Details of the Drug

General Information of Drug (ID: DMAPO0T)

Drug Name
Ciglitazone
Synonyms
ciglitazone; 74772-77-3; Ciglitizone; ADD-3878; Ciglitazonum; Ciglitazona; Ciglitazonum [Latin]; Ciglitazona [Spanish]; Ciglitazone [USAN:INN]; ADD 3878; CHEBI:64227; U-63287; (+-)-5-(p-((1-Methylcyclohexyl)methoxy)benzyl)-2,4-thiazolidinedione; C18H23NO3S; 5-(4-((1-methylcyclohexyl)methoxy)benzyl)thiazolidine-2,4-dione; YZFWTZACSRHJQD-UHFFFAOYSA-N; (+/-)-5-[4-(1-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione; U 63287; 5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione; NCGC00164446-01
Indication
Disease Entry ICD 11 Status REF
Pulmonary fibrosis CB03.4 Preclinical [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 333.4
Logarithm of the Partition Coefficient (xlogp) 4.8
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C18H23NO3S
IUPAC Name
5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
Canonical SMILES
CC1(CCCCC1)COC2=CC=C(C=C2)CC3C(=O)NC(=O)S3
InChI
InChI=1S/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21)
InChIKey
YZFWTZACSRHJQD-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2750
ChEBI ID
CHEBI:64227
CAS Number
74772-77-3
DrugBank ID
DB09201
TTD ID
D03GWY
INTEDE ID
DR0322

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Peroxisome proliferator-activated receptor gamma (PPAR-gamma) TTZMAO3 PPARG_HUMAN Agonist [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Acyl-CoA (FADS1) OTUYOYHX FADS1_HUMAN Gene/Protein Processing [4]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [5]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [5]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [6]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [7]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [8]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Gene/Protein Processing [9]
CREB-binding protein (CREBBP) OTPA4QGM CBP_HUMAN Drug Response [10]
Cyclin-A2 (CCNA2) OTPHHYZJ CCNA2_HUMAN Gene/Protein Processing [10]
Cyclin-dependent kinase 1 (CDK1) OTW1SC2N CDK1_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Pulmonary fibrosis
ICD Disease Classification CB03.4
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Peroxisome proliferator-activated receptor gamma (PPAR-gamma) DTT PPARG 2.41E-01 -0.06 -0.25
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 1.82E-04 -1.35E-01 -5.84E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.04E-02 6.29E-02 3.54E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Targeting metabolic dysregulation for fibrosis therapy. Nat Rev Drug Discov. 2020 Jan;19(1):57-75.
2 New drugs in development for the treatment of endometriosis. Expert Opin Investig Drugs. 2008 Aug;17(8):1187-202.
3 Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone. Clin Pharmacol Ther. 2005 May;77(5):404-14.
4 Delta5 desaturase mRNA levels are increased by simvastatin via SREBP-1 at early stages, not via PPARalpha, in THP-1 cells. Eur J Pharmacol. 2007 Oct 1;571(2-3):97-105.
5 Implication of peroxisome proliferator-activated receptor gamma and proinflammatory cytokines in gastric carcinogenesis: link to Helicobacter pylori-infection. J Pharmacol Sci. 2004 Oct;96(2):134-43. doi: 10.1254/jphs.fpj04016x. Epub 2004 Oct 9.
6 Ciglitazone induces caspase-independent apoptosis through down-regulation of XIAP and survivin in human glioma cells. Neurochem Res. 2008 Mar;33(3):551-61. doi: 10.1007/s11064-007-9475-x. Epub 2007 Oct 17.
7 Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
8 Activation of NFkappaB represents the central event in the neoplastic progression associated with Barrett's esophagus: a possible link to the inflammation and overexpression of COX-2, PPARgamma and growth factors. Dig Dis Sci. 2004 Aug;49(7-8):1075-83. doi: 10.1023/b:ddas.0000037790.11724.70.
9 Combined treatment with the Cox-2 inhibitor niflumic acid and PPARgama ligand ciglitazone induces ER stress/caspase-8-mediated apoptosis in human lung cancer cells. Cancer Lett. 2011 Jan 28;300(2):134-44.
10 Steroid receptor coactivator 1 deficiency increases MMTV-neu mediated tumor latency and differentiation specific gene expression, decreases metastasis, and inhibits response to PPAR ligands. BMC Cancer. 2010 Nov 16;10:629. doi: 10.1186/1471-2407-10-629.