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Suramin

A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.

A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties. Suramin is manufactured by Bayer in Germany as Germanin®.

Also known as: Naphuride, Germanin, Naganol, Belganyl, Fourneau, Farma, Antrypol, Suramine, Naganin

8,8′-{Carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]}di(1,3,5-naphthalenetrisulfonic acid) …FREE FORM

8,8′-[Ureylenebis[m-phenylenecarbonylimino(4-methyl-m-phenylene)carbonylimino]]di(1,3,5-naphthalenetrisulfonic acid) hexasodium salt

CAS  145-63-1 FREE FORM

129-46-4 of hexa sodium

LAUNCHED 1940 BAYER

Formula C51H40N6O23S6 
Mol. mass 1297.29

The molecular formula of suramin is C51H34N6O23S6. It is a symmetric molecule in the center of which lies ureaNH-CO-NH. Suramin contains eightbenzene rings, four of which are fused in pairs (naphthalene), four 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 a drug developed by Oskar Dressel and Richard Kothe of BayerGermany in 1916, and is still sold by Bayer under the brand nameGermanin.

Suramin sodium is a heparanase inhibitor that was first launched in 1940 by Bayer under the brand name Antrypol for the treatment of helminthic infection. It was later launched by Bayer for the treatment of trypanosomiasis (African sleeping sickness).

More recently, the product has entered early clinical development at Ohio State University for the treatment of platinum-pretreated patients with stage IIIB/IV non-small cell lung cancer, in combination with docetaxel or gemcitabine.

The National Cancer Institute (NCI) is conducting phase II clinical studies for the treatment of glioblastoma multiforme and for the treatment of adrenocortical carcinoma.

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:[1]

In addition to Germanin, the National Cancer Institute also lists the following “Foreign brand names”: 309 F or 309 Fourneau,[1] Bayer 205, Moranyl, Naganin, Naganine.

It is used for treatment of human sleeping sickness caused by trypanosomes.[2]

It has been used in the treatment of onchocerciasis.[3]

It has been investigated as treatment for prostate cancer.[4]

Also, suramin as treatment for autism is being evaluated. [5]

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

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 lifelongcorticosteroid 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. http://www.ncbi.nlm.nih.gov/pubmed/3548350

Suramin is also used in research as a broad-spectrum antagonist of P2 receptors[6][7] and agonist of Ryanodine receptors.[8]

ChemSpider 2D Image | 8,8'-{Carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]}di(1,3,5-naphthalenetrisulfonic acid) | C51H40N6O23S6suramin

Its effect on telomerase has been investigated.[9]

It may have some activity against RNA viruses.[10]

In addition to antagonism of P2 receptors, Suramin inhibits the acitivation 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.[11]

A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties. Suramin is manufactured by Bayer in Germany as Germanin®.

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InCl3-catalysed synthesis of 2-aryl quinazolin-4(3H)-ones and 5-aryl pyrazolo[4,3-d]pyrimidin-7(6H)-ones and their evaluation as potential anticancer agents.

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Identification of a sirtuin 3 inhibitor that displays selectivity over sirtuin 1 and 2.

European journal of medicinal chemistry

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Inhibition of the human deacylase Sirtuin 5 by the indole GW5074.

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Discovery of thieno[3,2-d]pyrimidine-6-carboxamides as potent inhibitors of SIRT1, SIRT2, and SIRT3.

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  1.  The formula of suramin was kept secret by Bayer for commercial reasons. But it was elucidated and published in 1924 by Fourneau and his team of the Pasteur Institute, and it is only on this date that its exact chemical composition was known. (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. 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.xPMID 14728611.
  3.  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.62.7.450PMC 1043255PMID 678497.
  4.  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.20655PMID 15484217.
  5.  http://medicalxpress.com/news/2013-03-drug-treatment-autism-symptoms-mouse.html
  6.  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.58.3.3PMID 16968944.
  7.  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.
  8.  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.0706359PMC 1751178.PMID 16056233.
  9.  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.
  10.  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
  11.  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.
  12. Drugs Fut 1986, 11(10): 860
  13. WO 2012159107
  14. WO 2012087336
  15. US 2011257109
  16. WO 2009022897
  17. WO 2009020613
  18. WO 2008094027
  19.   EP 0486809
  20. US 5158940
  21. US 5173509
  22. WO 1993007864
  23. WO 1994008574

SURAMIN

Enterovirus-71 (EV71) is one of the major causative reagents for hand-foot-and-mouth disease. In particular, EV71 causes severe central nervous system infections and leads to numerous dead cases. Although several inactivated whole-virus vaccines have entered in clinical trials, no antiviral agent has been provided for clinical therapy. In the present work, we screened our compound library and identified that suramin, which has been clinically used to treat variable diseases, could inhibit EV71 proliferation with an IC50 value of 40μM. We further revealed that suramin could block the attachment of EV71 to host cells to regulate the early stage of EV71 infection, as well as affected other steps of EV71 life cycle. Our results are helpful to understand the mechanism for EV71 life cycle and provide a potential for the usage of an approved drug, suramin, as the antiviral against EV71 infection.

  • Suramin Hexasodium
  • 129-46-4

Synonyms

  • 309 F
  • Antrypol
  • BAY 205
  • Bayer 205
  • CI-1003
  • EINECS 204-949-3
  • Fourneau 309
  • Germanin
  • Moranyl
  • Naganin
  • Naganine
  • Naganinum
  • Naganol
  • Naphuride sodium
  • NF060
  • NSC 34936
  • SK 24728
  • Sodium suramin
  • Suramin Hexasodium
  • Suramin sodium
  • Suramina sodica
  • Suramina sodica [INN-Spanish]
  • Suramine sodique
  • Suramine sodique [INN-French]
  • Suramine sodium
  • Suraminum natricum
  • Suraminum natricum [INN-Latin]
  • UNII-89521262IH

Suramin Sodium, is an anticancer agent with a wide variety of activities.

Recently suramin was shown to inhibit FSH binding to its receptor (Daugherty, R. L.; Cockett, A. T. K.; Schoen, S. R. and Sluss, P. M. “Suramin inhibits gonadotropon action in rat testis: implications for treatment of advanced prostate cancer” J. Urol. 1992, 147, 727-732).

This activity causes, at least in part, the decrease in testosterone production seen in rats and humans that were administered suramin(Danesi, R.; La Rocca, R. V.; Cooper, M. R.; Ricciardi, M. P.; Pellegrini, A.; Soldani, P.; Kragel, P. J.; Paparelli, A.; Del Tacca, M.; Myers, C. E, “Clinical and experimental evidence of inhibition of testosterone production by suramin.” J. Clin. Endocrinol. Metab. 1996, 81, 2238-2246).

Suramin is the only non-peptidic small molecule that has been reported to be an FSH receptor binding antagonist.

Figure US06200963-20010313-C00003

Suramin is 8,8′ – (carbonylbis(imino-3,1-phenylenecarbonylimino (4-methyl-3,1-phenylene) carbonylimino)) bis-1,3 ,5-naphthalenetrisulfonic acid (GB Patent No. 224849). This polyanionic compound has been used for many decades as a prophylactic and therapeutic agent for try- panosomiasis. It was subsequently shown that suramin is able to block the activity of a variety of proteins like cellular and viral enzymes and growth factors (Mitsuya, M. et al. Science 226 : 172 (1984), Hosang, M. J. Cell. Biochem. 29 : 265 (1985), De Clercq, E. Cancer Lett. 8 : 9 (1979)).

 

5-32-1977

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EP0183352A2 * Sep 27, 1985 Jun 4, 1986 THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce Use of suramin for clinical treatment of infection with any of the members of the family of human-t-cell leukemia (htvl) viruses including lymphadenopathy virus (lav)
EP0205077A2 * Jun 3, 1986 Dec 17, 1986 Bayer Ag Suramin sodium for use as an immunostimulant

EP0515523A1 * Feb 13, 1991 Dec 2, 1992 THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce Use of suramin to treat rheumatologic diseases
EP0755254A1 * Mar 24, 1995 Jan 29, 1997 The Trustees Of The University Of Pennsylvania Prevention and treatment of ischemia-reperfusion and endotoxin-related injury using adenosine and purino receptor antagonists
EP1460087A1 * Feb 17, 1997 Sep 22, 2004 The Kennedy Institute Of Rheumatology Methods of treating vascular disease with TNF antagonists
EP1940376A2 * Oct 3, 2006 Jul 9, 2008 Rottapharm S.P.A. Use of neboglamine in the treatment of toxicodependency
EP1945204A2 * Oct 27, 2006 Jul 23, 2008 Brane Discovery S.R.L. V-atpase inhibitors for use in the treatment of septic shock
US5453444 * Oct 6, 1994 Sep 26, 1995 Otsuka Pharmaceutical Co., Ltd. Method to mitigate or eliminate weight loss
US5534539 * Jun 12, 1995 Jul 9, 1996 Farmitalia Carlo Erba S.R.L. Biologically active ureido derivatives useful as anit-metastic agenst
US5596105 * Jan 13, 1995 Jan 21, 1997 Farmitalia Carlo Erba S.R.L. Therapeutically active naphthalenesulfonic pyrrolecarboxamido derivatives
US7476693 Mar 26, 2003 Jan 13, 2009 Eastern Virginia Medical School Suramin and derivatives thereof as topical microbicide and contraceptive
US7608262 Feb 16, 1996 Oct 27, 2009 The Kennedy Institute Of Rheumatology Methods of preventing or treating thrombosis with tumor necrosis factor antagonists
US8552064 Dec 19, 2008 Oct 8, 2013 Eastern Virginia Medical School Suramin and derivatives thereof as topical microbicide and contraceptive
WO1994008574A1 * Oct 12, 1993 Apr 28, 1994 Otsuka America Pharmaceutical Treatment of cachexia and inhibition of il-6 activity
WO1994010990A1 * Nov 12, 1993 May 26, 1994 British Bio Technology Inhibition of tnf production
WO1997030088A2 * Feb 17, 1997 Aug 21, 1997 Kennedy Inst Of Rheumatology Methods of treating vascular disease with tnf antagonists
WO2004113920A1 * Jun 18, 2004 Dec 29, 2004 Babon Jeff James Screening method for substances binding to merozoite surface protein-1/42
WO2008138943A2 * May 14, 2008 Nov 20, 2008 Mara Galli Prophylactic and therapeutic use of sirtuin inhibitors in tnf-alpha mediated pathologies
WO2009137471A2 * May 5, 2009 Nov 12, 2009 University Of Miami Azo dye related small molecule modulators of protein-protein interactions
WO2010016628A1 * Jul 10, 2009 Feb 11, 2010 Sammy Opiyo Conjugated suramin amino compounds for medical conditions
WO2012159107A1 * May 21, 2012 Nov 22, 2012 Rhode Island Hospital Inhibition of renal fibrosis

Title: Suramin Sodium

CAS Registry Number: 129-46-4

CAS Name: 8,8¢-[Carbonylbis[imino-3,1-phenylenecarbonylimino(4-methyl-3,1-phenylene)carbonylimino]]bis-1,3,5-naphthalenetrisulfonic acid hexasodium salt

Additional Names: hexasodium sym-bis(m-aminobenzoyl-m-amino-p-methylbenzoyl-1-naphthylamino-4,6,8-trisulfonate) carbamide

Manufacturers’ Codes: Bayer 205; Fourneau 309

Trademarks: Antrypol (AstraZeneca); Germanin (Bayer); Moranyl (Specia); Naganol; Naphuride

Molecular Formula: C51H34N6Na6O23S6

Molecular Weight: 1429.17

Percent Composition: C 42.86%, H 2.40%, N 5.88%, Na 9.65%, O 25.75%, S 13.46%

Literature References: Discovered in 1917 by O. Dressel and R. Kothe: J. Dressel, J. Chem. Educ. 38, 620 (1961). Prepn: E. Fourneau et al., Compt. Rend. 178, 675 (1924); J. Trefouel, E. Fourneau, GB 224849 (1923); B. Heymann, Angew. Chem. 37, 585 (1924). Pharmacology, toxicology and clinical antiparasitic activity: F. Hawking, Adv. Pharmacol. Chemother. 15, 289-322 (1978). Inhibition of reverse transcriptase in vitro: E. De Clercq, Cancer Lett. 8, 9 (1979); vs HIV: H. Mitsuya et al., Science 226, 172 (1984). HPLC determn in plasma: R. W. Klecker, J. M. Collins, J. Liq. Chromatogr. 8, 1685 (1985). Pharmacokinetics: J. M. Collins et al., J. Clin. Pharmacol. 26, 22 (1986). Pharmacology and virustatic effect in AIDS: S. Broder et al., Lancet 2, 627 (1985); A. M. Levine et al., Ann. Intern. Med. 105, 32 (1986). Clinical trial in onchocerciasis: H. Schultz-Key et al., Trop. Med. Parasitol. 36, 244 (1985); in prostate cancer: C. Myers et al., J. Clin. Oncol. 10, 881 (1992). Review: Olenick in Antibiotics vol. 3,J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 699-703; R. La Rocca et al., Cancer Cells 2, 106-115 (1990).

Properties: White or slightly pink or cream-colored powder. Slightly bitter taste. Hygroscopic. Freely sol in water, in physiological saline; sparingly sol in 95% alcohol. Insol in benzene, ether, petr ether, chloroform. Aq solns are neutral to litmus. LD50 in mice (mg/kg): ~620 i.v. (Hawking).

Toxicity data: LD50 in mice (mg/kg): ~620 i.v. (Hawking)

Therap-Cat: Anthelmintic (Nematodes); antiprotozoal (Trypanosoma).

Therap-Cat-Vet: Antiprotozoal (Trypanosoma).

Keywords: Anthelmintic (Nematodes); Antiprotozoal (Trypanosoma); Reverse Transcriptase Inhibitor.

Suramin Sodium

ANTHONY MELVIN CRASTO

THANKS AND REGARD’S

DR ANTHONY MELVIN CRASTO Ph.D

GLENMARK SCIENTIST , NAVIMUMBAI, INDIA

did you feel happy, a head to toe paralysed man’s soul in action for you round the clock

need help, email or call me

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I was  paralysed in dec2007, Posts dedicated to my family, my organisation Glenmark, Your readership keeps me going and brings smiles to my family


2 Comments

  1. A.J.Mostashari says:

    Dr. Anthony Melvin Castro Glenmark Generic India, Dear Dr. Castro, I want to thank you for your tremendous assistance rendered by you to researchers, faculty members and students of Medicine, Medicinal Chem, Pharmaceutical sciences and generally people in health care. I am 75 years old and been around almost everywhere in the world. But I have not witnessed anything similar to your work from anybody anywhere in the world. I personally feel grateful and believe we all owe you a lot.

    kindest Regards Abdoljalil Mostashari Professor of Chemistry Tehran Iran

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 year tenure till date Dec 2017, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 19 lakh plus views on New Drug Approvals Blog in 216 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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