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Dianhydrogalactitol

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Chemistry

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Also known as: 1,2:5,6-diepoxydulcitol, Dianhydromannitol, 23261-20-3, 1,2-bis(oxiran-2-yl)ethane-1,2-diol, Nsc 132313, 5,6-diepoxydulcitol

Molecular Formula

C₆H₁₀O₄

Molecular Weight

146.14 g/mol

InChI Key

AAFJXZWCNVJTMK-UHFFFAOYSA-N

One of the cytotoxic dihalohexitols that alkylates and cross-links DNA via an epoxide group during all phases of the cell cycle, resulting in a disruption of DNA function and cell cycle arrest. It has antineoplastic activity and also causes bone marrow toxicity.

1 2D Structure

Dianhydrogalactitol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,2-bis(oxiran-2-yl)ethane-1,2-diol

2.1.2 InChI

InChI=1S/C6H10O4/c7-5(3-1-9-3)6(8)4-2-10-4/h3-8H,1-2H2

2.1.3 InChI Key

AAFJXZWCNVJTMK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1C(O1)C(C(C2CO2)O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 1,2,5,6-dianhydrogalactitol

2. 1,2-5,6-dianhydrogalactitol

3. Dianhydrogalactitol

4. Diepoxydulcitol

5. Diepoxygalactitol

6. Nsc 132313

7. Nsc-132313

8. Nsc132313

2.2.2 Depositor-Supplied Synonyms

1. 1,2:5,6-diepoxydulcitol

2. Dianhydromannitol

3. 23261-20-3

4. 1,2-bis(oxiran-2-yl)ethane-1,2-diol

5. Nsc 132313

6. 5,6-diepoxydulcitol

7. 1,2-5,6-dianhydro-dulcitol

8. 1,2:5,6-dianhydrodulcitol

9. Galactitol, 1,2:5,6-dianhydro-

10. Dianhydrodulcitol;dianhydrogalactitol

11. Nsc132313

12. 19895-66-0

13. Nsc-133129

14. 1,6-diepoxydulcitol

15. 1,6-dianhydrodulcitol

16. 1,6-dianhydromannitol

17. 1,6-dianhydrogalactitol

18. 1,6-diepoxy-d-mannitol

19. 1,6-dianhydro-d-mannitol

20. 1,2:5,6-dianhydrohexitol

21. 1,6-di-anhydro-d-mannitol

22. Galactitol,2:5,6-dianhydro-

23. Schembl8375579

24. D-mannitol,2:5,6-dianhydro-

25. Chembl1987719

26. Dtxsid60941768

27. Mannitol,2:5,6-dianhydro-, D-

28. Nsc133129

29. Akos025396866

30. Nci60_000711

31. Ft-0667810

32. 261d203

2.3 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₀O₄
Molecular Weight	146.14 g/mol
XLogP3	-1.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	146.05790880 g/mol
Monoisotopic Mass	146.05790880 g/mol
Topological Polar Surface Area	65.5 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	122
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	4
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 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.)

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