Cilengitide

DRACPC ID  DRACPC0053

Active Ingredients   Cilengitide

Description  A cyclic Arg-Gly-Asp peptide with potential antineoplastic activity. Cilengitide binds to and inhibits the activities of the alpha(v)beta(3) and alpha(v)beta(5) integrins, thereby inhibiting endothelial cell-cell interactions, endothelial cell-matrix interactions, and angiogenesis.

Synonyms  cyclo(L-arginylglycyl-L-a-aspartyl-D-phenylalanyl-N-methyl-L-valyl); EMD 121974; EMD-121974; Cilengitide

Type  Small Molecule

Disease  Sarcoma, Gliomas, Lymphoma, Leukemia, Lung Cancer

Classification

  

Integrin αvβ3/αvβ5 inhibitor Peptide and derivative Cyclic Antiangiogenesis agent

Structure Information


Molecular Formula  C27H40N8O7

Molecular Weight  588.7

Active Sequence  RGDfX

Sequence Length  5

Modification  X=N(Me)Val

Structure

 

Show IUPAC/InChI/SMILES

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

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

InChI_Key AMLYAMJWYAIXIA-VWNVYAMZSA-N

SMILES  O=C(O)C[C@@H](C(N[C@H](CC1=CC=CC=C1)C(N(C)[C@@H](C(C)C)C(N[C@@H](CCC/N=C(N)\N)C(NC2)=O)=O)=O)=O)NC2=O

External Codes


PubChem CID  176873

DrugBank Accession Number  DB11890

NCI Thesaurus Code  C1834  

UNII  4EDF46E4GI   GSRS

CAS  188968-51-6



Drug approval


Drug indication
    Cilengitide has been used in trials studying the treatment of Sarcoma, Gliomas, Lymphoma, Leukemia, and Lung Cancer, among others.

    The drug is not approved.

ClinicalTrials.gov Identifier Title Condition or disease Phase Purpose
NCT01517776 Cilengitide and Metronomic Temozolomide for Relapsed or Refractory High Grade Gliomas or Diffuse Intrinsic Pontine Gliomas in Children and Adolescents - A Phase II Study HIT-HGG-CilMetro - A Clinical Phase II Trial of the HIT-HGG Study Group - Gliomas Phase 2 Treatment
NCT01118676 Phase I Trial Evaluating Continuous Infusion of Cilengitide Together With Radiochemotherapy in Patients With Locally Advanced Non Small Cell Lung Cancer Locally Advanced Non Small Cell Lung Cancer (NSCLC) Phase 1 Treatment
NCT01782976 A Phase II Trial of Cilengitide Plus Bevacizumab in Patients With Recurrent Glioblastoma Glioblastoma Phase 2 Treatment
NCT00121238 Phase II Evaluation of EMD 121974 (NSC 707544, Cilengitide) in Patients With Non-Metastatic Androgen Independent Prostate Cancer Recurrent Prostate Cancer; Stage I Prostate Cancer; Stage IIA Prostate Cancer; Stage IIB Prostate Cancer; Stage III Prostate Cancer Phase 2 Treatment
NCT00093964 A Multicenter, Open-label, Randomized, Uncontrolled, Phase IIa Trial in Subjects With Recurrent Glioblastoma Multiforme to Investigate the Clinical Activity, Safety, and Tolerability of Cilengitide (EMD 121,974) Administered as a Single Agent. Glioblastoma Multiforme Phase 2 Treatment

    More clinical information is obtained from ClinicalTrials.gov.





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