Raltitrexed: Difference between revisions
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{{ | {{Drugbox | ||
| IUPAC_name = | | verifiedrevid = 464379925 | ||
| image = Raltitrexed. | | IUPAC_name = ''N''-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}-2-thienyl)carbonyl]-<small>L</small>-glutamic acid | ||
| image = Raltitrexed.png | |||
| image2 = Raltitrexed ball-and-stick.png | |||
<!--Clinical data--> | |||
| tradename = | |||
| Drugs.com = {{drugs.com|CONS|raltitrexed}} | |||
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | |||
| pregnancy_US = <!-- A / B / C / D / X --> | |||
| pregnancy_category = | |||
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> | |||
| legal_UK = POM | |||
| legal_US = <!-- OTC / Rx-only --> | |||
| legal_status = Not available in U.S. | |||
| routes_of_administration = [[Intravenous therapy|Intravenous]] | |||
<!--Pharmacokinetic data--> | |||
| bioavailability = | |||
| protein_bound = | |||
| metabolism = | |||
| elimination_half-life = | |||
| excretion = | |||
<!--Identifiers--> | |||
| CASNo_Ref = {{cascite|correct|CAS}} | |||
| CAS_number_Ref = {{cascite|correct|??}} | |||
| CAS_number = 112887-68-0 | | CAS_number = 112887-68-0 | ||
| ATC_prefix = L01 | | ATC_prefix = L01 | ||
| ATC_suffix = BA03 | | ATC_suffix = BA03 | ||
| ATC_supplemental = | | ATC_supplemental = | ||
| PubChem = 104758 | | PubChem = 104758 | ||
| DrugBank = | | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ||
| C=21 | H=22 | N=4 | O=6 | S=1 | | DrugBank = DB00293 | ||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| ChemSpiderID = 94568 | |||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
| UNII = FCB9EGG971 | |||
| KEGG_Ref = {{keggcite|correct|kegg}} | |||
| KEGG = D01064 | |||
| ChEMBL_Ref = {{ebicite|correct|EBI}} | |||
| ChEMBL = 225071 | |||
| PDB_ligand = D16 | |||
<!--Chemical data--> | |||
| C=21 | H=22 | N=4 | O=6 | S=1 | |||
| molecular_weight = 458.489 g/mol | | molecular_weight = 458.489 g/mol | ||
| | | smiles = O=C(c3sc(N(C)Cc2cc1C(=O)\N=C(/Nc1cc2)C)cc3)N[C@H](C(=O)O)CCC(=O)O | ||
| InChI = 1/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 | |||
| InChIKey = IVTVGDXNLFLDRM-HNNXBMFYBV | |||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChI = 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 | |||
| | | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | ||
| StdInChIKey = IVTVGDXNLFLDRM-HNNXBMFYSA-N | |||
| | }}__NOTOC__ | ||
| | |||
| | |||
| | |||
}} | |||
{{CMG}} | |||
==Overview== | ==Overview== | ||
Latest revision as of 12:09, 24 February 2015
| File:Raltitrexed.png | |
 | |
| Clinical data | |
|---|---|
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| Routes of administration | Intravenous |
| ATC code | |
| Legal status | |
| Legal status |
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| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| PDB ligand | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C21H22N4O6S |
| Molar mass | 458.489 g/mol |
| 3D model (JSmol) | |
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| (verify) | |
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.