Unoprostone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 409092026

| IUPAC_name = (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)
cyclopentyl]hept-5-enoic acid

| image = Unoprostone.svg

| tradename = Rescula

| Drugs.com = {{drugs.com|CONS|unoprostone}}

| pregnancy_AU =

| pregnancy_US = C

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US = Discontinued

| legal_status =

| routes_of_administration = Topical (eye drops)

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life = 14 min

| excretion = Renal

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 120373-36-6

| CAS_supplemental = {{CAS|120373-24-2}} (isopropyl ester)

| ATC_prefix = S01

| ATC_suffix = EE02

| PubChem = 5311236

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB06826

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 6X4F561V3W

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08661

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201407

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4470755

| C=22 | H=38 | O=5

| smiles = O=C(O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CCC(=O)CCCCCCC

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C22H38O5/c1-2-3-4-5-8-11-17(23)14-15-19-18(20(24)16-21(19)25)12-9-6-7-10-13-22(26)27/h6,9,18-21,24-25H,2-5,7-8,10-16H2,1H3,(H,26,27)/b9-6-/t18-,19-,20+,21-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = TVHAZVBUYQMHBC-SNHXEXRGSA-N

}}

Unoprostone (INN) is a prostaglandin analogue. Its isopropyl ester, unoprostone isopropyl, was marketed under the trade name Rescula for the management of open-angle glaucoma and ocular hypertension.{{drugs.com|CONS|unoprostone}}{{cite journal | vauthors = Fung DS, Whitson JT | title = An evidence-based review of unoprostone isopropyl ophthalmic solution 0.15% for glaucoma: place in therapy | journal = Clinical Ophthalmology | location = Auckland, N.Z. | volume = 8 | issue = | pages = 543–54 | date = 2014 | pmid = 24648719 | pmc = 3958522 | doi = 10.2147/OPTH.S41562 | doi-access = free }}

It was approved by the Food and Drug Administration in 2000.{{cite news | url= https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/21214_Rescula.cfm | title=Drug Approval Package | publisher=Food and Drug Administration}}

In 2009, Sucampo Pharmaceuticals acquired the rights to the drug in the U.S. and Canada.{{cite press release | url=https://www.biospace.com/article/releases/sucampo-pharmaceuticals-inc-acquires-rights-to-rescula-for-u-s-and-canada-/ | title=Sucampo Pharmaceuticals, Inc. Acquires Rights to Rescula for U.S. and Canada | publisher=Business Wire | date=April 24, 2009}}

In 2015, the drug was discontinued in the U.S.{{cn|date=March 2022}}