Chemical Component Summary

Namepirtobrutinib
Synonyms5-amino-3-{4-[(5-fluoro-2-methoxybenzamido)methyl]phenyl}-1-[(2S)-1,1,1-trifluoropropan-2-yl]-1H-pyrazole-4-carboxamide
Identifiers5-azanyl-3-[4-[[(5-fluoranyl-2-methoxy-phenyl)carbonylamino]methyl]phenyl]-1-[(2~{S})-1,1,1-tris(fluoranyl)propan-2-yl]pyrazole-4-carboxamide
FormulaC22 H21 F4 N5 O3
Molecular Weight479.427
TypeNON-POLYMER
Isomeric SMILESC[C@@H](C(F)(F)F)n1c(c(c(n1)c2ccc(cc2)CNC(=O)c3cc(ccc3OC)F)C(=O)N)N
InChIInChI=1S/C22H21F4N5O3/c1-11(22(24,25)26)31-19(27)17(20(28)32)18(30-31)13-5-3-12(4-6-13)10-29-21(33)15-9-14(23)7-8-16(15)34-2/h3-9,11H,10,27H2,1-2H3,(H2,28,32)(H,29,33)/t11-/m0/s1
InChIKeyFWZAWAUZXYCBKZ-NSHDSACASA-N

Chemical Details

Formal Charge0
Atom Count55
Chiral Atom Count1
Bond Count57
Aromatic Bond Count17

Drug Info: DrugBank

DrugBank IDDB17472 
NamePirtobrutinib
Groups
  • approved
  • investigational
DescriptionPirtobrutinib is a small molecule and a highly selective non-covalent inhibitor of Bruton’s tyrosine kinase (BTK). Its high selectivity has been associated with lower discontinuation rates due to adverse events and a lower incidence of atrial fibrillation.[A256758] Unlike BTK covalent inhibitors, such as [ibrutinib], that bind to the cysteine 481 (Cys481) amino acid within the active site of BTK, the inhibitory activity of pirtobrutinib is maintained even in the presence of Cys481 mutations. Although the mechanisms of resistance to covalent BTK inhibitors have not been fully elucidated, it appears that the presence of Cys481 mutations is the most common reason for resistance to covalent BTK inhibitors.[A256758,A256773,L44863] However, other mutations may confer resistance to non-covalent BTK inhibitors such as pirtobrutinib.[A256788] In January 2023, the use of pirtobrutinib for the treatment of relapsed or refractory mantle cell lymphoma (MCL) after at least two lines of systemic therapy was approved under the FDA's Accelerated Approval pathway.[L44863,L44873]
Synonyms
  • Pirtobrutinib
  • (s)-5-amino-3-(4-((5-fluoro-2-methoxybenzamido)methyl)phenyl)-1-(1,1,1-trifluoropropan-2-yl)-1h-pyrazole-4-carboxamide
  • 5-amino-3-(4-((5-fluoro-2-methoxybenzamido)methyl)phenyl)-1-((2s)-1,1,1-trifluoropropan-2-yl)-1h-pyrazole-4-carboxamide
  • 1h-pyrazole-4-carboxamide, 5-amino-3-(4-(((5-fluoro-2-methoxybenzoyl)amino)methyl)phenyl)-1-((1s)-2,2,2-trifluoro-1-methylethyl)-
Brand NamesJaypirca
IndicationPirtobrutinib is indicated for the treatment of adult patients with relapsed or refractory mantle cell lymphoma (MCL) after at least two lines of systemic therapy, including a BTK inhibitor.[L44863]
Categories
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • BCRP/ABCG2 Inhibitors
  • BCRP/ABCG2 Substrates
  • Bruton's tyrosine kinase (BTK) inhibitors
CAS number2101700-15-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Tyrosine-protein kinase BTKMAAVILESIFLKRSQQKKKTSPLNFKKRLFLLTVHKLSYYEYDFERGRRG...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate,inhibitor,inducer
UDP-glucuronosyltransferase 1-8MARTGWTSPIPLCVSLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...unknownsubstrate
UDP-glucuronosyltransferase 1-9MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...unknownsubstrate
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknowninhibitor
View More
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

Related Resource References

Resource NameReference
PubChem 129269915
ChEMBL CHEMBL4650485