Raltitrexed

Raltitrexed

File:Raltitrexed.png
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Intravenous
ATC code	L01BA03 (WHO)
Legal status
Legal status	UK: POM (Prescription only) Not available in U.S.
Identifiers
IUPAC name N-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}-2-thienyl)carbonyl]-L-glutamic acid
CAS Number	112887-68-0 Y
PubChem CID	104758
DrugBank	DB00293 Y
ChemSpider	94568 Y
UNII	FCB9EGG971
KEGG	D01064 Y
ChEMBL	ChEMBL225071 Y
PDB ligand	D16 (PDBe, RCSB PDB)
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C21H22N4O6S
Molar mass	458.489 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(c3sc(N(C)Cc2cc1C(=O)\N=C(/Nc1cc2)C)cc3)N[C@H](C(=O)O)CCC(=O)O
InChI InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1 Y Key:IVTVGDXNLFLDRM-HNNXBMFYSA-N Y
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Raltitrexed (brand name Tomudex®) is a chemotherapy drug manufactured AstraZeneca Company, is an antimetabolite used in chemotherapy. It is an inhibitor of thymidylate synthase.

Uses

Used in treatment of colorectal cancer since 1998.

Mechanism of action

Raltitrexed is chemically similar to folic acid and is in the class of chemotherapy drugs called folate antimetabolites. It works by inhibiting enzyme used in pyrimidine synthesis —thymidylate synthase (TS). Raltitrexed is fully active after polyglutamylation. Inhibition of L1210 cell growth i culture IC₅₀ = 9 nM, is one of the strongest antimetabolite in use. By inhibiting the formation of precursor pyrimidine nucleotides, raltitrexed prevents the formation of DNA and RNA, which are required for the growth and survival of both normal cells and cancer cells.