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2D Structure
Also known as: 52205-73-9, Estramustine sodium phosphate, Estramustine phosphate disodium, Emcyt, Ro 21-8837/001, Chebi:31562
Molecular Formula
C23H30Cl2NNa2O6P
Molecular Weight
564.3  g/mol
InChI Key
IIUMCNJTGSMNRO-VVSKJQCTSA-L
FDA UNII
IQ856M1R16

A nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
disodium;[(8R,9S,13S,14S,17S)-3-[bis(2-chloroethyl)carbamoyloxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] phosphate
2.1.2 InChI
InChI=1S/C23H32Cl2NO6P.2Na/c1-23-9-8-18-17-5-3-16(31-22(27)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)32-33(28,29)30;;/h3,5,14,18-21H,2,4,6-13H2,1H3,(H2,28,29,30);;/q;2*+1/p-2/t18-,19-,20+,21+,23+;;/m1../s1
2.1.3 InChI Key
IIUMCNJTGSMNRO-VVSKJQCTSA-L
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2OP(=O)([O-])[O-])CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl.[Na+].[Na+]
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OP(=O)([O-])[O-])CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl.[Na+].[Na+]
2.2 Other Identifiers
2.2.1 UNII
IQ856M1R16
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Emcyt

2. Estracyt

3. Estramustin Phosphate

4. Estramustine

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. 52205-73-9

2. Estramustine Sodium Phosphate

3. Estramustine Phosphate Disodium

4. Emcyt

5. Ro 21-8837/001

6. Chebi:31562

7. 52205-73-9 (sodium)

8. Iq856m1r16

9. Estradiol 3-(bis(2-chloroethyl)carbamate) 17-(dihydrogen Phosphate), Disodium Salt

10. Ncgc00185756-01

11. Emcyt (tn)

12. Estramustine Phosphate Sodium (usan)

13. Sodium (8r,9s,13s,14s,17s)-3-((bis(2-chloroethyl)carbamoyl)oxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthren-17-yl Phosphate

14. Estramustine Phosphate Sodium [usan]

15. Estramustine Phosphate Sodium Hydrate

16. Ro-218837-001

17. Unii-iq856m1r16

18. Einecs 257-735-7

19. Estramustinephosphatesodium

20. Estramustine Phosphate Sodium [usan:ban:jan]

21. Dsstox_cid_28879

22. Dsstox_rid_83147

23. Dsstox_gsid_48953

24. Schembl19436

25. Chembl1200721

26. Dtxsid2048953

27. Tox21_113375

28. Mfcd00866320

29. Akos015915051

30. Ac-1612

31. Estramustine Sodium Phosphate [jan]

32. Cas-52205-73-9

33. Estramustine Sodium Phosphate [mart.]

34. Estramustine Phosphate Sodium [who-dd]

35. Estramustine Phosphate Sodium Anhydrous

36. Ro-21-8837/001

37. D02398

38. Estramustine Phosphate Sodium Anhyhdrous

39. Q27114436

40. Estramustine 17-(dihydrogenphosphate) Disodium Salt Anhydrous

41. Estramustine 17-(dihydrogenphosphate) Disodium Salt Anhydrous [mi]

42. Disodium (17beta)-3-{[bis(2-chloroethyl)carbamoyl]oxy}estra-1(10),2,4-trien-17-yl Phosphate

43. Disodium;[(8r,9s,13s,14s,17s)-3-[bis(2-chloroethyl)carbamoyloxy]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] Phosphate

44. Estra-1,3,5(10)-triene-3,17-diol (17.beta.)-, 3-(bis(2-chloroethyl)carbamate) 17-(dihydrogen Phosphate), Disodium Salt

45. Estra-1,3,5(10)-triene-3,17-diol (17beta)-, 3-(bis(2-chloroethyl)carbamate) 17-(dihydrogen Phosphate), Disodium Salt

46. Sodium (8r,9s,13s,14s,17s)-3-(bis(2-chloroethyl)carbamoyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthren-17-yl Phosphate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 564.3 g/mol
Molecular Formula C23H30Cl2NNa2O6P
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Exact Mass563.0983186 g/mol
Monoisotopic Mass563.0983186 g/mol
Topological Polar Surface Area102 Ų
Heavy Atom Count35
Formal Charge0
Complexity735
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameEmcyt
PubMed HealthEstramustine (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelEstramustine phosphate sodium, an antineoplastic agent, is an off-white powder readily soluble in water. EMCYT Capsules are white and opaque, each containing estramustine phosphate sodium as the disodium salt monohydrate equivalent to 140 mg estramus...
Active IngredientEstramustine phosphate sodium
Dosage FormCapsule
RouteOral
Strengtheq 140mg phosphate
Market StatusPrescription
CompanyPharmacia And Upjohn

2 of 2  
Drug NameEmcyt
PubMed HealthEstramustine (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelEstramustine phosphate sodium, an antineoplastic agent, is an off-white powder readily soluble in water. EMCYT Capsules are white and opaque, each containing estramustine phosphate sodium as the disodium salt monohydrate equivalent to 140 mg estramus...
Active IngredientEstramustine phosphate sodium
Dosage FormCapsule
RouteOral
Strengtheq 140mg phosphate
Market StatusPrescription
CompanyPharmacia And Upjohn

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Alkylating Drug [EPC]; Estradiol [CS]; Nitrogen Mustard Compounds [CS]; Alkylating Activity [MoA]