Details of the Drug

General Information of Drug (ID: DMEAOZ0)

Drug Name
Cilengitide
Synonyms
Cilengitide; 188968-51-6; EMD-121974; Cilengitide [USAN:INN]; UNII-4EDF46E4GI; EMD121974; EMD-12192; EMD 121974; 4EDF46E4GI; CHEMBL429876; 2-[(2S,5R,8S,11S)-5-benzyl-11-[3-(diaminomethylideneamino)propyl]-7-methyl-3,6,9,12,15-pentaoxo-8-propan-2-yl-1,4,7,10,13-pentazacyclopentadec-2-yl]acetic acid; Cyclo(L-arginylglycyl-L-aspartyl-D-phenylalanyl-N-methyl-L-valyl); Cyclo(L-arginylglycyl-L-alpha-aspartyl-D-phenylalanyl-N-methyl-L-valyl); Cilengitide (TFA salt)
Indication
Disease Entry ICD 11 Status REF
Rheumatoid arthritis FA20 Phase 3 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 588.7
Logarithm of the Partition Coefficient (xlogp) -1
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 7
Hydrogen Bond Acceptor Count (hbondacc) 8
Chemical Identifiers
Formula
C27H40N8O7
IUPAC Name
2-[(2S,5R,8S,11S)-5-benzyl-11-[3-(diaminomethylideneamino)propyl]-7-methyl-3,6,9,12,15-pentaoxo-8-propan-2-yl-1,4,7,10,13-pentazacyclopentadec-2-yl]acetic acid
Canonical SMILES
CC(C)[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](C(=O)N1C)CC2=CC=CC=C2)CC(=O)O)CCCN=C(N)N
InChI
InChI=1S/C27H40N8O7/c1-15(2)22-25(41)33-17(10-7-11-30-27(28)29)23(39)31-14-20(36)32-18(13-21(37)38)24(40)34-19(26(42)35(22)3)12-16-8-5-4-6-9-16/h4-6,8-9,15,17-19,22H,7,10-14H2,1-3H3,(H,31,39)(H,32,36)(H,33,41)(H,34,40)(H,37,38)(H4,28,29,30)/t17-,18-,19+,22-/m0/s1
InChIKey
AMLYAMJWYAIXIA-VWNVYAMZSA-N
Cross-matching ID
PubChem CID
176873
CAS Number
188968-51-6
DrugBank ID
DB11890
TTD ID
D09ZXO
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
Integrin alpha-V/beta-3 (ITGAV/B3) TT69TQN ITAV_HUMAN-ITB3_HUMAN Modulator [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Rheumatoid arthritis
ICD Disease Classification FA20
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Integrin alpha-V/beta-3 (ITGAV/B3) DTT ITGAV-ITGB3 8.19E-02 -0.16 -0.46
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: 6597).
2 The integrin antagonist cilengitide activates alphaVbeta3, disrupts VE-cadherin localization at cell junctions and enhances permeability in endothelial cells.PLoS One.2009;4(2):e4449.