(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

• ChemBase ID: 576
• Molecular Formular: C27H29NO10
• Molecular Mass: 527.51986
• Monoisotopic Mass: 527.17914613
• SMILES: O([C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)c(OC)ccc2)C(=O)C)[C@@H]1O[C@H]([C@@H](O)[C@@H](N)C1)C
• Canonical SMILES: COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)C(=O)C
• 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
• InChIKey: STQGQHZAVUOBTE-VGBVRHCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
• IUPAC Traditional name: daunorubicin
• Brand Name: Acetyladriamycin; Anthracyline; Antibiotics From Streptomyces Coeruleorubidus; Cerubidin; Cerubidine; DM1; Daunamycin; Daunarubicinum; Daunoblastin; Daunomycin; Daunomycin Hydrochloride; Daunomycin, Hydrochloride; Daunorrubicina; Daunorubicin Hcl; Daunorubicin Hydrochloride; Daunorubicin, Hydrochloride; Daunorubicine; Daunorubicinum [INN-Latin]; Daunoxome; Leukaemomycin C; Ondena; Rcra Waste No. U059; Rp 13057 Hydrochloride; Rubidomycin; Rubidomycin Hydrochloride; Rubomycin C
• Synonyms: Daunorubicin

Database IDs

• CAS Number: 20830-81-3
• PubChem SID: 160964039; 46508433
• PubChem CID: 30323
• CHEBI ID: 41977
• ATC CODE: L01DB02
• CHEMBL: 178
• Chemspider ID: 28163
• DrugBank ID: DB00694
• KEGG ID: C01907
• Unique Ingredient Identifier: ZS7284E0ZP
• Wikipedia Title: Daunorubicin
• Medline Plus: a682289

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.530939
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.6256268
• LogD (pH = 7.4): 0.54168487
• Log P: 1.7336931
• Molar Refractivity: 132.8915 cm^3
• Polarizability: 52.022972 Å^3
• Polar Surface Area: 185.84 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.68
• LOG S: -2.93
• Solubility (Water): 6.27e-01 g/l

PROPERTIES

Physical Property

• Solubility: 39.2 mg/L
• Hydrophobicity(logP): 0.1

Pharmacology Properties

• Admin Routes: Exclusively intravenous. Causes severe necrosis if administered intramuscularly or subcutaneously
• Excretion: Biliary and urinary
• Half Life: 26.7 hours (metabolite)
• Metabolism: Hepatic
• Legal Status: Rx-only (US)
• Pregnancy Category: D (U.S.)

DETAILS

DrugBank - DB00694

• Drug Groups: approved
• Description: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of leukemia and other neoplasms. [PubChem]
• Indication: For remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults.
• Pharmacology: Daunorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Daunorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Daunorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
• Toxicity: LD₅₀=20 mg/kg (mice, IV); LD₅₀=13 mg/kg (rat, IV)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Half Life: 18.5 hours
• Protein Binding: 97% binding-albumin
• Elimination: Twenty-five percent of an administered dose of daunorubicin hydrochloride is eliminated in an active form by urinary excretion and an estimated 40% by biliary excretion.
• External Links: Wikipedia; RxList; Drugs.com