Doxorubicinol hydrochloride

Modify Date: 2024-01-09 06:59:06

Doxorubicinol hydrochloride Structure
Doxorubicinol hydrochloride structure
Common Name Doxorubicinol hydrochloride
CAS Number 63950-05-0 Molecular Weight 581.99600
Density 1.61g/cm3 Boiling Point 828.7ºC at 760 mmHg
Molecular Formula C27H32ClNO11 Melting Point 188-192ºC
MSDS N/A Flash Point 455ºC

 Use of Doxorubicinol hydrochloride


Doxorubicinol hydrochloride (13-Dihydroadriamycin hydrochloride) is a secondary alcohol metabolite of Doxorubicin[1].

 Names

Name 13-Dihydroadriamycin hydrochloride

 Doxorubicinol hydrochloride Biological Activity

Description Doxorubicinol hydrochloride (13-Dihydroadriamycin hydrochloride) is a secondary alcohol metabolite of Doxorubicin[1].
Related Catalog
In Vitro Doxorubicinol hydrochloride is produced by a two-electron, NADPH-dependent reduction of the Doxorubicin side-chain carbonyl group (C13) to a secondary alcohol[1]. Doxorubicinol hydrochloride has been shown to have significantly lower DNA binding activity as compared to DOX. Moreover, while Doxorubicinol hydrochloride is retained in the cytoplasm or lysosomes, Doxorubicin is mainly accumulated in the nucleus[1].
In Vivo In vivo, in tumor-bearing mice, Nilotinib, acting as ABCB1 inhibitor, is found to increase the accumulation of Doxorubicin and Doxorubicinol hydrochloride in cancer tissues. This implies that weaker anticancer activity of Doxorubicinol hydrochloride may be related to its increased affinity to ABC transporters, thus leading to a lower intracellular concentration of the agent[1]. In comparison with wild-type mice, the terminal half-life and the area under the plasma concentration-time curve of Doxorubicin in mdr1a(-/-) mice are 1.6- and 1.2-fold higher respectively. The retention of both Doxorubicin and its metabolite Doxorubicinol hydrochloride in the hearts of mdr1a(-/-) mice is substantially prolonged[2].
References

[1]. Kamil Piska, et al. Metabolic carbonyl reduction of anthracyclines - role in cardiotoxicity and cancer resistance. Reducing enzymes as putative targets for novel cardioprotective and chemosensitizing agents. Invest New Drugs. 2017 Jun;35(3):375-385.

[2]. J van Asperen, et al. Increased accumulation of doxorubicin and doxorubicinol in cardiac tissue of mice lacking mdr1a P-glycoprotein. Br J Cancer. 1999 Jan;79(1):108-13.

 Chemical & Physical Properties

Density 1.61g/cm3
Boiling Point 828.7ºC at 760 mmHg
Melting Point 188-192ºC
Molecular Formula C27H32ClNO11
Molecular Weight 581.99600
Flash Point 455ºC
Exact Mass 581.16600
PSA 209.23000
LogP 1.29540
Index of Refraction 1.716

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QI9295800
CHEMICAL NAME :
5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosy l)oxy)-8-(1,2- dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy -1-methoxy-, hydrochloride
CAS REGISTRY NUMBER :
63950-05-0
LAST UPDATED :
198406
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C27-H31-N-O11.Cl-H
MOLECULAR WEIGHT :
582.05

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Mammal - species unspecified Lymphocyte
DOSE/DURATION :
52 umol/L
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 32,315,1977
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