STI

4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE

Created:	2001-04-11
Last modified:	2020-06-05

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Chemical Details
Formal Charge	0
Atom Count	68
Chiral Atom Count	0
Bond Count	72
Aromatic Bond Count	25

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Chemical Component Summary
Name	4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE
Synonyms	STI-571; IMATINIB
Systematic Name (OpenEye OEToolkits)	4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide
Formula	C₂₉ H₃₁ N₇ O
Molecular Weight	493.603
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(Nc3ccc(c(Nc2nc(c1cccnc1)ccn2)c3)C)c4ccc(cc4)CN5CCN(CC5)C
SMILES	CACTVS	3.341	CN1CCN(CC1)Cc2ccc(cc2)C(=O)Nc3ccc(C)c(Nc4nccc(n4)c5cccnc5)c3
SMILES	OpenEye OEToolkits	1.5.0	Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC(=O)c4ccc(cc4)CN5CCN(CC5)C
Canonical SMILES	CACTVS	3.341	CN1CCN(CC1)Cc2ccc(cc2)C(=O)Nc3ccc(C)c(Nc4nccc(n4)c5cccnc5)c3
Canonical SMILES	OpenEye OEToolkits	1.5.0	Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC(=O)c4ccc(cc4)CN5CCN(CC5)C
InChI	InChI	1.03	InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
InChIKey	InChI	1.03	KTUFNOKKBVMGRW-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB00619
Name	Imatinib
Groups	approved
Description	Imatinib is a small molecule kinase inhibitor that revolutionized the treatment of cancer, particularly chronic myeloid leukemia, in 2001.[A249305] It was deemed a "miracle drug" due to its clinical success, as oncologist Dr. Brian noted that "complete hematologic responses were observed in 53 of 54 patients with CML treated with a daily dosage of 300 mg or more and typically occurred in the first four weeks of therapy".[A249315]. The discovery of imatinib also established a new group of therapy called "targeted therapy", since treatment can be tailored specifically to the unique cancer genetics of each patient.[L42220] Imatinib was approved on February 1st ,2001 by the FDA and November 7th, 2001 by the EMA; however, its European approval has been withdrawn in October 2023.[A263036,L49746,L49751]
Synonyms	Imatinib Imatinib mesylate Imatinibum α-(4-methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-toluidide
Brand Names	Mint-imatinib Imatinib Accord Imatinib Teva Teva-imatinib Jamp Imatinib Imatinib Teva B.V. Imatinib Medac PMS-imatinib Sandoz Imatinib Imatinib Nat-imatinib Imatinib Mesylate Imatinib mesylate 400 mg Taro-imatinib Imatinib mesylate Apo-imatinib Mylan-imatinib Ach-imatinib Glivec Gleevec Imatinib Actavis Imatinib Koanaa
Indication	Imatinib is indicated for the treatment of adult and pediatric chronic myeloid leukemia with Philadelphia chromosome mutation (Ph+) in blast crisis, accelerated phase, or chronic phase after IFN-alpha therapy failure.[L42080] Additionally, imatinib is also indicated to treat adult and pediatric Ph+ acute lymphoblastic leukemia, adult myelodysplastic/myeloproliferative diseases, adult aggressive systemic mastocytosis, adult hypereosinophilic syndrome and/or chronic eosinophilic leukemia (CEL), adult dermatofibrosarcoma protuberans, and malignant gastrointestinal stromal tumors (GIST).[L42080]
Categories	Amides Antineoplastic Agents Antineoplastic and Immunomodulating Agents Bcr-Abl Tyrosine Kinase Inhibitors BCRP/ABCG2 Inhibitors BCRP/ABCG2 Substrates Benzamides and benzamide derivatives Benzene Derivatives BSEP/ABCB11 Substrates Cancer immunotherapy Cardiotoxic antineoplastic agents Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (moderate) Cytochrome P-450 CYP2C9 Inhibitors (strength unknown) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (strength unknown) Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Inhibitors Cytochrome P-450 CYP3A7 Inhibitors (strength unknown) Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Enzyme Inhibitors Highest Risk QTc-Prolonging Agents Immunosuppressive Agents Immunotherapy Kinase Inhibitor Myelosuppressive Agents OATP1B3 substrates OCT1 substrates OCT2 Inhibitors P-glycoprotein inhibitors P-glycoprotein substrates Photosensitizing Agents Piperazines Protein Kinase Inhibitors Pyrimidines QTc Prolonging Agents Tyrosine Kinase Inhibitors UDP Glucuronosyltransferases Inhibitors UGT2B17 Inhibitors
ATC-Code	L01EA01
CAS number	152459-95-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Breakpoint cluster region protein	MVDPVGFAEAWKAQFPDSEPPRMELRSVGDIEQELERCKASIRRLEQEVN...	unknown	inhibitor
Mast/stem cell growth factor receptor Kit	MRGARGAWDFLCVLLLLLRVQTGSSQPSVSPGEPSPPSIHPGKSDLIVRV...	unknown	antagonist
Proto-oncogene tyrosine-protein kinase receptor Ret	MAKATSGAAGLRLLLLLLLPLLGKVALGLYFSRDAYWEKLYVDQAAGTPL...	unknown	inhibitor
High affinity nerve growth factor receptor	MLRGGRRGQLGWHSWAAGPGSLLAWLILASAGAAPCPDACCPHGSSGLRC...	unknown	antagonist
Macrophage colony-stimulating factor 1 receptor	MGPGVLLLLLVATAWHGQGIPVIEPSVPELVVKPGATVTLRCVGNGSVEW...	unknown	antagonist
Platelet-derived growth factor receptor alpha	MGTSHPAFLVLGCLLTGLSLILCQLSLPSILPNENEKVVQLNSSFSLRCF...	unknown	antagonist
Epithelial discoidin domain-containing receptor 1	MGPEALSSLLLLLLVASGDADMKGHFDPAKCRYALGMQDRTIPDSDISAS...	unknown	antagonist
Tyrosine-protein kinase ABL1	MLEICLKLVGCKSKKGLSSSSSCYLEEALQRPVASDFEPQGLSEAARWNS...	unknown	inhibitor
Platelet-derived growth factor receptor beta	MRLPGAMPALALKGELLLLSLLLLLEPQISQGLVVTPPGPELVLNVSSTF...	unknown	antagonist
Discoidin domain-containing receptor 2	MILIPRMLLVLFLLLPILSSAKAQVNPAICRYPLGMSGGQIPDEDITASS...	unknown	antagonist
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate,inhibitor
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate,inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate,inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	substrate,inhibitor
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	binder
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	substrate
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate,inhibitor
ATP-binding cassette sub-family A member 3	MAVLRQLALLLWKNYTLQKRKVLVTVLELFLPLLFSGILIWLRLKIQSEN...	unknown	substrate
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	substrate
Multidrug resistance-associated protein 1	MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...	unknown	substrate,inhibitor
Solute carrier family 22 member 5	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	substrate
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	substrate
Multidrug resistance-associated protein 4	MLPVYQEVKPNPLQDANLCSRVFFWWLNPLFKIGHKRRLEEDDMYSVLPE...	unknown	substrate
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	substrate
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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