Misplaced Pages

Sulprostone

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	G02AD05 (WHO)
Identifiers
IUPAC name (Z)-7--5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide
CAS Number	60325-46-4
PubChem CID	5312153
ChemSpider	4471583
UNII	501Q5EQ1GM
KEGG	D02725
ChEMBL	ChEMBL284178
CompTox Dashboard (EPA)	DTXSID5049029
ECHA InfoCard	100.056.503
Chemical and physical data
Formula	C23H31NO7S
Molar mass	465.56 g·mol
3D model (JSmol)	Interactive image
SMILES CS(=O)(=O)NC(=O)CCC/C=C\C1((CC1=O)O)/C=C/(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 Key:UQZVCDCIMBLVNR-TWYODKAFSA-N
(what is this?)  (verify)

Sulprostone is an analogue of prostaglandin E2 (PGE₂) that has oxytocic activity in assays of rat kidney cells and tissues. 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.

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

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. hdl:11586/43242. 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. PMC 11055606. 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.

This drug article relating to the genito-urinary system is a stub. You can help Misplaced Pages by expanding it.

• v
• t
• e

• Eicosanoids
• Uterotonics
• Acylsulfonamides
• Cyclopentanes
• Genito-urinary system drug stubs