Ciclesonide

A synthetic corticosteroid prodrug used for the maintenance treatment of bronchial asthma and allergic rhinitis. Following inhalation or intranasal administration, ciclesonide is converted by esterases to its active metabolite, des-ciclesonide, which binds to glucocorticoid receptors and suppresses inflammatory mediator production, airway inflammation, and mucosal swelling. Its local activation and extensive first-pass metabolism help limit systemic corticosteroid exposure. It is not intended for the immediate relief of acute asthma attacks

CAS Number: 126544-47-6

Molecular Mass: 540.7 g/mol

Formula: C₃₂H₄₄O₇

Smiles: CC(C)C(=O)OCC(=O)[C@@]12O[C@H](C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]12C

Synonymes:

Ciclesonide, 126544-47-6, Alvesco, Omnaris, Zetonna, RPR251526, RPR-251526, Ciclesonida, DTXSID9046659, Alvesco 80, Alvesco 160, (R)-11beta,16alpha,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclohexanecarboxaldehyde, 21-isobutyrate, BI54903, DTXCID7026659, S59502J185, ciclesonidum, Aservo EquiHaler, RefChem:57392, R01AD13, R03BA08, 2-((1S,2S,4R,6R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo(10.8.0.02,?.0?,?.013,1?)icosa-14,17-dien-8-yl)-2-oxoethyl 2-methylpropanoate, Ciclesonide (Standard), Ciclesonide [INN], [2-[(1S,2S,4R,6R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 2-methylpropanoate, 141845-82-1, [2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-Cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 2-methylpropanoate, 2-{6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl}-2-oxoethyl 2-methylpropanoate, Osonase, Osonide, Omnair, RPR 251526, Alvesco HFA, Omnaris HFA, 2-((6aR,6bS,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-cyclohexyl-7-hydroxy-6a,8a-dimethyl-4-oxo-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl isobutyrate, Alvesco (TN), Omnaris (TN), Ciclesonide [USAN:INN], sobutyrate, BTR-15K, Ciclesonide (JAN/USAN/INN), BTR-15, TBN-15, Ciclesonide CRS, LUKZNWIVRBCLON-GXOBDPJESA-N, UNII-S59502J185, NCGC00167484-01, Zetonna (TN), Alvesco, Ciclesonide, BYK-20426, BY-9010, KS-1165, CICLESONIDE [MI], CICLESONIDE [JAN], CICLESONIDE [USAN], CICLESONIDE [VANDF], SCHEMBL3688, CICLESONIDE [MART.], CICLESONIDE [WHO-DD], B-9207-015, GTPL7469, orb1305357, orb3025781, el-87-6, CHEMBL2040682, CHEBI:31397, Ciclesonide, >=98% (HPLC), HY-B0625R, CICLESONIDE [ORANGE BOOK], WLZ3795, CICLESONIDE [EP MONOGRAPH], HMS3714N07, EX-A4195, HY-B0625, Tox21_112486, BDBM50247997, EBC-27297, MSK011037, s4646, Ciclesonide containing impurity A CRS, AKOS015994702, AC-1330, CCG-269962, DB01410, FC20428, MSK011037-1000A, NCGC00167972-01, Pregna-1,4-diene-3,20-dione, 16,17-(((R)-cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha)-, Pregna-1,4-diene-3,20-dione, 16,17-((cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha(R))-, Ciclesonide 100 microg/mL in Acetonitrile, C3701, CAS-141845-82-1, CS-0694790, NS00006507, C72110, D01703, Ciclesonide Solution in Acetonitrile, 1000ug/mL, EN300-19766990, SR-01000942227, Q5119448, SR-01000942227-1, BRD-K35245662-001-01-2, Ciclesonide, European Pharmacopoeia (EP) Reference Standard, (11?,16?)-16,17-[[(R)-Cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-pregna-1,4-diene-3,20-dione, (11beta,16alpha)-16,17-[[(R)-Cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)pregna-1,4-diene-3,20-dione, [2-[(1S,2S,4R,6R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxo-ethyl] 2-methylpropanoate, 2-((6aR,6bS,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-cyclohexyl-7-hydroxy-6a,8a-dimethyl-4-oxo-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl i, 2-[(1S,2S,4R,6R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate, 2-[(4aR,4bS,5S,6aS,6bS,8R,9aR,10aS,10bS)-8-cyclohexyl-5-hydroxy-4a,6a-dimethyl-2-oxo-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-phenanthro[1',2':1,2]cyclopenta[3,4-d][1,3]dioxol-6b-yl]-2-oxoethyl 2-methylpropanoate, 2H-Naphth (2',1':4,5) indeno (1,2-d) (1,3) dioxole, pregna-1,4-diene-3,20-dione deriv., PREGNA-1,4-DIENE-3,20-DIONE, 16,17-(((R)-CYCLOHEXYLMETHYLENE)BIS(OXY))-11-HYDROXY-21-(2-METHYL-1-OXOPROPOXY)-, (11.BETA.,16.ALPHA.)

Bioactivity: Glucocorticoid receptor agonist prodrug; anti-inflammatory corticosteroid

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	278.15	-	429.4	[98]
1-Butanol	280.65	-	442.2	[98]
1-Butanol	283.15	-	459.8	[98]
1-Butanol	285.65	-	477.4	[98]
1-Butanol	288.15	-	501.3	[98]
1-Butanol	290.65	-	525.3	[98]
1-Butanol	293.15	-	550.1	[98]
1-Butanol	295.65	-	581.3	[98]
1-Butanol	298.15	-	611.3	[98]
1-Butanol	300.65	-	646.5	[98]
1-Butanol	303.15	-	686.4	[98]
1-Butanol	305.65	-	728.8	[98]
1-Butanol	308.15	-	779.0	[98]
1-Butanol	310.65	-	822.3	[98]
1-Butanol	313.15	-	873.6	[98]
1-Propanol	278.15	-	105.0	[98]
1-Propanol	280.65	-	122.1	[98]
1-Propanol	283.15	-	142.2	[98]
1-Propanol	285.65	-	165.4	[98]
1-Propanol	288.15	-	186.0	[98]
1-Propanol	290.65	-	217.0	[98]
1-Propanol	293.15	-	249.8	[98]
1-Propanol	295.65	-	288.8	[98]
1-Propanol	298.15	-	328.7	[98]
1-Propanol	300.65	-	380.0	[98]
1-Propanol	303.15	-	430.3	[98]
1-Propanol	305.65	-	491.4	[98]
1-Propanol	308.15	-	559.2	[98]
1-Propanol	310.65	-	638.6	[98]
1-Propanol	313.15	-	722.2	[98]
Acetonitrile	278.15	-	51.28	[98]
Acetonitrile	280.65	-	55.66	[98]
Acetonitrile	283.15	-	60.54	[98]
Acetonitrile	285.65	-	65.59	[98]
Acetonitrile	288.15	-	71.78	[98]
Acetonitrile	290.65	-	76.98	[98]
Acetonitrile	293.15	-	83.0	[98]
Acetonitrile	295.65	-	89.59	[98]
Acetonitrile	298.15	-	96.77	[98]
Acetonitrile	300.65	-	104.0	[98]
Acetonitrile	303.15	-	112.0	[98]
Acetonitrile	305.65	-	119.8	[98]
Acetonitrile	308.15	-	128.7	[98]
Acetonitrile	310.65	-	137.5	[98]
Acetonitrile	313.15	-	145.3	[98]
Ethanol	278.15	-	21.81	[98]
Ethanol	280.65	-	26.0	[98]
Ethanol	283.15	-	31.28	[98]
Ethanol	285.65	-	37.34	[98]
Ethanol	288.15	-	44.72	[98]
Ethanol	290.65	-	53.08	[98]
Ethanol	293.15	-	62.88	[98]
Ethanol	295.65	-	74.15	[98]
Ethanol	298.15	-	87.19	[98]
Ethanol	300.65	-	102.0	[98]
Ethanol	303.15	-	119.8	[98]
Ethanol	305.65	-	140.1	[98]
Ethanol	308.15	-	163.3	[98]
Ethanol	310.65	-	189.2	[98]
Ethanol	313.15	-	220.0	[98]
Ethyl acetate	278.15	-	306.1	[98]
Ethyl acetate	280.65	-	332.8	[98]
Ethyl acetate	283.15	-	360.1	[98]
Ethyl acetate	285.65	-	390.0	[98]
Ethyl acetate	288.15	-	421.3	[98]
Ethyl acetate	290.65	-	456.0	[98]
Ethyl acetate	293.15	-	492.3	[98]
Ethyl acetate	295.65	-	531.0	[98]
Ethyl acetate	298.15	-	572.9	[98]
Ethyl acetate	300.65	-	614.5	[98]
Ethyl acetate	303.15	-	666.9	[98]
Ethyl acetate	305.65	-	712.8	[98]
Ethyl acetate	308.15	-	766.4	[98]
Ethyl acetate	310.65	-	827.4	[98]
Ethyl acetate	313.15	-	882.3	[98]
Isopropanol	278.15	-	58.97	[98]
Isopropanol	280.65	-	68.59	[98]
Isopropanol	283.15	-	80.22	[98]
Isopropanol	285.65	-	93.9	[98]
Isopropanol	288.15	-	109.0	[98]
Isopropanol	290.65	-	126.2	[98]
Isopropanol	293.15	-	146.5	[98]
Isopropanol	295.65	-	168.9	[98]
Isopropanol	298.15	-	195.8	[98]
Isopropanol	300.65	-	225.7	[98]
Isopropanol	303.15	-	260.3	[98]
Isopropanol	305.65	-	298.7	[98]
Isopropanol	308.15	-	343.0	[98]
Isopropanol	310.65	-	392.5	[98]
Isopropanol	313.15	-	449.0	[98]
Toluene	278.15	-	158.2	[98]
Toluene	280.65	-	169.3	[98]
Toluene	283.15	-	182.1	[98]
Toluene	285.65	-	195.4	[98]
Toluene	288.15	-	208.7	[98]
Toluene	290.65	-	224.2	[98]
Toluene	293.15	-	239.1	[98]
Toluene	295.65	-	255.2	[98]
Toluene	298.15	-	272.5	[98]
Toluene	300.65	-	290.3	[98]
Toluene	303.15	-	309.3	[98]
Toluene	305.65	-	329.4	[98]
Toluene	308.15	-	350.2	[98]
Toluene	310.65	-	372.2	[98]
Toluene	313.15	-	394.9	[98]

Molecule 3D descriptors

Descriptor	Value
PMI1	3937.8204
PMI2	7752.4042
PMI3	8594.3930
NPR1	0.4582
NPR2	0.9020
RadiusOfGyration	4.3310
InertialShapeFactor	0.0002
Eccentricity	0.8889
Asphericity	0.1796
SpherocityIndex	0.5224
PBF	1.5659