Drug Information

General Information
Drug ID
DR00032
Drug Name
Imatinib
Synonyms
112GI019; 4-(4-METHYL-PIPERAZIN-1-YLMETHYL)-N-[4-METHYL-3-(4-PYRIDIN-3-YL-PYRIMIDIN-2-YLAMINO)-PHENYL]-BENZAMIDE; 4-[(4-Methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-phenyl]benzamide; 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide methanesulfonate; 4-[(4-methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzamide; 4-[(4-methylpiperazin-1-yl)methyl]-N-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide; 4-[(4-methylpiperazin-1-yl)methyl]-N-{4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl}benzamide; Alpha-(4-Methyl-1-piperazinyl)-3'-((4-(3-pyridyl)-2-pyrimidinyl)amino)-p-tolu-p-toluidide; Benzamide, 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-(9CI); CGP 57148B; Cgp 57148; Glamox; Glamox (TN); Gleevec (TN); Glivec (TN); Imatinib (INN); Imatinib Methansulfonate; Imatinib [INN:BAN]; Imatinib free base; N-(3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylphenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide; STI; STI 571; STI571; Sti-571
Drug Type
Small molecular drug
Indication Gastrointestinal stromal tumor [ICD11:2B5B] Approved [1]
Chronic myelogenous leukemia [ICD11:2A20.0] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
Formula
C29H31N7O
Canonical SMILES
CC1=C(C=C(C=C1)NC(=O)C2=CC=C(C=C2)CN3CCN(CC3)C)NC4=NC=CC(=N4)C5=CN=CC=C5
InChI
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
KTUFNOKKBVMGRW-UHFFFAOYSA-N
CAS Number
CAS 152459-95-5
Pharmaceutical Properties Molecular Weight 493.6 Topological Polar Surface Area 86.3
Heavy Atom Count 37 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
XLogP
3.5
PubChem CID
5291
PubChem SID
14859628 ,22394533 ,24424247 ,26697112 ,26737110 ,29215405 ,29215406 ,29224346 ,46392211 ,46393540 ,46505055 ,46507948 ,46513933 ,49655235 ,50066026 ,50070642 ,50100104 ,50109856 ,50353059 ,53788935 ,53799240 ,5619104 ,56311252 ,56311284 ,56311359 ,56311779 ,56311988 ,56312022 ,56312838 ,56313109 ,56313183 ,56313522 ,56313562 ,56314521 ,57288246 ,57288452 ,57288559 ,57288780 ,57322698 ,57551951 ,57578266 ,584799 ,7890613 ,7979593 ,8153249 ,822644 ,828861 ,832827 ,841977 ,85171056
ChEBI ID
ChEBI:45783
TTD Drug ID
D0AZ3C
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
BCRP Transporter Info Breast cancer resistance protein Substrate [3]
OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [4]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [5]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [5]
P-GP Transporter Info P-glycoprotein 1 Substrate [6]
References
1 Imatinib was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Pharmacologic markers and predictors of responses to imatinib therapy in patients with chronic myeloid leukemia. Leuk Lymphoma. 2008 Apr;49(4):639-42.
3 Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood. 2004 Nov 1;104(9):2940-2.
4 Environmental and genetic factors affecting transport of imatinib by OATP1A2. Clin Pharmacol Ther. 2011 Jun;89(6):816-20.
5 Contribution of OATP1B1 and OATP1B3 to the disposition of sorafenib and sorafenib-glucuronide. Clin Cancer Res. 2013 Mar 15;19(6):1458-66.
6 Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50.

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