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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO11
Molecular Weight 543.5193
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXORUBICIN

SMILES

COC1=C2C(=O)C3=C(O)C4=C(C[C@](O)(C[C@@H]4O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)C(=O)CO)C(O)=C3C(=O)C2=CC=C1

InChI

InChIKey=AOJJSUZBOXZQNB-TZSSRYMLSA-N
InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H29NO11
Molecular Weight 543.5193
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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

PubMed

PubMed

TitleDatePubMed
Experimental animal models of adriamycin cardiotoxicity.
1979 May
Protective effects of carvedilol against doxorubicin-induced cardiomyopathy in rats.
1999
Doxorubicin-induced congestive heart failure in elderly patients with metastatic breast cancer, with long-term follow-up: the M.D. Anderson experience.
1999
Inhibitory effects of combinations of HER-2/neu antibody and chemotherapeutic agents used for treatment of human breast cancers.
1999 Apr 1
Anticancer drug sensitivity and expression of multidrug resistance markers in early passage human sarcomas.
1999 Aug
Sodium bicarbonate treatment reduces renal injury, renal production of transforming growth factor-beta, and urinary transforming growth factor-beta excretion in rats with doxorubicin-induced nephropathy.
1999 Aug
Doxorubicin induces slow ceramide accumulation and late apoptosis in cultured adult rat ventricular myocytes.
1999 Aug 1
Phase II trial of doxorubicin and paclitaxel plus granulocyte colony-stimulating factor in metastatic breast cancer: an Eastern Cooperative Oncology Group Study.
1999 Dec
Doxorubicin cardiotoxicity: growing importance.
1999 Jul
Correlation between serum levels of cardiac troponin-T and the severity of the chronic cardiomyopathy induced by doxorubicin.
1999 Jul
Toxic epidermal necrolysis and graft vs. host disease: a clinical spectrum but a diagnostic dilemma.
1999 Jul
Effect of proteinuria reduction on prevention of focal glomerulosclerosis by angiotensin-converting enzyme inhibition is modifiable.
1999 Jul
Abdominal-wall myositis secondary to intra-arterial chemotherapy for femoral osteosarcoma.
1999 Jul
Coordinate alterations in the expression of BRCA1, BRCA2, p300, and Rad51 in response to genotoxic and other stresses in human prostate cancer cells.
1999 Jun 15
Phase II of doxorubicin/taxol in metastatic breast cancer. Argentine Multicenter Taxol Group.
1999 May
Dose-finding study of docetaxel and doxorubicin in first-line treatment of patients with metastatic breast cancer.
1999 May
Role of thromboxane in the altered vascular reactivity of pregnant rats with adriamycin nephropathy.
1999 May
Zinc accumulation in adriamycin-induced cardiomyopathy in rats: effects of melatonin, a cardioprotective antioxidant.
1999 May
Phase II trial of high-dose liposome-encapsulated doxorubicin with granulocyte colony-stimulating factor in metastatic breast cancer. TLC D-99 Study Group.
1999 May
Primary desmoplastic small cell tumor of soft tissues and bone of the hand.
1999 Nov
Nonmetastatic osteosarcoma of the extremity: results of a neoadjuvant chemotherapy protocol (IOR/OS-3) with high-dose methotrexate, intraarterial or intravenous cisplatin, doxorubicin, and salvage chemotherapy based on histologic tumor response.
1999 Nov-Dec
Low-dose vincristine-associated bilateral vocal cord paralysis.
1999 Oct
Antifungal activities of antineoplastic agents: Saccharomyces cerevisiae as a model system to study drug action.
1999 Oct
A canine model of heart failure by intracoronary adriamycin injection: hemodynamic and energetic results.
1999 Sep
Decreased cortisol secretion by adrenal glands perfused with the P-glycoprotein inhibitor valspodar and mitotane or doxorubicin.
2000 Apr
Adriamycin-induced heart failure: mechanism and modulation.
2000 Apr
Doxorubicin-induced late cardiotoxicity: delayed impairment of Ca2+-handling mechanisms in the sarcoplasmic reticulum in the rat.
2000 Apr
Anthracyclines trigger apoptosis of both G0-G1 and cycling peripheral blood lymphocytes and induce massive deletion of mature T and B cells.
2000 Apr 1
Pegylated liposomal doxorubicin (doxil): reduced clinical cardiotoxicity in patients reaching or exceeding cumulative doses of 500 mg/m2.
2000 Aug
The influence of coordinate overexpression of glutathione phase II detoxification gene products on drug resistance.
2000 Aug
Deregulated manganese superoxide dismutase expression and resistance to oxidative injury in p53-deficient cells.
2000 Aug 15
Progressive cardiac dysfunction in adriamycin-induced cardiomyopathy rats.
2000 Dec
Neural crest-derived defects in experimental esophageal atresia.
2000 Feb
Comparison of doxorubicin- and MEN 10755-induced long-term progressive cardiotoxicity in the rat.
2000 Jan
Differential sensitivities of MRP1-overexpressing lung tumor cells to cytotoxic metals.
2000 Jan 3
Mechanism of doxorubicin-induced inhibition of sarcoplasmic reticulum Ca(2+)-ATPase gene transcription.
2000 Jan 7-21
Influence of Adriamycin and paraquat on antioxidant enzyme expression in primary rat hepatocytes.
2000 Jul
Doxorubicin-induced cardiomyopathy.
2000 Jul
Effects of probucol on changes of antioxidant enzymes in adriamycin-induced cardiomyopathy in rats.
2000 Jun
Beta-blockade in adriamycin-induced cardiomyopathy.
2000 Jun
Deficiency of the stress kinase p38alpha results in embryonic lethality: characterization of the kinase dependence of stress responses of enzyme-deficient embryonic stem cells.
2000 Mar 6
The influence of thymoquinone on doxorubicin-induced hyperlipidemic nephropathy in rats.
2000 Mar 7
Caffeine-potentiated radiochemotherapy and function-saving surgery for high-grade soft tissue sarcoma.
2000 May-Jun
Phase II study of pegylated liposomal doxorubicin: inactive in recurrent small-cell lung cancer. A Hellenic Cooperative Oncology Group Study.
2000 Nov
Renal antioxidant enzymes and fibrosis-related markers in the rat adriamycin model.
2000 Oct
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy.
2000 Sep
Phase 2 trial of liposomal doxorubicin (40 mg/m(2)) in platinum/paclitaxel-refractory ovarian and fallopian tube cancers and primary carcinoma of the peritoneum.
2000 Sep
Long-term cardiac sequelae in operable breast cancer patients given adjuvant chemotherapy with or without doxorubicin and breast irradiation.
2001 Jan 1
Characterization of adriamycin-induced G2 arrest and its abrogation by caffeine in FL-amnion cells with or without p53.
2001 Jan 1
Repression of cyclin B1 expression after treatment with adriamycin, but not cisplatin in human lung cancer A549 cells.
2001 Jan 26
Patents

Sample Use Guides

In Vivo Use Guide
When used in combination with other chemotherapy drugs, the most commonly used dosage of doxorubicin is 40 to 60 mg/m2 IV every 21 to 28 days. Alternatively, 60 to 75 mg/m2 IV once every 21 days.
Route of Administration: Intravenous
In Vitro Use Guide
Alkalinization of extracellular pH by urease (2 U/ml) and urea (> or = 2 mM) was found to enhance the antitumor efficacy of doxorubicin (50 uM)
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:56:34 UTC 2019
Edited
by admin
on Mon Oct 21 20:56:34 UTC 2019
Record UNII
80168379AG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOXORUBICIN
HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
DOXORUBICIN [HSDB]
Common Name English
DOXORUBICIN [VANDF]
Common Name English
ADRIABLASTIN
Common Name English
DOXORUBICIN [MART.]
Common Name English
DOXORUBICIN [MI]
Common Name English
NSC-123127
Code English
5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-
Common Name English
EPIRUBICIN HYDROCHLORIDE IMPURITY C [EP]
Common Name English
DOXORUBICIN [WHO-DD]
Common Name English
EPIRUBICIN IMPURITY C
Common Name English
EPIRUBICIN HYDROCHLORIDE IMPURITY, DOXORUBICIN- [USP]
Common Name English
VALRUBICIN IMPURITY, DOXORUBICIN [USP]
Common Name English
EPIRUBICIN HYDROCHLORIDE SPECIFIED IMPURITY C [EP]
Common Name English
DOXORUBICIN [INN]
Common Name English
ADRIBLASTINA
Brand Name English
(8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE
Common Name English
DOXORUBICIN [USAN]
Common Name English
HYDROXYDAUNORUBICIN
Common Name English
Classification Tree Code System Code
NDF-RT N0000007530
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
FDA ORPHAN DRUG 276009
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
FDA ORPHAN DRUG 553116
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
FDA ORPHAN DRUG 199904
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
NDF-RT N0000007530
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
FDA ORPHAN DRUG 248107
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
FDA ORPHAN DRUG 469215
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
WHO-VATC QL01DB01
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
NDF-RT N0000000176
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
NDF-RT N0000007530
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
FDA ORPHAN DRUG 139800
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
FDA ORPHAN DRUG 286109
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
NCI_THESAURUS C67502
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
NDF-RT N0000175414
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
FDA ORPHAN DRUG 117398
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
LIVERTOX 328
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
EU-Orphan Drug EU/3/15/1513
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
WHO-ATC L01DB01
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
Code System Code Type Description
EPA CompTox
23214-92-8
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
RXCUI
3639
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY RxNorm
ChEMBL
CHEMBL53463
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
EVMPD
SUB35582
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
IUPHAR
7069
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
LactMed
23214-92-8
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
CAS
23214-92-8
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
ECHA (EC/EINECS)
245-495-6
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
MESH
D004317
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
DRUG BANK
DB00997
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
INN
3005
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
WIKIPEDIA
DOXORUBICIN
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
NCI_THESAURUS
C456
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
MERCK INDEX
M4757
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY Merck Index
EVMPD
SUB06391MIG
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
PUBCHEM
31703
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
HSDB
23214-92-8
Created by admin on Mon Oct 21 20:56:34 UTC 2019 , Edited by admin on Mon Oct 21 20:56:34 UTC 2019
PRIMARY
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