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Pemetrexed Disodium Heptahydrate

Pemetrexed Disodium Heptahydrate

Synopsis, Chemistry

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Also known as: 150399-23-8, Alimta, Rolazar, Pemetrexed sodium salt, Tifolar, Ly231514 disodium

Molecular Formula

C₂₀H₁₉N₅Na₂O₆

Molecular Weight

471.4 g/mol

InChI Key

NYDXNILOWQXUOF-GXKRWWSZSA-L

FDA UNII

2PKU919BA9

A guanine-derived ANTINEOPLASTIC AGENT that functions as a NUCLEIC ACID SYNTHESIS INHIBITOR through its binding to, and inhibition of, THYMIDYLATE SYNTHASE.

1 2D Structure

Pemetrexed Disodium Heptahydrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

disodium;(2S)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioate

2.1.2 InChI

InChI=1S/C20H21N5O6.2Na/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);;/q;2*+1/p-2/t13-;;/m0../s1

2.1.3 InChI Key

NYDXNILOWQXUOF-GXKRWWSZSA-L

2.1.4 Canonical SMILES

C1=CC(=CC=C1CCC2=CNC3=C2C(=O)NC(=N3)N)C(=O)NC(CCC(=O)[O-])C(=O)[O-].[Na+].[Na+]

2.1.5 Isomeric SMILES

C1=CC(=CC=C1CCC2=CNC3=C2C(=O)NC(=N3)N)C(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-].[Na+].[Na+]

2.2 Other Identifiers

2.2.1 UNII

2PKU919BA9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 231,514, Ly

2. 231514, Ly

3. Alimta

4. Disodium, Pemetrexed

5. Ly 231,514

6. Ly 231514

7. Ly-231,514

8. Ly-231514

9. Ly231514

10. Mta

11. N-(4-(2-(2-amino-3,4-dihydro-4-oxo-7h-pyrrolo(2,3-d)pyrimdin-5-yl)ethyl)benzoyl)glutamic Acid

12. Pemetrexed

2.3.2 Depositor-Supplied Synonyms

1. 150399-23-8

2. Alimta

3. Rolazar

4. Pemetrexed Sodium Salt

5. Tifolar

6. Ly231514 Disodium

7. Chebi:63722

8. Ly231514 Disodium Salt

9. Ly-231514 Disodium Salt

10. Pemetrexed Disodium [usan]

11. 2pku919ba9

12. Pemetrexed Sodium Hydrate

13. Ly-231514

14. N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic Acid Disodium Salt

15. Sodium (s)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-1h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioate

16. Alimta (tn)

17. Pemetrexed (disodium)

18. Pemetrexed Disodium (usan)

19. Disodium;(2s)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioate

20. Ly 231514

21. L-glutamic Acid, N-(4-(2-(2-amino-4,7-dihydro-4-oxo-1h-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-, Disodium Salt

22. Pemetrexed-[d5]

23. N-(4-[2-(2-amino-4,7-dihydro-4-oxo-1h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl)-l-glutamic Acid Disodium Salt

24. Ncgc00167486-01

25. Pemetrexed Disodium, 95%

26. Dsstox_cid_26660

27. Dsstox_rid_81803

28. Unii-2pku919ba9

29. Dsstox_gsid_46660

30. Schembl18348

31. Chembl2360464

32. Dtxsid8046660

33. Ex-a836

34. Hms3264h07

35. Hms3715p06

36. Pemetrexed Sodium Salt [mi]

37. Tox21_112487

38. Bdbm50512141

39. Mfcd07779402

40. Pemetrexed Disodium [usp-rs]

41. Pemetrexed Disodium [who-dd]

42. S1135

43. Akos025149477

44. Akos025392176

45. Ac-1326

46. Ccg-213071

47. Ccg-221272

48. Cs-w004541

49. Ks-5001

50. Pemetrexed Disodium [orange Book]

51. 1129408-57-6

52. Disodium (2s)-2-({4-[2-(2-amino-4-oxo-4,7-dihydro-1h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}amino)pentanedioate

53. Pemetrexed Disodium [usp Monograph]

54. Cas-150399-23-8

55. Ly 231,514

56. D03828

57. A809041

58. Pemetrexed Disodium Is Known As A Thymidylate Synthase Inhibitor.

59. Disodium N-(p-(2-((2-amino-4,7-dihydro-4-oxo-1h-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-l-glutamate

60. Disodium N-(p-(2-(2-amino-4,7-dihydro-4-oxo-1h-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-l-glutamate

61. Disodium N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-l-glutamate

62. N-(4-[2-(2-amino-4,7-dihydro-4-oxo-1h-pyrrolo[2,3-d]pyrimidin-5yl)ethyl]benzoyl)-l-glutamic Acid Disodium Salt

63. N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1h-pyrrolo[2.3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic Acid Disodium Salt

64. N-[4[2-(-amino-3,4-dihydro-4-oxo-7h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamate Sodium Salt

65. Sodium (s)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-3h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioate

66. Sodium(s)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-1h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioate

2.4 Create Date

2019-01-15

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₉N₅Na₂O₆
Molecular Weight	471.4 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Exact Mass	471.11307191 g/mol
Monoisotopic Mass	471.11307191 g/mol
Topological Polar Surface Area	193 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	737
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	3

4 Drug and Medication Information

4.1 Drug Indication

* Malignant pleural mesothelioma:

Pemetrexed Krka in combination with cisplatin is indicated for the treatment of chemotherapy nave patients with unresectable malignant pleural mesothelioma.

* Non-small cell lung cancer :

Pemetrexed Krka in combination with cisplatin is indicated for the first-line treatment of patients with locally advanced or metastatic non-small cell lung cancer other than predominantly squamous cell histology.

Pemetrexed Krka is indicated as monotherapy for the maintenance treatment of locally advanced or metastatic non-small cell lung cancer other than predominantly squamous cell histology in patients whose disease has not progressed immediately following platinum-based chemotherapy.

Pemetrexed Krka is indicated as monotherapy for the second-line treatment of patients with locally advanced or metastatic non-small cell lung cancer other than predominantly squamous cell histology.

* Malignant pleural mesothelioma:

Alimta in combination with cisplatin is indicated for the treatment of chemotherapy-nave patients with unresectable malignant pleural mesothelioma.

* Non-small-cell lung cancer :

Alimta in combination with cisplatin is indicated for the first-line treatment of patients with locally advanced or metastatic non-small-cell lung cancer other than predominantly squamous cell histology.

Alimta is indicated as monotherapy for the maintenance treatment of locally advanced or metastatic non-small-cell lung cancer other than predominantly squamous cell histology in patients whose disease has not progressed immediately following platinum-based chemotherapy.

Alimta is indicated as monotherapy for the second line treatment of patients with locally advanced or metastatic non-small-cell lung cancer other than predominantly squamous cell histology.

Carcinoma of the head and neck (Covered by class waiver: oropharyngeal epithelial carcinoma, excluding nasopharyngeal carcinoma), Malignant pleural mesothelioma

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Nucleic Acid Synthesis Inhibitors

Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

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.)

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Folic Acid Metabolism Inhibitors [MoA]; Folate Analog Metabolic Inhibitor [EPC]

5.3 ATC Code

L01BA04