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3385-03-3 molecular structure
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(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one

ChemBase ID: 65
Molecular Formular: C24H31FO6
Molecular Mass: 434.4977432
Monoisotopic Mass: 434.21046693
SMILES and InChIs

SMILES:
F[C@H]1C[C@H]2[C@H]3[C@@]([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)(C[C@H](O)[C@@H]2[C@@]2(C1=CC(=O)C=C2)C)C
Canonical SMILES:
OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1C[C@@H](C1=CC(=O)C=C[C@]21C)F)(C)C
InChI:
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
InChIKey:
XSFJVAJPIHIPKU-XWCQMRHXSA-N

Cite this record

CBID:65 http://www.chembase.cn/molecule-65.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
(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
IUPAC Traditional name
soluzione
flunisolide
Brand Name
Aerobid
Bronalide
Lunis
Nasalide
Nasarel
Rhinalar
Synaclyn
Syntaris
Synonyms
Flunisolide [anhydrous]
flunisolide
Flunisolide
AeroBid
Nasalide
Nasarel
(6α,11β,16α)-6-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione
6α-Fluoro-11β,21-dihydroxy-16α,17α-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione
Aerobid M
Bronalide
Lunis
Nisolid
RS 3999
Rhinalar
Soluzione
Synaclyn
Syntaris
CAS Number
3385-03-3
PubChem SID
160963528
46507894
PubChem CID
82153

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.726746  H Acceptors
H Donor LogD (pH = 5.5) 1.5607916 
LogD (pH = 7.4) 1.5607915  Log P 1.5607916 
Molar Refractivity 111.8852 cm3 Polarizability 43.367012 Å3
Polar Surface Area 93.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.2  LOG S -4.07 
Solubility (Water) 3.74e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Practically insoluble expand Show data source
Apperance
White Solid expand Show data source
Melting Point
237-240°C (dec.) expand Show data source
Hydrophobicity(logP)
1.1 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
MSDS Link
Download expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals TRC TRC
DrugBank - DB00180 external link
Item Information
Drug Groups approved; investigational
Description Flunisolide (marketed as AeroBid, Nasalide, Nasarel) is a corticosteroid often prescribed as treatment for allergic rhinitis.

The principle mechanism of action of flunisolide is to activate glucocorticoid receptors. It also has anti-inflammatory action.
Indication For the maintenance treatment of asthma as a prophylactic therapy.
Pharmacology Flunisolide is a synthetic corticosteroid. It is administered either as an oral metered-dose inhaler for the treatment of asthma or as a nasal spray for treating allergic rhinitis. Corticosteroids are naturally occurring hormones that prevent or suppress inflammation and immune responses. When given as an intranasal spray, flunisolide reduces watery nasal discharge (rhinorrhea), nasal congestion, postnasal drip, sneezing, and itching oat the back of the throat that are common allergic symptoms.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic, converted to the S beta-OH metabolite.
Absorption Absorbed rapidly
Half Life 1.8 hours
Protein Binding Approximately 40% after oral inhalation
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S1513 external link
Research Area: Inflammation
Biological Activity:
Flunisolide (AeroBid, Nasalide, Nasarel) is a corticosteroid often prescribed as treatment for allergic rhinitis. The principal mechanism of action of Flunisolide is to activate glucocorticoid receptors. It also has anti-inflammatory action. [1]
Toronto Research Chemicals - F500485 external link
Synthetic fluorinated corticosteroid related to Prednisolone (P703740). Antiasthmatic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Flunisolide
  • • Chu, N.I., et al.: Drug Metab. Dispos., 7, 81 (1979)
  • • Pakes, G.E., et al.: Drugs, 19, 397 (1979)
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PATENTS

PATENTS

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INTERNET

INTERNET

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