Structure via PubChem · Public domain (PubChem)
cilengitide
Sign in to saveAlso known as EMD-12192, EMD-121974
Cilengitide (EMD 121974) is a molecule designed and synthesized at the Technical University Munich in collaboration with Merck KGaA in Darmstadt. It is based on the cyclic peptide cyclo(-RGDfV-), which is selective for αv integrins, which are important in angiogenesis (forming new blood vessels), and other aspects of tumor biology. Hence, it is under investigation for the treatment of glioblastoma, where it may act by inhibiting angiogenesis, and influencing tumor invasion and proliferation.
In the Vinony graph
Within Vinony's link graph, cilengitide is referenced by 5 other articles, and connects out to mass density, Darmstadt and Wayback Machine.
Vinony files it under Chembox image size set, Cyclic peptides and Drugs developed by Merck.
Its subject is documented across 6 Wikipedia language editions.
Chemical data
- Formula
- C27H40N8O7
- Molecular weight
- 588.7 g/mol
- 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
- 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
- InChIKey
- AMLYAMJWYAIXIA-VWNVYAMZSA-N
- XLogP
- -1
- Polar surface area
- 238 Ų
- H-bond donors
- 7
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Protein
- Indications
- neoplasm, sarcoma, glioblastoma multiforme, gliosarcoma
via ChEMBL · EBI
Research
411 papers- Cilengitide Merck.Current opinion in investigational drugs (London, England : 2000) · 2003
- Cilengitide: an integrin-targeting arginine-glycine-aspartic acid peptide with promising activity for glioblastoma multiforme.Expert opinion on investigational drugs · 2008
- Cilengitide sensitivity is predicted by overall integrin expression in breast cancer.Breast cancer research : BCR · 2024
- Cilengitide inhibits osteoclast adhesion through blocking the α(v)β(3)-mediated FAK/Src signaling pathway.Heliyon · 2023
- Cilengitide: the first anti-angiogenic small molecule drug candidate design, synthesis and clinical evaluation.Anti-cancer agents in medicinal chemistry · 2010
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 588.302
Show 4 more facts
- chemical formula
- C₂₇H₄₀N₈O₇
- canonical SMILES
- CC(C)C1C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N1C)CC2=CC=CC=C2)CC(=O)O)CCCN=C(N)N
- isomeric 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
- physically interacts with
- Integrin subunit beta 3
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
2 sectionsContents
- Clinical trials
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 460036937 | ImageFile = Cilengitide.svg | ImageClass = skin-invert-image | ImageSize = 300px | IUPACName = 2-[(2S,5R,8S,11S)-5-benzyl-11-{3-[(diaminomethylidene)amino]propyl}-7-methyl-3,6,9,12,15-pentaoxo-8-(propan-2-yl)-1,4,7,10,13-pentaazacyclopentadecan-2-yl]acetic acid | OtherNames = |Section1= |Section2= |Section3= }} Cilengitide (EMD 121974) is a molecule designed and synthesized at the Technical University Munich in collaboration with Merck KGaA in Darmstadt. It is based on the cyclic peptide cyclo(-RGDfV-), which is selective for αv integrins, which are important in angiogenesis (forming new blood vessels), and other aspects of tumor biology. Hence, it is under investigation for the treatment of glioblastoma, where it may act by inhibiting angiogenesis, and influencing tumor invasion and proliferation.
The European Medicines Agency has granted cilengitide orphan drug status.
Excerpted from Wikipedia’s “cilengitide” article, available under the CC BY-SA 4.0 licence.