X3N

N~2~-{(4S,11aP)-2-[(4S)-4-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl}-L-alaninamide

Created:	2022-10-26
Last modified:	2022-11-30

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3 entries where X3N is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	48
Chiral Atom Count	2
Bond Count	51
Aromatic Bond Count	11

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Chemical Component Summary
Name	N~2~-{(4S,11aP)-2-[(4S)-4-(difluoromethyl)-2-oxo-1,3-oxazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl}-L-alaninamide
Systematic Name (OpenEye OEToolkits)	(2~{S})-2-[[2-[(4~{S})-4-[bis(fluoranyl)methyl]-2-oxidanylidene-1,3-oxazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide
Formula	C₁₈ H₁₉ F₂ N₅ O₄
Molecular Weight	407.371
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	FC(F)C1COC(=O)N1c1nc2c3ccc(NC(C)C(N)=O)cc3OCCn2c1
SMILES	CACTVS	3.385	C[CH](Nc1ccc2c(OCCn3cc(nc23)N4[CH](COC4=O)C(F)F)c1)C(N)=O
SMILES	OpenEye OEToolkits	2.0.7	CC(C(=O)N)Nc1ccc-2c(c1)OCCn3c2nc(c3)N4C(COC4=O)C(F)F
Canonical SMILES	CACTVS	3.385	C[C@H](Nc1ccc2c(OCCn3cc(nc23)N4[C@@H](COC4=O)C(F)F)c1)C(N)=O
Canonical SMILES	OpenEye OEToolkits	2.0.7	C[C@@H](C(=O)N)Nc1ccc-2c(c1)OCCn3c2nc(c3)N4[C@@H](COC4=O)C(F)F
InChI	InChI	1.06	InChI=1S/C18H19F2N5O4/c1-9(16(21)26)22-10-2-3-11-13(6-10)28-5-4-24-7-14(23-17(11)24)25-12(15(19)20)8-29-18(25)27/h2-3,6-7,9,12,15,22H,4-5,8H2,1H3,(H2,21,26)/t9-,12-/m0/s1
InChIKey	InChI	1.06	SGEUNORSOZVTOL-CABZTGNLSA-N

Drug Info: DrugBank

DrugBank ID	DB15275
Name	Inavolisib
Groups	approved investigational
Description	_PIK3CA_ is one of the most frequently mutated oncogenes, with the resulting mutated p110α protein it encodes playing a central role in tumor cell proliferation.[A264563] Chemotherapeutic agents targeting the PI3K p110α catalytic subunit have shown antitumor activity and a manageable safety profile - some of which are in clinical use, like [alpelisib] - but preclinical studies have shown that PI3K pathway inhibition releases negative feedback and activates receptor tyrosine kinase signaling, reengaging the pathway and attenuating drug activity.[A264563] Newer PI3K inhibitors, like inavolisib, seek to mitigate this attenuation. Inavolisib is an inhibitor of PI3Kα that was approved by the FDA in October 2024 for the treatment of certain patients with advanced breast cancers.[L51748,L51738]
Synonyms	(2S)-2-((2-((4S)-4-(difluoromethyl)-2-oxo-3-oxazolidinyl)-5,6-dihydroimidazo(1,2-D)(1,4)benzoxazepin-9-yl)amino)propanamide Inavolisib propanamide, 2-((2-((4S)-4-(difluoromethyl)-2-oxo-3-oxazolidinyl)-5,6-dihydroimidazo(1,2-D)(1,4)benzoxazepin-9-yl)amino)-, (2S)-
Brand Names	Itovebi
Indication	Inavolisib is indicated in combination with [palbociclib] and [fulvestrant] for the treatment of adults with endocrine-resistant, PIK3CA-mutated, hormone receptor (HR)-positive, human epidermal growth factor receptor 2 (HER2)-negative, locally advanced or metastatic breast cancer, as detected by an FDA-approved test, following recurrence on or after completing adjuvant endocrine therapy.[L51738]
Categories	BCRP/ABCG2 Substrates Cytochrome P-450 CYP2B6 Inducers Cytochrome P-450 CYP2B6 Inducers (strength unknown) Cytochrome P-450 Enzyme Inducers Enzyme Inhibitors Phosphatidylinositol-3-kinase (Pi3K) inhibitors Phosphoinositide-3 Kinase Inhibitors
CAS number	2060571-02-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	MELENYKQPVVLREDNCRRRRRMKPRSAAASLSSMELIPIEFVLPTSQRK...	unknown	inhibitor
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	MPPRPSSGELWGIHLMPPRILVECLLPNGMIVTLECLREATLITIKHELF...	unknown	degradation
Cytochrome P450 3A Subfamily	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor,inducer
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	inducer
ATP-binding cassette sub-family B member 5	MENSERAEEMQENYQRNGTAEEQPKLRKEAVGSIEIFRFADGLDITLMIL...	unknown	substrate
Broad substrate specificity ATP-binding cassette transporter ABCG2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682