Compound: doxorubicin
SMILES: O=C1c2c(O)c3c(C[C@@](O)(C(=O)CO)C[C@@H]3O[C@@H]4O[C@H]([C@@H](O)[C@H](C4)N)C)c(c2C(=O)c5c1c(OC)ccc5)O
InChIKey: AOJJSUZBOXZQNB-TZSSRYMLSA-N
Synonyms: doxorubicin, Adriamycin, 23214-92-8, Adriablastin, Doxorubicine, 14-Hydroxydaunomycin, Doxorubicinum, Doxorubicina, 14-Hydroxydaunorubicine, NDC 38242-874, NSC 123127, NSC-123127, (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, NSC-759155, 80168379AG, DTXSID8021480, CHEBI:28748, (1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside, (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione, 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-, hydroxydaunomycin, KW-125, (8S-cis)-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, doxorrubicina, Adriablastine, Hydroxyldaunorubicin, (7S,9S)-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione, Hydroxyl Daunorubicin, RefChem:5780, DTXCID301480, L01DB01, (8S-cis)-10-((3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroacetyl)-1-methoxy-5,12-naphthacenedione, 245-495-6, Doxil, Adriblastina, Hydroxydaunorubicin, Doxorubicine [INN-French], Doxorubicinum [INN-Latin], Doxorubicina [INN-Spanish], Adriamycin semiquinone, MFCD00869292, CHEMBL53463, (8S,10S)-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione, ADM hydrochloride, NCI-C01514, ADM, (1S,3S)-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-trideoxy-alpha-L-lyxo-hexopyranoside, (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-, Doxorubicin [USAN:INN:BAN], ThermoDox, MLS000028393, C27H29NO11, DM2, Doxorubicin-hLL1, (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside, (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-alpha-L-lyxo hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, Adriblastina (TN), CCRIS 739, Doxorubicin-P4/D10, HSDB 3070, EINECS 245-495-6, Doxorubicin (USAN/INN), Doxorubicin-hLL1 conjugate, Doxorubicin-P4/D10 conjugate, Doxorubicin?, UNII-80168379AG, DOXORUBICIN [MI], Prestwick0_000438, Prestwick1_000438, Prestwick2_000438, Prestwick3_000438, DOXORUBICIN [INN], ADR, DOX, DOXORUBICIN [HSDB], DOXORUBICIN [USAN], Probes1_000151, Probes2_000129, DOXORUBICIN [VANDF], SCHEMBL3243, DOXORUBICIN [MART.], BSPBio_000456, BSPBio_001031, DOXORUBICIN [WHO-DD], (1S,3S)-3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-(3-amino-2,3,6-tridesoxy-alpha-L-lyxo-hexopyranosid), (8S,10S)-10-((3-Amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-glycoloyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione, 1,2,3,4,6,11-Hexahydro-4beta,5,12-trihydroxy-4-(hydroxyacetyl)-10-methoxy-6,11-dioxonaphthacen-1beta-yl-3-amino-2,3,6-trideoxy-alpha-L-lyxohexopyranoside, 10-((3-Amino-2,3,6-trideoxy-D-lyxohexopyranosyl)oxy)-8-glycolcyl-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione, Caelyx (liposomal doxorubicin), SPBio_002395, BPBio1_000502, cid_443939, GTPL7069, orb1308571, orb2279710, Valrubicin impurity, doxorubicin, SCHEMBL29459849, BDBM22984, BDBM32022, HMS2089H06, (8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE, 5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-, EBC-27299, GR-319, HY-15142A, LMPK13050001, AKOS015951330, Conjugate of doxorubicin with humanized monoclonal antibody LL1 against CD74, Conjugate of doxorubicin with monoclonal antibody P4/D10 against GP120, DB00997, SMP1_000106, NCGC00024415-35, NCGC00024415-37, NCGC00024415-38, NCGC00024415-40, NCGC00024415-41, NCGC00024415-42, NCGC00024415-61, AC-37453, BP-23114, BP-44119, SY224845, NS00002473, (8S,10S)-10-(((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracen, C01661, D03899, EN300-120698, Epirubicin hydrochloride impurity, doxorubicin-, H11954, Q18936, BRD-K92093830-003-04-3, BRD-K92093830-003-25-8, BRD-K92093830-003-30-8, BRD-K92093830-003-31-6, BRD-K92093830-003-33-2, VALRUBICIN IMPURITY, DOXORUBICIN [USP IMPURITY], EPIRUBICIN HYDROCHLORIDE IMPURITY C [EP IMPURITY], DAUNORUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY], Epirubicin Hydrochloride EP Impurity C; Daunorubicin EP Impurity D, EPIRUBICIN HYDROCHLORIDE IMPURITY, DOXORUBICIN- [USP IMPURITY], (7S,9R)-7-[(2S,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-9-glycoloyl-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride, (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-4-methoxy-6,9,11-tris(oxidanyl)-9-(2-oxidanylethanoyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride, (7S,9S)-7-[(4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione, (7S,9S)-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride, (8S,10S)-10-[(3-Amino-2,3,6-trideoxy-|_-L-lyxo hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, (8S,10S)-10-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-2-tetrahydropyranyl]oxy]-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione, (8S-cis)-10-[(3-Amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, 1392315-46-6, 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S,10S)-, 5,12-Naphthacenedione, 10-[(3-amino-2,3,6-trideoxy-|A-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-, (8S,10S)-
Theoretical properties:
molecular_formula: C27H29NO11
molecular_weight: 543.5 g/mol
exact_mass: 543.17406074 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 5
heavy_atom_count: 39
topological_polar_surface_area: 206 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Red, crystalline solid
color: Red, crystalline solid
melting_point: 229-231 °C
solubility: ~10 mg/ml
Descriptions:
pubchem: Doxorubicin is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a member of p-quinones, a deoxy hexoside, an aminoglycoside, an anthracycline, an anthracycline antibiotic and a member of tetracenequinones. It has a role as an Escherichia coli metabolite. It is functionally related to an Adriamycinone. It is a conjugate base of a doxorubicin(1+). It derives from a hydride of a tetracene.
chembl: DOXORUBICIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Doxorubicin, sold under the brand name Adriamycin among others, is a chemotherapy medication used to treat cancer. This includes breast cancer, bladder cancer, Kaposi's sarcoma, lymphoma, and acute lymphocytic leukemia. It is often used together with other chemotherapy agents. Doxorubicin is given by injection into a vein.
Common side effects include hair loss, bone marrow suppression, vomiting, rash, and inflammation of the mouth. Other serious side effects may include allergic reactions such as anaphylaxis, heart damage, tissue damage at the site of injection, radiation recall, and treatment-related leukemia. People often experience red discoloration of the urine for a few days. Doxorubicin is in the anthracycline and antitumor antibiotic family of medications. It works in part by interfering with the function of DNA.
Doxorubicin was approved for medical use in the United States in 1974. It is on the World Health Organization's List of Essential Medicines. Versions that are pegylated and in liposomes are also available; however, they are more expensive. Doxorubicin was originally made from the bacterium Streptomyces peucetius.