Prostaglandin F2alpha: Difference between revisions
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{{Drugbox | |||
| Verifiedfields = changed | |||
| Watchedfields = changed | |||
| verifiedrevid = 406310380 | |||
| IUPAC_name = (''Z'')-7-[(1''R'',2''R'',3''R'',5''S'')-3,5-dihydroxy-2-[(''E'',3''S'')- 3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid | |||
| image = Dinoprost.png | |||
| drug_name = Dinoprost Tromethamine | |||
<!--Clinical data--> | |||
| tradename = | |||
| Drugs.com = {{drugs.com|international|dinoprost-tromethamine}} | |||
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | |||
| pregnancy_US = <!-- A / B / C / D / X --> | |||
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | |||
| legal_UK = <!-- GSL / P / POM / CD --> | |||
| legal_US = <!-- OTC / Rx-only --> | |||
| routes_of_administration = [[Intravenous therapy|Intravenous]] (to induce labor), [[amniotic fluid|intra-amniotic]] (to induce abortion) | |||
<!--Pharmacokinetic data--> | |||
| elimination_half-life = 3 to 6 hours in [[amniotic fluid]], less than 1 minute in [[blood plasma]] | |||
<!--Identifiers--> | |||
| CASNo_Ref = {{cascite}} | |||
| CAS_number_Ref = {{cascite|correct|??}} | |||
| CAS_number = 551-11-1 | |||
| CAS_supplemental = {{CAS|38562-01-5}} | |||
| ATC_prefix = G02 | |||
| ATC_suffix = AD01 | |||
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | |||
| ChemSpiderID = 4444062 | |||
| smiles = O=C(O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC | |||
| InChI = 1/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 | |||
| InChIKey = PXGPLTODNUVGFL-YNNPMVKQBA | |||
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} | |||
| StdInChI = 1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1 | |||
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | |||
| StdInChIKey = PXGPLTODNUVGFL-YNNPMVKQSA-N | |||
| PubChem = 5280363 | |||
| IUPHAR_ligand = 1884 | |||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | |||
| DrugBank = DB01160 | |||
| KEGG_Ref = {{keggcite|changed|kegg}} | |||
| KEGG = D01352 | |||
| ChEMBL_Ref = {{ebicite|changed|EBI}} | |||
| ChEMBL = 815 | |||
<!--Chemical data--> | |||
| C=20 | H=34 | O=5 | |||
| molecular_weight = 354.48 g/mol | |||
}} | |||
__NOTOC__ | |||
{{SI}} | {{SI}} | ||
{{ | {{CMG}} | ||
==Overview== | |||
'''[[Prostaglandin]] F<sub>2α</sub>''' ('''PGF<sub>2α</sub>''' in [[prostanoid]] nomenclature), pharmaceutically termed '''dinoprost''' ([[International Nonproprietary Name|INN]]), is a naturally occurring prostaglandin used in medicine to [[induction (birth)|induce labor]] and as an [[abortifacient]]. | |||
In domestic mammals, it is produced by the uterus when stimulated by [[oxytocin]], in the event that there has been no implantation during the follicular phase. It acts on the [[corpus luteum]] to cause [[luteolysis]], forming a [[corpus albicans]] and stopping the production of progesterone. Action of PGF<sub>2α</sub> is dependent on the number of receptors on the corpus luteum membrane. | |||
The PGF<sub>2α</sub> isoform ''8-iso-PGF<sub>2α</sub>'' was found in significantly increased amounts in patients with [[endometriosis]], thus being a potential causative link in endometriosis-associated oxidative stress. | |||
==Mechanism of action== | |||
PGF<sub>2α</sub> acts by binding to the [[prostaglandin F2α receptor]]. | |||
==Synthesis== | |||
In 2012 a concise and highly stereoselective total synthesis of PGF<sub>2α</sub> was described. The synthesis requires only seven steps, a huge improvement on the original 17-steps synthesis of Corey and Cheng,<ref name="coreybook">{{cite book|title=The Logic of Chemical Synthesis|first1=E.J.|last1=Corey|first2=X.M.|last2=Cheng|publisher=Wiley|year=1995}}</ref> and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with ''S''-[[proline]] as an asymmetric catalyst. | |||
==Analogs== | |||
The following medications are [[Prostaglandin analogue|analogs]] of prostaglandin F<sub>2α</sub>: | |||
*[[Latanoprost]] | |||
*[[Bimatoprost]] | |||
*[[Travoprost]] | |||
*[[Carboprost]] | |||
== | == References == | ||
{{Reflist|2}} | |||
{{ | {{Prostaglandins}} | ||
[[Category:Abortifacients]] | |||
[[Category:Prostaglandins|F2]] | |||
[[Category:Drug]] | |||
Latest revision as of 17:01, 20 August 2015
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| Clinical data | |
|---|---|
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Intravenous (to induce labor), intra-amniotic (to induce abortion) |
| ATC code | |
| Pharmacokinetic data | |
| Elimination half-life | 3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| KEGG | |
| ChEMBL | |
| 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 | C20H34O5 |
| Molar mass | 354.48 g/mol |
| 3D model (JSmol) | |
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  (what is this?) (verify) | |
Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
Overview
Prostaglandin F2α (PGF2α in prostanoid nomenclature), pharmaceutically termed dinoprost (INN), is a naturally occurring prostaglandin used in medicine to induce labor and as an abortifacient.
In domestic mammals, it is produced by the uterus when stimulated by oxytocin, in the event that there has been no implantation during the follicular phase. It acts on the corpus luteum to cause luteolysis, forming a corpus albicans and stopping the production of progesterone. Action of PGF2α is dependent on the number of receptors on the corpus luteum membrane.
The PGF2α isoform 8-iso-PGF2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress.
Mechanism of action
PGF2α acts by binding to the prostaglandin F2α receptor.
Synthesis
In 2012 a concise and highly stereoselective total synthesis of PGF2α was described. The synthesis requires only seven steps, a huge improvement on the original 17-steps synthesis of Corey and Cheng,[1] and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with S-proline as an asymmetric catalyst.
Analogs
The following medications are analogs of prostaglandin F2α:
References
- ↑ Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.
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- Abortifacients
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