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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 of SULPROSTONE

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

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostaglandin E2 receptor EP1 subtype
2
Target ID: P34995
Gene ID: 5731.0
Gene Symbol: PTGER1
Target Organism: Homo sapiens (Human)
Agonist
2752
Prostaglandin E2 receptor EP3 subtype
4
Target ID: P43115|||Q16546
Gene ID: 5733.0
Gene Symbol: PTGER3
Target Organism: Homo sapiens (Human)
Agonist
2752
 1.6 nM [EC50]
PubMed

PubMed

TitleDatePubMed
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
1997 Dec 11
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
1997 Sep
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
[Circulatory arrest following sulprostone administration in postpartum hemorrhage].
1998 Jan 24
[Acute myocardial infarct following sulprostone administration].
1998 Jan 24
Cardiac arrest associated with sulprostone use during caesarean section.
1998 Jun
Spinal EP receptors mediating prostaglandin E2-induced mechanical hyperalgesia, thermal hyperalgesia, and touch-evoked allodynia in rats.
2003 Sep

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 Wed Apr 02 07:48:17 GMT 2025
Edited
by admin
on Wed Apr 02 07:48:17 GMT 2025
Record UNII
501Q5EQ1GM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CP-34,089
Preferred Name English
SULPROSTONE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
sulprostone [INN]
Common Name English
CP-34089
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
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
NCI_THESAURUS C78568
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
WHO-ATC G02AD05
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
Code System Code Type Description
WIKIPEDIA
Sulprostone
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
CAS
60325-46-4
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
NCI_THESAURUS
C84191
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL1472830
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
MERCK INDEX
m10390
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID5049029
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
PUBCHEM
5312153
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
EVMPD
SUB10760MIG
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
DRUG BANK
DB12708
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
INN
4243
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
MESH
C016767
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
DRUG CENTRAL
2538
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
FDA UNII
501Q5EQ1GM
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
SMS_ID
100000092603
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
262-173-0
Created by admin on Wed Apr 02 07:48:17 GMT 2025 , Edited by admin on Wed Apr 02 07:48:17 GMT 2025
PRIMARY
Related Record Type Details
PROSTAGLANDIN E2 RECEPTOR EP1 SUBTYPE
TARGET -> AGONIST
Ki
PROSTAGLANDIN E2 RECEPTOR EP3 SUBTYPE
TARGET -> AGONIST
Ki
PROSTAGLANDIN E2 RECEPTOR EP2 SUBTYPE
OFF TARGET->NON-INHIBITOR
Ki
PROSTAGLANDIN F2-ALPHA RECEPTOR
TARGET -> AGONIST
Ki
PROSTAGLANDIN E2 RECEPTOR EP4 SUBTYPE
TARGET->WEAK AGONIST
Ki
PROSTAGLANDIN E2 RECEPTOR EP3 SUBTYPE
TARGET -> AGONIST
Inhibition of 3H-NE release
EC50
Related Record Type Details
Structure of SULPROSTONE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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