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
CHEMBL7002
CAS Number
74772-77-3
UNII
U8QXS1WU8G
DrugBank ID
DB09201
TTD ID
D03GWY
INTEDE ID
DR0322
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
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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]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [5]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [6]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [7]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [8]
E3 ubiquitin-protein ligase XIAP OT24GP9B XIAP_HUMAN Gene/Protein Processing [5]
Eukaryotic translation initiation factor 2-alpha kinase 3 (EIF2AK3) OT0DZGY4 E2AK3_HUMAN Post-Translational Modifications [8]
Eukaryotic translation initiation factor 2A (EIF2A) OTWXELQP EIF2A_HUMAN Post-Translational Modifications [8]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [7]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Gene/Protein Processing [9]
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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 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.
6 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.
7 Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. World J Gastroenterol. 2009 Jan 21;15(3):310-20.
8 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.
9 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.