Details of the Drug

General Information of Drug (ID: DMIK6C9)

Drug Name
Zibotentan
Synonyms
ZD4054; ZD-4054; ZD4054, Zibotentan; Zibotentan (JAN/INN); Trans,trans-2(4-methoxyphenyl)-4-(1-3-benzodiazol-5-yl)-1-(dibutylaminocarbonylmethyl)pyrrolidine-3-carboxylic acid; N-(3-methoxy-5-methyl-pyrazin-2-yl)-2-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyridine-3-sulfonamide
Indication
Disease Entry ICD 11 Status REF
Prostate cancer 2C82.0 Discontinued in Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 424.4
Logarithm of the Partition Coefficient (xlogp) 1.4
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 10
Chemical Identifiers
Formula
C19H16N6O4S
IUPAC Name
N-(3-methoxy-5-methylpyrazin-2-yl)-2-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyridine-3-sulfonamide
Canonical SMILES
CC1=CN=C(C(=N1)OC)NS(=O)(=O)C2=C(N=CC=C2)C3=CC=C(C=C3)C4=NN=CO4
InChI
InChI=1S/C19H16N6O4S/c1-12-10-21-17(19(23-12)28-2)25-30(26,27)15-4-3-9-20-16(15)13-5-7-14(8-6-13)18-24-22-11-29-18/h3-11H,1-2H3,(H,21,25)
InChIKey
FJHHZXWJVIEFGJ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
9910224
ChEBI ID
CHEBI:94573
CAS Number
186497-07-4
DrugBank ID
DB06629
TTD ID
D02HVW
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Endothelin A receptor (EDNRA) TTKRD0G EDNRA_HUMAN Antagonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Endothelin-1 (EDN1) OTZCACEG EDN1_HUMAN Gene/Protein Processing [3]
Endothelin-converting enzyme 1 (ECE1) OTPFHC6F ECE1_HUMAN Gene/Protein Processing [3]
Neprilysin (MME) OT5Q39P8 NEP_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 02 Neoplasm
Disease Class ICD-11: 2C82 Prostate cancer
The Studied Tissue Prostate
The Studied Disease Prostate cancer [ICD-11:2C82]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Endothelin A receptor (EDNRA) DTT EDNRA 3.19E-05 -2.69 -1.71
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3539).
2 Clinical pipeline report, company report or official report of AstraZeneca (2009).
3 ETAR antagonist ZD4054 exhibits additive effects with aromatase inhibitors and fulvestrant in breast cancer therapy, and improves in vivo efficacy of anastrozole. Breast Cancer Res Treat. 2010 Sep;123(2):345-57. doi: 10.1007/s10549-009-0644-2. Epub 2009 Nov 27.