NAV

Gemeprost

Identification

Summary

Gemeprost is a prostaglandin E1 analogue used for cervical dilation and, in combination with mifepristone, for pregnancy termination.

Generic Name
Gemeprost
DrugBank Accession Number
DB08964
Background

Gemeprost is a prostaglandin E1 (PGE1) analog and antiprogestogen used for preoperative dilation of the cervix before surgical abortion. It is available as vaginal suppositories and also used in combination with the antiprogestin and mifepristone for termination of 1st- and 2nd-trimester pregnancy 1. It is not FDA-approved but available in Japan marketed as Preglandin.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 394.552
Monoisotopic: 394.271924324
Chemical Formula
C23H38O5
Synonyms
  • 16,16-Dimethyl-trans-delta-2-PGE1 methyl ester
  • 16,16-Dimethyl-trans-delta(sup 2)-prostaglandin E1 methyl ester
  • Gemeprost
  • SC-37681
External IDs
  • SC-37681
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Pharmacology

Indication

Indicated for the softening and dilatation of the cervix uteri prior to transcervical, intrauterine operative procedures in the first trimester of pregnancy or facilitating therapeutic termination of pregnancy in patients in the second trimester of gestation.

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Gemeprost softens and dilates of the cervix prior to transcervical intrauterine operative procedures. It is a prostaglandin E1 analog that potently stimulates uterine contractions and causes cervical ripening and relaxation 1.

Mechanism of action

As a prostaglandin analog, gemeprost binds to prostaglandin E2 and E3 receptors as an agonist to cause myometrial contractions and progressive cervical dilation via tissue sensitization to oxytocin 4.

TargetActionsOrganism
AProstaglandin E2 receptor EP3 subtype
agonist
Humans
UProstaglandin E2 receptor EP2 subtype
agonist
Humans
Absorption

Systemic absorption of gemeprost is limited with about 12-28% of administered dose of gemeprost reaching the systemic circulation 5. Following vaginal administration, peak plasma concentration is reached after 2-3 hours 1.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

After intravenous administration, gemeprost is rapidly metabolized via hydrolysis to the free acid with half life of 10-15 minutes. The free acid is then inactivated by β- and ω-oxidation 1.

Route of elimination

About 50% of the dose eliminated as metabolites in the urine during the first 24 hours.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Serious or life-threatening adverse effects include coronary spasms with subsequent myocardial infarctions and uterine rupture following prolonged uterine hypertonia or abnormal uterine pain. More common adverse effects are nausea, vomiting, loose stools, diarrhea, lower abdominal or back pain, headache, mild pyrexia and flushing. Less common side effects include hypotension, chest pain palpitations, tachycardia, muscle weakness, dyspnea, chills and headache. Oral LD50 is 300 mg/kg in mouse, 980 mg/kg in rat and 3200 mg/kg in rabbit MSDS.

Pathways
Not Available
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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
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Tenofovir alafenamideThe serum concentration of Tenofovir alafenamide can be increased when it is combined with Gemeprost.
Food Interactions
Not Available

Products

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International/Other Brands
Cergem (MSD Merck Sharp & Dohme) / Cervagem (Sanofi) / Cervagème (Sanofi-Aventis) / Cervidil (Merck Serono)

Categories

ATC Codes
G02AD03 — Gemeprost
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty alcohols
Direct Parent
Fatty alcohols
Alternative Parents
Fatty acid esters / Cyclopentanols / Methyl esters / Enoate esters / Cyclic ketones / Cyclic alcohols and derivatives / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homomonocyclic compound / Alpha,beta-unsaturated carboxylic ester / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Cyclic ketone / Cyclopentanol / Enoate ester
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
45KZB1FOLS
CAS number
64318-79-2
InChI Key
KYBOHGVERHWSSV-VNIVIJDLSA-N
InChI
InChI=1S/C23H38O5/c1-5-6-15-23(2,3)21(26)14-13-18-17(19(24)16-20(18)25)11-9-7-8-10-12-22(27)28-4/h10,12-14,17-18,20-21,25-26H,5-9,11,15-16H2,1-4H3/b12-10+,14-13+/t17-,18-,20-,21-/m1/s1
IUPAC Name
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
SMILES
CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCC\C=C\C(=O)OC

References

Synthesis Reference

U.S. Patent 4,052,512.

General References
  1. Bygdeman M: Pharmacokinetics of prostaglandins. Best Pract Res Clin Obstet Gynaecol. 2003 Oct;17(5):707-16. [Article]
  2. Bartley J, Baird DT: A randomised study of misoprostol and gemeprost in combination with mifepristone for induction of abortion in the second trimester of pregnancy. BJOG. 2002 Nov;109(11):1290-4. [Article]
  3. Wong KS, Ngai CS, Wong AY, Tang LC, Ho PC: Vaginal misoprostol compared with vaginal gemeprost in termination of second trimester pregnancy. A randomized trial. Contraception. 1998 Oct;58(4):207-10. [Article]
  4. Husslein P: [Causes of labor initiation in man: role of oxytocin and prostaglandins]. Z Geburtshilfe Perinatol. 1985 May-Jun;189(3):95-102. [Article]
  5. CERVAGEM (Gemeprost) Product information [Link]
KEGG Drug
D02073
PubChem Compound
5282237
PubChem Substance
310264927
ChemSpider
4445416
RxNav
12449
ChEBI
135626
ChEMBL
CHEMBL1908315
ZINC
ZINC000004216393
Wikipedia
Gemeprost
MSDS
Download (78.8 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentCervical Ripening2
3CompletedTreatmentCervical Ripening / Induction of Labour1
3CompletedTreatmentCervical Ripening / Induction of Labour / Reducing Time to Vaginal Delivery1
3TerminatedTreatmentInduction of Labor Affected Fetus / Newborn1
2RecruitingTreatmentIncomplete Abortion / Medical; Abortion, Fetus / Missed Abortion1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SuppositoryVaginal
SuppositoryVaginal1 mg
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0176 mg/mLALOGPS
logP4.02ALOGPS
logP4.71Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)14.68Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area83.83 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity113.05 m3·mol-1Chemaxon
Polarizability46.3 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-ce8cfd01eb62929bb015
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-e38d8aded5867040c9c9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6v-0019000000-2fe55988dd0a5a7c1b16
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-4449000000-348569c73751864b1892
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9400000000-c0b105c31c88a21ac6e3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006t-2359000000-fc157aa899f20f170261
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-201.96
predicted
DeepCCS 1.0 (2019)
[M+H]+204.35793
predicted
DeepCCS 1.0 (2019)
[M+Na]+210.271
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Prostaglandin E2 receptor EP3 subtype
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Rna polymerase ii transcription factor activity, ligand-activated sequence-specific dna binding
Specific Function
Receptor for prostaglandin E2 (PGE2); the EP3 receptor may be involved in inhibition of gastric acid secretion, modulation of neurotransmitter release in central and peripheral neurons, inhibition ...
Gene Name
PTGER3
Uniprot ID
P43115
Uniprot Name
Prostaglandin E2 receptor EP3 subtype
Molecular Weight
43309.335 Da
References
  1. Qian YM, Jones RL, Chan KM, Stock AI, Ho JK: Potent contractile actions of prostanoid EP3-receptor agonists on human isolated pulmonary artery. Br J Pharmacol. 1994 Oct;113(2):369-74. [Article]
  2. Matsuya H, Sekido N, Kida J, Mashimo H, Wakamatsu D, Okada H: Effects of an EP2 and EP3 Receptor Dual Agonist, ONO-8055, on a Radical Hysterectomy-Induced Underactive Bladder Model in Monkeys. Low Urin Tract Symptoms. 2017 Apr 25. doi: 10.1111/luts.12166. [Article]
Details2. Prostaglandin E2 receptor EP2 subtype
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Prostaglandin e receptor activity
Specific Function
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the ...
Gene Name
PTGER2
Uniprot ID
P43116
Uniprot Name
Prostaglandin E2 receptor EP2 subtype
Molecular Weight
39759.945 Da
References
  1. Matsuya H, Sekido N, Kida J, Mashimo H, Wakamatsu D, Okada H: Effects of an EP2 and EP3 Receptor Dual Agonist, ONO-8055, on a Radical Hysterectomy-Induced Underactive Bladder Model in Monkeys. Low Urin Tract Symptoms. 2017 Apr 25. doi: 10.1111/luts.12166. [Article]

Drug created at June 09, 2014 15:01 / Updated at June 12, 2021 10:54