Sulprostone: Difference between revisions

{{Short description|Chemical compound}}

| verifiedrevid = 458942413

| IUPAC_name = (Z)-7-[(1R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 60325-46-4

| PubChem = 5312153

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4471583

| UNII_Ref = {{fdacite|correct|FDA}}

| ChEMBL = 284178

<!--Chemical data-->

| smiles = CS(=O)(=O)NC(=O)CCC/C=C\C[C@@H]1[C@H]([C@@H](CC1=O)O)/C=C/[C@H](COc2ccccc2)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = UQZVCDCIMBLVNR-TWYODKAFSA-N

'''Sulprostone''' is an analogue of [[prostaglandin E2]] (PGE₂) that has [[oxytocic]] 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 PGE₂: [[prostaglandin EP1 receptor]], [[prostaglandin EP2 receptor]], [[prostaglandin EP3 receptor]], and [[prostaglandin EP4 receptor]]. Sulprosotone binds to and activates the [[prostaglandin EP3 receptor]] with far greater efficacy than the other PGE₂ receptors and also has the advantage of being relatively resistant, compared with PGE₂, to becoming metabolically degraded. It is listed as a comparatively weak [[receptor agonist]] of the prostaglandin EP1 receptor. In all events, this as well as other potent synthetic EP₃ [[receptor antagonist]]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>

Sulprostone (as well as other [[prostanoids]] receptor agonists) is in use for inducing [[medical abortion#side effects|medical abortion]] 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 [[postpartum hemorrhage]] 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 EP₃ 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>

{{Reflist|2}}

{{Oxytocics}}

{{Prostanoidergics}}

[[Category:Cyclopentanes]]

[[Category:Uterotonics]]

{{Genito-urinary-drug-stub}}