Gemeprost: Difference between revisions

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Revision as of 10:43, 6 August 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - updated 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Misplaced Pages talk:WikiProject_Pharmacology\|er← Previous edit		Revision as of 06:17, 31 August 2011 edit undoBogBot (talk \| contribs)Bots53,132 edits populated new fields in {{drugbox}} and reordered per bot approval. Report errors and suggestions to User_talk:BogBot Next edit →
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	{{~~drugbox~~		{{Drugbox
	\| Verifiedfields = changed		\| Verifiedfields = changed
		⚫	\| verifiedrevid = 400098742
⚫	\| UNII_Ref = {{fdacite\|changed\|FDA}}
		⚫	\| IUPAC_name = methyl (2''E'',11α,13''E'',15''R'')-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
⚫	~~\| UNII = 45KZB1FOLS~~\| verifiedrevid = 400098742
		⚫	\| image = Gemeprost.svg
	\|

⚫	\| IUPAC_name = methyl (2''E'',11α,13''E'',15''R'')-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
			<!--Clinical data-->
⚫	\|synonyms=<small>methyl (''E'')-7--5-oxo-cyclopentyl]hept-2-enoate</small>
			\| tradename =
⚫	\| image = Gemeprost.svg
			\| Drugs.com = {{drugs.com\|international\|gemeprost}}
		⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	\| 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 = ]

			<!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| protein_bound =
		⚫	\| metabolism =
		⚫	\| elimination_half-life =
		⚫	\| excretion =

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

			<!--Chemical data-->
		⚫	\| 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
	\| 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		\| 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		\| InChIKey = KYBOHGVERHWSSV-VNIVIJDLBY
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	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = KYBOHGVERHWSSV-VNIVIJDLSA-N		\| StdInChIKey = KYBOHGVERHWSSV-VNIVIJDLSA-N
		⚫	\| synonyms = <small>methyl (''E'')-7--5-oxo-cyclopentyl]hept-2-enoate</small>
⚫	\| CAS_number = 64318-79-2
⚫	\| ATC_prefix = G02
⚫	\| ATC_suffix = AD03
⚫	\| PubChem = 5282237
⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
⚫	\| DrugBank =
⚫	\| KEGG_Ref = {{keggcite\|changed\|kegg}}
⚫	\| KEGG = D02073
⚫	\| 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
⚫	\| bioavailability =
⚫	\| protein_bound =
⚫	\| metabolism =
⚫	\| elimination_half-life =
⚫	\| excretion =
⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	\| 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 = ]
	}}		}}
	'''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 ] E<sub>1</sub>.

Revision as of 06:17, 31 August 2011

Pharmaceutical compound

Gemeprost
Clinical data

Other names	methyl (E)-7--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
ChemSpider	4445416
UNII	45KZB1FOLS
KEGG	D02073
CompTox Dashboard (EPA)	DTXSID40895073
ECHA InfoCard	100.058.869
Chemical and physical data
Formula	C₂₃H₃₈O₅
Molar mass	394.545 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C1C(O)(/C=C/(O)C(C)(C)CCCC)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
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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 RU486 to terminate pregnancy up to 24 weeks gestation.

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.