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daunorubicin

Trade name: cerubidine

Small moleculeapproved

Approved

Dec 19, 1979

Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically, it is used for acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. Similar to doxorubicin, daunorubicin interacts with DNA by intercalation and inhibition of macromolecular biosynthesis. This inhibits the progression of the enzyme topoisomerase II, which relaxes supercoils in DNA for transcription. Daunorubicin stabilizes the topoisomerase II complex after it has broken the DNA chain for replication, preventing the DNA double helix from being resealed and thereby stopping the process of replication. On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. It has the highest preference for two adjacent G/C base pairs flanked on the 5' side by an A/T base pair. Daunorubicin should only be administered in a rapid intravenous infusion. It should not be administered intramuscularly or subcutaneously, since it may cause extensive tissue necrosis. It should also never be administered intrathecally (into the spinal canal), as this will cause extensive damage to the nervous system and may lead to death. — NCATS

Clinical trial activity

363 trials · 264 clinical orgs · 13 marketing orgs

Phase 1
82
Phase 2
252
Phase 3
118
Phase 4
18

Earliest trial started Nov 1, 1986 (NCT01324063)

Timeline

1970s

  1. Dec 19, 1979

    Wyeth — Earliest FDA Approval

  2. Dec 19, 1979

    American Home Products — NDA Secondary Org

  3. Dec 19, 1979

    Wyeth — NDA Organization

1980s

  1. Feb 5, 1980

    Sanofi-Aventis — Marketing Organization

  2. Jan 1, 1986

    Earliest Phase 3 Sponsor(trial)

1990s

  1. Jan 1, 1990

    Earliest Phase 2 Sponsor(trial)

  2. Feb 3, 1995

    West-Ward Pharmaceutical — NDA Secondary Org

  3. Apr 8, 1996

    Galen — NDA Secondary Org

  4. Jan 1, 1997

    Earliest Phase 1 Sponsor(trial)

  5. Jan 30, 1998

    Hikma — Marketing Organization

  6. Jan 30, 1998

    Hikma — NDA Secondary Org

  7. Jun 23, 1998

    Teva — Marketing Organization

  8. May 25, 1999

    Fresenius — Marketing Organization

2000s

  1. Jan 24, 2000

    Eu Yan Sang — Marketing Organization

  2. Jan 24, 2000

    Meitheal — Marketing Organization

2010s

  1. Aug 3, 2017

    Celator Pharmaceuticals — NDA Secondary Org

  2. Aug 3, 2017

    Jazz Pharmaceuticals — NDA Secondary Org

  3. Apr 12, 2019

    Zhejiang Hisun Pharmaceutical Co. Ltd. — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • vyxeos

    with cytarabine

    Also known as cytarabine and daunorubicin

Approval history

  • approvedPriority reviewDec 19, 1979

Chemistry & pharmacology

Loading structure…

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(C)=O)C(O)=C3C(=O)C2=CC=C1
Mol. weight
527.5199 g/mol
Lipinski Ro5
2 violation(s)
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Parenteral
Availability
Discontinued

Oral

No

Parenteral

Yes

Topical

No

Black box warning

Sources

Also known as

  • (8s-cis)-8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione
  • (8s-cis)-8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione
  • acetyladriamycin
  • acetyladriamycin
  • acetyladriamycin
  • anthracycline
  • anthracycline
  • cerubidin
  • cerubidine
  • cerubidine
  • cerubidine
  • cerubidine
  • daunoblastina
  • daunomycin
  • daunomycin
  • daunomycin
  • (+)-daunomycin
  • (+)-daunomycin
  • daunomycine
  • daunorubcin hydrochloride
  • daunorubicin
  • daunorubicin
  • daunorubicin
  • daunorubicin
  • daunorubicin
  • daunorubicin
  • daunorubicin
  • daunorubicin
  • daunorubicin
  • daunorubicin
  • daunorubicina
  • daunorubicina
  • daunorubicin citrate
  • daunorubicin citrate
  • daunorubicin citrate
  • daunorubicin citrate
  • daunorubicine
  • daunorubicine
  • daunorubicine
  • daunorubicin hcl
  • daunorubicin hcl
  • daunorubicin hcl
  • daunorubicin hydrochloride
  • daunorubicin hydrochloride
  • daunorubicin hydrochloride
  • daunorubicin hydrochloride
  • daunorubicin hydrochloride
  • daunorubicinum
  • daunorubicinum
  • daunoxome
  • daunoxome
  • daunoxome
  • fi-6339
  • fi-6339
  • fi-6339 [as the base]
  • fi-6339 [as the base]
  • leukaemomycin c
  • leukaemomycin c
  • leukaemomycin c
  • liposomal daunorubicin
  • liposomal daunorubicin citrate
  • ndc-0082-4155
  • ndc-0082-4155
  • rp-13057
  • rp-13057
  • rp-13057 [as the base]
  • rp-13057 [as the base]
  • rubidomycin
  • rubidomycin
  • rubidomycin

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07072585Phase 2/Phase 3 (Phase 3)Mar 30, 2026National Cancer Institute (NCI)
NCT07255872Phase 2/Phase 3 (Phase 3)Dec 31, 2025Baili Pharmaceutical Group
NCT07223814Phase 3Dec 31, 2025German-Austrian Acute Myeloid Leukemia Study Group, HOVON - Dutch Haemato-Oncology Association
NCT07228273Phase 2Dec 24, 2025OHSU Knight Cancer Institute, Oregon Health and Science University
NCT06770257Phase 2Dec 10, 2025China Academy of Chinese Medical Sciences, CSPC Zhongnuo Pharmaceutical (Shijiazhuang) Co., Ltd.
NCT07052994Phase 1Dec 1, 2025University of Texas at Houston
NCT06917911Phase 2Nov 20, 2025National Cancer Institute (NCI)
NCT06918431Phase 2Oct 10, 2025City of Hope National Medical Center, National Cancer Institute (NCI)
NCT07007312Phase 3Sep 26, 2025Kura Oncology, Inc.
NCT07132684Phase 3Aug 31, 2025China Academy of Chinese Medical Sciences, People's Liberation Army of China
NCT07232134Phase 3Jul 24, 2025Federal Research Institute of Pediatric Hematology, Oncology and Immunology
NCT07008638Phase 1/Phase 2 (Phase 2)Jul 7, 2025University of Minnesota
NCT07078591Phase 2Jun 20, 2025People's Liberation Army of China
NCT06697327N/AFeb 1, 2025Anhui Medical University
NCT06317662Phase 2Jan 26, 2025National Cancer Institute (NCI)
NCT06533748Phase 2Dec 31, 2024Amgen, Pfizer, St. Jude Children's Hospital
NCT06390319Phase 2Dec 31, 2024AbbVie, St. Jude Children's Hospital
NCT06289673Phase 4Dec 31, 2024St. Jude Children's Hospital
NCT06744504Phase 3Dec 25, 2024China Academy of Chinese Medical Sciences
NCT06744556Phase 2Dec 20, 2024China Academy of Chinese Medical Sciences
Showing 20 of 363 trials
Page 1 / 19

Organizations

Research & Development (264)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Cancer Institute (NCI)Government1187541992
Jazz PharmaceuticalsFor profit24432009
St. Jude Children's HospitalAcademic/Hospital161441993
PfizerFor profit12432012
University of ParisAcademic/Hospital11421986
University of Texas at HoustonAcademic/Hospital11932000
Cornell UniversityAcademic/Hospital9831990
Gruppo Italiano Malattie EMatologiche dell'AdultoAcademic/Hospital9731996
NovartisFor profit9432001
Southwest Oncology GroupAcademic/Hospital9621995
J. W. Goethe UniversityAcademic/Hospital8731993
Ohio State UniversityAcademic/Hospital8422002
PETHEMA FoundationAcademic/Hospital8821996
University of South FloridaAcademic/Hospital8531999
Chinese Academy of Medical SciencesAcademic/Hospital7532015
Deutsche Krebshilfe e.V.Academic/Hospital7021993
European Organisation for Research and Treatment of CancerAcademic/Hospital7711986
Harvard UniversityAcademic/Hospital7631993
University of WashingtonAcademic/Hospital7342001
Cancer and Leukemia Group B (CALGB)Academic/Hospital6021998
264 organizations
Page 1 / 14

Marketing (16)

OrganizationOrg typeRelationshipDate
American Home ProductsFor profitNDA2Dec 19, 1979
Celator PharmaceuticalsFor profitNDA2Aug 3, 2017
Eu Yan SangFor profitMKTGJan 24, 2000
FreseniusFor profitMKTGMay 25, 1999
GalenFor profitNDA2Apr 8, 1996
HikmaFor profitSYNFeb 3, 1995
HikmaFor profitMKTGJan 30, 1998
HikmaFor profitNDA2Jan 30, 1998
Jazz PharmaceuticalsFor profitNDA2Aug 3, 2017
MeithealFor profitMKTGJan 24, 2000
Sanofi-AventisFor profitMKTGFeb 5, 1980
TevaFor profitMKTGJun 23, 1998
TevaFor profitSYNJan 24, 2000
West-Ward PharmaceuticalFor profitNDA2Feb 3, 1995
WyethFor profitNDADec 19, 1979
Zhejiang Hisun Pharmaceutical Co. Ltd.For profitMKTGApr 12, 2019