Ponatinib

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Ponatinib are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Ponatinib?

The molecule Ponatinib presents a molecular formula of C29H27F3N6O and its IUPAC name is 3-(2-imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide.

Ponatinib (Iclusig) is a kinase inhibitor indicated for the treatment of patients with chronic phase, accelerated phase, or blast phase chronic myeloid leukemia (CML) or Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL) that is resistant to or intolerant of prior tyrosine kinase inhibitor (TKI) therapy. Ponatinib is a small molecule that targets BCR-ABL, the abnormal fusion protein that is the driver of CML and Ph+ ALL. Ponatinib has shown activity in patients with CML or Ph+ ALL with mutations that confer resistance to other TKIs, including imatinib, dasatinib, and nilotinib..

Ponatinib was approved by the FDA in December 2012, based on the results of a single-arm, open-label, multicenter clinical trial (n=132) in patients with CML or Ph+ ALL who had resistance or intolerance to prior TKI therapy. The primary endpoint was major cytogenetic response (MCyR), defined as the percentage of patients with a >= 35% reduction in the BCR-ABL transcript level. At 12 weeks, the MCyR rate was 54% in the overall trial population. The most common adverse reactions (>= 20%) were thrombocytopenia, neutropenia, anemia, rash, diarrhea, musculoskeletal pain, fatigue, pyrexia, and dry skin..

3D structure

Cartesian coordinates

Geometry of Ponatinib in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Ponatinib PHXJVRSECIGDHY-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Ponatinib

 

Molecule descriptors

 
IUPAC name3-(2-imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide
InChI codeInChI=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)
InChI KeyPHXJVRSECIGDHY-UHFFFAOYSA-N
SMILESCc1ccc(C(=O)Nc2ccc(CN3CCN(C)CC3)c(C(F)(F)F)c2)cc1C#Cc1cnc2cccnn12

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 0LI
  • 3-(2-(Imidazo(1,2-b)pyridazin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1- yl)methyl)-3-(trifluoromethyl)phenyl)benzamide
  • 3-(2-(Imidazo[1,2-b]pyridazin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide
  • 3-(2-Imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]-benzamide
  • 3-(2-Imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methyl-1-piperazinyl)methyl]-3-(trifluoromethyl)phenyl]benzamide
  • 3-(2-imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide
  • 3-(Imidazo[1,2-B]pyridazin-3-Ylethynyl)-4-Methyl-N-{4-[(4-Methylpiperazin-1-Yl)methyl]-3-(Trifluoromethyl)phenyl}benzamide
  • 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide
  • 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide.
  • 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}benzam
  • 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}benzam ide
  • 3-[2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl]-4-methyl-n-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl}benzamide
  • 4340891KFS
  • 943319-70-8
  • 943319-70-8 (free base)
  • A24930
  • AB01565847_03
  • AC-26973
  • AM81261
  • AP 24534
  • AP-24534
  • AP24534
  • AP24534 - Ponatinib
  • AP24534,Ponatinib
  • AS-19133
  • BCP02037
  • BCP9000307
  • BCPP000397
  • BDBM50322535
  • BENZAMIDE, 3-(2-IMIDAZO[1,2-B]PYRIDAZIN-3-YLETHYNYL)-4-METHYL-N-[4-[(4-METHYL-1-PIPERAZINYL)METHYL]-3-(TRIFLUOROMETHYL)PHENYL]-
  • Benzamide, 3-(2-imidazo(1,2-b)pyridazin-3-ylethynyl)-4-methyl-N-(4-((4-methyl-1- piperazinyl)methyl)-3-(trifluoromethyl)phenyl)-
  • CCG-264900
  • CS-0204
  • D09950
  • DB08901
  • EX-A067
  • FT-0660376
  • GTPL5890
  • HMS3295I23
  • HMS3654H16
  • HSDB 8184
  • HY-12047
  • MFCD17215203
  • MLS006010166
  • NCGC00263152-01
  • NCGC00263152-02
  • NCGC00263152-12
  • NCGC00263152-14
  • NSC-758487
  • NSC-800855
  • NSC758487
  • NSC800855
  • PB34916
  • PONATINIB
  • Ponatinib
  • Ponatinib (AP24534)
  • Ponatinib (USAN/INN)
  • Ponatinib, Free Base
  • Ponatinib;3-(2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide
  • Q198728
  • S1490
  • SMR004701274
  • SW218091-2
  • ponatinibum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC36701290
  • UNII-4340891KFS
  • AKOS015995214
  • BRD-K44227013-001-02-3
  • DTXSID50241426
  • CHEMBL1171837
  • CHEBI:78543
  • SCHEMBL589260

Physico-Chemical properties

IUPAC name3-(2-imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide
Molecular formulaC29H27F3N6O
Molecular weight532.559
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity150.10
LogP4.4
Topological polar surface area65.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.