Basic information
- CAS
25316-40-9- Standard SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.[Cl-].[H+]- InChIKey
MWWSFMDVAYGXBV-RUELKSSGSA-N- Molecular formula
- C27H30ClNO11
- Average molar mass
- 580 g/mol
- Monoisotopic mass
- 579.1507385
Overview
See also: Doxorubicin Hydrochloride (preferred); Doxorubicin (has active moiety).
Names & identifiers
- Preferred name
- (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;hydron;chloride
- IUPAC
- (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;hydron;chloride
- English name
- Doxorubicin hydrochloride
- Molecular formula
- C27H29NO11.ClH
- Molecular weight
- 579.98
Names & synonyms
SCHEMBL28158260DOXDOXORUBICIN HCLADRDoxorubicin HCIDOX HClCAELYXDOX HYDROCHLORIDEADRIAMYCIN HYDROCHLORIDEDoxorubicin hydrochlorid(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-methoxynaphthacene-5,12-dione hydrochloride
Database identifiers
- CAS
25316-40-9- PubChem CID
- 657367
Properties
Computed structural properties
- Topological polar surface area
- 206 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 5
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 977
Physicochemical properties
- Melting point
- 216 °C · 216 °C (dec.)(lit.)
- alpha
- 20 · D20 +248±2° (c = 0.1 in methanol)
- storage temp.
- 2 · 2-8°C
- solubility
- 100 mg/ml; · Soluble in DMSO at 100 mg/ml; very poorly soluble in ethanol; soluble in water at 10 mg/ml with slight warming.
- pka
- 8.25 · pKa 8.25±0.60 (Uncertain);8.43±0.70 (Uncertain);11.9±0.4 (Uncertain);12.95±0.1 (Uncertain);13.8±0.70 (Uncertain)
- form
- solid
- color
- orange to dark red
- biological source
- synthetic (organic)
- Water Solubility
- Soluble in water.
- λmax
- 497 nm · 497nm(H2O)(lit.)
- Merck
- 14 · 14,3439
- BRN
- 4229251 · 4229251
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
- InChIKey
- MWWSFMDVAYGXBV-RUELKSSGSA-N
- SMILES
- Cl[H].COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO
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
- 10-21
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- QI9295900
- ridadr
- UN2811
- hs_code
- 29419090
- Toxicity
- LD50 i.v. in mice: 21.1 mg/kg (Bertazzoli, 1970)
- risk_code
- 45-22-40-26/27/28-36/38
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- T,T+,Xi
- safety_code
- 53-45-36/37/39-22-7/9
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H302-H340-H350-H360FD
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 4 OralCarc. 1BMuta. 1BRepr. 1B
- Precautionary statements
- P201-P202-P264-P270-P301+P312-P308+P313
Chemistry & industry
Applications
UsesStrong fluorescent dye intercalating into DNA. Antitumour antibiotic. Effect of adriamycin on heart mitochondrial DNA. Inhibitor of reverse transcriptase and RNA polymerase; immunosuppressive agent.
UsesDoxorubicin hydrochloride (adriamycin hydrochloride) is an antitumour agent that has been formulated as a salt to achieve higher water solubility. While the salt shares the same pharmacological properties as doxorubicin free base, its greater water solubility may offer advantages in some in vitro applications. Physicochemical properties and chromatographic behaviour will depend on whether the pH is buffered. In non-pH controlled systems the free base and salt may behave differently.
UsesDoxorubicin is an anthracycline antitumor antibiotic that inhibits DNA topoisomerase II by inducing double-stranded DNA breaks. By intercalating within DNA, doxorubicin inhibits nucleic acid synthesis and induces apoptosis by inducing the accumulation of the p53 tumor suppressor protein.[Cayman Chemical]
General DescriptionAdriamycin hydrochloride appears as orange-red thin needles. Aqueous solutions yellow-orange at acid pHs, orange-red at neutral pHs, and violet blue over pH 9. Doxorubicin is available as both the conventional dosageform and a liposomal preparation, both of which are administeredby infusion. Doxorubicin HCl powder is available in10-, 20-, 50-, and 150-mg vials and is widely used in treatingvarious cancers, including leukemias, soft and bone tissuesarcomas, Wilms tumor, neuroblastoma, small cell lungcancer, and ovarian and testicular cancer.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers
Related reactions
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Compound notes
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