing==
Also, suramin as treatment for [[autism]] is being evaluated<ref>http://medicalxpress.com/news/2013-03-drug-treatment-autism-symptoms-mouse.html</ref> and there are promising results in adult mice.<ref>http://news.sciencemag.org/biology/2014/06/century-old-drug-reverses-signs-autism-mice</ref><ref>http://www.nature.com/tp/journal/v4/n6/full/tp201433a.html</ref>
Suramin is admistered by a single weekly [[intravenous injection]] for six weeks. The dose per injection is 1 g.


==Adverse reactions==
==Adverse reactions==
The most frequent adverse reactions are [[nausea]] and [[vomiting]].  
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 cortex|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.
About 90% of patients will get an [[urticaria]]l rash that disappears in a few days without needing to stop treatment.  There is a greater than 50% chance of [[adrenal cortex|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.
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.<ref>{{cite journal | pmid=3548350}}</ref>
==Chemistry==
The molecular formula of suramin is C<sub>51</sub>H<sub>40</sub>N<sub>6</sub>O<sub>23</sub>S<sub>6</sub>. It is a [[symmetry|symmetric]] [[molecule]] in the center of which lies a [[urea]] (NH–CO–NH) functional group. Suramin contains eight [[benzene ring]]s, 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==
==Research==
Suramin is also used in research as a broad-spectrum antagonist of P2 receptors ([[adenosine triphsophate|ATP]] receptors) and agonist of [[Ryanodine receptor]]s.  
According to the National Cancer Institute there are no active clinical trials.<ref>Completed and closed clinical trials are listed here: [http://www.cancer.gov/search/ResultsClinicalTrialsAdvanced.aspx?protocolsearchid=4504138]</ref>
 
Suramin is also used in research as a broad-spectrum antagonist of [[P2 receptors]]<ref name="pmid16968944">{{cite journal |author=Abbracchio MP, Burnstock G, Boeynaems JM, Barnard EA, Boyer JL, Kennedy C, Knight GE, Fumagalli M, Gachet C, Jacobson KA, Weisman GA. |title=International Union of Pharmacology LVIII: update on the P2Y G protein-coupled nucleotide receptors: from molecular mechanisms and pathophysiology to therapy |journal=Pharmacol Rev. |volume=58 |issue=3 |pages=281–341 |date=September 2006 |pmid=16968944 |doi=10.1124/pr.58.3.3 |pmc=3471216}}</ref><ref name="pmid11171941">{{cite journal |author=Khakh BS, Burnstock G, Kennedy C, King BF, North RA, Séguéla P, Voigt M, Humphrey PP. |title=International union of pharmacology. XXIV. Current status of the nomenclature and properties of P2X receptors and their subunits |journal=Pharmacol Rev. |volume=53 |issue=1 |pages=107–118 |date=March 2001 |pmid=11171941}}</ref> and agonist of [[Ryanodine receptor]]s.<ref name="pmid16056233">{{cite journal |author=Wolner I, Kassack MU, Ullmann H, Karel A, Hohenegger M |title=Use-dependent inhibition of the skeletal muscle ryanodine receptor by the suramin analogue NF676 |journal=Br. J. Pharmacol. |volume=146 |issue=4 |pages=525–33 |date=October 2005 |pmid=16056233 |pmc=1751178 |doi=10.1038/sj.bjp.0706359}}</ref>
 
Its effect on [[telomerase]] has been investigated.<ref name="pmid18667993">{{cite journal |author=Erguven M, Akev N, Ozdemir A, Karabulut E, Bilir A |title=The inhibitory effect of suramin on telomerase activity and spheroid growth of C6 glioma cells |journal=Med. Sci. Monit. |volume=14 |issue=8 |pages=BR165–73 |date=August 2008 |pmid=18667993 |doi= |url=http://www.medscimonit.com/fulltxt.php?ICID=865765}}</ref>
 
It may have some activity against RNA viruses.<ref name=Mastrangelo2012>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</ref>
 
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]].<ref name="pmid8700151">{{cite journal |author=Beindl W, Mitterauer T, Hohenegger M, Ijzerman AP, Nanoff C, Freissmuth M. |title=Inhibition of receptor/G protein coupling by suramin analogues |journal=ol. Pharmacology. |volume=50 |issue=2 |pages=415–23 |date=August 1996 |pmid=8700151 |doi= |url=http://molpharm.aspetjournals.org/content/50/2/415.long}}</ref>


== Manufacturing and availability ==
==References==
Suramin is manufactured by [[Bayer]] in Germany as '''Germanin'''®.  Each vial contains 1g of suramin powder to be reconstituted for injection.
{{Reflist|2}}


== External links ==
== External links ==
 
* [http://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=SVR Suramin bound to proteins] in the [[Protein Data Bank|PDB]]
* [http://www.drugs.com/cons/Suramin.html Drug information]
* [http://www.drugs.com/cons/Suramin.html Drug information]
* [http://www.jbc.org/cgi/content/full/273/20/12281 Suramin, drug information by JBC Online]
* [http://www.jbc.org/cgi/content/full/273/20/12281 Suramin, drug information by JBC Online]
* [http://www.clinicaltrials.gov/ct/show/NCT00006476?order=11 Suramin in treating patients with recurrent bladder cancer]
* [http://www.clinicaltrials.gov/ct/show/NCT00006476?order=11 Suramin in treating patients with recurrent bladder cancer]
* [http://www.cancer.gov/Templates/drugdictionary.aspx?CdrID=40052 National Cancer Institute]
{{Anthelmintics}}


{{Agents against leishmaniasis and trypanosomiasis}}
[[Category:Anthelmintics]]
[[Category:Anthelmintics]]
[[Category:Ureas]]
[[Category:Ureas]]
 
[[Category:Antiprotozoal agents]]
[[de:Suramin]]
[[Category:Drug]]
[[he:סוראמין]]

Latest revision as of 20:08, 14 April 2015

{{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 }}

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

Overview

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

Protozoa

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

Helminthiasis

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

Other

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

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

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

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

  1. ↑ E. Fourneau, J. and Th. Tréfouël and J. Vallée (1924). "Sur une nouvelle série de médicaments trypanocides", C. R. Séances Acad. Sci. 178: 675.)
  2. ↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
  3. ↑ Darsaud A, Chevrier C, Bourdon L, Dumas M, Buguet A, Bouteille B (January 2004). "Megazol combined with suramin improves a new diagnosis index of the early meningo-encephalitic phase of experimental African trypanosomiasis". Trop. Med. Int. Health. 9 (1): 83–91. doi:10.1046/j.1365-3156.2003.01154.x. PMID 14728611.
  4. ↑ Anderson J, Fuglsang H (July 1978). "Further studies on the treatment of ocular onchocerciasis with diethylcarbamazine and suramin". Br J Ophthalmol. 62 (7): 450–7. doi:10.1136/bjo.62.7.450. PMC 1043255. PMID 678497.
  5. ↑ Ahles TA, Herndon JE, Small EJ; et al. (November 2004). "Quality of life impact of three different doses of suramin in patients with metastatic hormone-refractory prostate carcinoma: results of Intergroup O159/Cancer and Leukemia Group B 9480". Cancer. 101 (10): 2202–8. doi:10.1002/cncr.20655. PMID 15484217.
  6. ↑ http://medicalxpress.com/news/2013-03-drug-treatment-autism-symptoms-mouse.html
  7. ↑ http://news.sciencemag.org/biology/2014/06/century-old-drug-reverses-signs-autism-mice
  8. ↑ http://www.nature.com/tp/journal/v4/n6/full/tp201433a.html
  9. ↑ . PMID 3548350. Missing or empty |title= (help)
  10. ↑ Completed and closed clinical trials are listed here: [1]
  11. ↑ Abbracchio MP, Burnstock G, Boeynaems JM, Barnard EA, Boyer JL, Kennedy C, Knight GE, Fumagalli M, Gachet C, Jacobson KA, Weisman GA. (September 2006). "International Union of Pharmacology LVIII: update on the P2Y G protein-coupled nucleotide receptors: from molecular mechanisms and pathophysiology to therapy". Pharmacol Rev. 58 (3): 281–341. doi:10.1124/pr.58.3.3. PMC 3471216. PMID 16968944.
  12. ↑ Khakh BS, Burnstock G, Kennedy C, King BF, North RA, Séguéla P, Voigt M, Humphrey PP. (March 2001). "International union of pharmacology. XXIV. Current status of the nomenclature and properties of P2X receptors and their subunits". Pharmacol Rev. 53 (1): 107–118. PMID 11171941.
  13. ↑ Wolner I, Kassack MU, Ullmann H, Karel A, Hohenegger M (October 2005). "Use-dependent inhibition of the skeletal muscle ryanodine receptor by the suramin analogue NF676". Br. J. Pharmacol. 146 (4): 525–33. doi:10.1038/sj.bjp.0706359. PMC 1751178. PMID 16056233.
  14. ↑ Erguven M, Akev N, Ozdemir A, Karabulut E, Bilir A (August 2008). "The inhibitory effect of suramin on telomerase activity and spheroid growth of C6 glioma cells". Med. Sci. Monit. 14 (8): BR165–73. PMID 18667993.
  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. ↑ Beindl W, Mitterauer T, Hohenegger M, Ijzerman AP, Nanoff C, Freissmuth M. (August 1996). "Inhibition of receptor/G protein coupling by suramin analogues". ol. Pharmacology. 50 (2): 415–23. PMID 8700151.

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