Page last updated: 2024-12-10

gemeprost

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Description

gemeprost: used for preoperative dilation of cervix before surgical abortion; RN given refers to (2E,11alpha,13E,15R)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5282237
CHEMBL ID1908315
CHEBI ID135626
SCHEMBL ID343075
MeSH IDM0075715

Synonyms (52)

Synonym
cervagem
preglandin
gemeprost
sc-37681
einecs 264-775-9
methyl (e)-7-((1r,2r,3r)-3-hydroxy-2-((e)-(3r)-3-hydroxy-4,4-dimethyl-1-octenyl)-5-oxocyclopentyl)-2-heptenoate
(2e,11alpha,13e,15r)-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oic acid, methyl ester
carprost
16,16-dimethyl-trans-delta(sup 2)-prostaglandin e1 methyl ester
16,16-dimethyl-trans-delta-2-prostaglandin e1 methyl ester
16,16-dimethyl-trans-delta-2-pge1 methyl ester
ono 802
gemeprost [usan:inn:ban:jan]
trans-2,3-didehydro-16,16-dimethyl pge1 methyl ester
sc 37681
gemeprostum [inn-latin]
prosta-2,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, methyl ester, (2e,11alpha,13e,15r)-
methyl 16,16-dimethyl-trans-delta-2-pge1
gemoprost
preglandin (tn)
gemeprost (jan/usan/inn)
D02073
64318-79-2
CHEBI:135626
methyl (e)-7-[(1r,2r,3r)-3-hydroxy-2-[(e,3r)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-oxocyclopentyl]hept-2-enoate
unii-45kzb1fols
45kzb1fols ,
gemeprostum
CHEMBL1908315
u-37026
prosta-2,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-oxo-, methyl ester, (2e,11.alpha.,13e,15r)-
gemeprost [mi]
gemeprost [mart.]
gemeprost [usan]
gemeprost [jan]
methyl (e)-7-[(1r,2r,3r)-3-hydroxy-2-[(e)-(3r)-3-hydroxy-4,4-dimethyl-1-octenyl]-5-oxocyclopentyl]-2-heptenoate
gemeprost [who-dd]
gemeprost [inn]
SCHEMBL343075
J-502050
(e)-methyl 7-(3-hydroxy-2-((e)-3-hydroxy-4,4-dimethyloct-1-en-1-yl)-5-oxocyclopentyl)hept-2-enoate
AC-31144
DB08964
DTXSID40895073
Q2760221
methyl (e)-7-((1r,2r,3r)-3-hydroxy-2-((r,e)-3-hydroxy-4,4-dimethyloct-1-en-1-yl)-5-oxocyclopentyl)hept-2-enoate
A854966
(e)-methyl 7-((1r,2r,3r)-3-hydroxy-2-((r,e)-3-hydroxy-4,4-dimethyloct-1-en-1-yl)-5-oxocyclopentyl)hept-2-enoate
methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(3r)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-oxocyclopentyl]hept-2-enoate
methyl (2e)-7-[(1r,2r,3r)-3-hydroxy-2-[(1e,3r)-3-hydroxy-4,4-dimethyloct-1-en-1-yl]-5-oxocyclopentyl]hept-2-enoate
EN300-22411584
AKOS040744718

Research Excerpts

Overview

Gemeprost pessaries are an effective alternative to the more invasive methods previously used for induction of second-trimester termination.

ExcerptReferenceRelevance
"Gemeprost pessaries are an effective alternative to the more invasive methods previously used for the induction of second-trimester termination."( Second-trimester termination with 16,16 dimethyl-PGE1-methyl ester (gemeprost), compared with a regimen that included intra-amniotic PGF2 alpha and hypertonic saline.
Healy, DL; Lolatgis, N; Mamers, PM; Morris, ND; Oldham, J; Renou, PM; Waldron, KW, 1990
)
1.24

Effects

Gemeprost (Cervagem) has been used widely compared with Misoprostol (Cytotec) alone in second trimester pregnancy termination. Gemeprost has profound effects on utero-placental circulation in the first trimester.

ExcerptReferenceRelevance
"Gemeprost has been reported to be associated with acute cardiovascular accidents in a few cases, but no adverse cardiovascular events have been reported with misoprostol."( Acute coronary artery vasospasm associated with misoprostol for termination of pregnancy.
Bennasar, M; Berge, R; Eixarch, E; Font, C; Illa, M; Palacio, M, 2010
)
1.08
"Gemeprost (Cervagem) has been used widely compared with Misoprostol (Cytotec) alone in second trimester pregnancy termination. "( Misoprostol (alone) in second trimester terminations of pregnancy: as effective as Gemeprost?
Abdullah, HS; Jamil, MA; Nor Azlin, MI; Zainul Rashid, MR, 2006
)
2
"Gemeprost has profound effects on utero-placental circulation in the first trimester and can induce embryonic/fetal bradycardia and sometimes embryonic/fetal demise. "( Effect of a prostaglandin E1 analogue (gemeprost) on uterine and luteal circulation in normal first trimester pregnancies. A Doppler velocimetry study.
Laurini, R; Marsál, K; Olofsson, P; Sladkevicius, P; Söderberg, H; Valentin, L, 1995
)
2

Actions

ExcerptReferenceRelevance
"Gemeprost produces an increase in uterine contractility which may be additional to cervical softening properties and which may be responsible for the adverse effects of pain and bleeding experienced by some women prior to termination."( Intra-amniotic pressures following vaginal gemeprost prior to first and second trimester termination of pregnancy.
Fisk, NM; Robson, SC; Ronderos-Dumit, D; Spencer, JA; Tannirandorn, Y, 1992
)
1.27

Treatment

Gemeprost treatment was more like physiological labor than was Sulprostone treatment. Pretreatment with gemeprost resulted in abdominal pain in 73% of women and vaginal bleeding in 32% compared with 3% and 0%, respectively, after isosorbide mononitrate.

ExcerptReferenceRelevance
"Gemeprost treatment increased free passibility (the size of the largest dilator which could be passed without encountering resistance) (P < 0.01), reduced the forces required to dilate the cervix (P < 0.01) reduced blood loss (P < 0.05), reduced the collagen concentration (P < 0.01) and was associated with a modest neutrophil influx (P < 0.02) as compared to placebo."( Gemeprost-induced cervical ripening: histological and biophysical effects.
Calder, AA; Greer, IA; Millar, M, 1992
)
2.45
"Gemeprost treatment was more like physiological labor than was Sulprostone treatment."( Uterine motility and cervical ripening in second trimester elective abortion by two different PGE analogues.
Albano, G; Catalano, D; Civetta, A; Di Lieto, A; Ferrara, R; Fimiani, R; Paladini, A; Pontillo, M; Uccello, N, 1991
)
0.9
"Pretreatment with gemeprost resulted in abdominal pain in 73% of women and vaginal bleeding in 32% compared with 3% and 0%, respectively, after isosorbide mononitrate, whereas, more women developed headache after isosorbide mononitrate (27%) than after gemeprost (0%)."( Randomised trial of nitric oxide donor versus prostaglandin for cervical ripening before first-trimester termination of pregnancy.
Cameron, IT; Greer, IA; Howat, RC; Ledingham, M; Lunan, CB; Norman, JE; Thomson, AJ, 1998
)
0.62

Pharmacokinetics

ExcerptReferenceRelevance
" In amniotic fluid the half-life was between 31 and 37 hours."( Pharmacokinetics of prostaglandins.
Bygdeman, M, 2003
)
0.32

Compound-Compound Interactions

Two regimens of the prostaglandin E1 analogue, gemeprost, in combination with mifepristone were compared in a randomised trial for termination of pregnancy between 12-19 weeks. Findings are presented from a prospective randomized study conducted to compare the efficacy of misoprostol withgemeprost.

ExcerptReferenceRelevance
" A randomised study was carried out to determine the efficacy of mifepristone and dilapan in combination with gemeprost for second trimester termination between 12-18 weeks' gestation."( A study of gemeprost alone, dilapan or mifepristone in combination with gemeprost for the termination of second trimester pregnancy.
Baird, DT; Thong, KJ, 1992
)
0.89
"Abortion was attempted in 39 women in early pregnancy (less than 56 days amenorrhea) with the progesterone antagonist RU486 alone (150 mg per day for 4 days) or in combination with a PG analogue, 16,16-dimethyl-trans-delta 2-PGE1 (Gemeprost) in the form of a 1 mg vaginal pessary."( Therapeutic abortion in early pregnancy with antiprogestogen RU486 alone or in combination with prostaglandin analogue (gemeprost).
Baird, DT; Cameron, IT; Michie, AF, 1986
)
0.66
"Abortion was attempted in 39 women in early pregnancy (less than 56 days amenorrhea) with the progesterone antagonist RU486 alone (150 mg per day for 4 days) or in combination with a PG analogue, 16,16-dimethyl-trans-delta2-PGE1 (Gemeprost) in the form of a 1 mg vaginal pessary."( Therapeutic abortion in early pregnancy with antiprogestogen RU486 alone or in combination with prostaglandin analogue (gemeprost).
Baird, DT; Cameron, IT; Michie, AF, 1986
)
0.66
"Mifepristone (600 mg) in combination with a prostaglandin has been demonstrated to be a safe, acceptable alternative to vacuum aspiration for induction of abortion in the first 9 weeks of pregnancy."( Randomized trial of misoprostol and cervagem in combination with a reduced dose of mifepristone for induction of abortion.
Baird, DT; Sukcharoen, N; Thong, KJ, 1995
)
0.29
" The authors' previous research had indicated there is no difference in clinical efficacy between 200 mg and 600 mg (standard dose) of mifepristone in combination with 600 mcg of misoprostol."( Randomized trial of misoprostol and cervagem in combination with a reduced dose of mifepristone for induction of abortion.
Baird, DT; Sukcharoen, N; Thong, KJ, 1995
)
0.29
"A prospective randomized study was conducted to compare the efficacy of misoprostol with gemeprost when combined with mifepristone for termination of second trimester pregnancy."( Misoprostol is as effective as gemeprost in termination of second trimester pregnancy when combined with mifepristone: a randomised comparative trial.
Chan, YF; Ho, PC; Lau, W, 1996
)
0.8
"Findings are presented from a prospective randomized study conducted to compare the efficacy of misoprostol with gemeprost when combined with mifepristone to terminate second trimester pregnancy."( Misoprostol is as effective as gemeprost in termination of second trimester pregnancy when combined with mifepristone: a randomised comparative trial.
Chan, YF; Ho, PC; Lau, W, 1996
)
0.79
"Two regimens of the prostaglandin E1 analogue, gemeprost, in combination with mifepristone were compared in a randomised trial for termination of pregnancy between 12-19 weeks."( A randomised study of two doses of gemeprost in combination with mifepristone for induction of abortion in the second trimester of pregnancy.
Baird, DT; Lynch, P; Thong, KJ, 1996
)
0.83
"Two regimens of prostaglandin E1 analogue, gemeprost, in combination with mifepristone were compared in a randomized trial for termination of pregnancy at 12-19 weeks."( A randomised study of two doses of gemeprost in combination with mifepristone for induction of abortion in the second trimester of pregnancy.
Baird, DT; Lynch, P; Thong, KJ, 1996
)
0.83
"Mifepristone in combination with prostaglandin has been used since 1988 for induction of early abortion."( Interruption of early pregnancy with mifepristone in combination with gemeprost.
Brooks, L; Grinsted, J; Grinsted, L; Jacobsen, JD; Nielsen, SP; Sandstrøm, O; Schantz, A, 1999
)
0.54
"Gemeprost and misoprostol are two of the most widely used prostaglandins in combination with mifepristone for medical abortion in early pregnancy."( Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation.
Baird, DT; Bartley, J; Brown, A; Elton, R, 2001
)
1.98
"To compare the effectiveness of gemeprost and misoprostol as prostaglandins used in combination with mifepristone for induction of mid-trimester termination."( A randomised study of misoprostol and gemeprost in combination with mifepristone for induction of abortion in the second trimester of pregnancy.
Baird, DT; Bartley, J, 2002
)
0.87
"We aimed to assess the efficacy and safety of midtrimester termination of pregnancy using gemeprost in combination with laminaria in women who had previously undergone cesarean section and in women who had not."( Midtrimester termination of pregnancy using gemeprost in combination with laminaria in women who have previously undergone cesarean section.
Abe, K; Fujiki, Y; Hamada, H; Nakamura, Y; Obata-Yasuoka, M; Ogura, T; Shimura, R; Takeshima, K; Toyoda, M; Watanabe, H; Yagi, H; Yoshikawa, H, 2009
)
0.84
"Medical regimens using mifepristone in combination with prostaglandins have been widely available for women undergoing termination of pregnancy (TOP) at 10-16 weeks' gestation in China."( Mifepristone in combination with prostaglandins for termination of 10-16 weeks' gestation: a systematic review.
Chen, QJ; Cheng, LN; Hong, QQ; Hou, SP; Huang, YM; Meads, C; Zhu, HP, 2011
)
0.37
"In combination with osmotic dilators and gemeprost, gestational age and parity are independent factors that affected the induction to abortion interval of second-trimester medical abortion."( Effects of parity and gestational age on second-trimester induction-abortion interval in combination with osmotic dilators and gemeprost.
Kai, K; Karakida, S; Kono, M; Narahara, H; Nishida, Y; Sasaki, T; Togo, K; Tsuno, A, 2012
)
0.85

Dosage Studied

ExcerptRelevanceReference
" Further studies on dosage and treatment protocols would be justified."( The efficacy of oral Mifepristone (RU 38,486) with a prostaglandin E1 analog vaginal pessary for the termination of early pregnancy: complications and patient acceptability.
Ferguson, J; Hill, NC; MacKenzie, IZ, 1990
)
0.28
" Water consumption was increased both during and after the dosing period for the mid and high dose dams."( Two-phase teratology study with the synthetic prostaglandin ONO-802 given intravaginally to rats.
de la Iglesia, FA; Fitzgerald, JE; Humphrey, RR; Petrere, JA; Sakowski, R, 1984
)
0.27
" Additional studies with larger sample sizes are recommended to determine the optimal misoprostol dosage and frequency of administration."( Comparative study of intravaginal misoprostol with gemeprost as an abortifacient in second trimester missed abortion.
Eng, NS; Guan, AC, 1997
)
0.55
" A short regimen of gemeprost was used: over a 24-h period, 1 mg vaginal gemeprost was given every 3 h up to three doses after which, if abortion did not occur, another course at the same dosage schedule was administered up to 4 days."( A short-scheme protocol of gemeprost for midtrimester termination of pregnancy with uterine scar.
Pontrelli, G; Santamato, S; Scioscia, M; Selvaggi, L; Vimercati, A, 2005
)
0.95
"Second trimester TOP on scarred uterus warrants careful usage of abortifacient with minimal cumulative dosage and should be carried out in early second trimester gestation whenever feasible."( Incidence and contributing factors for uterine rupture in patients undergoing second trimester termination of pregnancy in a large tertiary hospital - a 10-year case series.
Daniel Seow Choon, K; Eek Chaw, T; Hester Chang Qi, QL; Kok Hian, T; Mor Jack, NG; Wan Shi, T, 2018
)
0.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aliphatic alcoholAn alcohol derived from an aliphatic compound.
[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]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID227700Anticonvulsant activity2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (261)

TimeframeStudies, This Drug (%)All Drugs %
pre-199069 (26.44)18.7374
1990's124 (47.51)18.2507
2000's52 (19.92)29.6817
2010's14 (5.36)24.3611
2020's2 (0.77)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 46.11

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 Index46.11 (24.57)
Research Supply Index5.88 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index73.13 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (46.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials86 (31.62%)5.53%
Reviews23 (8.46%)6.00%
Case Studies27 (9.93%)4.05%
Observational0 (0.00%)0.25%
Other136 (50.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (2)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Gemeprost Versus Dinoprostone in the Medical Management of First Trimester Miscarriages: a Randomized Controlled Study [NCT05342467]Phase 2174 participants (Anticipated)Interventional2021-11-11Recruiting
Programmed Intermittent Epidural Bolus Versus Continuous Epidural Infusion for Second Trimester Voluntary Termination of Pregnancy Analgesia: a Randomized Study. [NCT01860521]104 participants (Actual)Interventional2011-09-30Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT01860521 (4) [back to overview]Degree of Satisfaction of the Patients With the Analgesia Procedure
NCT01860521 (4) [back to overview]Incidence of Motor Block
NCT01860521 (4) [back to overview]Total Levobupivacaine Consumption
NCT01860521 (4) [back to overview]Total Sufentanil Consumption.

Degree of Satisfaction of the Patients With the Analgesia Procedure

"At discharge from the hospital, patients were requested to answer the following question Taking into consideration the variations in pain symptoms, as well as the adverse events experienced, if any, how would you define the grade of satisfaction with your analgesic treatment? The grade of satisfaction was assessed using a visual analog scale (VAS) where 0 corresponded to completely unsatisfied and 100 to completely satisfied." (NCT01860521)
Timeframe: At discharge from the hospital (up to 72 hours from starting of the procedure).

Interventionmm (Mean)
Continuous Epidural Infusion73.2
Programmed Intermittent Epidural Bolus84.4

[back to top]

Incidence of Motor Block

The assessment of the degree of motor block was performed in the right and left lower extremities using the Breen modified Bromage score: 1 = complete block (unable to move feet or knees), 2 = almost complete block (able to move feet only), 3 = partial block (just able to move knees), 4 = detectable weakness of hip flexion while supine (between scores 3 and 5), 5 = no detectable weakness of hip flexion while supine (full flexion of knees), and 6 = able to stand and to perform partial knee bend. Patients with a Bromage score < 6 were considered to have motor block. (NCT01860521)
Timeframe: Assessed every hour from starting the analgesia procedure (up to 66 hours from starting of the procedure).

Interventionparticipants (Number)
Continuous Epidural Infusion24
Programmed Intermittent Epidural Bolus3

[back to top]

Total Levobupivacaine Consumption

(NCT01860521)
Timeframe: At the moment of fetal expulsion (up to 66 hours from starting of the procedure).

Interventionmg (Mean)
Continuous Epidural Infusion86.2
Programmed Intermittent Epidural Bolus75.5

[back to top]

Total Sufentanil Consumption.

(NCT01860521)
Timeframe: During the whole analgesia procedure (assessed between the starting of the procedure until 66 hours).

Interventionmicrog (Mean)
Continuous Epidural Infusion69.0
Programmed Intermittent Epidural Bolus60.4

[back to top]