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Birinapant

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Data Packages
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Identification

Generic Name
Birinapant
DrugBank Accession Number
DB11782
Background

Birinapant has been investigated for the treatment of Myelodysplastic Syndrome (MDS) and Chronic Myelomonocytic Leukemia (CMML).

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 806.957
Monoisotopic: 806.429087881
Chemical Formula
C42H56F2N8O6
Synonyms
  • Birinapant
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AE3 ubiquitin-protein ligase XIAP
modulator
Humans
ABaculoviral IAP repeat-containing protein 2
modulator
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Alanine and derivatives / 3-alkylindoles / N-acylpyrrolidines / Substituted pyrroles / Aryl fluorides / Benzenoids / Tertiary carboxylic acid amides / Heteroaromatic compounds
show 9 more
Substituents
3-alkylindole / Alanine or derivatives / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl fluoride
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6O4Z07B57R
CAS number
1260251-31-7
InChI Key
PKWRMUKBEYJEIX-DXXQBUJASA-N
InChI
InChI=1S/C42H56F2N8O6/c1-7-33(49-39(55)21(3)45-5)41(57)51-19-27(53)15-25(51)17-31-29-11-9-23(43)13-35(29)47-37(31)38-32(30-12-10-24(44)14-36(30)48-38)18-26-16-28(54)20-52(26)42(58)34(8-2)50-40(56)22(4)46-6/h9-14,21-22,25-28,33-34,45-48,53-54H,7-8,15-20H2,1-6H3,(H,49,55)(H,50,56)/t21-,22-,25-,26-,27-,28-,33-,34-/m0/s1
IUPAC Name
(2S)-N-[(2S)-1-[(2R,4S)-2-[(6,6'-difluoro-3'-{[(2R,4S)-4-hydroxy-1-[(2S)-2-[(2S)-2-(methylamino)propanamido]butanoyl]pyrrolidin-2-yl]methyl}-1H,1'H-[2,2'-biindole]-3-yl)methyl]-4-hydroxypyrrolidin-1-yl]-1-oxobutan-2-yl]-2-(methylamino)propanamide
SMILES
CC[C@H](NC(=O)[C@H](C)NC)C(=O)N1C[C@@H](O)C[C@H]1CC1=C(NC2=CC(F)=CC=C12)C1=C(C[C@@H]2C[C@H](O)CN2C(=O)[C@H](CC)NC(=O)[C@H](C)NC)C2=CC=C(F)C=C2N1

References

General References
Not Available
PubChem Compound
49836020
PubChem Substance
347828132
ChemSpider
27444380
BindingDB
50071920
ChEMBL
CHEMBL3039522
ZINC
ZINC000096941868
PDBe Ligand
GT6
PDB Entries
4kmp

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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2TerminatedTreatmentAbdominal wall neoplasm / Epithelial Ovarian Cancer / Fallopian Tube Neoplasms1somestatusstop reasonjust information to hide
2TerminatedTreatmentChronic Myelomonocytic Leukemia / Myelodysplastic Syndrome1somestatusstop reasonjust information to hide
1Active Not RecruitingTreatmentAcute Myeloid Leukemia / Chondrosarcomas / Chronic Lymphocytic Leukemia / Colorectal Cancer / Non-Hodgkin's Lymphoma (NHL) / Sarcomas / Small Lymphocytic Lymphoma / Solid Tumors1somestatusstop reasonjust information to hide
1CompletedTreatmentCancer1somestatusstop reasonjust information to hide
1CompletedTreatmentRelapsed Epithelial Ovarian Cancer / Relapsed Fallopian Tube Cancer / Relapsed Primary Peritoneal Cancer1somestatusstop reasonjust information to hide

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 Solubility0.0352 mg/mLALOGPS
logP2.21ALOGPS
logP1.62Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.28Chemaxon
pKa (Strongest Basic)8.9Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area194.92 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity214.65 m3·mol-1Chemaxon
Polarizability86.23 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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/MSsplash10-0a4i-3200000980-12bee5b3aae187d3122f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-016r-1100002900-48f88a361f701bac72c6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-6110021920-2210d9ca7bb776d06ece
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-6100003900-53e52f32fcab37a1da76
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9100012200-13efd99da855be71883f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-005i-7600004920-eaa25cc54c67116e66fa
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-272.98846
predicted
DeepCCS 1.0 (2019)
[M+H]+274.78293
predicted
DeepCCS 1.0 (2019)
[M+Na]+281.0411
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. E3 ubiquitin-protein ligase XIAP
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Modulator
General Function
Multi-functional protein which regulates not only caspases and apoptosis, but also modulates inflammatory signaling and immunity, copper homeostasis, mitogenic kinase signaling, cell proliferation, as well as cell invasion and metastasis (PubMed:11257230, PubMed:11257231, PubMed:11447297, PubMed:12121969, PubMed:12620238, PubMed:17560374, PubMed:17967870, PubMed:19473982, PubMed:20154138, PubMed:22103349, PubMed:9230442). Acts as a direct caspase inhibitor (PubMed:11257230, PubMed:11257231, PubMed:12620238). Directly bind to the active site pocket of CASP3 and CASP7 and obstructs substrate entry (PubMed:11257230, PubMed:11257231, PubMed:16352606, PubMed:16916640). Inactivates CASP9 by keeping it in a monomeric, inactive state (PubMed:12620238). Acts as an E3 ubiquitin-protein ligase regulating NF-kappa-B signaling and the target proteins for its E3 ubiquitin-protein ligase activity include: RIPK1, RIPK2, MAP3K2/MEKK2, DIABLO/SMAC, AIFM1, CCS, PTEN and BIRC5/survivin (PubMed:17560374, PubMed:17967870, PubMed:19473982, PubMed:20154138, PubMed:22103349, PubMed:22607974, PubMed:29452636, PubMed:30026309). Acts as an important regulator of innate immunity by mediating 'Lys-63'-linked polyubiquitination of RIPK2 downstream of NOD1 and NOD2, thereby transforming RIPK2 into a scaffolding protein for downstream effectors, ultimately leading to activation of the NF-kappa-B and MAP kinases signaling (PubMed:19667203, PubMed:22607974, PubMed:29452636, PubMed:30026309). 'Lys-63'-linked polyubiquitination of RIPK2 also promotes recruitment of the LUBAC complex to RIPK2 (PubMed:22607974, PubMed:29452636). Regulates the BMP signaling pathway and the SMAD and MAP3K7/TAK1 dependent pathways leading to NF-kappa-B and JNK activation (PubMed:17560374). Ubiquitination of CCS leads to enhancement of its chaperone activity toward its physiologic target, SOD1, rather than proteasomal degradation (PubMed:20154138). Ubiquitination of MAP3K2/MEKK2 and AIFM1 does not lead to proteasomal degradation (PubMed:17967870, PubMed:22103349). Plays a role in copper homeostasis by ubiquitinating COMMD1 and promoting its proteasomal degradation (PubMed:14685266). Can also function as E3 ubiquitin-protein ligase of the NEDD8 conjugation pathway, targeting effector caspases for neddylation and inactivation (PubMed:21145488). Ubiquitinates and therefore mediates the proteasomal degradation of BCL2 in response to apoptosis (PubMed:29020630). Protects cells from spontaneous formation of the ripoptosome, a large multi-protein complex that has the capability to kill cancer cells in a caspase-dependent and caspase-independent manner (PubMed:22095281). Suppresses ripoptosome formation by ubiquitinating RIPK1 and CASP8 (PubMed:22095281). Acts as a positive regulator of Wnt signaling and ubiquitinates TLE1, TLE2, TLE3, TLE4 and AES (PubMed:22304967). Ubiquitination of TLE3 results in inhibition of its interaction with TCF7L2/TCF4 thereby allowing efficient recruitment and binding of the transcriptional coactivator beta-catenin to TCF7L2/TCF4 that is required to initiate a Wnt-specific transcriptional program (PubMed:22304967)
Specific Function
Cysteine-type endopeptidase inhibitor activity
Gene Name
XIAP
Uniprot ID
P98170
Uniprot Name
E3 ubiquitin-protein ligase XIAP
Molecular Weight
56684.41 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Details2. Baculoviral IAP repeat-containing protein 2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Modulator
General Function
Multi-functional protein which regulates not only caspases and apoptosis, but also modulates inflammatory signaling and immunity, mitogenic kinase signaling, and cell proliferation, as well as cell invasion and metastasis. Acts as an E3 ubiquitin-protein ligase regulating NF-kappa-B signaling and regulates both canonical and non-canonical NF-kappa-B signaling by acting in opposite directions: acts as a positive regulator of the canonical pathway and suppresses constitutive activation of non-canonical NF-kappa-B signaling. The target proteins for its E3 ubiquitin-protein ligase activity include: RIPK1, RIPK2, RIPK3, RIPK4, CASP3, CASP7, CASP8, TRAF2, DIABLO/SMAC, MAP3K14/NIK, MAP3K5/ASK1, IKBKG/NEMO, IKBKE and MXD1/MAD1. Can also function as an E3 ubiquitin-protein ligase of the NEDD8 conjugation pathway, targeting effector caspases for neddylation and inactivation. Acts as an important regulator of innate immune signaling via regulation of Toll-like receptors (TLRs), Nodlike receptors (NLRs) and RIG-I like receptors (RLRs), collectively referred to as pattern recognition receptors (PRRs). Protects cells from spontaneous formation of the ripoptosome, a large multi-protein complex that has the capability to kill cancer cells in a caspase-dependent and caspase-independent manner. Suppresses ripoptosome formation by ubiquitinating RIPK1 and CASP8. Can stimulate the transcriptional activity of E2F1. Plays a role in the modulation of the cell cycle
Specific Function
Cysteine-type endopeptidase inhibitor activity involved in apoptotic process
Gene Name
BIRC2
Uniprot ID
Q13490
Uniprot Name
Baculoviral IAP repeat-containing protein 2
Molecular Weight
69899.005 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at October 20, 2016 20:47 / Updated at August 27, 2024 19:15