Sulprostone

Sulprostone is an analogue of prostaglandin E2 (PGE2) that has oxytocic activity in assays of rat kidney cells and tissues.[1] 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 antagonists have the realized or potential ability to promote the beneficial effects of prostaglandin EP3 receptor activation.[2]

Sulprostone
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.056.503
Chemical and physical data
FormulaC23H31NO7S
Molar mass465.56 g·mol−1
3D model (JSmol)
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
InChI
  • InChI=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 N
  • Key:UQZVCDCIMBLVNR-TWYODKAFSA-N N
 NY (what is this?)  (verify)

Sulprostone (as well as other prostanoids receptor agonists) is in use for inducting medical abortion and ending pregnancy after fetal death,[3] for the treatment of severe atonic postpartum hemorrhage after vaginal delivery,[4] and for removal of the placenta in patients with retained placenta.[5] 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.[6]

References
  1. Tamma G, Wiesner B, Furkert J, et al. (August 2003). "The prostaglandin E2 analogue sulprostone antagonizes vasopressin-induced antidiuresis through activation of Rho". Journal of Cell Science. 116 (Pt 16): 3285–94. doi:10.1242/jcs.00640. PMID 12829746.
  2. Moreno JJ (2017). "Eicosanoid receptors: Targets for the treatment of disrupted intestinal epithelial homeostasis". European Journal of Pharmacology. 796: 7–19. doi:10.1016/j.ejphar.2016.12.004. PMID 27940058. S2CID 1513449.
  3. Van Mensel K, Claerhout F, Debois P, Keirse MJ, Hanssens M (2009). "A randomized controlled trial of misoprostol and sulprostone to end pregnancy after fetal death". Obstetrics and Gynecology International. 2009: 496320. doi:10.1155/2009/496320. PMC 2778817. PMID 19960062.
  4. Schmitz T, Tararbit K, Dupont C, Rudigoz RC, Bouvier-Colle MH, Deneux-Tharaux C (2011). "Prostaglandin E2 analogue sulprostone for treatment of atonic postpartum hemorrhage". Obstetrics and Gynecology. 118 (2 Pt 1): 257–65. doi:10.1097/AOG.0b013e3182255335. PMID 21775840. S2CID 11989341.
  5. Grillo-Ardila CF, Ruiz-Parra AI, Gaitán HG, Rodriguez-Malagon N (2014). "Prostaglandins for management of retained placenta". The Cochrane Database of Systematic Reviews (5): CD010312. doi:10.1002/14651858.CD010312.pub2. PMID 24833288.
  6. Markovič T, Jakopin Ž, Dolenc MS, Mlinarič-Raščan I (2017). "Structural features of subtype-selective EP receptor modulators". Drug Discovery Today. 22 (1): 57–71. doi:10.1016/j.drudis.2016.08.003. PMID 27506873.
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