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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 408915067 |
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| verifiedrevid = 458942413 |
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| IUPAC_name = (''Z'')-7-[(1''R'',3''R'')-3-Hydroxy-2-[(''E'',3''R'')-3-hydroxy-4- |
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| IUPAC_name = (Z)-7--5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide |
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| image = Sulprostone.png |
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| image = Sulprostone.png |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = 60325-46-4 |
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| CAS_number = 60325-46-4 |
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| ATC_prefix = G02 |
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| ATC_prefix = G02 |
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| ATC_suffix = AD05 |
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| ATC_suffix = AD05 |
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| PubChem = 6917982 |
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| PubChem = 5312153 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4471583 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 501Q5EQ1GM |
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| UNII = 501Q5EQ1GM |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| smiles = CS(=O)(=O)NC(=O)CCC/C=C\C1((CC1=O)O)/C=C/(COc2ccccc2)O |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C23H31NO7S/c1-32(29,30)24-23(28)12-8-3-2-7-11-19-20(22(27)15-21(19)26)14-13-17(25)16-31-18-9-5-4-6-10-18/h2,4-7,9-10,13-14,17,19-20,22,25,27H,3,8,11-12,15-16H2,1H3,(H,24,28)/b7-2-,14-13+/t17-,19-,20-,22-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = UQZVCDCIMBLVNR-TWYODKAFSA-N |
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| C=23 | H=31 | N=1 | O=7 | S=1 |
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| C=23 | H=31 | N=1 | O=7 | S=1 |
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| molecular_weight = 465.56 g/mol |
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}} |
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'''Sulprostone''' is an analogue of ] (PGE<sub>2</sub>) that has ] activity in assays of rat kidney cells and tissues.<ref name="pmid12829746">{{Cite journal |vauthors=Tamma G, Wiesner B, Furkert J, etal |title=The prostaglandin E2 analogue sulprostone antagonizes vasopressin-induced antidiuresis through activation of Rho |journal=Journal of Cell Science |volume=116 |issue=Pt 16 |pages=3285–94 |date=August 2003 |pmid=12829746 |doi=10.1242/jcs.00640 |hdl=11586/43242 |url=http://jcs.biologists.org/cgi/pmidlookup?view=long&pmid=12829746|doi-access=free }}</ref> There are four known receptors which mediate various but often different cellular and tissue responses to PGE<sub>2</sub>: ], ], ], and ]. Sulprosotone binds to and activates the ] with far greater efficacy than the other PGE<sub>2</sub> receptors and also has the advantage of being relatively resistant, compared with PGE<sub>2</sub>, to becoming metabolically degraded. It is listed as a comparatively weak ] of the prostaglandin EP1 receptor. In all events, this as well as other potent synthetic EP<sub>3</sub> ]s have the realized or potential ability to promote the beneficial effects of prostaglandin EP3 receptor activation.<ref name="pmid27940058">{{cite journal | vauthors = Moreno JJ | title = Eicosanoid receptors: Targets for the treatment of disrupted intestinal epithelial homeostasis | journal = European Journal of Pharmacology | volume = 796 | pages = 7–19 | year = 2017 | pmid = 27940058 | doi = 10.1016/j.ejphar.2016.12.004 | s2cid = 1513449 }}</ref> |
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'''Sulprostone''' is an ]. |
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Sulprostone (as well as other ] receptor agonists) is in use for inducing ] and ending pregnancy after fetal death,<ref name="pmid19960062">{{cite journal | vauthors = Van Mensel K, Claerhout F, Debois P, Keirse MJ, Hanssens M | title = A randomized controlled trial of misoprostol and sulprostone to end pregnancy after fetal death | journal = Obstetrics and Gynecology International | volume = 2009 | pages = 496320 | year = 2009 | pmid = 19960062 | pmc = 2778817 | doi = 10.1155/2009/496320 | doi-access = free }}</ref> for the treatment of severe atonic ] after vaginal delivery,<ref name="pmid21775840">{{cite journal | vauthors = Schmitz T, Tararbit K, Dupont C, Rudigoz RC, Bouvier-Colle MH, Deneux-Tharaux C | title = Prostaglandin E2 analogue sulprostone for treatment of atonic postpartum hemorrhage | journal = Obstetrics and Gynecology | volume = 118 | issue = 2 Pt 1 | pages = 257–65 | year = 2011 | pmid = 21775840 | doi = 10.1097/AOG.0b013e3182255335 | s2cid = 11989341 }}</ref> and for removal of the placenta in patients with retained placenta.<ref name="pmid24833288">{{cite journal | vauthors = Grillo-Ardila CF, Ruiz-Parra AI, Gaitán HG, Rodriguez-Malagon N | title = Prostaglandins for management of retained placenta | journal = The Cochrane Database of Systematic Reviews | issue = 5 | pages = CD010312 | year = 2014 | pmid = 24833288 | doi = 10.1002/14651858.CD010312.pub2 | doi-access = free | pmc = 11055606 }}</ref> Currently, sulprostone along with SC-46275, MB-28767, ONO-AE-248 and other EP<sub>3</sub> receptor agonists are in development as drugs for the possible treatment of stomach ulcers in humans.<ref name="pmid27506873">{{cite journal | vauthors = Markovič T, Jakopin Ž, Dolenc MS, Mlinarič-Raščan I | title = Structural features of subtype-selective EP receptor modulators | journal = Drug Discovery Today | volume = 22 | issue = 1 | pages = 57–71 | year = 2017 | pmid = 27506873 | doi = 10.1016/j.drudis.2016.08.003 | doi-access = free }}</ref> |
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It is an analogue of prostaglandin E2.<ref name="pmid12829746">{{Cite journal|author=Tamma G, Wiesner B, Furkert J, ''et al.'' |title=The prostaglandin E2 analogue sulprostone antagonizes vasopressin-induced antidiuresis through activation of Rho |journal=Journal of cell science |volume=116 |issue=Pt 16 |pages=3285–94 |year=2003 |month=August |pmid=12829746 |doi=10.1242/jcs.00640 |url=http://jcs.biologists.org/cgi/pmidlookup?view=long&pmid=12829746}}</ref> |
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==References== |
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==References== |
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{{Reflist}} |
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{{Reflist|2}} |
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{{Eicosanoids}} |
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{{Oxytocics}} |
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{{Oxytocics}} |
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{{Prostanoidergics}} |
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{{Eicosanoids}} |
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{{Genito-urinary-drug-stub}} |
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{{Genito-urinary-drug-stub}} |
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