Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C30H30Cl2F2N2O8S |
| Molecular Weight | 687.536 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(=O)(=O)NC1=CC=C(C=C1OCC2CC2)C(=O)O[C@@H](CC3=C(Cl)C=[N+]([O-])C=C3Cl)C4=CC=C(OC(F)F)C(OCC5CC5)=C4
InChI
InChIKey=VCFBPAOSTLMYIV-SANMLTNESA-N
InChI=1S/C30H30Cl2F2N2O8S/c1-45(39,40)35-24-8-6-20(11-27(24)41-15-17-2-3-17)29(37)43-26(12-21-22(31)13-36(38)14-23(21)32)19-7-9-25(44-30(33)34)28(10-19)42-16-18-4-5-18/h6-11,13-14,17-18,26,30,35H,2-5,12,15-16H2,1H3/t26-/m0/s1
| Molecular Formula | C30H30Cl2F2N2O8S |
| Molecular Weight | 687.536 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
CHF6001 is a phosphodiesterase 4 (PDE4) inhibitor optimised for inhaled delivery and tolerability, for the treatment of Asthma and Chronic Obstructive Pulmonary Disease. CHF6001 was 7- and 923-fold more potent than roflumilast and cilomilast, respectively, in inhibiting PDE4 enzymatic activity. CHF6001 inhibited PDE4 isoforms A-D with equal potency, showed an elevated ratio of high-affinity rolipram binding site versus low-affinity rolipram binding site and displayed >20,000-fold selectivity versus PDE4 compared with a panel of phosphodiesterases. CHF6001 effectively inhibited the release of tumor necrosis factor-α from human peripheral blood mononuclear cells, human acute monocytic leukemia cell line macrophages (THP-1), and rodent macrophages (RAW264.7 and NR8383). CHF6001 has the potential to be an effective topical treatment of conditions associated with pulmonary inflammation, including asthma and chronic obstructive pulmonary disease.
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:14:05 GMT 2023
by
admin
on
Sat Dec 16 10:14:05 GMT 2023
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| Record UNII |
0984EU6E2F
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| Record Status |
Validated (UNII)
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| Record Version |
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KL-128
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70662473
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C171863
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0984EU6E2F
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300000010799
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CHF-6001
Created by
admin on Sat Dec 16 10:14:05 GMT 2023 , Edited by admin on Sat Dec 16 10:14:05 GMT 2023
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PRIMARY | MedKoo CAT NO.: 522557, CAS NO.: 1239278-59-1Description: CHF-6001 is a novel PDE4 inhibitor designed for treating pulmonary inflammatory diseases via inhaled administration. CHF6001 was 7- and 923-fold more potent than roflumilast and cilomilast, respectively, in inhibiting PDE4 enzymatic activity (IC50 = 0.026 +/- 0.006 nM). CHF6001 inhibited PDE4 isoforms A-D with equal potency, showed an elevated ratio of high-affinity rolipram binding site versus low-affinity rolipram binding site (i.e., >40) and displayed >20,000-fold selectivity versus PDE4 compared with a panel of PDEs. CHF6001 effectively inhibited (subnanomolar IC50 values) the release of tumor necrosis factor-.ALPHA. from human peripheral blood mononuclear cells, human acute monocytic leukemia cell line macrophages (THP-1), and rodent macrophages (RAW264.7 and NR8383). CHF6001 has the potential to be an effective topical treatment of conditions associated with pulmonary inflammation, including asthma and chronic obstructive pulmonary disease. (last updated: 1/3/2016). | ||
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DB12800
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11075
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1239278-59-1
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| Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
cell free
INHIBITOR
IC50
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
CHF6001 was 7- and 923-fold more potent than roflumilast and cilomilast, respectively, in inhibiting PDE4 enzymatic activity (IC50 = 0.026 +/- 0.006 nM). CHF6001 inhibited PDE4 isoforms A-D with equal potency, showed an elevated ratio of high-affinity rolipram binding site versus low-affinity rolipram binding site (i.e., >40) and displayed >20,000-fold selectivity versus PDE4 compared with a panel of PDEs. CHF6001 effectively inhibited (subnanomolar IC50 values) the release of tumor necrosis factor-.ALPHA. from human peripheral blood mononuclear cells, human acute monocytic leukemia cell line macrophages (THP-1), and rodent macrophages (RAW264.7 and NR8383). When administered intratracheally to rats as a micronized dry powder, CHF6001 inhibited liposaccharide-induced pulmonary neutrophilia (ED50 = 0.205 .MU.mol/kg) and leukocyte infiltration (ED50 = 0.188 .MU.mol/kg) with an efficacy comparable to a high dose of budesonide (1 .MU.mol/kg i.p.). In sum, CHF6001 has the potential to be an effective topical treatment of conditions associated with pulmonary inflammation, including asthma and chronic obstructive pulmonary disease.
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