Synonym
GW-870086; GW-870086X; 870086; GW870086; GW870086X; GW 870086; GW 870086X
IUPAC/Chemical Name
Androsta-1,4-diene-17-carboxylic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(((2,2,3,3-tetramethylcyclopropyl)carbonyl)oxy)-, cyanomethyl ester, (6alpha,11beta,16alpha,17alpha)-
InChi Key
WUBKGTSFJSEIEM-NSHBDUGJSA-N
InChi Code
InChI=1S/C31H39F2NO6/c1-16-12-18-19-14-21(32)20-13-17(35)8-9-28(20,6)30(19,33)22(36)15-29(18,7)31(16,25(38)39-11-10-34)40-24(37)23-26(2,3)27(23,4)5/h8-9,13,16,18-19,21-23,36H,11-12,14-15H2,1-7H3/t16-,18+,19+,21+,22+,28+,29+,30+,31+/m1/s1
SMILES Code
C[C@@]12[C@](C(OCC#N)=O)(OC(C3C(C)(C)C3(C)C)=O)[C@H](C)C[C@@]1([H])[C@]4([H])C[C@H](F)C5=CC(C=C[C@]5(C)[C@@]4(F)[C@@H](O)C2)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
In vitro activity:
Taken together, GW870086X differentially affected matrix generating and degrading processes in human TM cells compared with DEX and PRED. Both DEX and PRED shifted the balance toward matrix generation and decreased turnover. GW870086X was the only GC that increased a matrix-degrading component, tPA, and had a less pronounced effect on matrix deposition with an overall more favorable profile.
Reference: Invest Ophthalmol Vis Sci. 2013 Mar; 54(3): 2100–2107. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4601886/
In vivo activity:
As a close relative of fluticasone, GW870086 has pharmaceutical properties well suited for topical administration onto the skin or into the lungs. The anti-inflammatory activity of GW870086 on the skin was demonstrated using a simple delayed-type hypersensitivity reaction. Administration of oxazolone topically to the ears of sensitized mice generates a T-cell-mediated inflammation that results in swelling of the ears. Direct topical application of either FP or GW870086 showed potent dose-dependent anti-inflammatory activity on the treated ear (Figure 7C). Inhibition of inflammation in the contralateral ear was also observed with both compounds at higher doses as a result of systemic exposure following topical dosing.
Reference: Br J Pharmacol. 2013 Jul; 169(6): 1389–1403. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3831715/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
559.65
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Uings IJ, Needham D, Matthews J, Haase M, Austin R, Angell D, Leavens K, Holt J, Biggadike K, Farrow SN. Discovery of GW870086: a potent anti-inflammatory steroid with a unique pharmacological profile. Br J Pharmacol. 2013 Jul;169(6):1389-403. doi: 10.1111/bph.12232. PMID: 23639214; PMCID: PMC3831715.
2. Stamer WD, Hoffman EA, Kurali E, Krauss AH. Unique response profile of trabecular meshwork cells to the novel selective glucocorticoid receptor agonist, GW870086X. Invest Ophthalmol Vis Sci. 2013 Mar 1;54(3):2100-7. doi: 10.1167/iovs.12-11298. PMID: 23462748; PMCID: PMC4601886.
In vitro protocol:
1. Uings IJ, Needham D, Matthews J, Haase M, Austin R, Angell D, Leavens K, Holt J, Biggadike K, Farrow SN. Discovery of GW870086: a potent anti-inflammatory steroid with a unique pharmacological profile. Br J Pharmacol. 2013 Jul;169(6):1389-403. doi: 10.1111/bph.12232. PMID: 23639214; PMCID: PMC3831715.
2. Stamer WD, Hoffman EA, Kurali E, Krauss AH. Unique response profile of trabecular meshwork cells to the novel selective glucocorticoid receptor agonist, GW870086X. Invest Ophthalmol Vis Sci. 2013 Mar 1;54(3):2100-7. doi: 10.1167/iovs.12-11298. PMID: 23462748; PMCID: PMC4601886.
In vivo protocol:
1. Uings IJ, Needham D, Matthews J, Haase M, Austin R, Angell D, Leavens K, Holt J, Biggadike K, Farrow SN. Discovery of GW870086: a potent anti-inflammatory steroid with a unique pharmacological profile. Br J Pharmacol. 2013 Jul;169(6):1389-403. doi: 10.1111/bph.12232. PMID: 23639214; PMCID: PMC3831715.
1: Uings IJ, Needham D, Matthews J, Haase M, Austin R, Angell D, Leavens K, Holt J, Biggadike K, Farrow SN. Discovery of GW870086: a potent anti-inflammatory steroid with a unique pharmacological profile. Br J Pharmacol. 2013 Jul;169(6):1389-403. doi: 10.1111/bph.12232. PubMed PMID: 23639214; PubMed Central PMCID: PMC3831715.
2: Bareille P, Hardes K, Donald AC. Efficacy and safety of once-daily GW870086 a novel selective glucocorticoid in mild-moderate asthmatics: a randomised, two-way crossover, controlled clinical trial. J Asthma. 2013 Dec;50(10):1077-82. doi: 10.3109/02770903.2013.837480. PubMed PMID: 23991670.
3: Stamer WD, Hoffman EA, Kurali E, Krauss AH. Unique response profile of trabecular meshwork cells to the novel selective glucocorticoid receptor agonist, GW870086X. Invest Ophthalmol Vis Sci. 2013 Mar 1;54(3):2100-7. doi: 10.1167/iovs.12-11298. PubMed PMID: 23462748; PubMed Central PMCID: PMC4601886.
4: Leaker BR, O'Connor B, Singh D, Barnes PJ. The novel inhaled glucocorticoid receptor agonist GW870086X protects against adenosine-induced bronchoconstriction in asthma. J Allergy Clin Immunol. 2015 Aug;136(2):501-2.e6. doi: 10.1016/j.jaci.2015.01.034. PubMed PMID: 25784273.
5: Dölle S, Hielscher N, Bareille PJ, Hardes K, Robertson J, Worm M. Clinical efficacy and tolerability of a novel selective corticosteroid in atopic dermatitis--two randomised controlled trials. Skin Pharmacol Physiol. 2015;28(3):159-66. doi: 10.1159/000367696. PubMed PMID: 25614148.
6: Cazzola M, Coppola A, Rogliani P, Matera MG. Novel glucocorticoid receptor agonists in the treatment of asthma. Expert Opin Investig Drugs. 2015;24(11):1473-82. doi: 10.1517/13543784.2015.1078310. Review. PubMed PMID: 26293110.
7: Rider CF, Shah S, Miller-Larsson A, Giembycz MA, Newton R. Cytokine-induced loss of glucocorticoid function: effect of kinase inhibitors, long-acting β(2)-adrenoceptor [corrected] agonist and glucocorticoid receptor ligands. PLoS One. 2015 Jan 27;10(1):e0116773. doi: 10.1371/journal.pone.0116773. Erratum in: PLoS One. 2015;10(5):e0128728. PubMed PMID: 25625944; PubMed Central PMCID: PMC4308083.
