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Chemistry

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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

Estramustine

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 Formula	C₂₃H₃₁Cl₂NO₃
Molecular Weight	440.4 g/mol
XLogP3	4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	439.1680992 g/mol
Monoisotopic Mass	439.1680992 g/mol
Topological Polar Surface Area	49.8 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	585
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
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 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.

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