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{{short description|Chemical compound}}{{About|a ] drug|the village in Mykolaiv Oblast, Ukraine|Promin, Mykolaiv Oblast}}{{drugbox |
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{{drugbox| verifiedrevid = 441698882 |
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| verifiedrevid = 444223996 |
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| IUPAC_name = 2,3,4,5,6-pentahydroxy-1-phenyl]sulfonylanilino]hexane-1-sulfonic acid |
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| IUPAC_name = 2,3,4,5,6-pentahydroxy-1-phenyl]sulfonylanilino]hexane-1-sulfonic acid |
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| OtherNames = Sodium glucosulfone, Aceprosol, Promanide, Tasmin, Sulfona P |
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| synonyms = Sodium glucosulfone, Aceprosol, Promanide, Tasmin, Sulfona P |
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| image = Promin Molecular Structure Skeletal.svg |
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| image = Promin Molecular Structure Skeletal.svg |
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| image2 = Promin Molecular Structure Spacefill.png |
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| image2 = Promin Molecular Structure Spacefill.png |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| InChI = 1S/C24H36N2O18S3/c27-9-15(29)17(31)19(33)21(35)23(46(39,40)41)25-11-1-5-13(6-2-11)45(37,38)14-7-3-12(4-8-14)26-24(47(42,43)44)22(36)20(34)18(32)16(30)10-28/h1-8,15-36H,9-10H2,(H,39,40,41)(H,42,43,44) |
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| CAS_number = 554-18-7 |
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| InChIKey = SQQCWHCJRWYRLB-UHFFFAOYSA-N |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| smiles1 = |
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| UNII = I6RLN7D44F |
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| C=24 | H=36 | N=2 | O=18 | S=3 |
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| PubChem = 3481 |
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| PubChem = 71505 |
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| C=24|H=36|N=2|O=18|S=3 |
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| DrugBank = |
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| molecular_weight = 736.74024 g/mol |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| smiles = C1=CC(=CC=C1NC(C(C(C(C(CO)O)O)O)O)S(=O)(=O)O)S(=O)(=O)C2=CC=C(C=C2)NC(C(C(C(C(CO)O)O)O)O)S(=O)(=O)O |
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| ChemSpiderID = 64579 |
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| smiles = ..S(=O)(=O)(Nc1ccc(cc1)S(=O)(=O)c2ccc(N(S()(=O)=O)(O)(O)(O)(O)CO)cc2)(O)(O)(O)(O)CO |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C24H36N2O18S3.2Na/c27-9-15(29)17(31)19(33)21(35)23(46(39,40)41)25-11-1-5-13(6-2-11)45(37,38)14-7-3-12(4-8-14)26-24(47(42,43)44)22(36)20(34)18(32)16(30)10-28;;/h1-8,15-36H,9-10H2,(H,39,40,41)(H,42,43,44);;/q;2*+1/p-2/t15-,16-,17-,18-,19+,20+,21-,22-,23+,24+;;/m1../s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = NLLGJEMIZSAJFN-XRAGNMTMSA-L |
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'''Promin''', or '''sodium glucosulfone''' is a ] drug that was investigated for the treatment of ],<ref name="isbn0-8135-4438-6">{{cite book |author=Leo B. Slater |title=War and disease: biomedical research on malaria in the twentieth century |publisher=Rutgers University Press |location=New Brunswick, N.J |year=2009 |pages=102 |isbn=0-8135-4438-6 |oclc= |doi= |accessdate=}}</ref> ]<ref name="isbn0-8135-5009-2">{{cite book |author=Dr David Lilienfeld; Prof Dona Schneider |title=Public Health: The Development of a Discipline, Volume 2, Twentieth-Century Challenges, vol. 2 |publisher=Rutgers University Press |location=New Brunswick, N.J |year=2011 |pages=351 |isbn=0-8135-5009-2 |oclc= |doi= |accessdate=}}</ref> and ].<ref>Faget GH, et al. (1943) The Promin Treatment of Leprosy, Public Health Report 58:1729-1741, (Reprint Int J Lepr 34(3), 298-310, 1966)</ref> It is broken down in the body to ], which is the therapeutic form.<ref name="pmid498567">{{cite journal |author=McDougall AC |title=Dapsone |journal=Clin. Exp. Dermatol. |volume=4 |issue=2 |pages=139–42 |year=1979 |month=June |pmid=498567 |doi= |url=}}</ref> |
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'''Promin''', or '''sodium glucosulfone''' is a ] drug that was investigated for the treatment of ],<ref name="isbn0-8135-4438-6">{{cite book | vauthors = Slater LB |title=War and disease: biomedical research on malaria in the twentieth century |publisher=Rutgers University Press |location=New Brunswick, N.J |year=2009 |pages=102 |isbn=978-0-8135-4438-0 }}</ref> ]<ref name="isbn0-8135-5009-2">{{cite book | vauthors = Lilienfeld D, Schneider D |title=Public Health: The Development of a Discipline | volume = 2 Twentieth-Century Challenges |publisher=Rutgers University Press |location=New Brunswick, N.J |year=2011 |pages=351 |isbn=978-0-8135-5009-1 }}</ref> and ].<ref name="pmid19315949">{{cite journal | vauthors = Faget GH, Pogge RC, Johansen FA, Dinan JF, Prejean BM, Eccles CG | title = The Promin Treatment of Leprosy | journal = Public Health Reports | location = Washington, D.C. | volume = 58 | issue = 48 | pages = 1729–1741 | date = November 1943 | pmid = 19315949 | pmc = 2017027 | doi = 10.2307/4584691| jstor = 4584691 }}</ref><ref name="pmid5950351">{{cite journal | vauthors = Faget GH, Pogge RC, Johansen FA, Dinan JF, Prejean BM, Eccles CG | title = Reprint: The promin treatment of leprosy. A progress report | journal = International Journal of Leprosy and Other Mycobacterial Diseases | volume = 34 | issue = 3 | pages = 298–310 | date = 1966 | pmid = 5950351 }}</ref> It is broken down in the body to ], which is the therapeutic form.<ref name="pmid498567">{{cite journal | vauthors = McDougall AC | title = Dapsone | journal = Clinical and Experimental Dermatology | volume = 4 | issue = 2 | pages = 139–42 | date = June 1979 | pmid = 498567 | doi = 10.1111/j.1365-2230.1979.tb01608.x }}</ref> |
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==History== |
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==History== |
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The first synthesis of Promin is generally credited to W. H. Feldman of ] in 1940.<ref name=ravina2011evolution>{{cite book |author=Ravina, E. and Kubinyi, H. |title=The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs |publisher=John Wiley & Sons |year=2011 |pages=80 |isbn=9783527326693 |url=http://books.google.co.uk/books?id=iDNy0XxGqT8C }}</ref><ref>William Steenken, Jr. and Fred H. Heise (1943), , ''Proceedings of the Society for Experimental Biology and Medicine'' 52:180-183. doi:10.3181/00379727-52-14077</ref> However, although Parke-Davis did in fact synthesise the compound, it seems certain that they were not the first; in cooperation with J. Wittmann, ] synthesised various sulfone compounds in 1908, including both dapsone and some of its derivatives, such as promin. Fromm and Wittmann however were engaged on chemical rather than medical work, and no-one investigated the medical value of such compounds till some decades afterwards.<ref>Wozel, Gottfried; The Story of Sulfones in Tropical Medicine and Dermatology; International Journal of Dermatology, Volume 28, Issue 1, pages 17–21, January 1989. Published online as: DOI: 10.1111/j.1365-4362.1989.tb01301.x at URL: http://onlinelibrary.wiley.com/doi/10.1111/j.1365-4362.1989.tb01301.x/pdf</ref> The medical evaluation of sulfones was inspired by the discovery of the unprecedented value of synthetic compounds such as sulfonamides in treating microbial diseases. Early investigations yielded disappointing results, but subsequently promin and dapsone proved valuable in treating mycobacterial diseases. They were the first treatments to show more than a glimmer of hope of controlling such infections.<ref>Desikan, K. V. ; Multi-drug Regimen in Leprosy and its impact on Prevalence of the Disease ; MJAFI (Medical Journal, Armed Forces India) 2003; 59 : 2-4</ref> |
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The first synthesis of Promin is sometimes credited to Edward Tillitson and Benjamin F. Tullar of Parke, Davis, & Co. pharmaceuticals in August 1937.<ref name="johansen 2003 star reprint">{{cite news | vauthors = Johansen EA |title=Current Data on Promin Therapy; reprinted in The Star October-December 2003|url=http://www.fortyandeight.org/storage/The%20Star%20Oct_Dec_2003.pdf}}</ref><ref name=Wozel89>{{cite journal | vauthors = Wozel G | title = The story of sulfones in tropical medicine and dermatology | journal = International Journal of Dermatology | volume = 28 | issue = 1 | pages = 17–21 | date = 1989 | pmid = 2645226 | doi = 10.1111/j.1365-4362.1989.tb01301.x | s2cid = 30991934 }}</ref> However, although Parke-Davis did in fact synthesize the compound, it seems certain that they were not the first; in cooperation with J. Wittmann, ] synthesised various sulfone compounds in 1908, including both dapsone and some of its derivatives, such as promin. Fromm and Wittmann however were engaged on chemical rather than medical work, and no-one investigated the medical value of such compounds until some decades afterwards.<ref name=Wozel89 /> The medical evaluation of sulfones was inspired by the discovery of the unprecedented value of synthetic compounds such as sulfonamides in treating microbial diseases. Early investigations yielded disappointing results, but subsequently promin and dapsone proved valuable in treating mycobacterial diseases. They were the first treatments to show more than a glimmer of hope of controlling such infections.<ref name="pmid27407445">{{cite journal | vauthors = Desikan KV | title = Multi-drug Regimen in Leprosy and its impact on Prevalence of the Disease | journal = Medical Journal, Armed Forces India | volume = 59 | issue = 1 | pages = 2–4 | date = January 2003 | pmid = 27407445 | pmc = 4925770 | doi = 10.1016/S0377-1237(03)80092-8 }}</ref> |
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Initially, Promin appeared to be safer than dapsone, so it was further investigated at the ] as a treatment for tuberculosis in a ] model.<ref name="isbn0-471-89979-8">{{cite book |author=Sneader, Walter |title=Drug discovery: a history |publisher=Wiley |location=New York |year=2005 |pages= |isbn=0-471-89979-8 |oclc= |doi= |accessdate=}}</ref> Because it was already known that leprosy and tuberculosis were both caused by mycobacteria ('']'' and '']'', respectively), ] of the ] in Carville, Louisiana, requested information about the drug from Parke-Davis. They, in turn, informed him of the work being done on leprosy in rats by Edmund Cowdry at the ]. His successful results, published in 1941, convinced Faget to begin human studies, both with promin and ] sodium, a related compound from ]. The initial trials were on six volunteers, and were then expanded and replicated in different locations. Despite severe side effects that caused the initial tests to be suspended temporarily, the drug was shown to be effective.<ref name="isbn0-471-89979-8" /><ref>John Tayman (2006), '''', Simon and Schuster. Page 252.</ref> This breakthrough was reported worldwide, and led to a reduction in the stigma attached to leprosy, and consequent better treatment of patients, at the time still referred to as "inmates", and forbidden from using public transport.<ref name=time>{{cite news |title=Hope for Lepers |author= |url=http://www.time.com/time/printout/0,8816,934821,00.html |newspaper=Time Magazine |date=30 December 1946 |accessdate=22 July 2011}}</ref> |
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Initially, Promin appeared to be safer than dapsone, so it was further investigated at the ] as a treatment for tuberculosis in a ] model.<ref name="isbn0-471-89979-8">{{cite book | last = Sneader | first = Walter | name-list-style = vanc |title=Drug discovery: a history |publisher=Wiley |location=New York |year=2005 |isbn=978-0-471-89979-2 }}</ref> Because it was already known that leprosy and tuberculosis were both caused by mycobacteria ('']'' and '']'', respectively), ] of the ] in Carville, Louisiana, requested information about the drug from Parke-Davis. They, in turn, informed him of the work being done on leprosy in rats by Edmund Cowdry at the ]. His successful results, published in 1941, convinced Faget to begin human studies, both with promin and ] sodium, a related compound from ]. The initial trials were on six volunteers, and were then expanded and replicated in different locations. Despite severe side effects that caused the initial tests to be suspended temporarily, the drug was shown to be effective.<ref name="isbn0-471-89979-8" /><ref>{{cite book | first = John | last = Tayman | name-list-style = vanc | date = 2006 | url = https://books.google.com/books?id=7SXEMMraz0kC&pg=PA252 | title = The Colony | publisher = Simon and Schuster | page = 252 | isbn = 0-471-89979-8 }}</ref> This breakthrough was reported worldwide, and led to a reduction in the stigma attached to leprosy, and consequent better treatment of patients, at the time still referred to as "inmates", and forbidden from using public transport.<ref name=time>{{cite news |title=Hope for Lepers |url=http://content.time.com/time/magazine/article/0,9171,934821,00.html |newspaper=Time Magazine |date=30 December 1946 |access-date=22 July 2011}}</ref> |
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==Pharmacology== |
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==Pharmacology== |
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Promin is heat-stable and water soluble, and can therefore be heat-sterilized.<ref name=singh2002synthetic>{{cite book |author= Singh, R. |title= Synthetic Drugs |publisher= Mittal Publications |year= 2002 |pages= 291 |isbn= 9788170998310 |url=http://books.google.co.uk/books?id=QkmF7rcBaRIC }}</ref> It can be injected intravenously,<ref name=singh2002synthetic /> and is available in ampules.<ref name="isbn81-8061-283-X">{{cite book |author= |title=Clinical Leprosy |publisher=Jaypee Brothers Medical Publishers (P) Ltd |location= |year=2004 |pages= |isbn=81-8061-283-X |oclc= |doi= |accessdate=}}</ref> |
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Promin is heat-stable and water-soluble, and can therefore be heat-sterilized.<ref name=singh2002synthetic>{{cite book | vauthors = Singh R |title= Synthetic Drugs |publisher= Mittal Publications |year= 2002 |pages= 291 |isbn= 978-81-7099-831-0 |url=https://books.google.com/books?id=QkmF7rcBaRIC }}</ref> It can be injected intravenously,<ref name=singh2002synthetic /> and is available in ampules.<ref name="isbn81-8061-283-X">{{cite book |title=Clinical Leprosy |publisher=Jaypee Brothers Medical Publishers (P) Ltd |year=2004 |isbn=978-81-8061-283-1 }}</ref> |
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Beyond its solubility, however, promin was later found to have no real advantages over the simpler compound dapsone (which is administered in tablet form). Promin and other sulfones can also not be used as substitutes for dapsone when intolerance develops, as this is a general reaction to sulfones, and not specific to dapsone.<ref name=2008PharmText>{{cite book |author= |title=Textbook Of Pharmacology |publisher=Elsevier India Pvt. Ltd. |year=2008 |pages=X-87 |isbn=9788131211588 |url=http://books.google.co.uk/books?id=51ozlZRBvQwC }}</ref> |
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Beyond its solubility, however, promin was later found to have no real advantages over the simpler compound dapsone (which is administered in tablet form). Promin and other sulfones can also not be used as substitutes for dapsone when intolerance develops, as this is a general reaction to sulfones, and not specific to dapsone.<ref name=2008PharmText>{{cite book |title=Textbook Of Pharmacology |publisher=Elsevier India Pvt. Ltd. |year=2008 |pages=X–87 |isbn=978-81-312-1158-8 |url=https://books.google.com/books?id=51ozlZRBvQwC }}</ref> |
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Today, the drugs of choice for treating leprosy are dapsone, ] and ].<ref name=ravina2011evolution /> |
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Today, the drugs of choice for treating leprosy are dapsone, ] and ].<ref name=ravina2011evolution>{{cite book | vauthors = Ravina E, Kubinyi H |title=The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs |publisher=John Wiley & Sons |year=2011 |pages=80 |isbn=978-3-527-32669-3 |url=https://books.google.com/books?id=iDNy0XxGqT8C }}</ref> |
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==References== |
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== References == |
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