Ponatinib

Ponatinib, sold under the brand name Iclusig, is a medication developed by ARIAD Pharmaceuticals for the treatment of chronic myeloid leukemia (CML) and Philadelphia chromosome–positive (Ph+) acute lymphoblastic leukemia (ALL). It is a multi-targeted tyrosine-kinase inhibitor. Some forms of CML, those that have the T315I mutation, are resistant to current therapies such as imatinib. Ponatinib has been designed to be effective against these types of tumors.

Ponatinib
Clinical data
Pronunciation/poʊˈnætɪnɪb/ poh-NAT-i-nib
Trade namesIclusig
Other namesAP24534
AHFS/Drugs.comMonograph
MedlinePlusa613029
License data
Pregnancy
category
  • AU: D
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityUnknown
Protein binding>99% (in vitro)
MetabolismLiver (CYP3A4, 2C8, 2D6, 3A5)
Elimination half-life12–66 hours
ExcretionFeces (87%), urine (5%)
Identifiers
  • 3-(2-Imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H27F3N6O
Molar mass532.571 g·mol−1
3D model (JSmol)
  • Cc1ccc(cc1C#Cc2cnc3n2nccc3)C(=O)Nc4ccc(c(c4)C(F)(F)F)CN5CCN(CC5)C
  • InChI=1S/C29H27F3N6O/c1-20-5-6-22(16-21(20)8-10-25-18-33-27-4-3-11-34-38(25)27)28(39)35-24-9-7-23(26(17-24)29(30,31)32)19-37-14-12-36(2)13-15-37/h3-7,9,11,16-18H,12-15,19H2,1-2H3,(H,35,39)
  • Key:PHXJVRSECIGDHY-UHFFFAOYSA-N

The United States Food and Drug Administration approved the drug as a candidate in December 2012, but temporarily suspended sales in October 2013, because of "the risk of life-threatening blood clots and severe narrowing of blood vessels". The suspension was partially lifted on in December 2013, with ponatinib being issued revised prescribing information, a new "Black Box Warning" and a "Risk Evaluation and Mitigation Strategy" in place to better evaluate the risks and benefits of using the drug.

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