Cilengitide

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Cilengitide
Accession Number
DB11890
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Cilengitide HydrochlorideSW9AYG2XI2188969-00-8JSBRBZVFFMRGCI-LOPTWHKWSA-N
Categories
UNII
4EDF46E4GI
CAS number
188968-51-6
Weight
Average: 588.666
Monoisotopic: 588.30199566
Chemical Formula
C27H40N8O7
InChI Key
AMLYAMJWYAIXIA-VWNVYAMZSA-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
IUPAC Name
2-[(2S,5R,8S,11S)-5-benzyl-11-(3-carbamimidamidopropyl)-7-methyl-3,6,9,12,15-pentaoxo-8-(propan-2-yl)-1,4,7,10,13-pentaazacyclopentadecan-2-yl]acetic acid
SMILES
CC(C)[C@@H]1N(C)C(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
176873
PubChem Substance
347828225
ChemSpider
154046
BindingDB
50235980
ChEMBL
CHEMBL429876
Wikipedia
Cilengitide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableImpaired Renal Function1
1CompletedTreatmentAIDS-related Peripheral/Systemic Lymphoma / AIDS-related Primary CNS Lymphoma / Anaplastic Large Cell Lymphoma / Angioimmunoblastic T-Cell Lymphoma / Extranodal Marginal Zone B-cell Lymphoma of Mucosa-associated Lymphoid Tissue / Intraocular Lymphoma / Nodal marginal zone B-cell lymphomas / Recurrent Adult Burkitt Lymphoma / Recurrent Adult Diffuse Large Cell Lymphoma / Recurrent Adult Diffuse Mixed Cell Lymphoma / Recurrent Adult Diffuse Small Cleaved Cell Lymphoma / Recurrent Adult Hodgkin's Lymphoma / Recurrent Adult Immunoblastic Large Cell Lymphoma / Recurrent Adult Lymphoblastic Lymphoma / Recurrent Adult T-Cell Leukemia/Lymphoma / Recurrent Cutaneous T-Cell Non-Hodgkin Lymphoma / Recurrent Grade 1 Follicular Lymphoma / Recurrent Grade 2 Follicular Lymphoma / Recurrent Grade 3 Follicular Lymphoma / Recurrent Mantle Cell Lymphoma / Recurrent Marginal Zone Lymphoma / Recurrent Mycosis Fungoides/Sezary Syndrome / Recurrent Small Lymphocytic Lymphoma / Splenic Marginal Zone Lymphoma / Stage III Adult Burkitt Lymphoma / Stage III Adult Diffuse Large Cell Lymphoma / Stage III Adult Diffuse Mixed Cell Lymphoma / Stage III Adult Diffuse Small Cleaved Cell Lymphoma / Stage III Adult Hodgkin Lymphoma / Stage III Adult Immunoblastic Large Cell Lymphoma / Stage III Adult Lymphoblastic Lymphoma / Stage III Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage III Grade 1 Follicular Lymphoma / Stage III Grade 2 Follicular Lymphoma / Stage III Grade 3 Follicular Lymphoma / Stage III Mantle Cell Lymphoma / Stage III Marginal Zone Lymphoma / Stage III Mycosis Fungoides/Sezary Syndrome / Stage III Small Lymphocytic Lymphoma / Stage IV Adult Burkitt Lymphoma / Stage IV Adult Diffuse Large Cell Lymphoma / Stage IV Adult Diffuse Mixed Cell Lymphoma / Stage IV Adult Diffuse Small Cleaved Cell Lymphoma / Stage IV Adult Hodgkin Lymphoma / Stage IV Adult Immunoblastic Large Cell Lymphoma / Stage IV Adult Lymphoblastic Lymphoma / Stage IV Cutaneous T-Cell Non-Hodgkin Lymphoma / Stage IV Grade 1 Follicular Lymphoma / Stage IV Grade 2 Follicular Lymphoma / Stage IV Grade 3 Follicular Lymphoma / Stage IV Mantle Cell Lymphoma / Stage IV Marginal Zone Lymphoma / Stage IV Mycosis Fungoides/Sezary Syndrome / Stage IV Small Lymphocytic Lymphoma / Unspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentAdult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Neoplasm1
1CompletedTreatmentAdult Solid Neoplasm / Estrogen Receptor Negative / HER2/Neu Negative / Male Breast Carcinoma / Progesterone Receptor Negative / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer / Triple-Negative Breast Carcinoma1
1CompletedTreatmentChildhood Central Nervous System Germ Cell Tumor / Childhood Choroid Plexus Tumor / Childhood Craniopharyngioma / Childhood Ependymoblastoma / Childhood Grade I Meningioma / Childhood Grade II Meningioma / Childhood Grade III Meningioma / Childhood High-grade Cerebellar Astrocytoma / Childhood High-grade Cerebral Astrocytoma / Childhood Infratentorial Ependymoma / Childhood Low-grade Cerebellar Astrocytoma / Childhood Low-grade Cerebral Astrocytoma / Childhood Medulloepithelioma / Childhood Mixed Glioma / Childhood Oligodendroglioma / Childhood Supratentorial Ependymoma / Recurrent Childhood Brain Stem Glioma / Recurrent Childhood Brain Tumor / Recurrent Childhood Cerebellar Astrocytoma / Recurrent Childhood Cerebral Astrocytoma / Recurrent Childhood Ependymoma / Recurrent Childhood Medulloblastoma / Recurrent Childhood Pineoblastoma / Recurrent Childhood Subependymal Giant Cell Astrocytoma / Recurrent Childhood Supratentorial Primitive Neuroectodermal Tumor / Recurrent Childhood Visual Pathway and Hypothalamic Glioma1
1CompletedTreatmentChronic Myeloproliferative Disorders / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Precancerous/Nonmalignant Condition / Small Intestine Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1CompletedTreatmentDiffuse Intrinsic Pontine Glioma (DIPG)1
1CompletedTreatmentLocally Advanced Non Small Cell Lung Cancer (NSCLC)*1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
1TerminatedTreatmentAdult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Adult Solid Neoplasm / Recurrent Adult Brain Neoplasm1
1TerminatedTreatmentSarcomas1
1Unknown StatusTreatmentBrain and Central Nervous System Tumors / Lung Cancers1
1, 2CompletedTreatmentAdult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma1
1, 2CompletedTreatmentBrain and Central Nervous System Tumors1
2CompletedTreatmentAdult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Tumor1
2CompletedTreatmentChildhood High-grade Cerebellar Astrocytoma / Childhood High-grade Cerebral Astrocytoma / Recurrent Childhood Anaplastic Astrocytoma / Recurrent Childhood Anaplastic Oligoastrocytoma / Recurrent Childhood Anaplastic Oligodendroglioma / Recurrent Childhood Brain Tumor / Recurrent Childhood Cerebellar Astrocytoma / Recurrent Childhood Cerebral Astrocytoma / Recurrent Childhood Glioblastoma / Recurrent Childhood Visual Pathway and Hypothalamic Glioma1
2CompletedTreatmentGlioblastomas1
2CompletedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2CompletedTreatmentRecurrent Prostate Cancer / Stage I Prostate Cancer / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer / Stage III Prostate Cancer1
2CompletedTreatmentRecurrent Prostate Cancer / Stage IV Prostate Cancer1
2TerminatedTreatmentAdult Acute Basophilic Leukemia / Adult Acute Eosinophilic Leukemia / Adult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b)1
2TerminatedTreatmentGliomas1
2TerminatedTreatmentStage III Melanoma / Stage IV Melanoma1
2Unknown StatusTreatmentNewly Diagnosed Non Methylated Glioblastoma Multiforme Grade 41
2WithdrawnTreatmentGlioblastomas1
3CompletedTreatmentGlioblastomas1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.144 mg/mLALOGPS
logP-0.96ALOGPS
logP-3.7ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)12.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area235.91 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity159.97 m3·mol-1ChemAxon
Polarizability59.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Macrolactams / Alpha amino acids and derivatives / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Guanidines / Lactams / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Carboximidamides
show 6 more
Substituents
Alpha-oligopeptide / Macrolactam / Alpha-amino acid or derivatives / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide / Carboxamide group / Guanidine / Lactam / Secondary carboxylic acid amide
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on October 20, 2016 14:57 / Updated on June 02, 2018 09:47