doxorubicin
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kemia kombinaĵo
estas
speco de kemiaĵo
subaro de
anthracycline polyketide
parto de
uzado
kemia strukturo
maso
543,174 daltono[18]
stereoizomero de
epirubicin[34]
3,5,12-Trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxyhexopyranoside[34]
kemia formulo
C₂₇H₂₉NO₁₁[18]
ĉefforma SMILES
CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O[18]
izomera SMILES
C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O[18]
aktiva ingredienco en
Adriamycin[35]
Internacia Nekomerca Nomo de medikamento laŭ Internacia Organizaĵo pri Sano
doxorubicin[19]
en taksono
Streptomyces peucetius[36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62][63][64][65][66][67][68][69]
Actinoallomurus[70]
Ixora coccinea[72]
Dracocephalum kotschyi[73]
Xylopia laevigata[74]
Streptomyces venezuelae[76]
Xylopia aromatica[82]
Peniophora incarnata[83]
Ophioparma ventosa[84]
Moorea producens[85]
Streptomyces atratus[86]
Pestalotiopsis palmarum[88]
Viola abyssinica[89]
Ochrolechia parella[91]
Trichodesmium thiebautii[92]
Oscillatoria thiebautii[92]
Zinnia grandiflora[93]
Macrohyporia cocos[94]
Wolfiporia cocos[94]
Ipomoea nil[95]
Aspergillus sclerotiorum[96]
Laurencia tristicha[97]
Annona cherimolia[98]
Penicillium brocae[99]
Quambalaria cyanescens[100]
Schisandra chinensis[101]
Cordyceps farinosa[102]
Hamigera fusca[103]
Fusarium oxysporum[104]
Trichoderma cornu-damae[105]
Talaromyces aculeatus[78]
Fusarium solani[107]
Alstonia macrophylla[108]
Streptomyces violascens[109]
Teratosphaeria[116]
Dothiora[118]
Actinoalloteichus[119]
Alternaria[120]
Verrucosispora[121]
Myrothecium[122]
Nocardiopsis[123]
Dendrodochium[124]
Chrysosporium[125]
Oscillatoria[126]
Okeania[126]
kuracata malsano
ovaria kancero[127]
urinvezika kancero[127]
neuroblastoma, susceptibility to[128]
hepatoblastoma[128]
transitional cell carcinoma[128]
plasmablastic lymphoma[128]
mature T-cell and NK-cell lymphoma[128]
mantle cell lymphoma[128]
T-cell lymphoma[128]
precursor T-cell lymphoblastic leukemia[128]
chronic lymphocytic leukemia[128]
akuta mjeloida leŭkemio[128]
invasive ductal carcinoma[128]
precursor T-cell acute lymphoblastic leukemia[128]
ne-Hodgkin-a limfomo[128]
primary mediastinal B-cell lymphoma[128]
bone sarcoma[128]
post-transplant lymphoproliferative disorder[128]
hematologia kancero[128]
B-ĉela limfomo[128]
difuza limfomo de grandaj B-ĉeloj[128]
low-grade serous carcinoma
fizike interagas kun
medikamenta kategorio pri gravedo
Aŭstralia medikamenta prigraveda kategorio D
Usona medikamenta prigraveda kategorio D
subjekto havas rolon
DNA polymerase inhibitors[131]
topoisomerase inhibitor[131]
antineoplastic antibiotics[132]
topoisomerase II inhibitor[132]
anthracycline antibiotic[133]
stylized name
DOXOrubicin[134]
havas econ: Tall Man lettering
asignita de: Usona Manĝo kaj Drogo Servo
nomita kiel: Doxorubicin
Komuneja kategorio
Doxorubicin
Referenco
- ↑ 1,0 1,1 1,2 1,3 1,4 1,5 Global Substance Registration System, 17 nov. 2016, angla lingvo, doxorubicin, 80168379AG
- ↑ CAS Common Chemistry, 8 apr. 2021, AOJJSUZBOXZQNB-TZSSRYMLSA-N, https://commonchemistry.cas.org/detail?cas_rn=23214-92-8
- ↑ 3,0 3,1 ChEMBL, 17 nov. 2016, angla lingvo, DOXORUBICIN, CHEMBL53463
- ↑ 4,0 4,1 4,2 inferred from InChIKey
- ↑ 5,0 5,1 5,2 5,3 5,4 5,5 5,6 AOJJSUZBOXZQNB-TZSSRYMLSA-N, InChIKey
- ↑ ECHA Substance Infocard database, 27 dec. 2018, 100.041.344, Doxorubicin, CAS no.: 23214-92-8
- ↑ Proteina Datenbazo, 19 okt. 2016, angla lingvo, 1D12, 1D12
- ↑ Proteina Datenbazo, 19 okt. 2016, angla lingvo, 1I1E, 1I1E
- ↑ Proteina Datenbazo, 19 okt. 2016, angla lingvo, 4DX7, 4DX7
- ↑ Proteina Datenbazo, 19 okt. 2016, angla lingvo, 1P20, 1P20
- ↑ Proteina Datenbazo, 19 okt. 2016, angla lingvo, 2DR6, 2DR6
- ↑ Proteina Datenbazo, 19 okt. 2016, angla lingvo, 4ZVM, 4ZVM
- ↑ Proteina Datenbazo, 19 okt. 2016, angla lingvo, 151D, 151D
- ↑ Proteina Datenbazo, 19 okt. 2016, angla lingvo, 1DA9, 1DA9
- ↑ 15,0 15,1 UniChem
- ↑ Freebase Data Dumps, 28 okt. 2013
- ↑ Komuna Norma Datumaro
- ↑ 18,0 18,1 18,2 18,3 18,4 18,5 18,6 PubChem, 17 nov. 2016, angla lingvo, 31703, doxorubicin
- ↑ 19,0 19,1 Kemiaj Entoj de Biologia Intereso, 19 okt. 2016, angla lingvo, doxorubicin, 28748
- ↑ 20,0 20,1 OpenAlex, 26 jan. 2022, https://docs.openalex.org/download-snapshot/snapshot-data-format
- ↑ KBpedia, 9 jul. 2020
- ↑ ChEBI release 2020-09-01
- ↑ ChEBI release 2019-10-02
- ↑ Internacia Kemia Identigilo, 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
- ↑ National Library of Israel Names and Subjects Authority File
- ↑ DrugBank, angla lingvo, 17 nov. 2015, 00997, Doxorubicin
- ↑ IUPHAR/BPS Guide to PHARMACOLOGY, 17 nov. 2016, angla lingvo, 7069, doxorubicin
- ↑ UMLS 2023, 25 maj. 2023, inferred by common MeSH mappings on source and on Wikidata
- ↑ Mapping file of InChIStrings, InChIKeys and DTXSIDs for the EPA CompTox Dashboard
- ↑ ChemSpider, 17 nov. 2016, angla lingvo, 29400, Doxorubicin
- ↑ GF WordNet
- ↑ Hazardous Substances Data Bank, 10 maj. 2021, 28 okt. 2019, DOXORUBICIN, 3070
- ↑ 33,0 33,1 33,2 33,3 Gene Ontology release 2019-11-16
- ↑ 34,0 34,1 inferred from InChI
- ↑ RxNorm, 42512, 14 feb. 2018
- ↑ Characterization of the Streptomyces peucetius ATCC 29050 genes encoding doxorubicin polyketide synthase
- ↑ Expression of doxorubicin-daunorubicin resistance genes in different anthracycline-producing mutants of Streptomyces peucetius
- ↑ Identification and characterization of the afsR homologue regulatory gene from Streptomyces peucetius ATCC 27952.
- ↑ A bacterial analog of the mdr gene of mammalian tumor cells is present in Streptomyces peucetius, the producer of daunorubicin and doxorubicin
- ↑ Exploration of geosmin synthase from Streptomyces peucetius ATCC 27952 by deletion of doxorubicin biosynthetic gene cluster
- ↑ Enhancement of doxorubicin production by expression of structural sugar biosynthesis and glycosyltransferase genes in Streptomyces peucetius.
- ↑ Self-resistance mechanism in Streptomyces peucetius: overexpression of drrA, drrB and drrC for doxorubicin enhancement
- ↑ Isolation and genetic manipulation of the antibiotic down-regulatory gene, wblA ortholog for doxorubicin-producing Streptomyces strain improvement
- ↑ Superoxide dismutase (SOD) genes in Streptomyces peucetius: effects of SODs on secondary metabolites production.
- ↑ Enhancing macrolide production in Streptomyces by coexpressing three heterologous genes.
- ↑ Exploration of two epimerase homologs in Streptomyces peucetius ATCC 27952.
- ↑ The DrrAB efflux system of Streptomyces peucetius is a multidrug transporter of broad substrate specificity
- ↑ Switching antibiotics production on and off in actinomycetes by an IclR family transcriptional regulator from Streptomyces peucetius ATCC 27952.
- ↑ One-Pot Combinatorial Biosynthesis of Glycosylated Anthracyclines by Cocultivation of Streptomyces Strains Producing Aglycones and Nucleotide Deoxysugars.
- ↑ Complete genome sequence of Streptomyces peucetius ATCC 27952, the producer of anticancer anthracyclines and diverse secondary metabolites
- ↑ Implication of orphan histidine kinase (OhkAsp) in biosynthesis of doxorubicin and daunorubicin in Streptomyces peucetius ATCC 27952
- ↑ Isolation and characterization of a gene from Streptomyces sp. strain C5 that confers the ability to convert daunomycin to doxorubicin on Streptomyces lividans TK24
- ↑ Expression and characterization of DrrA and DrrB proteins of Streptomyces peucetius in Escherichia coli: DrrA is an ATP binding protein
- ↑ Minimal Streptomyces sp. strain C5 daunorubicin polyketide biosynthesis genes required for aklanonic acid biosynthesis
- ↑ Production of the antitumor drug epirubicin (4'-epidoxorubicin) and its precursor by a genetically engineered strain of Streptomyces peucetius
- ↑ The Streptomyces peucetius dpsY anddnrX Genes Govern Early and Late Steps of Daunorubicin and Doxorubicin Biosynthesis
- ↑ Purification, properties, and characterization of recombinant Streptomyces sp. strain C5 DoxA, a cytochrome P-450 catalyzing multiple steps in doxorubicin biosynthesis
- ↑ Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene
- ↑ Glucose kinases from Streptomyces peucetius var. caesius.
- ↑ NdgR, an IclR-like regulator involved in amino-acid-dependent growth, quorum sensing, and antibiotic production in Streptomyces coelicolor
- ↑ Precursor for biosynthesis of sugar moiety of doxorubicin depends on rhamnose biosynthetic pathway in Streptomyces peucetius ATCC 27952.
- ↑ Identification of the duplicated genes for S-adenosyl-l-methionine synthetase (metK1-sp and metK2-sp) in Streptomyces peucetius var. caesius ATCC 27952.
- ↑ Improvement in doxorubicin productivity by overexpression of regulatory genes in Streptomyces peucetius
- ↑ Enhanced doxorubicin production by Streptomyces peucetius using a combination of classical strain mutation and medium optimization
- ↑ The Streptomyces peucetius drrC gene encodes a UvrA-like protein involved in daunorubicin resistance and production
- ↑ Interspecies DNA microarray analysis identifies WblA as a pleiotropic down-regulator of antibiotic biosynthesis in Streptomyces
- ↑ Genome analyses of Streptomyces peucetius ATCC 27952 for the identification and comparison of cytochrome P450 complement with other Streptomyces
- ↑ Limitations in doxorubicin production from Streptomyces peucetius
- ↑ Isolation and characterization of stable mutants of Streptomyces peucetius defective in daunorubicin biosynthesis
- ↑ Halogenated Spirotetronates from Actinoallomurus
- ↑ A comprehensive genome-scale reconstruction of Escherichia coli metabolism--2011.
- ↑ Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea
- ↑ Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent
- ↑ Cytotoxic Alkaloids from the Stem of Xylopia laevigata.
- ↑ Antioxidant and cell growth activities of beet root pomace extracts
- ↑ Development of a Streptomyces venezuelae-based combinatorial biosynthetic system for the production of glycosylated derivatives of doxorubicin and its biosynthetic intermediates
- ↑ Varitatin A, a Highly Modified Fatty Acid Amide from Penicillium variabile Cultured with a DNA Methyltransferase Inhibitor
- ↑ 78,0 78,1 Inducing Secondary Metabolite Production by Combined Culture of Talaromyces aculeatus and Penicillium variabile.
- ↑ Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata
- ↑ New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata
- ↑ Two new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annomuricins A and B, from the leaves of Annona muricata
- ↑ Bioactive annonaceous acetogenins from the bark of Xylopia aromatica
- ↑ Cytotoxic Xanthone Derivatives from the Mangrove-Derived Endophytic Fungus Peniophora incarnata Z4
- ↑ Minor Pyranonaphthoquinones from the Apothecia of the Lichen Ophioparma ventosa
- ↑ Cytotoxic Microcolin Lipopeptides from the Marine Cyanobacterium Moorea producens
- ↑ Antitubercular Ilamycins from Marine-Derived Streptomyces atratus SCSIO ZH16 ΔilaR
- ↑ Bioactive ent-kaurene diterpenoids from Annona senegalensis
- ↑ Sinopestalotiollides A-D, cytotoxic diphenyl ether derivatives from plant endophytic fungus Pestalotiopsis palmarum
- ↑ Cyclotides from an extreme habitat: characterization of cyclic peptides from Viola abyssinica of the Ethiopian highlands
- ↑ 90,0 90,1 Quassinoids from Eurycoma longifolia
- ↑ Metabolites from the LichenOchrolechia parellaGrowing under Two Different Heliotropic Conditions⊥
- ↑ 92,0 92,1 Isolation of Isotrichophycin C and Trichophycins G-I from a Collection of Trichodesmium thiebautii
- ↑ Zinagrandinolides A-C, cytotoxic delta-elemanolide-type sesquiterpene lactones from Zinnia grandiflora
- ↑ 94,0 94,1 Cytotoxic Lanostanoids from Poria cocos
- ↑ Diterpene glycosides from the seeds of Pharbitis nil.
- ↑ Lovastatin Analogues from the Soil-Derived Fungus Aspergillus sclerotiorum PSU-RSPG178.
- ↑ Halogenated Sesquiterpenoids from the Red Alga Laurencia tristicha Collected in Taiwan.
- ↑ 98,0 98,1 Annomolin and annocherimolin, new cytotoxic annonaceous acetogenins from Annona cherimolia seeds
- ↑ Brocazines A-F, Cytotoxic Bisthiodiketopiperazine Derivatives from Penicillium brocae MA-231, an Endophytic Fungus Derived from the Marine Mangrove Plant Avicennia marina
- ↑ Quambalarine B, a Secondary Metabolite from Quambalaria cyanescens with Potential Anticancer Properties.
- ↑ Identification of key structural characteristics of Schisandra chinensis lignans involved in P-glycoprotein inhibition.
- ↑ Paecilosetin Derivatives as Potent Antimicrobial Agents from Isaria farinosa
- ↑ Non-geminal Aliphatic Dihalogenation Pattern in Dichlorinated Diaporthins from Hamigera fusca NRRL 35721
- ↑ Search for cell motility and angiogenesis inhibitors with potential anticancer activity: beauvericin and other constituents of two endophytic strains of Fusarium oxysporum
- ↑ Macrocyclic Trichothecene Mycotoxins from a Deadly Poisonous Mushroom, Podostroma cornu-damae
- ↑ A novel constituent from Rollinia mucosa, rollicosin, and a new approach to develop annonaceous acetogenins as potential antitumor agents
- ↑ Cytotoxic Naphthoquinone and Azaanthraquinone Derivatives from an Endophytic Fusarium solani
- ↑ Alstoniaphyllines A-C, unusual nitrogenous derivatives from the bark of Alstonia macrophylla
- ↑ Violapyrones A-G, α-pyrone derivatives from Streptomyces violascens isolated from Hylobates hoolock feces
- ↑ Meliponamycins: Antimicrobials from Stingless Bee-Associated Streptomyces sp
- ↑ Cytotoxic Dibohemamines D-F from a Streptomyces Species.
- ↑ Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species.
- ↑ Komodoquinone A, a Novel Neuritogenic Anthracycline, from Marine Streptomyces sp. KS3
- ↑ Cytotoxic Bagremycins from Mangrove-Derived Streptomyces sp. Q22.
- ↑ Bioactive Streptoglutarimides A-J from the Marine-Derived Streptomyces sp. ZZ741
- ↑ Cytotoxic and Noncytotoxic Metabolites from Teratosphaeria sp. FL2137, a Fungus Associated with Pinus clausa.
- ↑ Condensation of Macrocyclic Polyketides Produced by Penicillium sp. DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway
- ↑ Hormonemate Derivatives from Dothiora sp., an Endophytic Fungus.
- ↑ Bioactive Alkaloids from the Actinomycete Actinoalloteichus sp. ZZ1866
- ↑ Chlorinated Dehydrocurvularins and Alterperylenepoxide A from Alternaria sp. AST0039, a Fungal Endophyte of Astragalus lentiginosus
- ↑ Cytotoxic Kendomycins Containing the Carbacylic Ansa Scaffold from the Marine-Derived Verrucosispora sp. SCSIO 07399
- ↑ Cytotoxic and Antibacterial Quinone Sesquiterpenes from a Myrothecium Fungus
- ↑ Cytotoxic p-Terphenyls from a Marine-Derived Nocardiopsis Species
- ↑ Polyhydroxy Cyclohexanols from a Dendrodochium sp. Fungus Associated with the Sea Cucumber Holothuria nobilis Selenka
- ↑ Chrysosporazines F-M: P-Glycoprotein Inhibitory Phenylpropanoid Piperazines from an Australian Marine Fish Derived Fungus, Chrysosporium sp. CMB-F294
- ↑ 126,0 126,1 Ikoamide, an Antimalarial Lipopeptide from an Okeania sp. Marine Cyanobacterium
- ↑ 127,0 127,1 127,2 N0000147829, 13 dec. 2016, NDF-RT, angla lingvo
- ↑ 128,00 128,01 128,02 128,03 128,04 128,05 128,06 128,07 128,08 128,09 128,10 128,11 128,12 128,13 128,14 128,15 128,16 128,17 128,18 128,19 Drug Indications Extracted from FAERS, 2 okt. 2018
- ↑ IUPHAR/BPS Guide to PHARMACOLOGY, 17 aŭg. 2016, 7069, angla lingvo
- ↑ Open Targets Platform, 14 aŭg. 2023, https://platform.opentargets.org/drug/CHEMBL53463
- ↑ 131,0 131,1 N0000147829, 5 mar. 2018, NDF-RT
- ↑ 132,0 132,1 Medical Subject Headings, 15 mar. 2018, D004317
- ↑ N0000147829, 27 feb. 2018, NDF-RT
- ↑ https://www.fda.gov/drugs/medication-errors-related-cder-regulated-drug-products/fda-name-differentiation-project, 2 sep. 2022