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    Evofosfamide

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: Th-302, 918633-87-1, Th302, Th 302, Hap-302, N,n'-bis(2-bromoethyl)phosphorodiamidic acid (1-methyl-2-nitro-1h-imidazol-5-yl)methyl ester
    Molecular Formula
    C9H16Br2N5O4P
    Molecular Weight
    449.04  g/mol
    InChI Key
    UGJWRPJDTDGERK-UHFFFAOYSA-N
    FDA UNII
    8A9RZ3HN8W
    Evofosfamide is a hypoxia-activated prodrug of the cytotoxin bromo-isophosphoramide mustard (Br-IPM) conjugated with 2-nitroimidazole, with potential antineoplastic activity. When exposed to hypoxic conditions, such as those found in hypoxic tumors, the 2-nitroimidazole moiety of evofosfamide is reduced. This releases the DNA-alkylating Br-IPM moiety, which introduces intra- and inter-strand DNA crosslinks in nearby cells; the crosslinks inhibit both DNA replication and cell division, and may lead to apoptosis of cells in the tumor. The inactive form of the prodrug is stable under normoxic conditions, which may limit systemic toxicity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine
    2.1.2 InChI
    InChI=1S/C9H16Br2N5O4P/c1-15-8(6-12-9(15)16(17)18)7-20-21(19,13-4-2-10)14-5-3-11/h6H,2-5,7H2,1H3,(H2,13,14,19)
    2.1.3 InChI Key
    UGJWRPJDTDGERK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C(=CN=C1[N+](=O)[O-])COP(=O)(NCCBr)NCCBr
    2.2 Other Identifiers
    2.2.1 UNII
    8A9RZ3HN8W
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Th 302

    2. Th-302

    3. Th302 Cpd

    2.3.2 Depositor-Supplied Synonyms

    1. Th-302

    2. 918633-87-1

    3. Th302

    4. Th 302

    5. Hap-302

    6. N,n'-bis(2-bromoethyl)phosphorodiamidic Acid (1-methyl-2-nitro-1h-imidazol-5-yl)methyl Ester

    7. 2-bromo-n-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine

    8. 8a9rz3hn8w

    9. Compound 3b

    10. Th-302; Evofosfamide;hap-302

    11. Phosphorodiamidic Acid, N,n'-bis(2-bromoethyl)-, (1-methyl-2-nitro-1h-imidazol-5-yl)methyl Ester

    12. Phosphorodiamidic Acid, N,n'-bis(2-bromoethyl)-, (1-methyl-2-nitro-1h-imidazol-5-yl)methyl Ester.

    13. Evofosfamide [usan:inn]

    14. Unii-8a9rz3hn8w

    15. Evofosfamide(th 302)

    16. Evofosfamide(th-302)

    17. Evofosfamide [inn]

    18. Evofosfamide [jan]

    19. Evofosfamide [usan]

    20. Evofosfamide [who-dd]

    21. Chembl260046

    22. Evofosfamide (jan/usan/inn)

    23. Gtpl8695

    24. Schembl2357174

    25. Schembl15691894

    26. Dtxsid60238721

    27. Amy16615

    28. Bcp06074

    29. Ex-a1740

    30. Bdbm50543112

    31. S2757

    32. Zinc29053729

    33. Akos026673946

    34. Ccg-269225

    35. Cs-0616

    36. Db06091

    37. Sb17116

    38. Ac-29025

    39. As-74462

    40. Hy-10535

    41. Ft-0696771

    42. J3.504.735b

    43. D10704

    44. A901406

    45. J-523214

    46. Q7670203

    47. (1-methyl-2-nitro-1h-imidazol-5-yl)methyl N,n'-bis(2-bromoethyl)diamidophosphate

    48. (1-methyl-2-nitro-1h-imidazole-5-yl)methyl N,n'-bis(2-bromoethyl) Diamidophosphate

    49. 1-methyl-2-nitro-l H-imidazole-5-yl) N,n-bis(2-bromoethyl)diamidophosphate

    50. (2-bromoethyl)({[(2-bromoethyl)amino][(1-methyl-2-nitro-1h-imidazol-5-yl)methoxy]phosphoryl})amine

    51. Th302n,n'-bis(2-bromoethyl)phosphorodiamidic Acid (1-methyl-2-nitro-1h-imidazol-5-yl)methyl Ester

    2.4 Create Date
    2007-01-10
    3 Chemical and Physical Properties
    Molecular Weight 449.04 g/mol
    Molecular Formula C9H16Br2N5O4P
    XLogP30.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count9
    Exact Mass448.92862 g/mol
    Monoisotopic Mass446.93067 g/mol
    Topological Polar Surface Area114 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity374
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in solid tumors.

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    TH-302 combines a 2-nitroimidazole oxygen-sensing trigger with a masked DNA crosslinker. Upon activation in oxygen deficient zones, TH-302 is converted selectively to the drug's active form, dibromo isophosphoramide mustard, a potent alkylator. TH-302 targets levels of severe hypoxia that are found in tumors but are rare in normal tissues - this is how selective targeting of the tumor occurs. After conversion to the active form of the drug, the hypoxic cells are exposed to high concentrations of released cytotoxic agent, which can also diffuse into the adjacent regions of the tumor.