1N1

N-(2-CHLORO-6-METHYLPHENYL)-2-({6-[4-(2-HYDROXYETHYL)PIPERAZIN-1-YL]-2-METHYLPYRIMIDIN-4-YL}AMINO)-1,3-THIAZOLE-5-CARBOXAMIDE

Created:	2006-04-24
Last modified:	2021-03-01

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23 entries where 1N1 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	59
Chiral Atom Count	0
Bond Count	62
Aromatic Bond Count	17

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Chemical Component Summary
Name	N-(2-CHLORO-6-METHYLPHENYL)-2-({6-[4-(2-HYDROXYETHYL)PIPERAZIN-1-YL]-2-METHYLPYRIMIDIN-4-YL}AMINO)-1,3-THIAZOLE-5-CARBOXAMIDE
Synonyms	Dasatinib
Systematic Name (OpenEye OEToolkits)	N-(2-chloranyl-6-methyl-phenyl)-2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methyl-pyrimidin-4-yl]amino]-1,3-thiazole-5-carboxamide
Formula	C₂₂ H₂₆ Cl N₇ O₂ S
Molecular Weight	488.006
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	Clc1cccc(c1NC(=O)c2sc(nc2)Nc4nc(nc(N3CCN(CCO)CC3)c4)C)C
SMILES	CACTVS	3.370	Cc1nc(Nc2sc(cn2)C(=O)Nc3c(C)cccc3Cl)cc(n1)N4CCN(CCO)CC4
SMILES	OpenEye OEToolkits	1.7.2	Cc1cccc(c1NC(=O)c2cnc(s2)Nc3cc(nc(n3)C)N4CCN(CC4)CCO)Cl
Canonical SMILES	CACTVS	3.370	Cc1nc(Nc2sc(cn2)C(=O)Nc3c(C)cccc3Cl)cc(n1)N4CCN(CCO)CC4
Canonical SMILES	OpenEye OEToolkits	1.7.2	Cc1cccc(c1NC(=O)c2cnc(s2)Nc3cc(nc(n3)C)N4CCN(CC4)CCO)Cl
InChI	InChI	1.03	InChI=1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
InChIKey	InChI	1.03	ZBNZXTGUTAYRHI-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank ID	DB01254
Name	Dasatinib
Groups	approved investigational
Description	Dasatinib is an orally available multikinase inhibitor indicated for the treatment of Philadelphia chromosome (Ph)-positive leukemias.[A2224,L45171] Ph is a chromosomal abnormality found in patients with chronic myelogenous leukemia (CML) and acute lymphocytic leukemia (ALL), where the ABL tyrosine kinase and the breakpoint cluster region (BCR) gene transcribe the chimeric protein BCR-ABL. BCR-ABL is associated with the uncontrolled activity of the ABL tyrosine kinase and is involved in the pathogenesis of CML and 15-30% of ALL cases.[A11377,A33432] Dasatinib also inhibits a spectrum of kinases involved in cancer, including several SRC-family kinases.[A11377] Unlike [imatinib], another tyrosine kinase used for the treatment of CML and Ph-positive ALL, dasatinib inhibits the active and inactive conformations of the ABL kinase domain.[A2226,A11377] Also, mutations in the kinase domain of BCR-ABL may lead to relapse during imatinib treatment. Since dasatinib does not interact with some of the residues involved in those mutations, the use of this drug represents a therapeutic alternative for patients with cancers that have developed imatinib-resistance.[A2226] The use of dasatinib was first approved by the FDA in 2006.[L45171,L45186]
Synonyms	Dasatinib (anh.) dasatinib (anhydrous) Dasatinibum Dasatinib Dasatinib anhydrous Dasatinib monolauryl sulfate Anh. dasatinib N-(2-CHLORO-6-methylphenyl)-2-({6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl}amino)-1,3-thiazole-5-carboxamide BMS dasatinib Dasatinib monohydrate Anhydrous dasatinib
Brand Names	Dasatinib Accord Reddy-dasatinib Dasatinib Accordpharma Apo-dasatinib Teva-dasatinib Taro-dasatinib Sprycel
Indication	Dasatinib is indicated for the treatment of newly diagnosed adults with Philadelphia chromosome-positive (Ph+) chronic myeloid leukemia (CML) in chronic phase, as well as adults with chronic, accelerated, or myeloid or lymphoid blast phase Ph+ CML with resistance or intolerance to prior therapy including imatinib, and adults with Philadelphia chromosome-positive acute lymphoblastic leukemia (Ph+ ALL) with resistance or intolerance to prior therapy. Dasatinib is also indicated for the treatment of pediatric patients 1 year of age and older with Ph+ CML in chronic phase or newly diagnosed Ph+ ALL in combination with chemotherapy.[L45171]
Categories	Antineoplastic Agents Antineoplastic and Immunomodulating Agents Bcr-Abl Tyrosine Kinase Inhibitors BCRP/ABCG2 Inhibitors BCRP/ABCG2 Substrates Cytochrome P-450 CYP1A2 Substrates Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (weak) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Enzyme Inhibitors Immunosuppressive Agents Kinase Inhibitor Myelosuppressive Agents Narrow Therapeutic Index Drugs P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Photosensitizing Agents Potential QTc-Prolonging Agents Protein Kinase Inhibitors Pyrimidines QTc Prolonging Agents Sulfur Compounds Thiazoles Tyrosine Kinase Inhibitors
ATC-Code	L01EA02
CAS number	302962-49-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Tyrosine-protein kinase ABL1	MLEICLKLVGCKSKKGLSSSSSCYLEEALQRPVASDFEPQGLSEAARWNS...	unknown	inhibitor,multitarget
Proto-oncogene tyrosine-protein kinase Src	MGSNKSKPKDASQRRRSLEPAENVHGAGGGAFPASQTPSKPASADGHRGP...	unknown	inhibitor,multitarget
Ephrin type-A receptor 2	MELQAARACFALLWGCALAAAAAAQGKEVVLLDFAAAGGELGWLTHPYGK...	unknown	antagonist
Tyrosine-protein kinase Lck	MGCGCSSHPEDDWMENIDVCENCHYPIVPLDGKGTLLIRNGSEVRDPLVT...	unknown	inhibitor,multitarget
Tyrosine-protein kinase Yes	MGCIKSKENKSPAIKYRPENTPEPVSTSVSHYGAEPTTVSPCPSSSAKGT...	unknown	inhibitor
Mast/stem cell growth factor receptor Kit	MRGARGAWDFLCVLLLLLRVQTGSSQPSVSPGEPSPPSIHPGKSDLIVRV...	unknown	antagonist
Platelet-derived growth factor receptor beta	MRLPGAMPALALKGELLLLSLLLLLEPQISQGLVVTPPGPELVLNVSSTF...	unknown	antagonist
Signal transducer and activator of transcription 5B	MAVWIQAQQLQGEALHQMQALYGQHFPIEVRHYLSQWIESQAWDSVDLDN...	unknown	inhibitor
Tyrosine-protein kinase ABL2	MGQQVGRVGEAPGLQQPQPRGIRGSSAARPSGRRRDPAGRTTETGFNIFT...	unknown	multitarget
Tyrosine-protein kinase Fyn	MGCVQCKDKEATKLTEERDGSLNQSSGYRYGTDPTPQHYPSFGVTSIPNY...	unknown	inhibitor,multitarget
Tyrosine-protein kinase BTK	MAAVILESIFLKRSQQKKKTSPLNFKKRLFLLTVHKLSYYEYDFERGRRG...	unknown	inhibitor
Nuclear receptor subfamily 4 group A member 3	MPCVQAQYSPSPPGSSYAAQTYSSEYTTEIMNPDYTKLTMDLGSTEITAT...	unknown	inhibitor
Breakpoint cluster region protein	MVDPVGFAEAWKAQFPDSEPPRMELRSVGDIEQELERCKASIRRLEQEVN...	unknown	inhibitor
Tyrosine-protein kinase CSK	MSAIQAAWPSGTECIAKYNFHGTAEQDLPFCKGDVLTIVAVTKDPNWYKA...	unknown	inhibitor
Ephrin type-A receptor 5	MRGSGPRGAGRRRPPSGGGDTPITPASLAGCYSAPRRAPLWTCLLLCAAL...	unknown	inhibitor
Ephrin type-B receptor 4	MELRVLLCWASLAAALEETLLNTKLETADLKWVTFPQVDGQWEELSGLDE...	unknown	inhibitor
Tyrosine-protein kinase Fgr	MGCVFCKKLEPVATAKEDAGLEGDFRSYGAADHYGPDPTKARPASSFAHI...	unknown	inhibitor
Tyrosine-protein kinase FRK	MSNICQRLWEYLEPYLPCLSTEADKSTVIENPGALCSPQSQRHGHYFVAL...	unknown	binder
Heat shock cognate 71 kDa protein	MSKGPAVGIDLGTTYSCVGVFQHGKVEIIANDQGNRTTPSYVAFTDTERL...	unknown	binder
Tyrosine-protein kinase Lyn	MGCIKSKGKDSLSDDGVDLKTQPVRNTERTIYVRDPTSNKQQRPVPESQL...	unknown	inhibitor
Mitogen-activated protein kinase kinase kinase MLT	MSSLGASFVQIKFDDLQFFENCGGGSFGSVYRAKWISQDKEVAVKKLLKI...	unknown	binder
Mitogen-activated protein kinase 14	MSQERPTFYRQELNKTIWEVPERYQNLSPVGSGAYGSVCAAFDTKTGLRV...	unknown	binder
Amidophosphoribosyltransferase	MELEELGIREECGVFGCIASGEWPTQLDVPHVITLGLVGLQHRGQESAGI...	unknown	binder
Cytochrome P450 1A1	MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...	unknown	substrate
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	substrate
Cytochrome P450 1B1	MGTSLSPNDPWPLNPLSIQQTTLLLLLSVLATVHVGQRLLRQRRRQLRSA...	unknown	substrate
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Dimethylaniline monooxygenase [N-oxide-forming] 3	MGKKVAIIGAGVSGLASIRSCLEEGLEPTCFEKSNDIGGLWKFSDHAEEG...	unknown	substrate
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate,inhibitor
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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