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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 400098742 | verifiedrevid = 447612599
| IUPAC_name = methyl (2''E'',11α,13''E'',15''R'')-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate | IUPAC_name = methyl (2''E'',11α,13''E'',15''R'')-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
| image = Gemeprost.svg | image = Gemeprost.svg


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Cervagem
| Drugs.com = {{drugs.com|international|gemeprost}} | Drugs.com = {{drugs.com|international|gemeprost}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = B3
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = S4
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = POM
| legal_UK_comment = <ref>{{cite web | title=Cervagem 1 mg Pessary - Summary of Product Characteristics (SmPC) | website=(emc) | date=16 August 2019 | url=https://www.medicines.org.uk/emc/product/2202 | access-date=7 September 2020}}</ref>
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = | legal_status =
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 64318-79-2 | CAS_number = 64318-79-2
| ATC_prefix = G02 | ATC_prefix = G02
| ATC_suffix = AD03 | ATC_suffix = AD03
| PubChem = 5282237 | PubChem = 5282237
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = | DrugBank = DB08964
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4445416 | ChemSpiderID = 4445416
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 45KZB1FOLS | UNII = 45KZB1FOLS
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02073 | KEGG = D02073


<!--Chemical data--> <!--Chemical data-->
| C=23 | H=38 | O=5 | C=23 | H=38 | O=5
| molecular_weight = 394.545 g/mol
| smiles = O=C1C(O)(/C=C/(O)C(C)(C)CCCC)1CCCC\C=C\C(=O)OC | smiles = O=C1C(O)(/C=C/(O)C(C)(C)CCCC)1CCCC\C=C\C(=O)OC
| InChI = 1/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
| InChIKey = KYBOHGVERHWSSV-VNIVIJDLBY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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| synonyms = <small>methyl (''E'')-7--5-oxo-cyclopentyl]hept-2-enoate</small> | synonyms = <small>methyl (''E'')-7--5-oxo-cyclopentyl]hept-2-enoate</small>
}} }}

'''Gemeprost''' (16, 16-dimethyl-trans-delta2 PGE<sub>1</sub> methyl ester) is an ] of ] E<sub>1</sub>. '''Gemeprost''' (16, 16-dimethyl-trans-delta2 PGE<sub>1</sub> methyl ester) is an ] of ].


==Clinical use== ==Clinical use==


It is used as a treatment for ]. It is used as a treatment for ].{{fact|date=September 2021}}


It is used with ] to terminate pregnancy up to 24 weeks gestation. <ref name="pmid11574498">{{cite journal |author=Bartley J, Brown A, Elton R, Baird DT |title=Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation |journal=Human reproduction (Oxford, England) |volume=16 |issue=10 |pages=2098–102 |year=2001 |month=October |pmid=11574498 |doi= 10.1093/humrep/16.10.2098|url=http://humrep.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11574498 |accessdate=2008-10-29}}</ref> It is used with ] to terminate pregnancy up to 24 weeks gestation.<ref name="pmid11574498">{{cite journal | vauthors = Bartley J, Brown A, Elton R, Baird DT | title = Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation | journal = Human Reproduction | volume = 16 | issue = 10 | pages = 2098–102 | date = October 2001 | pmid = 11574498 | doi = 10.1093/humrep/16.10.2098 | doi-access = free }}</ref>


==Side effects== ==Side effects==


Vaginal bleeding, cramps, nausea, vomiting, loose stools or diarrhea, headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild ]. Rare: Uterine rupture, severe ], coronary spasms with subsequent ]s. Vaginal bleeding, cramps, nausea, vomiting,<ref name="Meyler">{{cite book | last=Aronson | first=J. K. | title=Meyler's Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and Interactions | publisher=Elsevier Science | year=2015 | isbn=978-0-4445-3716-4 | url=https://books.google.com/books?id=NOKoBAAAQBAJ | page=524}}</ref> loose stools or diarrhea,<ref name="Meyler"/> headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild ].<ref name="Meyler"/> Rare: Uterine rupture, severe ], coronary spasms with subsequent ]s.{{fact|date=September 2021}}


==References== ==References==
{{reflist}} {{Reflist}}

== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/gemeprost | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Gemeprost }}


⚫ {{Oxytocics}}
{{Eicosanoids}} {{Eicosanoids}}
⚫ {{Oxytocics}}
{{Prostanoidergics}}
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{{genito-urinary-drug-stub}} {{genito-urinary-drug-stub}}

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