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

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
[Cardio-circulatory arrest with mifepristone sulprostone combination for pregnancy interruption].	1991 Sep-Oct	1754984
[Cardiocirculatory arrest after administration of combined mifepristone (Mifegyne) and sulprostone (Nalador) for induced abortion. Possible role of coronary vasospasm].	1992 Jan	1550429
[Prolonged angina after the administration of a synthetic PGE2 derivative].	1993 Jul	8405838
Cardiac arrest associated with sulprostone use during caesarean section.	1998 Jun	9619226
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.	2002 Apr	11999132
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
Spinal EP receptors mediating prostaglandin E2-induced mechanical hyperalgesia, thermal hyperalgesia, and touch-evoked allodynia in rats.	2003 Sep	14622681

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

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