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D8809

Daunorubicin hydrochloride

Name: Daunorubicin hydrochloride
Brand: SIAL

meets USP testing specifications

Synonym(s):

Daunomycin hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₂₉NO₁₀ · HCl

CAS Number:

23541-50-6

Molecular Weight:

563.98

UNSPSC Code:

41116107

NACRES:

NA.21

PubChem Substance ID:

24894229

EC Number:

245-723-4

Beilstein/REAXYS Number:

4229221

MDL number:

MFCD04974507

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Properties

Quality Segment

200

agency

USP/NF, meets USP testing specifications

form

solid

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl.COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(C)=O

InChI

1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1

InChI key

GUGHGUXZJWAIAS-QQYBVWGSSA-N

Gene Information

human ... TOP2A(7153)

Description

Biochem/physiol Actions

Naturally fluorescent anthracycline antibiotic, anticancer drug. Substrate for Pgp, MRP-1 and BCRP. Fluorescent property has been exploited for the measurement of drug efflux pump activities as well as resolving the important question of intracellular localization of various multidrug resistance proteins and the role of subcellular organelles (golgi and lysosome) in the sequestration of drugs and its implication in drug resistant phenotypes. Daunorubicin is sequestered into lysosomes according to a pH partitioning type mechanism. Strong inhibitor of DNA and RNA synthesis.

Potent anticancer agent. Inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent.