Cilengitide
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Also known as CilengitidaEMD 121974EMD-12192EMD-121974c(RGDfMeV)cyclo(Arg-Gly-Asp-D-Phe-[N-Me]Val)cyclo-[Arg-Gly-Asp-D-Phe-(N-Me)val]c[Arg-Gly-Asp-D-Phe-N(Me)-Val]CILENGITIDE TRIFLUOROACETATE
Summary
Cilengitide (CHEMBL429876) is a phase-3 clinical-stage protein; indicated across 22 conditions including glioblastoma and gliosarcoma.
At a glance
- Status: Max clinical phase 3 (not approved)
- Modality: Protein
- Indications: 22 conditions
- Clinical trials: 27
- Chemistry: 588.7 Da · C27H40N8O7
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL429876 |
| Name | Cilengitide |
| Type | Protein |
| Max phase | 3 |
| FDA approved | no |
| PubChem CID | 176873 |
| Molecular formula | C27H40N8O7 |
| Molecular weight | 588.7 |
| InChIKey | AMLYAMJWYAIXIA-VWNVYAMZSA-N |
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
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
Also known as: Cilengitida, Cilengitide, EMD 121974, EMD-12192, EMD-121974, c(RGDfMeV), cilengitide, cyclo(Arg-Gly-Asp-D-Phe-[N-Me]Val), CILENGITIDE, cyclo-[Arg-Gly-Asp-D-Phe-(N-Me)val], c[Arg-Gly-Asp-D-Phe-N(Me)-Val], CILENGITIDE TRIFLUOROACETATE
Patent coverage: 2,608 distinct patent families (10,123 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 8,881 (88%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| integrin αVβ3 | Antagonist | 8.5 |
Broader ChEMBL bioactivity targets: 7 (assay-derived). Sample: Integrin alpha-V/beta-3, Integrin alpha-IIb/beta-3, Integrin alpha-5/beta-1, Integrin alpha-V/beta-5, Integrin alpha-V/beta-6, Integrin alpha-V/alpha-5, Integrin alpha-V/beta-3/alpha-V/beta-5.
Bioactivity
ChEMBL activities: 57 potent at pChembl ≥ 5 of 59 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| ITGAV | 9.89 | IC50 | 0.13 | nM | CHEMBL_ACT_1655725 |
| ITGAV | 9.89 | IC50 | 0.13 | nM | CHEMBL_ACT_1688065 |
| ITGAV | 9.89 | IC50 | 0.13 | nM | CHEMBL_ACT_2116232 |
| ITGAV | 9.89 | IC50 | 0.13 | nM | CHEMBL_ACT_2146181 |
| ITGAV | 9.89 | IC50 | 0.13 | nM | CHEMBL_ACT_2610663 |
| ITGB3 | 9.29 | IC50 | 0.51 | nM | CHEMBL_ACT_13506391 |
| ITGB3 | 9.27 | IC50 | 0.54 | nM | CHEMBL_ACT_12675370 |
| ITGB3 | 9.27 | IC50 | 0.54 | nM | CHEMBL_ACT_14566673 |
| ITGB3 | 9.27 | IC50 | 0.54 | nM | CHEMBL_ACT_18377745 |
| ITGB3 | 9.27 | IC50 | 0.54 | nM | CHEMBL_ACT_19132385 |
| ITGB3 | 9.27 | IC50 | 0.54 | nM | CHEMBL_ACT_20706874 |
| ITGB3 | 9.27 | IC50 | 0.54 | nM | CHEMBL_ACT_22992147 |
| ITGB3 | 9.24 | IC50 | 0.58 | nM | CHEMBL_ACT_16436915 |
| ITGB3 | 9.22 | IC50 | 0.6 | nM | CHEMBL_ACT_3302250 |
| ITGB3 | 9.21 | IC50 | 0.61 | nM | CHEMBL_ACT_29282578 |
| ITGB3 | 9.19 | IC50 | 0.65 | nM | CHEMBL_ACT_15035124 |
| ITGB3 | 9.07 | IC50 | 0.86 | nM | CHEMBL_ACT_1894491 |
| ITGB3 | 9 | Ki | 1 | nM | CHEMBL_ACT_18401281 |
| ITGAV | 8.68 | IC50 | 2.1 | nM | CHEMBL_ACT_1894499 |
| ITGB3 | 8.52 | IC50 | 3 | nM | CHEMBL_ACT_1197641 |
| ITGAV | 8.12 | IC50 | 7.6 | nM | CHEMBL_ACT_12675369 |
| ITGAV | 8.1 | IC50 | 8 | nM | CHEMBL_ACT_20706880 |
| ITGAV | 7.93 | IC50 | 11.7 | nM | CHEMBL_ACT_15039433 |
| ITGB1 | 7.88 | IC50 | 13.2 | nM | CHEMBL_ACT_15039437 |
| ITGB1 | 7.83 | IC50 | 14.9 | nM | CHEMBL_ACT_29282587 |
| ITGB1 | 7.82 | IC50 | 15 | nM | CHEMBL_ACT_12675371 |
| ITGB1 | 7.81 | IC50 | 15.4 | nM | CHEMBL_ACT_14566680 |
| ITGB1 | 7.81 | IC50 | 15.4 | nM | CHEMBL_ACT_18377760 |
| ITGB1 | 7.81 | IC50 | 15.4 | nM | CHEMBL_ACT_19132386 |
| ITGB1 | 7.81 | IC50 | 15.4 | nM | CHEMBL_ACT_20706886 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
22 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| glioblastoma | 3 | MONDO:0018177 | EFO:0000519 |
| gliosarcoma | 2 | MONDO:0016681 | EFO:1001465 |
| melanoma | 2 | MONDO:0005105 | EFO:0000756 |
| anaplastic astrocytoma | 2 | MONDO:0016684 | EFO:0002499 |
| anaplastic oligodendroglioma | 2 | MONDO:0016696 | EFO:0002501 |
| non-small cell lung carcinoma | 2 | MONDO:0005233 | EFO:0003060 |
| astrocytoma (excluding glioblastoma) | 2 | MONDO:0019781 | MONDO:0021633 |
| brain neoplasm | 2 | MONDO:0021211 | EFO:0003833 |
| paraganglioma | 2 | MONDO:0000448 | EFO:1000453 |
| neoplasm | 1 | MONDO:0005070 | EFO:0000616 |
| sarcoma | 1 | MONDO:0005089 | EFO:0000691 |
| squamous cell carcinoma | 1 | MONDO:0005096 | EFO:0000707 |
| male breast carcinoma | 1 | MONDO:0005628 | EFO:0006861 |
| myelodysplastic syndrome | 1 | MONDO:0018881 | EFO:0000198 |
| leukemia | 1 | MONDO:0005059 | EFO:0000565 |
| plasma cell myeloma | 1 | MONDO:0009693 | EFO:0001378 |
| myeloproliferative neoplasm | 1 | MONDO:0020076 | EFO:0002428 |
| kidney disorder | 1 | MONDO:0005240 | EFO:0003086 |
| diffuse intrinsic pontine glioma | 1 | MONDO:0006033 | EFO:1000026 |
| central nervous system neoplasm | 1 | MONDO:0006130 | EFO:1000158 |
2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 27.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 12 |
| PHASE1 | 12 |
| PHASE1/PHASE2 | 2 |
| PHASE3 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00689221 | PHASE3 | COMPLETED | Cilengitide, Temozolomide, and Radiation Therapy in Treating Patients With Newly Diagnosed Glioblastoma and Methylated Gene Promoter Status |
| NCT00006093 | PHASE1/PHASE2 | COMPLETED | EMD 121974 in Treating Patients With Progressive or Recurrent Glioma |
| NCT00082875 | PHASE2 | TERMINATED | Cilengitide in Treating Patients With Unresectable or Metastatic Melanoma |
| NCT00085254 | PHASE1/PHASE2 | COMPLETED | Cilengitide, Temozolomide, and Radiation Therapy in Treating Patients With Newly Diagnosed Glioblastoma Multiforme |
| NCT00089388 | PHASE2 | TERMINATED | Cilengitide in Treating Patients With Acute Myeloid Leukemia |
| NCT00093964 | PHASE2 | COMPLETED | Cilengitide (EMD 121974) for Recurrent Glioblastoma Multiforme (Brain Tumor) |
| NCT00103337 | PHASE2 | COMPLETED | Cilengitide in Treating Patients With Metastatic Prostate Cancer |
| NCT00112866 | PHASE2 | TERMINATED | Cilengitide in Treating Patients Who Are Undergoing Surgery for Recurrent or Progressive Glioblastoma Multiforme |
| NCT00121238 | PHASE2 | COMPLETED | Cilengitide in Treating Patients With Prostate Cancer |
| NCT00679354 | PHASE2 | COMPLETED | Cilengitide in Treating Younger Patients With Recurrent or Progressive High-Grade Glioma That Has Not Responded to Standard Therapy |
| NCT00813943 | PHASE2 | COMPLETED | Cilengitide, Temozolomide, and Radiation Therapy in Treating Patients With Newly Diagnosed Glioblastoma and Unmethylated Gene Promoter Status |
| NCT00842712 | PHASE2 | COMPLETED | Cilengitide and Cetuximab in Combination With Platinum-based Chemotherapy as First-line Treatment for Subjects With Advanced Non Small Cell Lung Cancer (NSCLC) |
| NCT01124240 | PHASE2 | UNKNOWN | Temozolomide and Procarbazine With Cilengitide for Patients With Glioblastoma Multiforme Without Methylation of the MGMT Promoter Gene |
| NCT01517776 | PHASE2 | TERMINATED | Cilengitide and Metronomic Temozolomide for Relapsed or Refractory High Grade Gliomas or Diffuse Intrinsic Pontine Gliomas in Children and Adolescents |
| NCT01782976 | PHASE2 | WITHDRAWN | Ph II Cilengitide Plus Bevacizumab for Recurrent Glioblastoma (GBM) |
| NCT00004258 | PHASE1 | COMPLETED | EMD 121974 in Treating Patients With Locally Advanced or Metastatic Cancer |
| NCT00006222 | PHASE1 | TERMINATED | EMD 121974 in Treating Patients With HIV-Related Kaposi’s Sarcoma |
| NCT00022113 | PHASE1 | COMPLETED | EMD 121974 in Treating Patients With Advanced Solid Tumors |
| NCT00063973 | PHASE1 | COMPLETED | Cilengitide in Treating Children With Refractory Primary Brain Tumors |
| NCT00077155 | PHASE1 | COMPLETED | Cilengitide (EMD 121974) in Treating Patients With Advanced Solid Tumors or Lymphoma |
| NCT00884598 | PHASE1 | COMPLETED | Cilengitide and Whole-Brain Radiation Therapy in Treating Patients With Brain Metastases From Lung Cancer |
| NCT00979862 | PHASE1 | COMPLETED | Cediranib Maleate and Cilengitide in Treating Patients With Progressive or Recurrent Glioblastoma |
| NCT01118676 | PHASE1 | COMPLETED | Cilengitide Together With Radiochemotherapy in Patients With Locally Advanced Non Small Cell Lung Cancer |
| NCT01122888 | PHASE1 | TERMINATED | Cilengitide and Sunitinib Malate in Treating Patients With Advanced Solid Tumors or Glioblastoma Multiforme |
| NCT01165333 | PHASE1 | COMPLETED | Cilengitide in Combination With Irradiation in Children With Diffuse Intrinsic Pontine Glioma |
| NCT01276496 | PHASE1 | COMPLETED | Weekly Doses of Cilengitide and Paclitaxel in Treating Patients With Advanced Solid Tumors That Cannot Be Removed by Surgery |
| NCT01504165 | PHASE1 | COMPLETED | Pharmacokinetics in Subjects With Renal Impairment |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).
Related Atlas pages
- Diseases: glioblastoma