Drug Details

General Information of the Drug (ID: DR3046)
Name
Raltitrexed
Synonyms
Raltitrexed; Tomudex; 112887-68-0; ZD1694; ZD-1694; ICI-D1694; D-1694; ICI D1694; UNII-FCB9EGG971; D1694; CHEBI:5847; C21H22N4O6S; Raltitrexed (Tomudex); ZD-16; FCB9EGG971; ZD 1694; CHEMBL225071; N-(5-(N-(3,4-Dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino)-2-thenoyl)-L-glutamic acid; ICI-D-1694; NSC-639186; NCGC00229704-01; DSSTox_CID_26482; DSSTox_RID_81653; DSSTox_GSID_46482; (S)-2-(5-(Methyl((2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)-methyl)amino)thiophene-2-carboxamido)pentanedioic acid; (S)-2-(5-(methyl((2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl)amino)thiophene-2-carboxamido)pentanedioic acid; N-(5-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino]-2-thenoyl)-L-glutamic acid; (2S)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid; (S)-2-(5-(methyl((2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)amino)thiophene-2-carboxamido)pentanedioic acid; D16; Tomudex (TN); D 1694; CAS-112887-68-0; Raltitrexed (JAN/USAN/INN); (2S)-2-[[5-[methyl-[(2-methyl-4-oxo-1H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid; 1hvy; 2kce; 2tsr; ZN-D1694; KS-5069; ZD1694; Raltitrexed; SCHEMBL7438; MLS001424225; MLS006010125; N-(5-(((3,4-Dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thenoyl)-L-glutamic acid; Raltitrexed [USAN:INN:BAN]; GTPL7403; DTXSID0046482; BDBM18795; QCR-125; 1i00; HMS2052I03; HMS3715P08; AMY42113; ZINC3832372; Tox21_112237; BDBM50027655; MFCD00864168; NSC639186; s1192; AKOS015894877; AKOS015994729; Tox21_112237_1; CCG-101075; CCG-221273; DB00293; NC00325; NCGC00263534-02; HY-10821; L-Glutamic acid, N-((5-(((1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thienyl)carbonyl)-; L-Glutamic acid, N-[[5-[[(3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-; NCI60_013008; SMR000469217; SMR002529608; BCP0726000267; SW197705-2; C11372; D01064; S-7682; AB00698356-05; 134189-EP2275102A1; 134189-EP2292233A2; 887R680; SR-01000763351; J-524216; SR-01000763351-3; BRD-K89839824-001-01-2; Q15304877; (2S)-2-[[5-[methyl-[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid; N-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)carbonyl]-L-glutamic acid; N-[[5-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-L-glutamic acid
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Molecular Type
Small molecule
Disease Rectum cancer [ICD-11: 2B92] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.9 mL/min/kg
Elimination
50% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 198 hours
Metabolism
The drug is metabolized via a reduced folate carrier
Unbound Fraction
The unbound fraction of drug in plasma is 0.05%
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 6.57 L/kg
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Formula
C21H22N4O6S
PubChem CID
135400182
Canonical SMILES
CC1=NC2=C(C=C(C=C2)CN(C)C3=CC=C(S3)C(=O)NC(CCC(=O)O)C(=O)O)C(=O)N1
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
InChIKey
IVTVGDXNLFLDRM-HNNXBMFYSA-N
CAS Number
CAS 112887-68-0
ChEBI ID
CHEBI:5847
TTD Drug ID
D01KKQ
DrugBank ID
DB00293
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Fluoroorotic acid      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model LoVo CVCL_0399 Colon adenocarcinoma Homo sapiens
HT-29 CVCL_0320 Colon adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Histone deacetylase inhibitor NVP-LAQ824 sensitizes human nonsmall cell lung cancer to the cytotoxic effects of ionizing radiation.
Target and Pathway
Target(s) Candida thymidylate synthase (Candi TMP1)  Molecule Info  [3]
BioCyc Pyrimidine deoxyribonucleotides biosynthesis from CTP Click to Show/Hide
2 Pyrimidine deoxyribonucleotides de novo biosynthesis
3 Superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis
4 Superpathway of pyrimidine deoxyribonucleoside salvage
5 DTMP de novo biosynthesis (mitochondrial)
6 Pyrimidine deoxyribonucleosides salvage
KEGG Pathway Pyrimidine metabolism Click to Show/Hide
2 One carbon pool by folate
3 Metabolic pathways
Panther Pathway De novo pyrimidine deoxyribonucleotide biosynthesis Click to Show/Hide
2 Formyltetrahydroformate biosynthesis
Pathwhiz Pathway Pyrimidine Metabolism Click to Show/Hide
Pathway Interaction Database E2F transcription factor network Click to Show/Hide
Reactome E2F mediated regulation of DNA replication Click to Show/Hide
2 Pyrimidine biosynthesis
3 G1/S-Specific Transcription
WikiPathways Trans-sulfuration and one carbon metabolism Click to Show/Hide
2 Retinoblastoma (RB) in Cancer
3 One Carbon Metabolism
4 Integrated Pancreatic Cancer Pathway
5 miR-targeted genes in muscle cell - TarBase
6 miR-targeted genes in lymphocytes - TarBase
7 miR-targeted genes in leukocytes - TarBase
8 miR-targeted genes in epithelium - TarBase
9 Metabolism of nucleotides
10 Fluoropyrimidine Activity
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7403).
Reference 2 Histone deacetylase inhibitor NVP-LAQ824 sensitizes human nonsmall cell lung cancer to the cytotoxic effects of ionizing radiation. Anticancer Drugs. 2007 Aug;18(7):793-800.
Reference 3 DNA damage and homologous recombination signaling induced by thymidylate deprivation. Biochem Pharmacol. 2008 Oct 15;76(8):987-96.
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