Drug Information

General Information
Drug ID
DR00318
Drug Name
Pemetrexed
Synonyms
(2R)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid; (2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid; 2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid; 2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-PENTANEDIOIC ACID; Alimta; Alimta (TN); LY 231,514; LY 231514; LY-231,514; LY-2315; LY-231514; LY231514; LYA; N-(4-(2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimdin-5-yl)ethyl)benzoyl)glutamic acid; N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-d-glutamic acid; Pemetrexed (INN); Pemetrexed [INN:BAN]
Drug Type
Small molecular drug
Indication Malignant pleural mesothelioma [ICD11:2C26.0] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
Formula
C20H21N5O6
Canonical SMILES
C1=CC(=CC=C1CCC2=CNC3=C2C(=O)NC(=N3)N)C(=O)NC(CCC(=O)O)C(=O)O
InChI
InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m0/s1
InChIKey
WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
CAS Number
CAS 150399-23-8
Pharmaceutical Properties Molecular Weight 427.4 Topological Polar Surface Area 187
Heavy Atom Count 31 Rotatable Bond Count 9
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 7
XLogP
0.2
PubChem CID
135410875
PubChem SID
104321790 ,117542033 ,126665655 ,134337377 ,134338975 ,134339784 ,134457174 ,135945851 ,137002681 ,152035380 ,160963987 ,175437774 ,177748645 ,178103443 ,189306395 ,223392020 ,223658518 ,223705327 ,224164966 ,226399254 ,250180319 ,252216021 ,43118181 ,46505640 ,50064379 ,50524509 ,53788923 ,57314144 ,90342403
ChEBI ID
CHEBI:63616
TTD Drug ID
D0Y4GO
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
FLOT1 Transporter Info Folate transporter 1 Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [4]
MRP5 Transporter Info Multidrug resistance-associated protein 5 Substrate [5]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [6]
PCFT Transporter Info Proton-coupled folate transporter Substrate [7]
Drug-Transporter Activity Data
Drug-Transporter Activity Data FLOT1 Transporter Info Km =0.2 microM Human liver cancer cells (HepG2)-FLOT1 [8]
MRP5 Transporter Info Km =281 microM Human embryonic kidney cells (HEK293)-MRP5 [5]
PCFT Transporter Info Km =0.2 microM Human liver cancer cells (HepG2)-PCFT [7]
References
1 Pemetrexed was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 pH-Dependent transport of pemetrexed by breast cancer resistance protein. Drug Metab Dispos. 2011 Sep;39(9):1478-85.
3 Biology of the major facilitative folate transporters SLC19A1 and SLC46A1. Curr Top Membr. 2014;73:175-204.
4 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
5 Kinetic validation of the use of carboxydichlorofluorescein as a drug surrogate for MRP5-mediated transport. Eur J Pharm Sci. 2006 Apr;27(5):524-32.
6 Substrate- and pH-specific antifolate transport mediated by organic anion-transporting polypeptide 2B1 (OATP2B1-SLCO2B1). Mol Pharmacol. 2012 Feb;81(2):134-42.
7 The proton-coupled folate transporter: impact on pemetrexed transport and on antifolates activities compared with the reduced folate carrier. Mol Pharmacol. 2008 Sep;74(3):854-62.
8 Antifolates in cancer therapy: structure, activity and mechanisms of drug resistance. Drug Resist Updat. 2012 Aug;15(4):183-210.

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