Prostaglandin F2alpha
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| Systematic (IUPAC) name | |
|---|---|
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(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)- 3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Intravenous (to induce labor), intra-amniotic (to induce abortion) |
| Pharmacokinetic data | |
| Biological half-life | 3 to 6 hours in amniotic fluid, less than 1 minute in blood plasma |
| Identifiers | |
| CAS Number |
551-11-1  38562-01-5 |
| ATC code | G02AD01 (WHO) |
| PubChem | CID 5280363 |
| IUPHAR/BPS | 1884 |
| DrugBank |
DB01160 |
| ChemSpider |
4444062  |
| KEGG |
D01352 |
| ChEMBL |
CHEMBL815 |
| Chemical data | |
| Formula | C20H34O5 |
| Molar mass | 354.48 g/mol |
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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.[1]
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.[2] The synthesis requires only seven steps, a huge improvement on the original 17-steps synthesis of Corey and Cheng,[3] and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with S-proline as an asymmetric catalyst.
Analogues
The following medications are analogues of prostaglandin F2α:
References
- ↑ Sharma, I.; Dhaliwal, L.; Saha, S.; Sangwan, S.; Dhawan, V. (2010). "Role of 8-iso-prostaglandin F2alpha and 25-hydroxycholesterol in the pathophysiology of endometriosis". Fertility and Sterility 94 (1): 63–70. doi:10.1016/j.fertnstert.2009.01.141. PMID 19324352.
- ↑ Coulthard, G.; Erb, W.; Aggarwal, V. K. (2012). "Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps". Nature 489 (7415): 278–281. doi:10.1038/nature11411. PMID 22895192.
- ↑ Corey, E.J.; Cheng, X.M. (1995). The Logic of Chemical Synthesis. Wiley.
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