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ZD1694; Raltitrexed

ZD1694; Raltitrexed

Chemistry

Chemistry

Also known as: Tomudex, 112887-68-0, Zd1694, Zd-1694, Ici-d1694, D-1694

Molecular Formula

C₂₁H₂₂N₄O₆S

Molecular Weight

458.5 g/mol

InChI Key

IVTVGDXNLFLDRM-HNNXBMFYSA-N

FDA UNII

FCB9EGG971

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

1 2D Structure

ZD1694; Raltitrexed

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[[5-[methyl-[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid

2.1.2 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

2.1.3 InChI Key

IVTVGDXNLFLDRM-HNNXBMFYSA-N

2.1.4 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

2.1.5 Isomeric SMILES

CC1=NC2=C(C=C(C=C2)CN(C)C3=CC=C(S3)C(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)N1

2.2 Other Identifiers

2.2.1 UNII

FCB9EGG971

2.3 Synonyms

2.3.1 MeSH Synonyms

1. D 1694

2. D-1694

3. D1694

4. Ici D1694

5. Ici-d1694

6. N-(5-(n-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-n-methylamino)-2-thenoyl)-l-glutamic Acid

7. Tomudex

8. Zd 1694

9. Zd-1694

10. Zd1694

2.3.2 Depositor-Supplied Synonyms

1. Tomudex

2. 112887-68-0

3. Zd1694

4. Zd-1694

5. Ici-d1694

6. D-1694

7. D1694

8. Ici D1694

9. Zd-16

10. Chebi:5847

11. (2s)-2-[[5-[methyl-[(2-methyl-4-oxo-1h-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic Acid

12. Raltitrexed (tomudex)

13. Fcb9egg971

14. Zd 1694

15. Chembl225071

16. N-(5-(n-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-n-methylamino)-2-thenoyl)-l-glutamic Acid

17. Ici-d-1694

18. Nsc-639186

19. N-(5-(((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thenoyl)-l-glutamic Acid

20. Ncgc00229704-01

21. Dsstox_cid_26482

22. Dsstox_rid_81653

23. Dsstox_gsid_46482

24. (s)-2-(5-(methyl((2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)-methyl)amino)thiophene-2-carboxamido)pentanedioic Acid

25. (s)-2-(5-(methyl((2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl)amino)thiophene-2-carboxamido)pentanedioic Acid

26. L-glutamic Acid, N-((5-(((1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thienyl)carbonyl)-

27. N-(5-[n-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-n-methylamino]-2-thenoyl)-l-glutamic Acid

28. (2s)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic Acid

29. (2s)-2-[[5-[methyl-[(2-methyl-4-oxo-3h-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic Acid

30. D16

31. Tomudex (tn)

32. D 1694

33. Cas-112887-68-0

34. Unii-fcb9egg971

35. Raltitrexed (jan/usan/inn)

36. 1hvy

37. 2kce

38. 2tsr

39. Zn-d1694

40. Ks-5069

41. Zd1694; Raltitrexed

42. Raltitrexed [mi]

43. Raltitrexed [inn]

44. Raltitrexed [jan]

45. Raltitrexed [usan]

46. Schembl7438

47. Raltitrexed [mart.]

48. Raltitrexed [who-dd]

49. Mls001424225

50. Mls006010125

51. Raltitrexed [usan:inn:ban]

52. Gtpl7403

53. Dtxsid0046482

54. Bdbm18795

55. 1i00

56. Hms2052i03

57. Hms3715p08

58. (s)-2-(5-(methyl((2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)amino)thiophene-2-carboxamido)pentanedioic Acid

59. Amy42113

60. Zinc3832372

61. Tox21_112237

62. Bdbm50027655

63. Mfcd00864168

64. Nsc639186

65. S1192

66. Akos015894877

67. Akos015994729

68. Tox21_112237_1

69. Ccg-101075

70. Ccg-221273

71. Db00293

72. Nc00325

73. Ncgc00263534-02

74. Hy-10821

75. L-glutamic Acid, N-[[5-[[(3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-

76. Nci60_013008

77. Smr000469217

78. Smr002529608

79. Bcp0726000267

80. R0208

81. Sw197705-2

82. D01064

83. Ab00698356-05

84. 887r680

85. Sr-01000763351

86. J-524216

87. Sr-01000763351-3

88. Brd-k89839824-001-01-2

89. Q15304877

90. N-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)carbonyl]-l-glutamic Acid

91. N-[[5-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-l-glutamic Acid

2.4 Create Date

2019-01-15

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₂N₄O₆S
Molecular Weight	458.5 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	9
Exact Mass	458.12600561 g/mol
Monoisotopic Mass	458.12600561 g/mol
Topological Polar Surface Area	177 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	790
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of malignant neoplasm of colon and rectum

Mesothelioma of the pleura

5 Pharmacology and Biochemistry

5.1 Pharmacology

Raltitrexed belongs to a group of medicines known as antimetabolites. It is used to treat cancer of the colon and rectum. It may also be used to treat other kinds of cancer, as determined by your doctor. Raltitrexed blocks an enzyme needed by the cell to live. This interferes with the growth of cancer cells, which are eventually destroyed. Since the growth of normal body cells may also be affected by raltitrexed, other effects will also occur. Some of these may be serious and must be reported to your doctor. Other effects, like hair loss, may not be serious but may cause concern.

5.2 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

Folic Acid Antagonists

Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Folic Acid Antagonists.)

5.3 ATC Code

L01BA03

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01B - Antimetabolites

L01BA - Folic acid analogues

L01BA03 - Raltitrexed

5.4 Metabolism/Metabolites

Raltitrexed is transported into cells via a reduced folate carrier. Inside the cell it is extensively polyglutamated by the enzyme folyl polyglutamate synthetase to polyglutamate forms.

5.5 Biological Half-Life

198 hours

5.6 Mechanism of Action

Raltitrexed is an antineoplastic Agents and folic acid antagonists. Raltitrexed inhibits thymidylate synthase (TS) leading to DNA fragmentation and cell death. It is transported into cells via a reduced folate carrier. Inside the cell Raltitrexed is extensively polyglutamated, which enhances thymidylate synthase inhibitory power and duration. Inhibition of this enzyme results in decreased synthesis of thymidine triphosphate which is required for DNA synthesis.