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^N
PubChem CID	5312153
ChemSpider	4471583^N
UNII	501Q5EQ1GM
KEGG	D02725^Y
ChEMBL	CHEMBL284178^N
ECHA InfoCard	100.056.503
Chemical and physical data
Formula	C₂₃H₃₁NO₇S
Molar mass	465.56 g/mol
3D model (Jmol)	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^N Key:UQZVCDCIMBLVNR-TWYODKAFSA-N^N
^NY (what is this?)

Sulprostone is an analogue of prostaglandin E2 (PGE₂) that has 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 EP₃receptor 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 inducting 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.

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Wikipedia