flunisolide

{{Short description|Chemical compound}}

{{Infobox drug

| Verifiedfields = changed

| verifiedrevid = 461101454

| IUPAC_name = (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

| image = Flunisolide.png

| image2 = Flunisolide ball-and-stick.png

| tradename = Aerobid, Nasalide, Nasarel, others

| Drugs.com = {{drugs.com|monograph|flunisolide}}

| MedlinePlus = a681048

| pregnancy_category =

| legal_status =

| routes_of_administration = Inhaled

| bioavailability =

| protein_bound = 40% after inhalation

| metabolism =

| elimination_half-life = 1.8 hours

| IUPHAR_ligand = 7076

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

| CAS_number = 3385-03-3

| ATC_prefix = R01

| ATC_suffix = AD04

| ATC_supplemental = {{ATC|R03|BA03}}

| PubChem = 82153

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00180

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 74144

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 78M02AA8KF

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D00324

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 5106

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1512

| C=24 | H=31 | F=1 | O=6

| smiles = O=C\1\C=C/[C@]2(/C(=C/1)[C@@H](F)C[C@H]3[C@H]4[C@](C[C@H](O)[C@H]23)([C@@]5(OC(O[C@@H]5C4)(C)C)C(=O)CO)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C24H31FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h5-7,13-14,16-17,19-20,26,28H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XSFJVAJPIHIPKU-XWCQMRHXSA-N

| synonyms = 6α-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione acetone cyclic 16,17-acetal

}}

Flunisolide (marketed as AeroBid among others) is a corticosteroid often prescribed as a treatment for allergic rhinitis.{{cite web | title = Flunisolide | url = http://www.drugbank.ca/drugs/DB00180 | work = DrugBank }} Intranasal corticosteroids are the most effective medication for controlling symptoms.{{cite journal | vauthors = Wallace DV, Dykewicz MS, Bernstein DI, Blessing-Moore J, Cox L, Khan DA, Lang DM, Nicklas RA, Oppenheimer J, Portnoy JM, Randolph CC, Schuller D, Spector SL, Tilles SA | display-authors = 6 | title = The diagnosis and management of rhinitis: an updated practice parameter | journal = The Journal of Allergy and Clinical Immunology | volume = 122 | issue = 2 Suppl | pages = S1-84 | date = August 2008 | pmid = 18662584 | doi = 10.1016/j.jaci.2008.06.003 | doi-access = free }}

Flunisolide's principal mechanism of action is to activate glucocorticoid receptors, indicating an anti-inflammatory action. The effects of topical corticosteroids are not immediate and must be used for at least a few days for noticeable relief. As-needed use is less effective than regular recommended use. Flunisolide should not be used for nasal infections. It should not be continued if symptoms are not relieved after regular use for over two to three weeks.{{cite web | title = Flunisolide Nasal Solution | url = http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8ba9cc1c-55e5-40ed-9efe-f7abb73976ea | work = DailyMed | publisher = U.S. National Library of Medicine }}

Patented in 1958 and approved for medical use in 1978,{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=486 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA486 |language=en}} it is on the World Health Organization's List of Essential Medicines.{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}

Side effects

Temporary nose and throat dryness, irritation, bleeding, or unpleasant taste or smell may occur.{{cite web|url=http://www.medicinenet.com/flunisolide-nasal/page2.htm|title=FLUNISOLIDE - NASAL (Nasalide, Nasarel) side effects, medical uses, and drug interactions | work = MedicineNet }} Nasal septum perforation has been rarely reported. Rare but localized infections of the nose and pharynx with Candida albicans have also been reported. Its long-term use may raise the chances of cataracts or glaucoma.

Flunisolide nasal spray is absorbed into the circulatory system (blood). Corticosteroid nasal sprays may affect the hypothalamic-pituitary-adrenal axis function in humans.{{cite web|url=http://www.rxlist.com/nasalide-drug/clinical-pharmacology.htm|title=Nasalide (Flunisolide (Nasal Spray)) Drug Information: Clinical Pharmacology - Prescribing Information | work = RxList }} After obtaining the desired clinical effect, the maintenance dose should be reduced to the smallest amount required to control the symptoms. The amount can be as low as one spray in each nostril daily. Utilizing the minimum effective dose reduces possibility of side effects. Recommended amounts of intranasal corticosteroids are generally not associated with systemic side effects.

Corticosteroids inhibit wound healing, so corticosteroid nasal sprays should be used cautiously in patients who have experienced recent nasal septal ulcers, recurrent epistaxis, nasal surgery or trauma, until healing. In pregnancy, recommended doses of intranasal corticosteroids are safe and effective.

References

{{Reflist|2}}

{{Glucocorticoids}}

{{Nasal preparations}}

{{Drugs for obstructive airway diseases}}

{{Glucocorticoidics}}

Category:Acetonides

Category:Corticosteroid cyclic ketals

Category:Diketones

Category:Diols

Category:Organofluorides

Category:Glucocorticoids