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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Rubidazone, Rubidazone monohydrochloride, Rp 22,050 hydrochloride, Nsc-164011, N-[(e)-1-[(2s,4s)-4-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]ethylideneamino]benzamide;hydrochloride, Nsc164011

Molecular Formula

C₃₄H₃₆ClN₃O₁₀

Molecular Weight

682.1 g/mol

InChI Key

NKFHKYQGZDAKMX-CBGHEUOKSA-N

Zorubicin Hydrochloride is a benzoyl-hydrazone derivative of the anthracycline antineoplastic antibiotic daunorubicin. Zorubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair and RNA and protein synthesis. (NCI04)

1 2D Structure

Rubidazone Monohydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(E)-1-[(2S,4S)-4-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]ethylideneamino]benzamide;hydrochloride

2.1.2 InChI

InChI=1S/C34H35N3O10.ClH/c1-15-28(38)20(35)12-23(46-15)47-22-14-34(44,16(2)36-37-33(43)17-8-5-4-6-9-17)13-19-25(22)32(42)27-26(30(19)40)29(39)18-10-7-11-21(45-3)24(18)31(27)41;/h4-11,15,20,22-23,28,38,40,42,44H,12-14,35H2,1-3H3,(H,37,43);1H/b36-16+;/t15?,20?,22-,23?,28?,34-;/m0./s1

2.1.3 InChI Key

NKFHKYQGZDAKMX-CBGHEUOKSA-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(=NNC(=O)C6=CC=CC=C6)C)O)N)O.Cl

2.1.5 Isomeric SMILES

CC1C(C(CC(O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(/C(=N/NC(=O)C6=CC=CC=C6)/C)O)N)O.Cl

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Daunomycin Benzoylhydrazone

2. Rp 22050

3. Rubidazone

4. Zorubicin

5. Zorubicin Hydrochloride, (l-xylo)-(2s-cis)-isomer

6. Zorubicin, (l-arabino)-(2s-cis)-isomer

7. Zorubicine

2.2.2 Depositor-Supplied Synonyms

1. Rubidazone

2. Rubidazone Monohydrochloride

3. Rp 22,050 Hydrochloride

4. Nsc-164011

5. N-[(e)-1-[(2s,4s)-4-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]ethylideneamino]benzamide;hydrochloride

6. Nsc164011

7. 36508-71-1

8. Rubidaz

9. Zorubicinhydrochlorid

10. Daunorubicin, Monohydrochloride

11. Chembl1975668

12. Rp 22050

13. Benzoic Acid Hydrazide, Monohydrochlorideone

14. 22050 R.p.

15. Benzoic Acid [1-[4-[(3-amino-2,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]ethylidene]hydrazide, (2s-cis)-, Monohydrochloride

16. Benzoic Acid,3,6-trideoxy-.alpha.-l-lyxo-hexopyranosyl)oxy]-1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-2-naphthacenyl]ethylidene]hydrazide, Monohydrochloride, (2s-cis)-

2.3 Create Date

2006-10-24

3 Chemical and Physical Properties

Molecular Formula	C₃₄H₃₆ClN₃O₁₀
Molecular Weight	682.1 g/mol
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	6
Exact Mass	681.2089220 g/mol
Monoisotopic Mass	681.2089220 g/mol
Topological Polar Surface Area	210 Å²
Heavy Atom Count	48
Formal Charge	0
Complexity	1230
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	4
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

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