SULPROSTONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H31NO7S
Molecular Weight	465.56
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(=O)(=O)NC(=O)CCC\C=C/C[C@@H]1[C@@H](\C=C\[C@@H](O)COC2=CC=CC=C2)[C@H](O)CC1=O

InChI

InChIKey=UQZVCDCIMBLVNR-TWYODKAFSA-N

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

HIDE SMILES / InChI

Molecular Formula	C23H31NO7S
Molecular Weight	465.56
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19960062 | https://www.ncbi.nlm.nih.gov/pubmed/21775840 | https://www.ncbi.nlm.nih.gov/pubmed/27506873

Sulprostone, a P1/EP3 prostanoid receptor agonist, participated in trials for ending pregnancy after fetal death between 14 and 42 weeks gestation. This drug was also studied for treating severe atonic postpartum hemorrhage after vaginal delivery and for management of retained placenta. Moreover, recent investigations have revealed, that sulprostone could be a valuable drug candidate in the therapy of many pathophysiological states, including ulcerative colitis, glaucoma, and bone healing.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin E2 receptor EP1 subtype 2 Target ID: P34995 Gene ID: 5731.0 Gene Symbol: PTGER1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27940058 \| https://www.ncbi.nlm.nih.gov/pubmed/8832065	Agonist 2678
Prostaglandin E2 receptor EP3 subtype 4 Target ID: P43115\|\|\|Q16546 Gene ID: 5733.0 Gene Symbol: PTGER3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27940058 \| https://www.ncbi.nlm.nih.gov/pubmed/8140121	Agonist 2678		1.6 nM [EC50]

PubMed

Title	Date	PubMed
Convulsions in epileptic women after administration of prostaglandin E2 derivative.	1990 Nov 3	1978020
[Prolonged angina after the administration of a synthetic PGE2 derivative].	1993 Jul	8405838
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.	1997 Dec 11	9537820
Pharmacology of [3H]prostaglandin E1/[3H]prostaglandin E2 and [3H]prostaglandin F2alpha binding to EP3 and FP prostaglandin receptor binding sites in bovine corpus luteum: characterization and correlation with functional data.	1998 Aug	9694973
[Acute myocardial infarct following sulprostone administration].	1998 Jan 24	9557026
Arachidonic acid and PGE2 regulation of hepatic lipogenic gene expression.	1999 Jun	10357836
Developmental regulation of endothelial nitric oxide synthase in cerebral vessels of newborn pig by prostaglandin E(2).	1999 Nov	10525081
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.	2000 Jan 17	10634944
Trophic effects of the cyclooxygenase-2 product prostaglandin E(2) in cardiac myocytes.	2002 Feb	11882577
Complete recovery after 2 h of cardiopulmonary resuscitation following high-dose prostaglandin treatment for atonic uterine haemorrhage.	2002 Oct	12366517
[Effect of guizhi tang and its active components on the fever induced by EP3 agonist].	2003 Nov	15615417
Acute myocardial infarction due to vasospasm induced by prostaglandin.	2009 Oct	19812811

Sample Use Guides

In Vivo Use Guide

at 1 μg/min (1 ampoule of 500 μg sulprostone in 250 mL NaCl 0.9%, at 30 mL/min) for 36 hours or until fetal and placental expulsion

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:23:23 UTC 2023` Edited by `admin` on `Sat Dec 16 16:23:23 UTC 2023`
Record UNII	501Q5EQ1GM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULPROSTONE

Official Name

English

sulprostone [INN]

Common Name

English

CP-34089

Code

English

CP-34,089

Code

English

SULPROSTONE [USAN]

Common Name

English

SULPROSTONE [MART.]

Common Name

English

5-HEPTENAMIDE, 7-(3-HYDROXY-2-(3-HYDROXY-4-PHENOXY-1-BUTENYL)-5-OXOCYCLOPENTYL)-N-(METHYLSULFONYL)-, (1R-(1A(Z),2B(1E,3R*),3A))-

Systematic Name

English

ZK-57+G1872671

Code

English

ZK 57 671

Code

English

SULPROSTONE [MI]

Common Name

English

Sulprostone [WHO-DD]

Common Name

English

(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(E)-(3R)-(3-hydroxy-4-phenoxy-1-butenyl)]-5-oxocyclopentyl]-N-(methylsulfonyl)-5-heptenamide

Systematic Name

English

ZK-57671

Code

English

Classification Tree Code System Code

WHO-VATC

QG02AD05