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    Estramustine

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

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    2D Structure
    Also known as: 2998-57-4, Estramustinum, Estramustina, Estramustinum [inn-latin], Estramustina [inn-spanish], Estradiol 3-(n,n-bis(2-chloroethyl)carbamate)
    Molecular Formula
    C23H31Cl2NO3
    Molecular Weight
    440.4  g/mol
    InChI Key
    FRPJXPJMRWBBIH-RBRWEJTLSA-N
    FDA UNII
    35LT29625A
    A nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties.
    Estramustine is an Alkylating Drug. The mechanism of action of estramustine is as an Alkylating Activity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate
    2.1.2 InChI
    InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
    2.1.3 InChI Key
    FRPJXPJMRWBBIH-RBRWEJTLSA-N
    2.1.4 Canonical SMILES
    CC12CCC3C(C1CCC2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
    2.1.5 Isomeric SMILES
    C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl
    2.2 Other Identifiers
    2.2.1 UNII
    35LT29625A
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Emcyt

    2. Estracyt

    3. Estramustin Phosphate

    4. Estramustine Phosphate Sodium

    5. Estramustinphosphate

    6. Leo 275

    7. Leo-275

    8. Leo275

    9. Nsc 89199

    10. Nsc-89199

    11. Nsc89199

    12. Phosphate Sodium, Estramustine

    13. Phosphate, Estramustin

    2.3.2 Depositor-Supplied Synonyms

    1. 2998-57-4

    2. Estramustinum

    3. Estramustina

    4. Estramustinum [inn-latin]

    5. Estramustina [inn-spanish]

    6. Estradiol 3-(n,n-bis(2-chloroethyl)carbamate)

    7. Nsc-89201

    8. 17beta-estradiol 3-(bis(2-chloroethyl)carbamate)

    9. Chembl1575

    10. Estradiol 3-(bis(2-chloroethyl)carbamate)

    11. Estradiol 3-[bis(2-chloroethyl)carbamate]

    12. Chebi:4868

    13. [(8r,9s,13s,14s,17s)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,n-bis(2-chloroethyl)carbamate

    14. Ro 22-2296/000

    15. 35lt29625a

    16. Leo 275

    17. Ncgc00164581-01

    18. Ro-222296000

    19. Estradiol, 3-[bis(2-chloroethyl)carbamate]

    20. Ro-22-2296000

    21. Dsstox_cid_26458

    22. Dsstox_rid_81632

    23. Dsstox_gsid_46458

    24. (8r,9s,13s,14s,17s)-17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthren-3-yl Bis(2-chloroethyl)carbamate

    25. Ro 21-8837

    26. Nsc 89201

    27. Estra-1,3,5(10)-triene-3,17beta-diol, 3-[bis(2-chloroethyl)carbamate]

    28. Disodium (1s,10r,11s,14s,15s)-5-{[bis(2-chloroethyl)carbamoyl]oxy}-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-yl Phosphate

    29. Cas-2998-57-4

    30. Estradiol, 3-(bis(2-chloroethyl)carbamate)

    31. Estradiol 3-[n,n-bis(2-chloroethyl)carbamate]

    32. Mls002701936

    33. 17.beta.-estradiol 3-[bis(2-chloroethyl)carbamate]

    34. Estramustine (usan/inn)

    35. Estramustin

    36. Nsc89201

    37. Estramustine [usan:inn:ban]

    38. Unii-35lt29625a

    39. Einecs 221-076-3

    40. Estramustine [mi]

    41. Estramustine [inn]

    42. Ro-22-2296/000

    43. Estramustine [usan]

    44. Schembl4252

    45. Estramustin Sodium Phosphate

    46. Estramustine [vandf]

    47. Bidd:gt0482

    48. Estramustine [who-dd]

    49. Gtpl9076

    50. Dtxsid8046458

    51. Hms3715d22

    52. Zinc4099032

    53. Tox21_112207

    54. Bdbm50333646

    55. Lmst02010038

    56. (17beta)-17-hydroxyestra-1(10),2,4-trien-3-yl Bis(2-chloroethyl)carbamate

    57. Akos025402444

    58. Tox21_112207_1

    59. Ac-9163

    60. Ccg-221220

    61. Db01196

    62. Estra-1,3,5(10)-triene-3,17-diol (17beta)-, 3-(bis(2-chloroethyl)carbamate)

    63. Ncgc00164581-02

    64. As-12259

    65. Nci60_041982

    66. Hy-103711

    67. Cs-0035073

    68. Ro-22-2296-000

    69. D04066

    70. 998e574

    71. A876334

    72. Q412939

    73. W-106963

    74. Carbamic Acid, Bis(2-chloroethyl)-, 17beta-hydroxyestra-1,3,5(10)-trien-3-yl Ester

    75. Estra-1,3,5(10)-triene-3,17-diol, 3-(bis(2-chloroethyl)carbamate), (17b)-

    76. Estra-1,3,5(10)-triene-3,17-diol, 3-(bis(2-chloroethyl)carbamate), (17beta)-

    77. Estra-1,5(10)-triene-3,17-diol (17.beta.)-, 3-[bis(2-chloroethyl)carbamate]

    78. Estra-1,5(10)-triene-3,17-diol, 3-[bis(2-chloroethyl)carbamate], (17.beta.)-

    79. Bis-(2-chloro-ethyl)-carbamic Acid 17-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthren-3-yl Ester

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 440.4 g/mol
    Molecular Formula C23H31Cl2NO3
    XLogP34
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count6
    Exact Mass439.1680992 g/mol
    Monoisotopic Mass439.1680992 g/mol
    Topological Polar Surface Area49.8 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity585
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    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

    For the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Estramustine is an antineoplastic agent indicated in the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate. Estramustine is a combination of estradiol with nitrogen mustard. In vivo, the nitrogen-mustard moiety becomes active and participates in alkylation of DNA or other cellular components.. This causes DNA damage in rapidly dividing cancerous cells leading to cell death and ideally, tumor shrinkage.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents, Alkylating

    A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)

    Antineoplastic Agents, Hormonal

    Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ESTRAMUSTINE
    5.3.2 FDA UNII
    35LT29625A
    5.3.3 Pharmacological Classes
    Chemical Structure [CS] - Nitrogen Mustard Compounds
    5.4 ATC Code

    L01XX11

    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

    L01X - Other antineoplastic agents

    L01XX - Other antineoplastic agents

    L01XX11 - Estramustine

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    The metabolic urinary patterns of the estradiol moiety of estramustine phosphate and estradiol itself are very similar, although the metabolites derived from estramustine phosphate are excreted at a slower rate.

    5.6 Biological Half-Life

    20 hours

    5.7 Mechanism of Action

    Estramustine is a derivative of estradiol with a nitrogen mustard moiety. This gives it alkylating properties. In vivo, the nitrogen mustard component is active and can alklyate DNA and other cellular components (such as tubulin components) of rapidly dividing cells. This causes DNA strandbreaks or misscoding events. This leads to apoptosis and cell death. Also, due to the drugs estrogen component, it can bind more selectively to active estrogen receptors.