Iloprost

{{Short description|Pharmaceutical drug}} {{Multiple issues|{{more citations needed|date=December 2010}} {{cleanup reorganize|date=February 2024}} {{cleanup rewrite|date=February 2024}}}} {{Use dmy dates|date=February 2024}} {{cs1 config | name-list-style=vanc | display-authors=6}} {{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443868674 | image = Iloprost 2D structure.svg | image_class = skin-invert-image | width = 250 | alt =  | image2 = Iloprost.png | image_class2 = bg-transparent | pronounce = | tradename = Ventavis, Ilomedine, Aurlumyn | Drugs.com = {{drugs.com|monograph|iloprost}} | MedlinePlus = a612032 | DailyMedID = Iloprost | pregnancy_AU =  | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = Inhalation, intravenous | class = | ATC_prefix = B01 | ATC_suffix = AC11 | ATC_supplemental = | legal_US = Rx-only | legal_US_comment = <ref name="Ventavis FDA label">{{cite web | title=Ventavis- iloprost solution | website=DailyMed | date=26 July 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d3bebc1c-f032-402a-bbc9-aff024276ed1 | access-date=19 February 2024 | archive-date=19 February 2024 | archive-url=https://web.archive.org/web/20240219031405/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d3bebc1c-f032-402a-bbc9-aff024276ed1 | url-status=live }}{{PD-notice}}</ref><ref name="Aurlumyn FDA label">{{cite web | title=Aurlumyn- iloprost injection, solution | website=DailyMed | date=11 March 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f3306add-2edd-8494-e053-2a95a90a7a78 | access-date=6 May 2024}}</ref> | legal_EU = Rx-only | legal_EU_comment = <ref name="Ventavis EPAR">{{cite web | title=Ventavis EPAR | website=European Medicines Agency (EMA) | date=26 August 2013 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/ventavis | access-date=19 February 2024 | archive-date=12 November 2020 | archive-url=https://web.archive.org/web/20201112033346/https://www.ema.europa.eu/en/medicines/human/EPAR/ventavis | url-status=live }}</ref> | legal_status = Rx-only

| bioavailability = Not determined<ref name="Ventavis FDA label" /> | metabolism = Via β-oxidation to inactive tetranor-iloprost<ref name="Ventavis FDA label" /> | elimination_half-life = 20–30 minutes<ref name="Ventavis FDA label" /> | excretion = Kidney (68%) and fecal (12%)<ref name="Ventavis FDA label" /> | protein_bound = 60%<ref name="Ventavis FDA label" />

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 78919-13-8 | CAS_supplemental = {{CAS|73873-87-7}} | PubChem = 5311181 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01088 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4470703 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = JED5K35YGL | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D02721 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 236025

| IUPAC_name = 5-<nowiki/>{(''E'')-(1''S'',5''S'',6''R'',7''R'')-7-hydroxy-6[(''E'')-(3''S'',4''RS'')-3-hydroxy-4-methyl-1-octen-6-ynyl]-bicyclo[3.3.0]octan-3-ylidene}pentanoic acid | C = 22 | H = 32 | O = 4 | smiles = CC#CCC(C)[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/C2)O)O | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20+,21+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = HIFJCPQKFCZDDL-ACWOEMLNSA-N }}

'''Iloprost''', sold under the brand name '''Ventavis''' among others, is a medication used to treat pulmonary arterial hypertension (PAH), scleroderma, Raynaud's phenomenon, frostbite, and other conditions in which the blood vessels are constricted and blood cannot flow to the tissues.<ref name=autogenerated1>{{cite web | title = Iloprost Information | url= http://raynauds.chicanes.net/potioncms/articlefiles/102-Iloprost.pdf | archive-url= https://web.archive.org/web/20160406164933/http://raynauds.chicanes.net/potioncms/articlefiles/102-Iloprost.pdf | url-status= dead | archive-date= 6 April 2016 | access-date = 5 February 2009 }}</ref> Iloprost is a prostacyclin mimetic.<ref name="Ventavis FDA label" />

For pulmonary arterial hypertension, iloprost is given via inhalation. Iloprost works by opening (dilating) the blood vessels to allow the blood to flow through them. It was developed by the pharmaceutical company Schering AG and is marketed by Bayer Schering Pharma AG in the European Union and by Actelion Pharmaceuticals in the US.

== Medical uses == In the US, iloprost is indicated for the treatment of pulmonary arterial hypertension (PAH) (WHO Group 1) to improve a composite endpoint consisting of exercise tolerance, symptoms (NYHA Class), and lack of deterioration.<ref name="Ventavis FDA label" />

In the EU, iloprost is indicated for the treatment of people with primary pulmonary hypertension, classified as New York Heart Association functional class III, to improve exercise capacity and symptoms.<ref name="Ventavis EPAR" />

In February 2024, the US Food and Drug Administration (FDA) approved iloprost (Aurlumyn) to treat severe frostbite to reduce the risk of finger or toe amputation.<ref name="Aurlumyn FDA label" /><ref name="FDA Aurlumyn">{{cite press release |url=https://www.fda.gov/news-events/press-announcements/fda-approves-first-medication-treat-severe-frostbite |title=FDA Approves First Medication to Treat Severe Frostbite |publisher=U.S. Food and Drug Administration (FDA) |date=14 February 2024 |access-date=16 February 2024 |archive-date=16 February 2024 |archive-url=https://web.archive.org/web/20240216003235/https://www.fda.gov/news-events/press-announcements/fda-approves-first-medication-treat-severe-frostbite |url-status=dead }} {{PD-notice}}</ref>

==Pharmacology== Iloprost is a synthetic analogue of prostacyclin PGI2. Iloprost dilates systemic and pulmonary arterial vascular beds. It also affects platelet aggregation but the relevance of this effect to the treatment of pulmonary hypertension is unknown. The two diastereoisomers of iloprost differ in their potency in dilating blood vessels, with the 4''S'' isomer substantially more potent than the 4''R'' isomer. While Iloprost is an analog of PGI2 that activates PGI2's receptor, the prostacyclin receptor, to stimulate vasodilation, it has little selectivity in that it binds to and activates all four receptors for prostaglandin E2 viz., prostaglandin EP1 receptor, prostaglandin EP2 receptor, prostaglandin EP3 receptor, and prostaglandin EP4 receptor.<ref name="pmid27940058">{{cite journal | vauthors = Moreno JJ | title = Eicosanoid receptors: Targets for the treatment of disrupted intestinal epithelial homeostasis | journal = European Journal of Pharmacology | volume = 796 | pages = 7–19 | date = February 2017 | pmid = 27940058 | doi = 10.1016/j.ejphar.2016.12.004 | s2cid = 1513449 }}</ref> Activation of the EP2 and EP4 receptors cause vasodilation but activation of the EP3 receptor causes vasoconstriction.

== Contraindications == Contraindications include: unstable angina; within 6 months of myocardial infarction; decompensated cardiac failure (unless under close medical supervision); severe arrhythmias; congenital or acquired heart-valve defects; within 3 months of cerebrovascular events; pulmonary veno-occlusive disease; conditions which increase risk of bleeding.

== Side effects == In clinical studies, common adverse reactions due to inhaled iloprost included: vasodilation (flushing, 27%), cough (39%), headache (30%), flu syndrome (14%), nausea (13%), neck spasms (12%), hypotension (11%), insomnia (8%), and fainting (syncope) (8%); other serious adverse events reported with the use of Ventavis included congestive heart failure, chest pain, supraventricular tachycardia, dyspnea, swelling of the limbs (especially around the ankles and feet), and kidney failure.

Serious adverse events reported with the use of inhaled iloprost include congestive heart failure, chest pain, supraventricular tachycardia, shortness of breath, peripheral edema, and kidney failure.

== References == {{reflist}}

== Further reading == {{refbegin}} * {{cite journal | vauthors = Olschewski H, Simonneau G, Galiè N, Higenbottam T, Naeije R, Rubin LJ, Nikkho S, Speich R, Hoeper MM, Behr J, Winkler J, Sitbon O, Popov W, Ghofrani HA, Manes A, Kiely DG, Ewert R, Meyer A, Corris PA, Delcroix M, Gomez-Sanchez M, Siedentop H, Seeger W | title = Inhaled iloprost for severe pulmonary hypertension | journal = The New England Journal of Medicine | volume = 347 | issue = 5 | pages = 322–329 | date = August 2002 | pmid = 12151469 | doi = 10.1056/NEJMoa020204 | doi-access = free }} * {{cite journal | vauthors = Meizer R, Meraner D, Meizer E, Radda C, Landsiedl F, Aigner N | title = Outcome of painful bone marrow edema of the femoral head following treatment with parenteral iloprost | journal = Indian Journal of Orthopaedics | volume = 43 | issue = 1 | pages = 36–39 | date = January 2009 | pmid = 19753177 | pmc = 2739485 |doi = 10.4103/0019-5413.45321 | doi-broken-date = 12 July 2025 |doi-access=free}} {{refend}}

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