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

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H42N4O13.ClH
Molecular Weight 787.209
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ALDOXORUBICIN HYDROCHLORIDE

SMILES

Cl.[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)C(\CO)=N\NC(=O)CCCCCN6C(=O)C=CC6=O

InChI

InChIKey=NGKHWQPYPXRQTM-UKFSEGPMSA-N
InChI=1S/C37H42N4O13.ClH/c1-17-32(46)20(38)13-27(53-17)54-22-15-37(51,23(16-42)39-40-24(43)9-4-3-5-12-41-25(44)10-11-26(41)45)14-19-29(22)36(50)31-30(34(19)48)33(47)18-7-6-8-21(52-2)28(18)35(31)49;/h6-8,10-11,17,20,22,27,32,42,46,48,50-51H,3-5,9,12-16,38H2,1-2H3,(H,40,43);1H/b39-23+;/t17-,20-,22-,27-,32+,37-;/m0./s1

HIDE SMILES / InChI

Description

Doxorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Doxorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Doxorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. Doxorubicin is used to produce regression in disseminated neoplastic conditions like acute lymphoblastic leukemia, acute myeloblastic leukemia, Wilms’ tumor, neuroblastoma, soft tissue and bone sarcomas, breast carcinoma, ovarian carcinoma, transitional cell bladder carcinoma, thyroid carcinoma, gastric carcinoma, Hodgkin’s disease, malignant lymphoma and bronchogenic carcinoma in which the small cell histologic type is the most responsive compared to other cell types. Doxorubicin is also indicated for use as a component of adjuvant therapy in women with evidence of axillary lymph node involvement following resection of primary breast cancer.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.67 µM [IC50]
2.67 µM [IC50]
200.0 nM [IC50]
24.68 µM [IC50]
0.074 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
DOXIL
Primary
DOXIL

Cmax

ValueDoseCo-administeredAnalytePopulation
2 μM
60 mg/m² 1 times / day steady-state, intravenous
DOXORUBICIN plasma
Homo sapiens
2 μM
60 mg/m² 1 times / day steady-state, intravenous
DOXORUBICIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
7.4 μM × h
60 mg/m² 1 times / day steady-state, intravenous
DOXORUBICIN plasma
Homo sapiens
7.4 μM × h
60 mg/m² 1 times / day steady-state, intravenous
DOXORUBICIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
34.8 h
60 mg/m² 1 times / day steady-state, intravenous
DOXORUBICIN plasma
Homo sapiens
34.8 h
60 mg/m² 1 times / day steady-state, intravenous
DOXORUBICIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
DOXORUBICIN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Aldoxorubicin is administered at 350 mg/m2 (260 mg/m2 doxorubicin equivalent) intravenously on Day 1 every 21-day cycles until tumor progression or unacceptable toxicity occurs.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown