Ibrutinib

Ibrutinib
Clinical data

Trade names	Imbruvica
License data	US FDA: Ibrutinib
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Oral (capsules)
ATC code	L01XE27 (WHO)
Legal status
Legal status	US: ℞-only ℞ (Prescription only)
Pharmacokinetic data
Protein binding	97.3%
Metabolism	Hepatic (CYP3A & CYP2D6)
Biological half-life	4–6 hours
Excretion	Feces (80%), urine (10%)
Identifiers
IUPAC name 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
CAS Number	936563-96-1
PubChem CID	24821094
IUPHAR/BPS	6912
ChemSpider	26637187
UNII	1X70OSD4VX
KEGG	D10223
ChEBI	CHEBI:76612
ChEMBL	CHEMBL1873475
ECHA InfoCard	100.232.543
Chemical and physical data
Formula	C₂₅H₂₄N₆O₂
Molar mass	440.4971
3D model (Jmol)	Interactive image
SMILES C=CC(=O)N1CCC[C@H](C1)N2C3=C(C(=N2)C4=CC=C(C=C4)OC5=CC=CC=C5)C(=NC=N3)N
InChI InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1 Key:XYFPWWZEPKGCCK-GOSISDBHBU

Ibrutinib (Imbruvica) is a small molecule drug that binds permanently to a protein, Bruton's tyrosine kinase (BTK), that is important in B cells; the drug is used to treat B cell cancers like mantle cell lymphoma, chronic lymphocytic leukemia, and Waldenström's macroglobulinemia, a form of non-Hodgkin's lymphoma.

Ibrutinib was created by scientists at Celera Genomics as a tool compound for studying BTK function, then developed by Pharmacyclics up to Phase II, then partnered with Johnson & Johnson. Pharmacyclics was acquired by AbbVie in May 2015, and Abbvie projected global sales of US$1 billion in 2016 and $5 billion in 2020.

According to the Wall Street Journal in January 2016 ibrutinib, a specialty drug, cost US$116,600 to $155,400 a year wholesale in the United States. In spite of discounts and medical insurance, the prohibitive price causes some patients to not fill their prescriptions.

Ibrutinib is used to treat mantle cell lymphoma, chronic lymphocytic leukemia, and Waldenstrom's macroglobulinemia.

Very common (>10% frequency) adverse effects include pneumonia, upper respiratory tract infection, sinusitis, skin infection, low neutrophil count, low platelet counts, headache, bleeding, bruising, diarrhea, vomiting, inflammation of mouth and lips, nausea, constipation, rash, joint pain, muscle spasms, musculoskeletal pain, fever, and edema.

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