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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
Structure of TRANIMILAST

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

HIDE SMILES / InChI

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

PubMed

PubMed

TitleDatePubMed
Novel class of benzoic acid ester derivatives as potent PDE4 inhibitors for inhaled administration in the treatment of respiratory diseases.
2014 Feb 13
Patents

Patents

Substance Class Chemical
Created
by admin
on Thu Jul 06 15:46:45 UTC 2023
Edited
by admin
on Thu Jul 06 15:46:45 UTC 2023
Record UNII
0984EU6E2F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRANIMILAST
USAN  
Official Name English
3-cyclopropylmethoxy-4[(methylsulfonyl)-amino]-1-(S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxido-4-pyridinyl)-benzoic acid ethylester
Systematic Name English
CHF6001
Code English
J3.309.618F
Code English
tanimilast [INN]
Common Name English
2.3,5-dichloro-4-[(2S)-2-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-([3-(cyclopropylmethoxy)-4-(methanesulfonamido)benzoyl]oxy}ethyl]pyridine 1-oxide
Systematic Name English
TRANIMILAST [USAN]
Common Name English
CHF-6001
Code English
TANIMILAST
INN  
Official Name English
Code System Code Type Description
USAN
KL-128
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
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PUBCHEM
70662473
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
PRIMARY
NCI_THESAURUS
C171863
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
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FDA UNII
0984EU6E2F
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
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SMS_ID
300000010799
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
PRIMARY
MANUFACTURER PRODUCT INFORMATION
CHF-6001
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
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).
DRUG BANK
DB12800
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
PRIMARY
INN
11075
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
PRIMARY
CAS
1239278-59-1
Created by admin on Thu Jul 06 15:46:45 UTC 2023 , Edited by admin on Thu Jul 06 15:46:45 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
cell free
INHIBITOR
IC50
Related Record Type Details
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.