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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H35N3O10
Molecular Weight 645.6571
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZORUBICIN

SMILES

C[C@@]1([H])[C@]([H])([C@]([H])(C[C@@]([H])(O1)O[C@@]2([H])C[C@@](Cc3c2c(c4c(C(=O)c5cccc(c5C4=O)OC)c3O)O)(C(=NN=C(c6ccccc6)O)C)O)N)O

InChI

InChIKey=FBTUMDXHSRTGRV-BJISBDEGSA-N
InChI=1S/C34H35N3O10/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)/t15-,20-,22-,23-,28+,34-/m0/s1

HIDE SMILES / InChI

Molecular Formula C34H35N3O10
Molecular Weight 645.6571
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Zorubicin is a benzoylhydrazone derivative of the anthracycline antineoplastic antibiotic daunorubicin, but it introduces lower cardiomyopathy and bone marrow toxicity. Zorubicin intercalates into DNA and interacts with topoisomerase II, thereby inhibiting DNA replication and repair as well as RNA and protein synthesis. The cytotoxic effect results from intercalation between DNA pairs. To minimize toxicity, individualized dose regimens are given preferentially over prolonged periods of time by carefully inspecting i.v. administration to prevent extravasation.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.46 µM [IC50]
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:43:57 UTC 2021
Edited
by admin
on Sat Jun 26 13:43:57 UTC 2021
Record UNII
V25F9362OP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ZORUBICIN
INN   MI   WHO-DD  
INN  
Official Name English
ZORUBICIN [MI]
Common Name English
BENZOIC ACID (1-(4-((3-AMINO-2,3,6-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, (2S-CIS)-
Common Name English
ZORUBICIN [INN]
Common Name English
ZORUBICIN [WHO-DD]
Common Name English
RP 22,050
Code English
BENZOIC ACID HYDRAZIDE, 3-HYDRAZONE WITH DAUNORUBICIN
Common Name English
RP-22050
Code English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
WHO-VATC QL01DB05
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
WHO-ATC L01DB05
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
Code System Code Type Description
WIKIPEDIA
ZORUBICIN
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
FDA UNII
V25F9362OP
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
MERCK INDEX
M11665
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY Merck Index
EVMPD
SUB00190MIG
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
MESH
C002205
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
PUBCHEM
57164040
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
DRUG CENTRAL
2874
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
NCI_THESAURUS
C91365
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
EPA CompTox
54083-22-6
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
CAS
54083-22-6
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL1697854
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
INN
4349
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
DRUG BANK
DB11618
Created by admin on Sat Jun 26 13:43:58 UTC 2021 , Edited by admin on Sat Jun 26 13:43:58 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY