Page last updated: 2024-11-11

sulprostone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

sulprostone: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5312153
CHEMBL ID1472830
CHEBI ID135755
SCHEMBL ID94842
MeSH IDM0066967

Synonyms (47)

Synonym
(z)-7-[(1r,2r,3r)-3-hydroxy-2-[(e,3r)-3-hydroxy-4-(phenoxy)but-1-enyl]-5-oxocyclopentyl]-n-methylsulfonylhept-5-enamide
gtpl1919
cp-34089
zk-57671
sulprostone (usan/inn)
D02725
16-phenoxy-omega-17,18,19,20-tetranor pge-2 methylsulfonylamide
shb 286
cp 34089
5-heptenamide, 7-(3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocyclopentyl)-n-(methylsulfonyl)-, (1r-(1alpha(z),2beta(1e,3r*),3alpha))-
sulprostone [usan:inn]
16-phenoxy-omega-17,18,19,20-tetranor prostaglandin e2 methylsulfonylamide
zk 57671
sulprostona [inn-spanish]
16-phenoxy-17,18,19,20 tetranor prostaglandin e(sub 2) methyl sulfonylamide
sulprostonum [inn-latin]
einecs 262-173-0
(z)-7-((1r,2r,3r)-3-hydroxy-2-((e)-(3r)-(3-hydroxy-4-phenoxy-1-butenyl))-5-oxocyclopentyl)-n-(methylsulfonyl)-5-heptenamide
sulprostone
CHEBI:135755
CHEMBL1472830
sulprostona
unii-501q5eq1gm
cp-34,089
5-heptenamide, 7-(3-hydroxy-2-(3-hydroxy-4-phenoxy-1-butenyl)-5-oxocyclopentyl)-n-(methylsulfonyl)-, (1r-(1a(z),2b(1e,3r*),3a))-
501q5eq1gm ,
sulprostonum
zk 57 671
(z)-7-[(1r,2r,3r)-3-hydroxy-2-[(e)-(3r)-(3-hydroxy-4-phenoxy-1-butenyl)]-5-oxocyclopentyl]-n-(methylsulfonyl)-5-heptenamide
zk-57+g1872671
sulprostone [who-dd]
sulprostone [inn]
sulprostone [mart.]
sulprostone [usan]
sulprostone [mi]
SCHEMBL94842
(5z)-7-[(1r,2r,3r)-3-hydroxy-2-[(1e,3r)-3-hydroxy-4-buten-1-yl]-5-oxocyclopentyl]-n-(methylsulfonyl)-5-heptenamide
AKOS024457401
HMS3648J09
HY-19360
CS-0015437
DB12708
SR-01000946436-1
sr-01000946436
Q410556
BRD-K14551499-001-01-7
sulprostone in 5mg/ml methyl acetate

Research Excerpts

Overview

Sulprostone is a prostaglandin with selective activity in the uterus. It is a tissue-specific PGE2-derivative with high abortifacient activity.

ExcerptReferenceRelevance
""Sulprostone: is a prostaglandin with selective activity in the uterus."( [Induction of abortion during the second and third trimester of pregnancy with sulprostone (author's transl)].
Heinzl, S; Winkler, C, 1981
)
1.11
"Sulprostone is a PG with selective activity in the uterus."( [Induction of abortion during the second and third trimester of pregnancy with sulprostone (author's transl)].
Heinzl, S; Winkler, C, 1981
)
1.11
"Sulprostone is a tissue-specific PGE2-derivative with high abortifacient activity in various species including man. "( Receptor binding in various tissues of PGE2, PGF2 alpha and sulprostone, a novel PGE2-derivative.
Prior, G; Schillinger, E; Speckenbach, A; Wellershoff, S, 1979
)
1.94

Effects

ExcerptReferenceRelevance
"Sulprostone has been demonstrated to be effective as a parenteral abortifacient, but not as a vaginal suppository. "( Early pregnancy-abortion model using sulprostone.
Blattner, P; Fayemi, A; Fleischer, A; Jagani, N; Schulman, H, 1982
)
1.98

Actions

ExcerptReferenceRelevance
"Sulprostone induced an increase in both the frequency and amplitude of contractions, reaching a maximum 12 hours after injection and fading out after 24 hours in vehicle-treated animals."( Effects of nomegestrol acetate on spontaneous and sulprostone-induced uterine contractions in pregnant cynomolgus monkeys monitored by telemetry.
Cabrol, D; Carbonne, B; Clerget, MS; Germain, G, 1998
)
1.27

Treatment

ExcerptReferenceRelevance
"Sulprostone (pretreatment or continuous infusion) had no effect on any of the haemodynamic parameters measured."( Sulprostone-induced reduction of myocardial infarct size in the rabbit by activation of ATP-sensitive potassium channels.
Hide, EJ; Thiemermann, C, 1996
)
2.46

Compound-Compound Interactions

ExcerptReferenceRelevance
" In group IV, 2 mg of the analogue was combined with oxytocin."( Termination of second trimester pregnancy with intraamniotic administration of 16-phenoxy-omega-tetranor-PgE2-methylsulfonamide (SHB 286) alone and combined with oxytocin and calcium gluconate.
Haspels, AA; van den Bergh, AS, 1978
)
0.26
" In Group 4, 2 mg of the analog was combined with oxytocin."( Termination of second trimester pregnancy with intraamniotic administration of 16-phenoxy-omega-tetranor-PgE2-methylsulfonamide (SHB 286) alone and combined with oxytocin and calcium gluconate.
Haspels, AA; van den Bergh, AS, 1978
)
0.26

Dosage Studied

In the 2nd and 3rd trimesters, Sulprostone was administered either by intravenous (mean dosage, 925 mcg), intragluteal or extraamniotic route. Intracervical administration of Sulpro stone (25-100 micrograms) 14-16 h before surgery required the lowest dosage and had no side effects.

ExcerptRelevanceReference
" This study compares 2 dosage regimens of intramuscular administration."( Clinical trials of intramuscular sulprostone for second trimester abortion.
Intaraprasert, S; Sugkraroek, P, 1988
)
0.56
" The 100-micrograms dosage proved to be the most effective method in nulliparae, achieving a mean free patency (i."( Preoperative cervical priming by intracervical application of a new sulprostone gel.
Dennemark, N; Gödicke, HD; Rath, W, 1985
)
0.5
" The dosage was lowest on extra-amnial administration (50 micrograms on the average), and highest on intramuscular application with a mean of 1760 micrograms."( [16-Phenoxy-prostaglandin-E2 for inducing abortion in intact and complicated pregnancy].
Lichtenegger, W, 1984
)
0.27
" Intracervical administration of Sulprostone (25-100 micrograms) 14-16 h before surgery required the lowest dosage and had no side effects."( Sulprostone for preoperative cervical dilatation in primigravidae scheduled for late first trimester termination of pregnancy.
Fylling, P; Jerve, F, 1983
)
1.99
" Intracervical administration of Sulprostone (25-100 mcg) 14-16 hours prior to surgery required the lowest dosage and had no side effects."( Sulprostone for preoperative cervical dilatation in primigravidae scheduled for late first trimester termination of pregnancy.
Fylling, P; Jerve, F, 1983
)
1.99
" In the second and third trimester Sulprostone was administered by the intravenous (mean dosage 925 mcg), the intragluteal (mean dosage 540 mcg) or the extra-amniotic (mean dosage 660 mcg) route."( [Clinical experience with sulprostone (author's transl)].
Bichler, A; Brabec, W; Dapunt, O, 1981
)
0.84
" In the 2nd and 3rd trimesters, Sulprostone was administered either by intravenous (mean dosage, 925 mcg), intragluteal (mean dosage, 540 mcg), or the extraamniotic (mean dosage 660 mcg) routes."( [Clinical experience with sulprostone (author's transl)].
Bichler, A; Brabec, W; Dapunt, O, 1981
)
0.84
" The drug was administered in a 500 mcg dosage every 4 hours up to a maximum of 6 injections."( First and midtrimester abortion with intramuscular injections of sulprostone.
Ballard, CA, 1981
)
0.5
" It appears that the dosage schedules of PGE2 and SHB 286 were equally effective in inducing labor."( Intravenous prostaglandin E2 and 16-phenoxy prostaglandin E2 methyl sulfonylamide for induction of fetal death in utero.
Baumgarten, K; Gruber, WS, 1980
)
0.26
" ATtempts have been made to shorten the induction-abortion interval and to lower dosage of the prostaglandins in order to reduce the incidence of side effects."( Termination of second trimester pregnancy with sulprostone and mifepristone: a randomized double-blind placebo-controlled trial.
Ho, PC; Ma, HK, 1993
)
0.54
" However, it was not possible to generate dose-response curves whereas significant correlations of uptake values with T50 values were found."( The effect of oxytocin, prostaglandin E2 and acetylsalicylic acid on flow distribution and on the transfer of alanine, glucose and water in isolated perfused guinea pig placentae.
Goepel, E; Niemax, K; Rybakowski, C; Schröder, HJ, 2000
)
0.31
" Dose-response relations for PGE2 and subtype receptors EP1/EP3 (sulprostone), EP2 (butaprost), and EP4 (1-OH PGE1) were assessed by cumulated doses of single agonists."( Duodenal secretion in humans mediated by the EP4 receptor subtype.
Bindslev, N; Hansen, MB; Larsen, R, 2005
)
0.57
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
prostanoidThe family of natural prostaglandins and prostaglandin-like compounds including prostacyclins and thromboxanes.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency70.79460.010039.53711,122.0200AID1479
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency2.51190.00798.23321,122.0200AID2551
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID76906Percent protection against histamine-induced bronchoconstriction in conscious guinea pig.1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: tissue-selective, uterine stimulants.
AID187316Relative potency (50 ug/kg) for inhibition of pentagastrin-stimulated gastric acid secretion in anesthetized rats1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: tissue-selective, uterine stimulants.
AID77488Relative ability to cause abortion in conscious guinea pigs compared to PGE-2.1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: tissue-selective, uterine stimulants.
AID118203Relative potency of compound versus PGE-2 (0.3-3.0mg/mL, iv) for induction of diarrhoea in conscious mice1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: tissue-selective, uterine stimulants.
AID58906Compound versus PGE-2 (0.1 ug/kg, iv) was tested for effects on blood pressure in anesthetized dogs; Depressor1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: tissue-selective, uterine stimulants.
AID77499Relative spasmogenic potency in an in vitro guinea pig uteri assay.1981Journal of medicinal chemistry, Nov, Volume: 24, Issue:11
N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: tissue-selective, uterine stimulants.
AID1346343Human EP3 receptor (Prostanoid receptors)1998The Journal of pharmacology and experimental therapeutics, Aug, Volume: 286, Issue:2
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.
AID1346345Rat EP1 receptor (Prostanoid receptors)1997European journal of pharmacology, Dec-11, Volume: 340, Issue:2-3
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
AID1346372Mouse EP1 receptor (Prostanoid receptors)1997British journal of pharmacology, Sep, Volume: 122, Issue:2
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
AID1346408Human EP1 receptor (Prostanoid receptors)2002The Journal of pharmacy and pharmacology, Apr, Volume: 54, Issue:4
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
AID1346343Human EP3 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346408Human EP1 receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346336Mouse EP3 receptor (Prostanoid receptors)1997British journal of pharmacology, Sep, Volume: 122, Issue:2
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.
AID1346394Human FP receptor (Prostanoid receptors)2000Biochimica et biophysica acta, Jan-17, Volume: 1483, Issue:2
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
AID1346396Rat EP3 receptor (Prostanoid receptors)1997European journal of pharmacology, Dec-11, Volume: 340, Issue:2-3
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (422)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990138 (32.70)18.7374
1990's131 (31.04)18.2507
2000's97 (22.99)29.6817
2010's51 (12.09)24.3611
2020's5 (1.18)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 45.89

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index45.89 (24.57)
Research Supply Index6.21 (2.92)
Research Growth Index4.33 (4.65)
Search Engine Demand Index73.40 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (45.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials58 (13.15%)5.53%
Reviews16 (3.63%)6.00%
Case Studies29 (6.58%)4.05%
Observational0 (0.00%)0.25%
Other338 (76.64%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
[NCT00206193]0 participants ObservationalRecruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]