Xevinapant
PubChem CID
25022340
Structure
Molecular Formula
Synonyms
- 1071992-99-8
- AT-406
- Xevinapant
- Debio-1143
- SM-406
Molecular Weight
561.7 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2008-11-10
- Modify:2025-01-18
Description
Xevinapant is an orally available mimetic of the natural second mitochondrial-derived activator of caspases (Smac) and inhibitor of Inhibitor of Apoptosis Proteins (IAPs), with potential immunomodulating, apoptotic-inducing, chemo-radio-sensitizing and antineoplastic activities. Upon oral administration,xevinapant targets and binds to the Smac binding groove on IAPs, including the direct caspase inhibitor X chromosome-linked IAP (XIAP), and the cellular IAPs 1 (c-IAP1) and 2 (c-IAP2). This inhibits the activities of these IAPs and promotes the induction of apoptosis. Additionally, as xevinapant inhibits the activity of IAPs, it may work synergistically with cytotoxic drugs and/or radiation to overcome tumor cell resistance to apoptosis. As IAPs regulate nuclear factor-kappa B (NFkB) signaling pathways, which drives the expression of genes involved in immune and inflammatory responses, xevinapant may enhance anti-tumor immune responses when administered with certain immunomodulating agents, such as immune checkpoint inhibitors. IAPs are overexpressed by many cancer cell types and suppress both intrinsic and extrinsic apoptosis by binding to and inhibiting active caspases via their baculoviral lAP repeat (BIR) domains. They contribute to chemo-radio-resistance of cancer cells to certain cytotoxic agents and radiation, promote tumor cell survival and are associated with poor prognosis in certain types of cancer. SMAC, a pro-apoptotic mitochondrial protein, is an endogenous inhibitor of the IAPs family of cellular proteins.
XEVINAPANT is a small molecule drug with a maximum clinical trial phase of III (across all indications) and has 7 investigational indications.
See also: Xevinapant Hydrochloride (is active moiety of).
Chemical Structure Depiction
(5S,8S,10aR)-N-benzhydryl-5-[[(2S)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C32H43N5O4/c1-21(2)19-28(38)36-18-17-25-15-16-27(37(25)32(41)26(20-36)34-30(39)22(3)33-4)31(40)35-29(23-11-7-5-8-12-23)24-13-9-6-10-14-24/h5-14,21-22,25-27,29,33H,15-20H2,1-4H3,(H,34,39)(H,35,40)/t22-,25+,26-,27-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
LSXUTRRVVSPWDZ-MKKUMYSQSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C[C@@H](C(=O)N[C@H]1CN(CC[C@H]2CC[C@H](N2C1=O)C(=O)NC(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)CC(C)C)NC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C32H43N5O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)
1071992-99-8
- AT 406
- AT-406
- AT406 cpd
- DEBIO1143
- N-benzhydryl-5-(2-(methylamino)propanamido)-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo(1,2-a)(1,5)diazocine-8-carboxamide
- SM 406
- SM-406
- SM406 cpd
- 1071992-99-8
- AT-406
- Xevinapant
- Debio-1143
- SM-406
- N65WC8PXDD
- UNII-N65WC8PXDD
- AT406
- (5S,8S,10aR)-N-benzhydryl-5-((S)-2-(methylamino)propanamido)-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
- Debio 1143
- QCR-136
- AT 406
- Debio1143
- Iap inhibitor AT-406
- SM 406
- Xevinapant [INN]
- AT-406(AT406)
- AT406 (SM-406)
- CHEMBL2158051
- DeBio-1143 (AT-406)
- D-1143
- MSC2735845A
- 1071992-99-8 (free base)
- (5S,8S,10aR)-N-benzhydryl-5-[[(2S)-2-(methylamino)propanoyl]amino]-3-(3-methylbutanoyl)-6-oxo-1,2,4,5,8,9,10,10a-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
- D 1143
- (5S,8S,10aR)-N-(Diphenylmethyl)decahydro-5-(((2S)-2-(methylamino)-1-oxopropyl)amino)-3-(3-methyl-1-oxobutyl)-6-oxopyrrolo(1,2-a)(1,5)diazocine-8-carboxamide
- PYRROLO(1,2-A)(1,5)DIAZOCINE-8-CARBOXAMIDE, N-(DIPHENYLMETHYL)DECAHYDRO-5-(((2S)-2-(METHYLAMINO)-1-OXOPROPYL)AMINO)-3-(3-METHYL-1-OXOBUTYL)-6-OXO-, (5S,8S,10AR)-
- Pyrrolo[1,2-a][1,5]diazocine-8-carboxamide, N-(diphenylmethyl)decahydro-5-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-3-(3-methyl-1-oxobutyl)-6-oxo-, (5S,8S,10aR)-
- MFCD22124467
- AT-406Xevinapant?
- XEVINAPANT [USAN]
- XEVINAPANT [WHO-DD]
- SMAC Mimetic Debio 1143
- IAPs Inhibitor Debio 1143
- Xevinapant (JAN/USAN/INN)
- IAPs Antagonist Debio 1143
- GTPL7729
- SCHEMBL2724374
- DTXSID50648496
- EX-A104
- BCP04668
- BDBM50393505
- NSC764757
- s2754
- AKOS027250726
- CCG-270056
- CS-0962
- NSC-764757
- NCGC00346675-01
- NCGC00346675-03
- (5S,8S,10aR)-N-(diphenylmethyl)-5-[(2S)-2-(methylamino)propanamido]-3-(3-methylbutanoyl)-6-oxo-octahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
- (5S,8S,10aR)-N-(Diphenylmethyl)-5-[(N-methyl-L-alanyl)amino]-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
- AC-30282
- AS-56453
- DA-61281
- HY-15454
- D1143
- D12565
- AT406 (SM-406, ARRY-334543)
- EN300-25327900
- J-501625
- Q27074566
- Z2740129972
- 1071992-99-8, 1071992-57-8 (HCl)
- Second Mitochondrial-derived Activator of Caspases Mimetic Debio 1143
- (5S,8S,10aR)-N-(diphenylmethyl)-5-[(2S)-2-(methylamino)propanamido]-3-(3-methylbutanoyl)-6-oxo-decahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
- (5S,8S,10aR)-N-(diphenylmethyl)-5-[(2S)-2-(methylamino)propanamido]-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamide
- (5S,8S,10aR)-N-(Diphenylmethyl)decahydro-5-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-3-(3-methyl-1-oxobutyl)-6-oxopyrrolo[1,2-a][1,5 ]diazocine-8-carboxamide
- Pyrrolo(1,2-a)(1,5)diazocine-8-carboxamide, n-((1,1'-biphenyl)-2-ylmethyl)decahydro-5-(((2s)-2-(methylamino)-1-oxopropyl)amino)-3-(3-methyl-1-oxobutyl)-6-oxo-, (5s,8s,10ar)
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
561.7 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
561.33150487 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
561.33150487 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
111 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
41
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
896
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Paediatric drug
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Xevinapant Hydrochloride (is active moiety of)
Treatment of head and neck epithelial malignant neoplasms
Type
Paediatric investigation
Active Substance
Therapeutic Area
Oncology
Drug Form
Oral solution
Administration Route
Oral use
Decision Type
W: decision granting a waiver in all age groups for all conditions or indications
Decision Date
2022-09-09
Human Drugs -> EU pediatric investigation plans
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=LSXUTRRVVSPWDZ-MKKUMYSQSA-N
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useXevinapanthttps://www.drugbank.ca/drugs/DB16305
- EPA DSSTox(5S,8S,10aR)-N-(Diphenylmethyl)-5-[(N-methyl-L-alanyl)amino]-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo[1,2-a][1,5]diazocine-8-carboxamidehttps://comptox.epa.gov/dashboard/DTXSID50648496CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ClinicalTrials.govLICENSEThe ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
- EU Clinical Trials Register
- European Medicines Agency (EMA)LICENSEInformation on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.https://www.ema.europa.eu/en/about-us/legal-noticexevinapant (P/0374/2022)https://www.ema.europa.eu/en/medicines/human/paediatric-investigation-plans/emea-003235-pip01-22
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licence
- IUPHAR/BPS Guide to PHARMACOLOGYLICENSEThe Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)https://www.guidetopharmacology.org/about.jsp#licenseGuide to Pharmacology Target Classificationhttps://www.guidetopharmacology.org/targets.jsp
- Therapeutic Target Database (TTD)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.keg
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- Wikidata
- WikipediaMasupirdinehttps://en.wikipedia.org/wiki/MasupirdineXevinapanthttps://en.wikipedia.org/wiki/Xevinapant
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlN-benzhydryl-5-(2-(methylamino)propanamido)-3-(3-methylbutanoyl)-6-oxodecahydropyrrolo(1,2-a)(1,5)diazocine-8-carboxamidehttps://www.ncbi.nlm.nih.gov/mesh/67559144
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 392320145https://pubchem.ncbi.nlm.nih.gov/substance/392320145
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