ChemFOnt: Showing chemical card for Flunisolide (CFc000008723)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:37 UTC

Chemfont ID

CFc000008723

Molecule Identification

Common Name

Flunisolide

Definition

Flunisolide is only found in individuals that have used or taken this drug. It is a corticosteroid often prescribed as treatment for allergic rhinitis.Flunisolide is a glucocorticoid receptor agonist. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Flunisolide binds to plasma transcortin, and it becomes active when it is not bound to transcortin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Flunisolida	ChEBI
Flunisolide anhydrous	ChEBI
Flunisolidum	ChEBI
Elan brand 2 OF flunisolide	HMDB
Nasalide	HMDB
Nasarel	HMDB
Flunisolide hemihydrate, (6alpha,11beta,16alpha)-isomer	HMDB
Flunisolide hydrofluoroalkane	HMDB
AeroBid	HMDB
Inhacort	HMDB
Flunisolide hfa	HMDB
Flunisolide, (6beta,11beta,16alpha)-isomer	HMDB
Ratio-flunisolide	HMDB
Apo-flunisolide	HMDB
Rhinalar	HMDB
6 alpha-Fluorodihydroxy-16 alpha,17 alpha-isopropylidenedioxy-1,4-pregnadiene-3,20- dione	HMDB
Elan brand 1 OF flunisolide	HMDB
Syntaris	HMDB

Chemical Formula

C₂₄H₃₁FO₆

Average Molecular Weight

434.4977

Monoisotopic Molecular Weight

434.210466929

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

Traditional Name

soluzione

CAS Registry Number

3385-03-3

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO

InChI Identifier

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

InChI Key

XSFJVAJPIHIPKU-XWCQMRHXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-1,4-steroid
3-oxosteroid
6-halo-steroid
Halo-steroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
Delta-1,4-steroid
Ketal
Meta-dioxolane
Alpha-hydroxy ketone
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alkyl halide
Alkyl fluoride
Alcohol
Organohalogen compound
Organofluoride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:5106 )
cyclic ketal (CHEBI:5106 )
20-oxo steroid (CHEBI:5106 )
fluorinated steroid (CHEBI:5106 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:5106 )
21-hydroxy steroid (CHEBI:5106 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014326)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.037 g/L	ALOGPS
logP	2.2	ALOGPS
logP	1.56	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	111.89 m³·mol⁻¹	ChemAxon
Polarizability	44.88 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon