Ixazomib

Systematic (IUPAC) name
N2-(2,5-Dichlorobenzoyl)-N-[(1R)-1-(dihydroxyboryl)-3-methylbutyl]glycinamide
Clinical data
Trade names	Ninlaro
AHFS/Drugs.com	entry
Legal status	US: ℞-only ℞ (Prescription only)
Routes of administration	Oral (capsules)
Pharmacokinetic data
Bioavailability	58%
Protein binding	99%
Metabolism	Hepatic (CYP: 3A4 (42%), 1A2 (26%), 2B6 (16%) and others)
Biological half-life	9.5 days
Excretion	Urine (62%), feces (22%)
Identifiers
CAS Number	1072833-77-2
ATC code	L01XX50 (WHO)
PubChem	CID: 25183872
ChemSpider	25027391
UNII	71050168A2
KEGG	D10130
ChEBI	CHEBI:90942 Y
Synonyms	MLN2238
Chemical data
Formula	C14H19BCl2N2O4
Molecular mass	361.03 g·mol−1
SMILES B([C@H](CC(C)C)NC(=O)CNC(=O)c1cc(ccc1Cl)Cl)(O)O
InChI InChI=1S/C14H19BCl2N2O4/c1-8(2)5-12(15(22)23)19-13(20)7-18-14(21)10-6-9(16)3-4-11(10)17/h3-4,6,8,12,22-23H,5,7H2,1-2H3,(H,18,21)(H,19,20)/t12-/m0/s1 Key:MXAYKZJJDUDWDS-LBPRGKRZSA-N

Ixazomib (trade name Ninlaro) is a drug for the treatment of multiple myeloma, developed by Takeda. It acts as a proteasome inhibitor and has orphan drug status in the US.

On November 20, 2015, the U.S. Food and Drug Administration approved ixazomib for use in combination with lenalidomide and dexamethasone for the treatment of multiple myeloma after at least one prior therapy.

Mechanism

Ixazomib is a peptide analogue that reversibly inhibits the protein proteasome subunit beta type-5 (PSMB5), which is part of the 20S proteasome complex.

Chemistry

Ixazomib citrate—a prodrug for ixazomib

Ixazomib citrate is a prodrug which rapidly hydrolyzes under physiological conditions to its biologically active form, ixazomib.