TOFIMILAST

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H21N5S
Molecular Weight	339.458
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=NN(C2CCCC2)C3=C1CCN4C(=NN=C34)C5=CC=CS5

InChI

InChIKey=DHCOPPHTVOXDKU-UHFFFAOYSA-N

InChI=1S/C18H21N5S/c1-2-14-13-9-10-22-17(15-8-5-11-24-15)19-20-18(22)16(13)23(21-14)12-6-3-4-7-12/h5,8,11-12H,2-4,6-7,9-10H2,1H3

HIDE SMILES / InChI

Molecular Formula	C18H21N5S
Molecular Weight	339.458
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800017360 | https://www.ncbi.nlm.nih.gov/pubmed/17228876 | https://www.ncbi.nlm.nih.gov/pubmed/18660832 | https://www.ncbi.nlm.nih.gov/pubmed/22077102

Tofimilast is a potent phosphodiesterase-4 (PDE4) inhibitor with low oral bioavailability and no emesis-associated behaviors in ferrets at plasma concentrations up to 152 ng/ml. Tofimilast exhibited an apparent slower absorption through the rat lung after administration as a dry powder, although absorption half-life values were <1 h and therefore the significance of a formulation effect for this compound is questionable. Tofimilast was tested as a therapeutic agent against asthma and chronic obstructive pulmonary disease but development has been discontinued due to lack of efficacy.

Originator

Approval Year

PubMed

Title	Date	PubMed
Rapid characterisation of the inherent dispersibility of respirable powders using dry dispersion laser diffraction.	2013-04-15	23434542
A new methodology for predicting human pharmacokinetics for inhaled drugs from oratracheal pharmacokinetic data in rats.	2012-01	22077102
GSK256066, an exceptionally high-affinity and selective inhibitor of phosphodiesterase 4 suitable for administration by inhalation: in vitro, kinetic, and in vivo characterization.	2011-04	21205923
Can the anti-inflammatory potential of PDE4 inhibitors be realized: guarded optimism or wishful thinking?	2008-10	18660832
SAR of a series of 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines as potent inhibitors of human eosinophil phosphodiesterase.	2007-01-25	17228876

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:16 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:16 GMT 2025`
Record UNII	5D7022962A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TOFIMILAST

Official Name

English

CP-325,366

Preferred Name

English

CP-325366

Code

English

Tofimilast [WHO-DD]

Common Name

English

TOFIMILAST [USAN]

Common Name

English

tofimilast [INN]

Common Name

English

9-Cyclopentyl-7-ethyl-6,9-dihydro-3-(2-thienyl)-5H-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-a]pyridine

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744