Daunorubicin
Daunorubicin, also known as daunomycin,
is a chemotherapy medication used to
treat cancer.[2] Specifically it is used for
acute myeloid leukemia (AML), acute
lymphoblastic leukemia (ALL), chronic
myelogenous leukemia (CML), and
Kaposi's sarcoma.[2] It is administered by
injection into a vein.[2] A liposomal
formulation known as liposomal
daunorubicin also exists.[2]
Common side
Daunorubicin
effects include hair
loss, vomiting, bone
marrow
suppression, and
inflammation of the
inside of the
mouth.[2] Other Clinical data
severe side effects Trade Cerubidine,
include heart names
others
disease and tissue AHFS/Drugs.com Mo
death at the site of (ht
injection.[2] Use in ww
pregnancy may om
harm the fetus.[2] rap
Daunorubicin is in oru
the anthracycline dro
family of e.h
medication.[3] It MedlinePlus a68228
works in part by (https://
blocking the medline
plus.go
function of
v/drugin
topoisomerase II.[2]
fo/med
Daunorubicin was s/a6822
89.htm
approved for
l)
medical use in the
Pregnancy AU: D[1]
United States in category
1979.[2] It is on the Routes of Exclu
World Health administration
intrav
Organization's List Caus
of Essential necro
Medicines.[4] It was admin
originally isolated intram
from bacteria of the or
subcu
Streptomyces
ATC code L01DB02
type.[5]
(WHO (ht
Medical uses tps://ww
w.whocc.
It slows or stops the no/atc_d
growth of cancer dd_inde
cells in the body. x/?code=
Treatment is usually L01DB0
2) )
performed together
with other Legal status
chemotherapy drugs Legal AU: S4
status
(such as (Prescription
only)
cytarabine), and its US: ℞-only
administration Pharmacokinetic
depends on the type data
of tumor and the Metabolism Liver
degree of response. Elimination 26.7 hou
half-life
(metabo
In addition to its
Excretion Biliary
major use in treating
and
AML, daunorubicin
urinary
is also used to treat
Identifiers
neuroblastoma.
Daunorubicin has IUPAC name
(8S,10S)-8-Acetyl-10-
been used with
[(2S,4S,5S,6S)-
other chemotherapy
4-amino-5-hydrox
agents to treat the
y-6-methyl-oxan-
blastic phase of 2-yl]oxy-6,8,11-tri
chronic hydroxy-1-methox
myelogenous y-
9,10-dihydro-7H-t
leukemia.
etracene-5,12-dio
Daunorubicin is also ne
used as the starting CAS 20830-
Number
material for semi- 81-3 (htt
synthetic ps://com
monchem
manufacturing of
istry.cas.
doxorubicin,
org/detai
epirubicin and
l?cas_rn=
idarubicin. 20830-81
-3)
PubChem 30323 (h
CID
ttps://pu
bchem.n
cbi.nlm.ni
Mechanism of h.gov/co
action mpound/
30323)
Similar to IUPHAR/BPS 7063
doxorubicin, (http
daunorubicin s://w
interacts with DNA ww.g
by intercalation and uideto
inhibition of phar
macromolecular macol
ogy.or
biosynthesis.[6][7]
g/GR
This inhibits the
AC/Li
progression of the
gand
enzyme Displ
topoisomerase II, ayFor
which relaxes ward?
supercoils in DNA; ligand
without action of Id=70
63)
topoisomerase II,
DrugBank DB00694
these DNA
(https://
supercoils interfere
www.dru
in transcription of
gbank.c
DNA. Daunorubicin
a/drugs/
stabilizes the DB0069
topoisomerase II 4)
complex after it has ChemSpider 28163
broken the DNA (http
chain for replication, s://ww
preventing the DNA w.che
double helix from mspid
being resealed and er.co
thereby stopping the m/Che
process of mical-
replication. On Struct
ure.28
binding to DNA,
163.ht
daunomycin
ml)
intercalates, with its
UNII ZS7284E0ZP
daunosamine
(https://preci
residue directed
sion.fda.go
toward the minor v/uniisearch/
groove. It has the srs/unii/ZS7
highest preference 284E0ZP)
for two adjacent KEGG C01907
G/C base pairs (https://
flanked on the 5' www.keg
side by an A/T base g.jp/entr
pair. Crystallography
shows that y/C0190
daunomycin induces 7)
a local unwinding ChEBI CHEBI:41977
angle of 8°, and (https://ww
other w.ebi.ac.uk/c
hebi/searchI
conformational
d.do?chebiId
disturbances of
=CHEBI:4197
adjacent and
7)
second-neighbour
ChEMBL ChEMBL178
base pairs.[8] It can
(https://ww
also induce histone
w.ebi.ac.uk/
eviction from chembldb/in
chromatin upon dex.php/co
intercalation.[9][10] mpound/ins
pect/ChEM
BL178)
CompTox DTXSID7
History Dashboard
(https://c
(EPA)
x.epa.gov
In the 1950s, an
board/che
Italian research
details/D
company, Farmitalia 022883)
Research ECHA 100.040.04
Laboratories, began InfoCard
(https://ech
an organized effort a.europa.e
to isolate anticancer u/substanc
compounds from -informatio
soil-based n/-/substan
microbes. A soil ceinfo/100.
040.048)
sample was
isolated from the Chemical and
physical data
area surrounding the
Castel del Monte, a Formula C H NO
27 29 10
13th-century castle Molar 527.526 g·mol
mass
in Apulia. A new
3D Interactive
strain of
model
image (htt
Streptomyces (JSmol)
ps://chem
peucetius which
apps.stol
produced a red
af.edu/jm
pigment was ol/jmol.ph
isolated, and an p?model=
antibiotic was C%5BC%4
produced from this 0H%5D1%
bacterium that was 5BC%40
found to have good H%5D%2
8%5BC%4
activity against
0H%5D%2
murine tumors.
8C%5BC%
Since a group of
French researchers 40%40H%
discovered the 5D%28O
same compound at 1%29O%5
BC%40
about the same
H%5D2
time, the two teams
C%5BC%4
named the
0%40%5
compound D%28Cc3
daunorubicin, c2c%28c4
combining the name c%28c3
Dauni, a pre-Roman O%29C%2
tribe that occupied 8%3DO%2
the area of Italy 9c5cccc%
28c5C4%
where the
3DO%29O
compound was
C%29O%2
isolated, with the
9%28C%2
French word for
ruby, rubis, 8%3DO%2
describing the 9C%29O%
color.[11][12][13] 29N%29
O)
Clinical trials began
in the 1960s, and the SMILES
C[C@H]1[C@H]([C
drug saw success in @H](C[C@@H]
treating acute (O1)O[C@H]2C
[C@@](Cc3c2c
leukemia and (c4c(c3O)C(=
O)c5cccc(c5C4
lymphoma.
=O)OC)O)(C(=
O)C)O)N)O
However, by 1967, it
InChI
was recognized that InChI=1S/C27H29
daunorubicin could NO10/c1-10-22
(30)14(28)7-17
produce fatal (37-10)38-16-9
-27(35,11(2)2
cardiac toxicity.[14]
9)8-13-19(16)2
6(34)21-20(24
(13)32)23(31)1
In 2015–16, a team 2-5-4-6-15(36-
3)18(12)25(21)
at Ohio State 33/h4-6,10,14,
16-17,22,30,32,
University "showed
34-35H,7-9,28
that, by carefully H2,1-3H3/t10-,
14-,16-,17-,22+,
manipulating 27-/m0/s1
strands of viral DNA, Key:STQGQHZAVU
OBTE-VGBVRH
an origami structure CVSA-N
with complex folds (verify) (https://en.
can be created in wikipedia.org/w/inde
just 10 minutes. x.php?title=Special:C
Incredibly, these omparePages&rev1
structures are only =458300140&page2
=Daunorubicin)
100 nanometers
across – that’s
1,000 times smaller than the width of a
human hair. Small volumes of daunorubicin
can be wrapped up in these minuscule
pods, which can then be released into a
leukemia cell-filled environment."[15]
Route of administration
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. Daunorubicin has
been used intravitreally (inside the eye) for
the purposes of preventing proliferative
vitreoretinopathy, a common complication
following retinal detachment surgery, but
has not been found to be effective and is
not used for any other ophthalmic
purposes at this time.[16]
See also
Doxorubicin
Idarubicin
References
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ttps://www.ncbi.nlm.nih.gov/pmc/articles/
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med.ncbi.nlm.nih.gov/1462166) .
12. Baruffa G (1966). "Clinical trials in
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2990030-7) . PMID 5332105 (https://pubm
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13. Camerino B, Palamidessi G (1960). "Derivati
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[Derivatives of parazine II. Sulfonamdopir].
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14. Tan C, Tasaka H, Yu KP, Murphy ML,
Karnofsky DA (March 1967). "Daunomycin,
an antitumor antibiotic, in the treatment of
neoplastic disease. Clinical evaluation with
special reference to childhood leukemia" (ht
tps://doi.org/10.1002%2F1097-0142%2819
67%2920%3A3%3C333%3A%3AAID-CNCR2
820200302%3E3.0.CO%3B2-K) . Cancer. 20
(3): 333–353. doi:10.1002/1097-
0142(1967)20:3<333::AID-
CNCR2820200302>3.0.CO;2-K (https://doi.
org/10.1002%2F1097-0142%281967%292
0%3A3%3C333%3A%3AAID-CNCR2820200
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ttps://pubmed.ncbi.nlm.nih.gov/4290058) .
S2CID 19272219 (https://api.semanticscho
lar.org/CorpusID:19272219) .
15. "Researchers kill drug-resistant leukemia
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e/researchers-kill-drug-resistant-leukemia-c
ells-using-dna-trojan-horse-attack) . IFL
Science. 25 February 2016.
16. Mortensen ME, Cecalupo AJ, Lo WD, Egorin
MJ, Batley R (1992). "Inadvertent
intrathecal injection of daunorubicin with
fatal outcome". Medical and Pediatric
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org/10.1002%2Fmpo.2950200315) .
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External links
"Daunorubicin" (https://druginfo.nlm.nih.
gov/drugportal/name/daunorubicin) .
Drug Information Portal. U.S. National
Library of Medicine.
Portal: Medicine
Retrieved from
"https://en.wikipedia.org/w/index.php?
title=Daunorubicin&oldid=1179705641"
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