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{{Short description|Chemical compound}}
{{Drugbox
{{Infobox drug
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 461101454
| verifiedrevid = 461101454
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| image2 = Flunisolide ball-and-stick.png
| image2 = Flunisolide ball-and-stick.png
<!--Clinical data-->
<!--Clinical data-->
| tradename = Aerobid
| tradename = Aerobid, Nasalide, Nasarel, others
| Drugs.com = {{drugs.com|monograph|flunisolide}}
| Drugs.com = {{drugs.com|monograph|flunisolide}}
| MedlinePlus = a681048
| MedlinePlus = a681048
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| legal_status =
| legal_status =
| routes_of_administration = Inhaled
| routes_of_administration = Inhaled

<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| protein_bound = 40% after oral inhalation
| protein_bound = 40% after inhalation
| metabolism =
| metabolism =
| elimination_half-life = 1.8 hours
| elimination_half-life = 1.8 hours

<!--Identifiers-->
<!--Identifiers-->
| IUPHAR_ligand = 7076
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3385-03-3
| CAS_number = 3385-03-3
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| PubChem = 82153
| PubChem = 82153
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00180
| DrugBank = DB00180
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 74144
| ChemSpiderID = 74144
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1512
| ChEMBL = 1512

<!--Chemical data-->
<!--Chemical data-->
| C=24 | H=31 | F=1 | O=6
| C=24 | H=31 | F=1 | O=6
| molecular_weight = 434.498 g/mol
| 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
| 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
| InChI = 1/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
| InChIKey = XSFJVAJPIHIPKU-XWCQMRHXBG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| 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
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| synonyms = <small>6α-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione acetone cyclic 16,17-acetal</small>
| synonyms = <small>6α-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione acetone cyclic 16,17-acetal</small>
}}
}}
<!-- Definition and medical uses -->
⚫
'''Flunisolide''' (marketed as '''AeroBid''' among others) is a [[corticosteroid]] often prescribed as a treatment for [[allergic rhinitis]].<ref>{{cite web | title = Flunisolide | url = http://www.drugbank.ca/drugs/DB00180 | work = DrugBank }}</ref> Intranasal corticosteroids are the most effective medication for controlling symptoms.<ref name="auto">{{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 }}</ref>


<!-- Side effects and mechanisms -->
⚫
'''Flunisolide''' (marketed as '''AeroBid''', '''Nasalide''', '''Nasarel''') is a [[corticosteroid]] often prescribed as treatment for [[allergic rhinitis]].<ref>See http://www.drugbank.ca/drugs/DB00180</ref> Intranasal corticosteroids are the most effective medication for controlling symptoms. <ref>{{cite journal|title=The diagnosis and management of rhinitis: an updated practice parameter|journal=Allergy and Clinical Immunology|date=Aug 2008|pmid=18662584}}</ref> In the [[United Kingdom]] it was formerly marketed as '''Syntaris''', but this was recently discontinued by the manufacturers.<ref>See http://www.pharphar.com/v/Syntaris</ref>
⚫
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.<ref name="auto"/> 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.<ref name="nih.gov">{{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 }}</ref>


<!-- Society and culture -->
⚫
The principal mechanism of action of flunisolide is to activate [[glucocorticoid]] receptors, meaning it has an [[anti-inflammatory]] action. The effects of topical corticosteroids is not immediate and requires regular use and at least a few days to start experiencing noticeable symptom relief. As-needed use has been shown to be not as effective as regular recommended use. <ref>{{cite journal|title=The diagnosis and management of rhinitis: an updated practice parameter|journal=Allergy and Clinical Immunology|date=Aug 2008|pmid=18662584}}</ref> Flunisolide should not be used in the presence of nasal infection. It should not be continued if there is no relief of symptoms after regular use over two to three weeks. <ref>http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8ba9cc1c-55e5-40ed-9efe-f7abb73976ea</ref>
Patented in 1958 and approved for medical use in 1978,<ref name=Fis2006>{{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}}</ref> it is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO22nd">{{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 }}</ref>


==Side effects==
==Side effects==
Temporary nose and throat dryness, irritation, bleeding or unpleasant taste or smell may occur.<ref>http://www.medicinenet.com/flunisolide-nasal/page2.htm</ref> [[Nasal septum perforation]] is rarely reported. <ref>{{cite journal|title=The diagnosis and management of rhinitis: an updated practice parameter|journal=Allergy and Clinical Immunology|date=Aug 2008|pmid=18662584}}</ref> Rare, but localized infections of the nose and pharynx with [[Candida albicans]] have been reported and long-term use may raise the chance of cataracts or glaucoma. <ref>http://www-uptodate-com.ucsf.idm.oclc.org/contents/flunisolide-nasal-patient-drug-information?source=search_result&search=flunisolide&selectedTitle=3~14</ref>
Temporary nose and throat dryness, irritation, bleeding, or unpleasant taste or smell may occur.<ref>{{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 }}</ref> [[Nasal septum perforation]] has been rarely reported.<ref name="auto"/> 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.<ref name="rxlist.com" />


Flunisolide nasal spray is absorbed into the [[circulatory system]] (blood).<ref>http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8ba9cc1c-55e5-40ed-9efe-f7abb73976ea</ref> Corticosteroid nasal sprays may affect the [[hypothalamic-pituitary-adrenal axis]] function in humans.<ref>http://www.rxlist.com/nasalide-drug/clinical-pharmacology.htm</ref> After the desired clinical effect is obtained, the [[maintenance dose]] should be reduced to the smallest amount necessary to control symptoms, which can be as low as 1 spray in each nostril a day. Utilizing the minimum [[effective dose]] will reduce possibility of side effects. <ref>http://www.rxlist.com/nasalide-drug/clinical-pharmacology.htm</ref>Recommended amounts of intranasal corticosteroids are generally not associated with [[systemic]] side effects.
Flunisolide nasal spray is absorbed into the [[circulatory system]] (blood).<ref name="nih.gov"/> Corticosteroid nasal sprays may affect the [[hypothalamic-pituitary-adrenal axis]] function in humans.<ref name="rxlist.com">{{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 }}</ref> 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 [[Effective dose (pharmacology)|minimum effective dose]] reduces possibility of side effects.<ref name="rxlist.com"/> Recommended amounts of intranasal corticosteroids are generally not associated with [[Systemic effect|systemic]] side effects.


Corticosteroids inhibit wound healing. Therefore, use of corticosteroid nasal sprays in patients who have experienced recent nasal septal ulcers, recurrent [[epistaxis]], nasal surgery or trauma, a nasal corticosteroid should be used with caution until healing has occurred. <ref>http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8ba9cc1c-55e5-40ed-9efe-f7abb73976ea</ref> In pregnancy, recommended doses of intranasal corticosteroids are safe and effective.<ref>{{cite journal|title=The diagnosis and management of rhinitis: an updated practice parameter|journal=Allergy and Clinical Immunology|date=Aug 2008|pmid=18662584}}</ref>
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.<ref name="nih.gov"/> In pregnancy, recommended doses of intranasal corticosteroids are safe and effective.<ref name="auto"/>


==References==
== References ==
{{Reflist|2}}
{{Reflist|2}}



{{Glucocorticoids}}
{{Glucocorticoids}}
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{{Glucocorticoidics}}
{{Glucocorticoidics}}


⚫
[[Category:Acetonides]]
[[Category:Corticosteroid cyclic ketals]]
[[Category:Diketones]]
[[Category:Diols]]
[[Category:Organofluorides]]
[[Category:Glucocorticoids]]
[[Category:Glucocorticoids]]
⚫
[[Category:Organofluorides]]


{{respiratory-system-drug-stub}}

Latest revision as of 23:16, 1 October 2024

Flunisolide
Clinical data
Trade namesAerobid, Nasalide, Nasarel, others
Other names6α-Fluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione acetone cyclic 16,17-acetal
AHFS/Drugs.comMonograph
MedlinePlusa681048
Routes of
administration		Inhaled
ATC code
Pharmacokinetic data
Protein binding40% after inhalation
Elimination half-life1.8 hours
Identifiers
  • (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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.177 Edit this at Wikidata
Chemical and physical data
FormulaC24H31FO6
Molar mass434.504 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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 checkY
  • Key:XSFJVAJPIHIPKU-XWCQMRHXSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Flunisolide (marketed as AeroBid among others) is a corticosteroid often prescribed as a treatment for allergic rhinitis.[1] Intranasal corticosteroids are the most effective medication for controlling symptoms.[2]

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.[2] 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.[3]

Patented in 1958 and approved for medical use in 1978,[4] it is on the World Health Organization's List of Essential Medicines.[5]

Side effects

[edit]

Temporary nose and throat dryness, irritation, bleeding, or unpleasant taste or smell may occur.[6] Nasal septum perforation has been rarely reported.[2] 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.[7]

Flunisolide nasal spray is absorbed into the circulatory system (blood).[3] Corticosteroid nasal sprays may affect the hypothalamic-pituitary-adrenal axis function in humans.[7] 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.[7] 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.[3] In pregnancy, recommended doses of intranasal corticosteroids are safe and effective.[2]

References

[edit]
  1. ^ "Flunisolide". DrugBank.
  2. ^ a b c d Wallace DV, Dykewicz MS, Bernstein DI, Blessing-Moore J, Cox L, Khan DA, et al. (August 2008). "The diagnosis and management of rhinitis: an updated practice parameter". The Journal of Allergy and Clinical Immunology. 122 (2 Suppl): S1-84. doi:10.1016/j.jaci.2008.06.003. PMID 18662584.
  3. ^ a b c "Flunisolide Nasal Solution". DailyMed. U.S. National Library of Medicine.
  4. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 486. ISBN 9783527607495.
  5. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  6. ^ "FLUNISOLIDE - NASAL (Nasalide, Nasarel) side effects, medical uses, and drug interactions". MedicineNet.
  7. ^ a b c "Nasalide (Flunisolide (Nasal Spray)) Drug Information: Clinical Pharmacology - Prescribing Information". RxList.
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