(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;hydron;chloride
Basic information
- CAS
23541-50-6- Standard SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)=O)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.[Cl-].[H+]- InChIKey
GUGHGUXZJWAIAS-QQYBVWGSSA-N- Molecular formula
- C27H30ClNO10
- Average molar mass
- 564 g/mol
- Monoisotopic mass
- 563.1558238
Overview
See also: Daunorubicin Hydrochloride (preferred); Daunorubicin (has active moiety); Idarubicin (related) ... View More ...
Names & identifiers
- Preferred name
- (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;hydron;chloride
- IUPAC
- (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;hydron;chloride
- English name
- Daunorubicin hydrochloride
- Molecular formula
- C27H29NO10.ClH
- Molecular weight
- 563.98
Names & synonyms
SCHEMBL14973357AKOS015896281DAUNORUBICIN HCLCerubidineDAUNOMYCIN HCLDAUNOMYCIN HYDROCHLORIDEErythromycin hydrochloride(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 hydrochlorideondenaCS-585daunoblastinndc0082-4155
Database identifiers
- CAS
23541-50-6- PubChem CID
- 657197
Properties
Computed structural properties
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 4
- Heavy atoms
- 39
- Formal charge
- 0
- Complexity
- 960
Physicochemical properties
- Melting point
- 190 °C · 190°C (dec)
- alpha
- 20 · D20 +248 ±5° (c = 0.05-0.1 in methanol)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Freely soluble in water and in methanol, slightly soluble in alcohol, practically insoluble in acetone.
- form
- solid
- color
- red to deep red
- Water Solubility
- Soluble in water (50 mM)
- λmax
- 477 nm · 477nm(H2O)(lit.)
- Sensitive
- Hygroscopic
- Merck
- 14 · 14,2832
- BRN
- 4229221 · 4229221
- Stability
- Stability
- InChIKey
- GUGHGUXZJWAIAS-SMLRDAARNA-N
- SMILES
- C1=CC2C(=O)C3=C(O)C4C[C@](C(C)=O)(O)C[C@H](O[C@@H]5O[C@@H](C)[C@@H](O)[C@@H](N)C5)C=4C(O)=C3C(=O)C=2C(OC)=C1.Cl |&1:10,16,18,20,22,24,r|
- NCI Dictionary of Cancer Terms
- Cerubidine; daunomycin hydrochloride; daunorubicin hydrochloride
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-10
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- HB7878000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29419059
- Toxicity
- LD50 in mice (mg/kg): 26 i.v. (DiMarco, 1969)
- risk_code
- 22-40-42/43-36/37/38-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- Xn,Xi
- safety_code
- 22-36/37-45-37/39-36-26
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301-H341-H351-H360FD
- Hazard Classifications
- Acute Tox. 3 OralCarc. 2Muta. 2Repr. 1B
- Precautionary statements
- P201-P202-P264-P270-P280-P301+P310
Chemistry & industry
Applications
DescriptionDaunorubicin HCl (23541-50-6) is an antitumor antibiotic used in the treatment of acute myeloid leukemias.1Induces DNA damage by intercalation.2Induces apoptosis in a variety of cell lines.3Inhibition of autophagy with chloroquine enhances daunorubicin-induced apoptosis in K562 cells.4Cell permeable.
UsesAnthracycline antibiotic related to the rhodomycins. Antineoplastic
UsesAntineoplastic;DNA intercaling
Usesanti-neoplastic LD50 in mice 26 mg/kg
UsesA DNA intercalator which may suppress acute leukemia proliferation
General DescriptionDaunorubicin is available in 20- and 100-mg vials for reconstitution.The agent is given intravenously for the treatmentof acute nonlymphocytic and lymphocytic leukemia. Otherunlabeled uses include CML and Kaposi sarcoma. In general,its use is more limited than that of doxorubicin.Daunorubicin lacks the hydroxyl groups found at C-14 ofdoxorubicin. This leads to an increase in the amount of thealcohol metabolite daunorubicinol (active) arising as a resultof reduction of the side chain ketone. This, however, doesnot appear to lead to a significant increase in the occurrenceof cardiotoxicity compared with doxorubicin. The mechanismsof resistance and toxicities of daunorubicin are similarto that of doxorubicin; the major difference betweenthe two agents being the spectrum of cancers that they areused treat.A liposomal form of daunorubicin is also availableknown as DaunoXome. The drug offers the same advantagesas those seen for the liposomal form of doxorubicin.
General DescriptionOrange-red powder. Thin red needles decomposing at 188-190°C. An anti-cancer drug.
Upstream & downstream products
Upstream raw materials
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…