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    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
    Pemetrexed Disodium
    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

    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 Weight 471.4 g/mol
    Molecular Formula C20H19N5Na2O6
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count7
    Exact Mass471.11307191 g/mol
    Monoisotopic Mass471.11307191 g/mol
    Topological Polar Surface Area193 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity737
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    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

    L01BA04

    API Reference Price

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    21-Jan-2021
    26-Apr-2024
    KGS
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