Gemeprost: Difference between revisions

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List of terms related to Gemeprost

Gemeprost
Clinical data
Synonyms	methyl (E)-7-[(1R,2S,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4,4-dimethyl-oct-1-enyl]-5-oxo-cyclopentyl]hept-2-enoate
AHFS/Drugs.com	International Drug Names
Routes of; administration	Pessary
ATC code	G02AD03 (WHO) ;
Identifiers
	IUPAC name methyl (2E,11α,13E,15R)-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate;
CAS Number	64318-79-2 ;
PubChem CID	5282237;
DrugBank	DB08964 ;
ChemSpider	4445416 ;
UNII	45KZB1FOLS;
KEGG	D02073 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C23H38O5
Molar mass	394.545 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C1C[C@@H](O)[C@H](/C=C/[C@@H](O)C(C)(C)CCCC)[C@H]1CCCC\C=C\C(=O)OC;
	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 ; Key:KYBOHGVERHWSSV-VNIVIJDLSA-N ;
(what is this?) (verify)

← Older edit

VisualWikitext

Latest revision as of 16:12, 13 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Gemeprost (16, 16-dimethyl-trans-delta2 PGE₁ methyl ester) is an analogue of prostaglandin E₁.

Clinical use

It is used as a treatment for obstetric bleeding.

It is used with mifepristone to terminate pregnancy up to 24 weeks gestation. ^[1]

Side effects

Vaginal bleeding, cramps, nausea, vomiting, loose stools or diarrhea, headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild pyrexia. Rare: Uterine rupture, severe hypotension, coronary spasms with subsequent myocardial infarctions.

References

↑ Bartley J, Brown A, Elton R, Baird DT (October 2001). "Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation". Human reproduction (Oxford, England). 16 (10): 2098–102. doi:10.1093/humrep/16.10.2098. PMID 11574498. Retrieved 2008-10-29.

Template:Eicosanoids

[pmid11574498-1] Bartley J, Brown A, Elton R, Baird DT (October 2001). "Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation". Human reproduction (Oxford, England). 16 (10): 2098–102. doi:10.1093/humrep/16.10.2098. PMID 11574498. Retrieved 2008-10-29.

[1]

@@ Line 1: / Line 1: @@
-{{drugbox |
+{{Drugbox
-| IUPAC_name        = methyl (''E'')-7-[(1''R'',2''S'',3''R'')-3-hydroxy-2-<br>[(''E'',3''R'')-3-hydroxy-4,4-dimethyl-oct-1-enyl]-<br>5-oxo-cyclopentyl]hept-2-enoate
+| Verifiedfields = changed
-| image             = Gemeprost.svg
+| verifiedrevid = 447612599
-| CAS_number        = 64318-79-2
+| IUPAC_name = methyl (2''E'',11α,13''E'',15''R'')-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
-| ATC_prefix        = G02
+| image = Gemeprost.png
-| ATC_suffix        = AD03
-| PubChem           = 5282237
+<!--Clinical data-->
-| DrugBank          =
+| tradename =
-| C = 23 | H = 38 | O = 5
+| Drugs.com = {{drugs.com|international|gemeprost}}
-| molecular_weight  = 394.545 g/mol
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
-| smiles            = CCCCC(C)(C)C(C=CC1C(CC(=O)C1CCCCC=CC(=O)OC)O)O
+| pregnancy_US = <!-- A / B            / C / D / X -->
-| bioavailability   =
+| pregnancy_category =
-| protein_bound     =
+| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
-| metabolism        =
+| legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| elimination_half-life =
+| legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
-| excretion         =
+| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
-| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
+| legal_status =
-| pregnancy_US      =  <!-- A / B            / C / D / X -->
-| pregnancy_category=
-| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
-| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| legal_UK          =  <!-- GSL         / P       / POM / CD / Class A, B, C -->
-| legal_US          =  <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
-| legal_status      =
 | routes_of_administration = [[Pessary]]
+<!--Pharmacokinetic data-->
+| bioavailability =
+| protein_bound =
+| metabolism =
+| elimination_half-life =
+| excretion =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 64318-79-2
+| ATC_prefix = G02
+| ATC_suffix = AD03
+| PubChem = 5282237
+| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
+| DrugBank = DB08964
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 4445416
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 45KZB1FOLS
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D02073
+<!--Chemical data-->
+| C=23 | H=38 | O=5
+| molecular_weight = 394.545 g/mol
+| smiles = O=C1C[C@@H](O)[C@H](/C=C/[C@@H](O)C(C)(C)CCCC)[C@H]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 = 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
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = KYBOHGVERHWSSV-VNIVIJDLSA-N
+| synonyms = <small>methyl (''E'')-7-[(1''R'',2''S'',3''R'')-3-hydroxy-2-[(''E'',3''R'')-3-hydroxy-4,4-dimethyl-oct-1-enyl]-5-oxo-cyclopentyl]hept-2-enoate</small>
 }}
+__NOTOC__
 {{SI}}
-{{EH}}
+{{CMG}}
+==Overview==
-'''Gemeprost''' (16, 16-dimethyl-trans-delta2 PGE<sub>1</sub> methyl ester) is an [[analog (chemistry)|analogue]] of [[prostaglandin]] E<sub>1</sub>.
+'''Gemeprost''' (16, 16-dimethyl-trans-delta2 PGE<sub>1</sub> methyl ester) is an [[analog (chemistry)|analogue]] of [[Prostaglandin E1|prostaglandin E<sub>1</sub>]].
 ==Clinical use==
+It is used as a treatment for [[Obstetrical hemorrhage|obstetric bleeding]].
-In [[pessary]] form as the second drug in [[medical abortion]] regimen in the UK and Sweden. Gemeprost softens and dilates the [[cervix]] and stimulates the [[uterus]] to contract.
+It is used with [[mifepristone]] 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 |date=October 2001 |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>
 ==Side effects==
+Vaginal bleeding, cramps, nausea, vomiting, loose stools or diarrhea, headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild [[pyrexia]]. Rare: Uterine rupture, severe [[hypotension]], coronary spasms with subsequent [[myocardial infarction]]s.
-[[Vaginal bleeding]], [[cramps]], [[nausea]], [[vomiting]], loose stools or [[diarrhea]], [[headache]], muscle weakness; [[dizziness]]; [[flushing]]; [[chills]]; [[backache]]; [[dyspnoea]]; [[chest pain]]; [[palpitations]] and mild [[pyrexia]]. Rare: Uterine rupture, severe [[hypotension]], coronary spasms with subsequent [[myocardial infarction]]s.
+==References==
+{{reflist|2}}
+{{Eicosanoids}}
 [[Category:Abortifacients]]
 [[Category:Prostaglandins]]
+[[Category:Drug]]
-{{SIB}}
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