(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

Base Information

• Chemical 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
• CAS No.: 25316-40-9
• Molecular Formula: C27H30ClNO11
• Molecular Weight: 579.988
• Hs Code.: 29419090
• Mol file: 25316-40-9.mol

Synonyms:

Chemical Property of (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

Chemical Property:

• Appearance/Colour: orange-red crystalline solid
• Vapor Pressure: 9.64E-28mmHg at 25°C
• Melting Point: 216 °C (dec.)(lit.)
• Boiling Point: 810.3 °C at 760 mmHg
• PKA: 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)
• Flash Point: 443.8 °C
• PSA: 206.07000
• LogP: 1.50360
• Storage Temp.: 2-8°C
• Solubility.: H2O: 10 mg/mL, clear, red-orange
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 5
• Exact Mass: 579.1507385
• Heavy Atom Count: 40
• Complexity: 977

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Doxorubicin Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,T+
• Hazard Codes: T,T+,Xi
• Statements: 45-22-40-26/27/28-36/38
• Safety Statements: 53-45-36/37/39-22-7/9

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [H+].CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.[Cl-]
• Isomeric SMILES: [H+].C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.[Cl-]
• Indications: Doxorubicin is a potent antitumour agent active against a wide spectrum of malignancies, including leukaemias, sarcomas, breast cancer, small cell lung cancer and ovarian cancer. Doxorubicin is used to produce regression in disseminated neoplastic conditions like acute lymphoblastic leukemia, acute myeloblastic leukemia, Wilms’ tumor, neuroblastoma, soft tissue and bone sarcomas, breast carcinoma, ovarian carcinoma, transitional cell bladder carcinoma, thyroid carcinoma, gastric carcinoma, Hodgkin's disease, malignant lymphoma and bronchogenic carcinoma in which the small cell histologic type is the most responsive compared to other cell types. Doxorubicin is also indicated for use as a component of adjuvant therapy in women with evidence of axillary lymph node involvement following resection of primary breast cancer. Doxorubicin does not playa crucial role in the treatment of tumours that can be cured with chemotherapy, such as testicular carcinoma, nephroblastoma, Burkitt's tumour and choriocarcinoma[3]. Like most other cytostatic agents, doxorubicin is not effective in the most frequently occurring malignancies such as colorectal cancer and non-small cell lung cancer.
• Description: Doxorubicin HCl (25316-40-9) is an antitumor antibiotic. Induces DNA damage by intercalation1 and inhibition of topoisomerase II. Doxorubicin HCl induces apoptosis in a variety of cell lines.2 Acts as a substrate for MDR1.3?Cell permeable.
• Uses: Strong fluorescent dye intercalating into DNA. Antitumour antibiotic. Effect of adriamycin on heart mitochondrial DNA. Inhibitor of reverse transcriptase and RNA polymerase; immunosuppressive agent. Antibacterial;DNA intercalant Doxorubicin 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. Doxorubicin 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]
• Therapeutic Function: Cancer chemotherapy
• Biological Functions: The C13 substituent of doxorubicin is hydroxymethyl, which retards the action of cytosolic aldoketoreductase and slows the conversion to the equally active, but chronically cardiotoxic, doxorubicinol.
• Clinical Use: Doxorubicin is utilized either alone or in combination therapy to treat a wide range of neoplastic disorders, including hematologic cancers and solid tumors in breast, ovary, stomach, bladder, and thyroid gland. A liposomal formulation of doxorubicin is used in the treatment of AIDS-related Kaposi's sarcoma and organoplatinum-resistant ovarian cancer.
• Drug interactions: Potentially hazardous interactions with other drugsAntipsychotics: avoid with clozapine, increased risk of agranulocytosis.Ciclosporin: increased risk of neurotoxicityCytotoxics: possible increased risk of cardiotoxicity with trastuzumab - avoid for 28 weeks after stopping trastuzumab.Avoid with live vaccines.

Technology Process of (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

There total 13 articles about (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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

14-bromodaunorubicin hydrochloride (29742-67-4) → doxorubicin hydrochloride (25316-40-9)

Guidance literature:

In water; dimethyl sulfoxide; at 80 ℃; for 2h;

DOI:10.1016/0008-6215(88)80021-1

Reference yield:

doxorubicin → doxorubicin hydrochloride (25316-40-9)

Guidance literature:

With 3,6-dimethyl-1,2,4,5-tetrazine; In acetonitrile; Reagent/catalyst;

Reference yield:

C47H55N5O20S2 → C21H30N4O10S3 + doxorubicin hydrochloride (25316-40-9)

Guidance literature:

C₄₇H₅₅N₅O₂₀S₂; With triethyl ammonium acetate; triethylamine; In aq. buffer; at 20 ℃; for 2h; pH=9.5 - 9.9; Darkness;

With acetic acid; In aq. buffer; pH=8.2; Darkness;

In aq. buffer; pH=6-7; Darkness;

DOI:10.1039/c7cc06843c

upstream raw materials:

14-bromodaunorubicin hydrochloride

daunomycin hydrochloride

Downstream raw materials:

Ac-LGLYL-Dox

Ac-PLGLYL-Dox

Ac-PLGLYAL-Dox

Ac-PLG-S(OMe)YL-Dox

Refernces

• 1、 -. "ADIPOCYTE MEDIATED DELIVERY OF ANTICANCER THERAPEUTICS". Page/Page column 29. . Retrieved 2020/05/28.
• 2、 -. "CHANNEL PROTEIN ACTIVATABLE LIPOSOMES". Page/Page column 112. . Retrieved 2014/06/11.