Sulprostone

Sulprostone
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	G02AD05 (WHO) ;
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	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−1
3D model (JSmol)	Interactive image;
	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 ; Key:UQZVCDCIMBLVNR-TWYODKAFSA-N ;
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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 (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

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.
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.
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.
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.
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.
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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[pmid12829746-1] 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.

[pmid27940058-2] 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.

[pmid19960062-3] 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.

[pmid21775840-4] 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.

[pmid24833288-5] 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.

[pmid27506873-6] 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.