(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 hydrochloride

• ChemBase ID: 72636
• Molecular Formular: C27H30ClNO10
• Molecular Mass: 563.9808
• Monoisotopic Mass: 563.15582385
• SMILES: c1ccc2c(c1OC)C(=O)c1c(C2=O)c(c2c(c1O)[C@H](C[C@](C2)(O)C(=O)C)O[C@H]1C[C@@H]([C@@H]([C@@H](O1)C)O)N)O.Cl
• 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.Cl
• InChI: InChI=1S/C27H29NO10.ClH/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;1H/t10-,14-,16-,17-,22+,27-;/m0./s1
• InChIKey: GUGHGUXZJWAIAS-QQYBVWGSSA-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 hydrochloride
• IUPAC Traditional name: daunorubicin hydrochloride
• Synonyms: (8S,10S)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione Hydrochloride; (8S-cis)-Daunomycin Hydrochloride; 13-Dihydrocarminomycin; Cerubidine; Daunoblastin; Daunomycin Chlorohydrate; NDC 0082-4155; Ondena; RP 13057 Hydrochloride; Daunorubicin Hydrochloride; Daunomycin hydrochloride; Daunorubicin; Rubidomycin hydrochloride; Cerubidine; Daunorubicin hydrochloride; (-)-Daunorubicin; WP900 hydrochloride; Daunorubicin HCl (Daunomycin HCl); Daunorubicinol hydrochloride; 道诺霉素 盐酸盐; 柔红霉素 盐酸盐

Database IDs

• CAS Number: 23541-50-6
• EC Number: 245-723-4
• MDL Number: MFCD04974507
• Beilstein Number: 4229221
• PubChem SID: 24858374; 24724666; 162037561; 24894229
• PubChem CID: 62770

CALCULATED PROPERTIES

• Acid pKa: 7.996109
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.49411148
• LogD (pH = 7.4): 0.9138854
• Log P: 1.3442496
• 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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Dark Red Solid; solid
• Melting Point: >180°C (dec)

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: HB7878000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-40-42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H334-H351; H302-H334-H351
• GHS Precautionary statements: P261-P281-P301 + P310-P342 + P311; P261-P281-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Target: Telomerase; Topoisomerase

Product Information

• Purity: ≥90% (HPLC); ≥95% (HPLC); 95+%
• Salt Data: HCL; Hydrochloride
• Suitability: meets USP testing specifications
• Empirical Formula (Hill Notation): C27H29NO10 · HCl; C27H30NO10Cl

DETAILS

Selleck Chemicals - S1216

Biological Activity:
Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is the hydrochloride salt of an anthracycline cytotoxic antibiotic produced by a strain of Streptomyces coeruleorubidus (IC50=0.5μM). On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) has the highest preference for two adjacent G/C base pairs flanked on the 5’ side by an A/T base pair. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) effectively binds to every 3 base pairs and induces a local unwinding angle of 11o, but negligible distortion of helical conformation. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is chemotherapeutic of the anthracycline family that is given as a treatment for some types of cancer. Cerubidine (Daunorubicin HCl, Rubidomycin HCl) is most commonly used to treat specific types of leukaemia (acute myeloid leukemia and acute lymphocytic leukemia). Cerubidine (Daunorubicin HCl, Rubidomycin HCl) was initially isolated from Streptomyces peucetius. [1][2][3]

Sigma Aldrich - 30450

Biochem/physiol Actions
Daunorubicin inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent. On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. Daunomycin effectively binds to every 3 base pairs which causes unwinding.
Potent anticancer agent. Inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent. Properties
Application
Daunorubicin hydrochloride is used in photostability 1, antileukemic, 2, and drug metabolism studies 3.

Sigma Aldrich - W4013

Biochem/physiol Actions
Synthetic left-handed enantiomer of (+)-daunorubicin, anti-tumor antibiotic, binds to right-handed B-form DNA under low salt conditions.

Sigma Aldrich - D8809

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
强效抗癌剂，已证明是 DNA 和 RNA 合成的强抑制剂。性质
自发荧光的蒽环类抗生素，抗癌药。Pgp、MRP-1 和 BCRP 的底物。已利用荧光特性来测量药物外排泵活性，以及解决许多重要问题，如多种多药耐药蛋白的胞内定位和亚细胞器（高尔基体和溶酶体）在药物螯合中的作用及其在耐药表型中的含义。根据 pH 分配型机理将柔红霉素螯合进溶酶体。1,2DNA 和 RNA 合成的强抑制剂。

Toronto Research Chemicals - D194500

Anthracycline antibiotic related to the rhodomycins. Antineoplastic.

REFERENCES

• http://www.cancer.gov/drugdictionary/?CdrID=39779
• Yang, Z., et al.: J. Pharmacol. Experim. Ther., 327, 474 (2008)
• Zhao, Y., et al.: Int. J. Pharm., 379, 90 (2008)
• Bayne, W., et al.: J. Pharm. Sci., 98, 2540 (2008)