Drug Information

General Information
Drug ID
DR00269
Drug Name
Mitoxantrone
Synonyms
1,4-Bis(2-(2-hydroxyethylamino)ethyl)amino)-5,8-dihydroxyanthraquinone; 1,4-DIHYDROXY-5,8-BIS({2-[(2-HYDROXYETHYL)AMINO]ETHYL}AMINO)-9,10-ANTHRACENEDIONE; 1,4-Dihydroxy-5,8-bis(2-((2-hydroxyethyl)amino)ethylamino)-9,10-anthracenedione; 1,4-Dihydroxy-5,8-bis(5-hydroxy-3-azapentylamino)anthrachinon; 1,4-Dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione; 1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione; 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthra-9,10-quinone; 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracene-9,10-dione; 5,8-Bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxyanthraquinone; 9,10-Anthracenedione, 1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-(9CI); AN-584/42007670; DHAD; DHAQ; DHAQ (*Diacetate salt*); DHAQ HCl; Dihydroxyanthraquinone; Liposome Encapsulated Mitoxantrone (LEM); MITOXANTRONE, 1,4-DIHYDROXY-5,8-BIS({2-[(2-HYDROXYETHYL)AMINO]ETHYL}AMINO)ANTHRA-9,10-QUINONE; MITOXANTRONE, Mitoxantrone Hydrochloride, Mitoxantrone dihydrochloride, MITOXANTHRONE HYDROCHLORIDE; MIX; Misostol; Misostol (TN); Mitoxanthrone; Mitoxantron; Mitoxantrona; Mitoxantrona [INN-Spanish]; Mitoxantrone (INN); Mitoxantrone (free base); Mitoxantrone 2HCl; Mitoxantrone [INN]; Mitoxantronum; Mitoxantronum [INN-Latin]; Mitozantrone; Mitozantrone hydrochloride; Novantrone (TN); Novantrone(R) (mitoxantrone for injection concentrate)
Drug Type
Small molecular drug
Indication Non-hodgkin's lymphoma [ICD11:2B33.5] Approved [1]
Metastatic breast cancer [ICD11:2C6Y] Approved [1]
Acute myeloid leukemia [ICD11:2A60] Approved [1]
Therapeutic Class
Analgesics
Structure
3D MOL 2D MOL
Formula
C22H28N4O6
Canonical SMILES
C1=CC(=C2C(=C1NCCNCCO)C(=O)C3=C(C=CC(=C3C2=O)O)O)NCCNCCO
InChI
InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2
InChIKey
KKZJGLLVHKMTCM-UHFFFAOYSA-N
CAS Number
CAS 65271-80-9
Pharmaceutical Properties Molecular Weight 444.5 Topological Polar Surface Area 163
Heavy Atom Count 32 Rotatable Bond Count 12
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 10
XLogP
1
PubChem CID
4212
PubChem SID
11111482 ,11111483 ,11335691 ,11360930 ,11364549 ,11367111 ,11369673 ,11372759 ,11374669 ,11377835 ,11406669 ,11406928 ,11461902 ,11466413 ,11467533 ,11484492 ,11486226 ,11488724 ,11491405 ,11492681 ,11495469 ,13376 ,142727 ,14710338 ,14857298 ,15047380 ,17417295 ,24769895 ,29223317 ,46394146 ,46504608 ,47216744 ,47365147 ,47440212 ,47440213 ,47515285 ,47662243 ,47736437 ,48035072 ,48035073 ,48184960 ,4873554 ,49698959 ,49870599 ,50111146 ,53790842 ,56352855 ,600874 ,7980008 ,8152633
ChEBI ID
ChEBI:50729
TTD Drug ID
D0R3JB
DT(s) Transporting This Drug ABCA3 Transporter Info ATP-binding cassette sub-family A member 3 Substrate [2]
BCRP Transporter Info Breast cancer resistance protein Substrate [3]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [4]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [5]
P-GP Transporter Info P-glycoprotein 1 Substrate [5]
Drug-Transporter Activity Data
Drug-Transporter Activity Data BCRP Transporter Info Km =7 microM Spodoptera frugiperda (Sf9) cells-BCRP [3]
References
1 Mitoxantrone was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 A distinct "side population" of cells with high drug efflux capacity in human tumor cells. Proc Natl Acad Sci U S A. 2004 Sep 28;101(39):14228-33.
3 Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells. Biochem Biophys Res Commun. 2001 Jul 6;285(1):111-7.
4 Multidrug resistance protein 1 (MRP1, ABCC1) mediates resistance to mitoxantrone via glutathione-dependent drug efflux. Mol Pharmacol. 2006 Apr;69(4):1499-505.
5 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.

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