U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C34H35N3O10.ClH
Molecular Weight 682.117
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ZORUBICIN HYDROCHLORIDE

SMILES

Cl.[H][C@@]1(C[C@@](O)(CC2=C(O)C3=C(C(=O)C4=C(C=CC=C4OC)C3=O)C(O)=C12)C(C)=NNC(=O)C5=CC=CC=C5)O[C@H]6C[C@H](N)[C@H](O)[C@H](C)O6

InChI

InChIKey=NKFHKYQGZDAKMX-QMFNWPJUSA-N
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/t15-,20-,22-,23-,28+,34-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C34H35N3O10
Molecular Weight 645.6558
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 1
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Fri Dec 15 15:35:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:35:05 GMT 2023
Record UNII
WXM8D9M6DE
Record Status Validated (UNII)
Record Version
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Name Type Language
ZORUBICIN HYDROCHLORIDE
MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
ZORUBICIN HCL
Common Name English
DAUNORUBICIN BENZOYLHYDRAZONE HYDROCHLORIDE
Common Name English
NSC-164011
Code English
BENZOIC ACID, 2-(1-((2S,4S)-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, HYDROCHLORIDE (1:1)
Systematic Name English
ZORUBICIN HYDROCHLORIDE [MI]
Common Name English
RUBIDAZONE
Brand Name English
ZORUBICIN HYDROCHLORIDE [MART.]
Common Name English
RP 22,050 HYDROCHLORIDE
Code English
Zorubicin hydrochloride [WHO-DD]
Common Name English
RP-22050 HYDROCHLORIDE
Code English
ZORUBICIN HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1594
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
253-076-4
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
NCI_THESAURUS
C1458
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
EVMPD
SUB05194MIG
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
SMS_ID
100000087889
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
MERCK INDEX
m11665
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY Merck Index
NSC
164011
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
PUBCHEM
76964555
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID4023755
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
CAS
36508-71-1
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
FDA UNII
WXM8D9M6DE
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL1697854
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
DRUG BANK
DBSALT001936
Created by admin on Fri Dec 15 15:35:05 GMT 2023 , Edited by admin on Fri Dec 15 15:35:05 GMT 2023
PRIMARY
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