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Berubicin Hydrochloride

Berubicin Hydrochloride

Synopsis, Chemistry

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Also known as: Berubicin hcl, Wp744, Berubicin hydrochloride [usan], Rta 744, Wp-744, 293736-67-1

Molecular Formula

C₃₄H₃₆ClNO₁₁

Molecular Weight

670.1 g/mol

InChI Key

GPMIHHFZKBVWAZ-LMMKTYIZSA-N

FDA UNII

7BA3X03948

Berubicin Hydrochloride is the hydrochloride salt of the anthracycline derivative berubicin with potential antineoplastic activity. Berubicin intercalates into DNA and interrupts topoisomerase II activity, resulting in the inhibition of DNA replication and repair, and RNA and protein synthesis. Unlike other anthracycline derivatives, this agent crosses the blood-brain barrier (BBB).

1 2D Structure

Berubicin Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride

2.1.2 InChI

InChI=1S/C34H35NO11.ClH/c1-16-33(44-15-17-7-4-3-5-8-17)20(35)11-24(45-16)46-22-13-34(42,23(37)14-36)12-19-26(22)32(41)28-27(30(19)39)29(38)18-9-6-10-21(43-2)25(18)31(28)40;/h3-10,16,20,22,24,33,36,39,41-42H,11-15,35H2,1-2H3;1H/t16-,20-,22-,24-,33+,34-;/m0./s1

2.1.3 InChI Key

GPMIHHFZKBVWAZ-LMMKTYIZSA-N

2.1.4 Canonical SMILES

CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OCC6=CC=CC=C6.Cl

2.1.5 Isomeric SMILES

C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OCC6=CC=CC=C6.Cl

2.2 Other Identifiers

2.2.1 UNII

7BA3X03948

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Rta744

2. Wp 744

3. Wp-744

4. Wp744 Cpd

2.3.2 Depositor-Supplied Synonyms

1. Berubicin Hcl

2. Wp744

3. Berubicin Hydrochloride [usan]

4. Rta 744

5. Wp-744

6. 293736-67-1

7. Rta-744

8. 7ba3x03948

9. Berubicin Hydrochloride (usan)

10. Unii-7ba3x03948

11. Wp 744

12. Chembl2103796

13. Dtxsid10951913

14. Berubicin Hydrochloride [who-dd]

15. 293736-67-1 (hcl)

16. D08871

17. Q27268015

18. (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride

19. (8s,10s)-10-(((2r,4s,5s,6s)-4-amino-5-(benzyloxy)-6-methyltetrahydro-2h-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

20. (8s,10s)-10-(((2r,4s,5s,6s)-4-amino-5-(benzyloxy)-6-methyltetrahydro-2h-pyran-2-yl)oxy)-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione Hydrochloride

21. (8s,10s)-10-((3-amino-4-o-benzyl-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)- 6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene- 5,12-dione Hydrochloride

22. 3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-4-o-benzyl-2,3,6-trideoxyhexopyranoside--hydrogen Chloride (1/1)

23. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-4-o-(phenylmethyl)-.alpha.-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8s,10s)-, Hydrochloride

24. 5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-4-o-(phenylmethyl)-alpha-l-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, Hydrochloride, (8s,10s)-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₄H₃₆ClNO₁₁
Molecular Weight	670.1 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	8
Exact Mass	669.1976887 g/mol
Monoisotopic Mass	669.1976887 g/mol
Topological Polar Surface Area	195 Å²
Heavy Atom Count	47
Formal Charge	0
Complexity	1130
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in brain cancer.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

RTA 744 is a substance being studied in the treatment of adult brain tumors. RTA 744 crosses the blood-brain barrier and blocks an enzyme needed for cancer growth. RTA 744 is a type of topoisomerase inhibitor. Also called topoisomerase II inhibitor RTA 744.