Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00284
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| Drug Name |
Daunorubicin
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| Synonyms |
(+)-Daunomycin; (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside; (7S,9R)-9-Acetyl-7-[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; (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-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione; Acetyladriamycin; Anthracyline; Antibiotics from Streptomyces coeruleorubidus; Cerubidin; Cerubidine; DAUNORUBICIN HCL; DM1; Daunamycin; Daunarubicinum; Dauno-Rubidomycine; DaunoXome; DaunoXome (TN); Daunoblastin; Daunoblastine; Daunomycin; Daunorrubicina; Daunorubicin (INN); Daunorubicin (liposomal); Daunorubicin [INN:BAN]; Daunorubicin, Hydrochloride; Daunorubicine; Daunorubicinum; Daunorubicinum [INN-Latin]; FI 6339; FI6339; Leukaemomycin C; RP 13057; Rubidomycin; Rubomycin; Rubomycin C; VS-103
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| Drug Type |
Small molecular drug
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| Indication | Acute myeloid leukemia [ICD11:2A60] | Approved | [1] | |||
| Therapeutic Class |
Anticancer Agents
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| Structure |
|
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| 3D MOL | 2D MOL | |||||
| Formula |
C27H29NO10
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| Canonical SMILES |
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O
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| InChI |
InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
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| InChIKey |
STQGQHZAVUOBTE-VGBVRHCVSA-N
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| CAS Number |
CAS 20830-81-3
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| Pharmaceutical Properties | Molecular Weight | 527.5 | Topological Polar Surface Area | 186 | ||
| Heavy Atom Count | 38 | Rotatable Bond Count | 4 | |||
| Hydrogen Bond Donor Count | 5 | Hydrogen Bond Acceptor Count | 11 | |||
| XLogP |
1.8
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| PubChem CID | ||||||
| PubChem SID |
103477782
,104066339
,104307942
,11114094
,117393873
,124766118
,124886869
,124886870
,124886871
,125299287
,126663226
,127301039
,127301040
,127301041
,14763056
,15481415
,24769892
,26697306
,26701813
,26704223
,26715132
,26718351
,26718779
,29215022
,34672588
,46508433
,47440436
,47736668
,48110630
,48415843
,49699346
,49855159
,50070917
,50104250
,5016
,53788227
,56465013
,57288764
,57310919
,596008
,74382025
,74462219
,7887073
,7979028
,8171488
,85788867
,866161
,92307396
,92308820
,96024474
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| ChEBI ID |
ChEBI:41977
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | BCRP | Transporter Info | Breast cancer resistance protein | Substrate | [2] | |
| MRP1 | Transporter Info | Multidrug resistance-associated protein 1 | Substrate | [3] | ||
| MRP6 | Transporter Info | Multidrug resistance-associated protein 6 | Substrate | [4] | ||
| P-GP | Transporter Info | P-glycoprotein 1 | Substrate | [5] | ||
| Drug-Transporter Activity Data | ||||||
| Drug-Transporter Activity Data | BCRP | Transporter Info | Km =2.5 microM | Spodoptera frugiperda (Sf9) cells-BCRP | [2] | |
| MRP1 | Transporter Info | Km =1.4 microM | Human small cell lung cancer cells | [6] | ||
| P-GP | Transporter Info | Km =1.74 microM | High five cells-MDR1 | [7] | ||
| References | ||||||
| 1 | Daunorubicin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019) | |||||
| 2 | Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells. Biochem Biophys Res Commun. 2001 Jul 6;285(1):111-7. | |||||
| 3 | Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. | |||||
| 4 | Characterization of the drug resistance and transport properties of multidrug resistance protein 6 (MRP6, ABCC6). Cancer Res. 2002 Nov 1;62(21):6172-7. | |||||
| 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. | |||||
| 6 | Competitive inhibition by genistein and ATP dependence of daunorubicin transport in intact MRP overexpressing human small cell lung cancer cells. Biochem Pharmacol. 1994 Sep 15;48(6):1129-36. | |||||
| 7 | Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. | |||||
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