Valrubicin

Base Information

• Chemical Name: Valrubicin
• CAS No.: 56124-62-0
• Molecular Formula: C34H36F3NO13
• Molecular Weight: 723.654
• Hs Code.: 2941906000
• Mol file: 56124-62-0.mol

Synonyms:Pentanoic acid,2-[1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-4-[[2,3,6-trideoxy-3-[(trifluoroacetyl)amino]-a-L-lyxo-hexopyranosyl]oxy]-2-naphthacenyl]-2-oxoethylester, (2S-cis)-;AD 32;Antibiotic AD 32;N-Trifluoroacetyladriamycin14-valerate;N-Trifluoroacetyldoxorubicin 14-valerate;NSC 246131;Trifluoroacetyladriamycin 14-valerate;Valstar;

Chemical Property of Valrubicin

Chemical Property:

• Vapor Pressure: 3.81E-32mmHg at 25°C
• Melting Point: 116-117 °C
• Refractive Index: 1.618
• Boiling Point: 867.711 °C at 760 mmHg
• PKA: 7.34±0.60(Predicted)
• Flash Point: 478.575 °C
• PSA: 215.22000
• Density: 1.54 g/cm³
• LogP: 2.85310
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: insoluble

Purity/Quality:

99% ^*data from raw suppliers

Valrubicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Description: Valrubicin was launched as a new 'chemotherapeutic agent for the treatment of bladder cancer, particularly in patients with BCG-refractory carcinoma in situ (CIS) of the bladder for whom immediate cystectomy is unacceptable. It belongs to the class of anthracyclines, the widest used in human cancers, and is a N-trifluoroacetyl 14-valerate derivative of doxorubicin.Valrubicin can be obtained in 3 steps from daunomycin by N-trifluoroacetylation of the sugar moiety then iodination of the 2-acetyl group and introduction of a valerate residue. A proposed mechanism involved in the cytotoxicity of Valrubicin coud be the blockade of SV40 large T antigen helicase; this cellular enzyme is involved in the formation of a ternary complex with DNA to maintain the topographic structure of DNA during transcription. In patients with CIS of bladder refractory to front line and second line therapies, intravesical instillation of Valrubicin resulted in a complete response with a significant rate and allowed a delay in cystectomy. Systemic absorption was minimal and accordingly produced a lower incidence of cardiotoxicity compared with doxorubicin.
• Uses: Chemotherapy drug used to treat cancer of the bladder.
• Therapeutic Function: Antineoplastic
• Clinical Use: Valrubicin currently has orphan drug status in the treatment of bacille Calmette-Guérin (BCG)–refractory bladder cancer (the total patient population is ~1,000 individuals) and is used with patients for whom surgical intervention would result in high morbidity or death.

Technology Process of Valrubicin

There total 5 articles about Valrubicin 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:

adriamycin 14-valerate (80287-44-1) + trifluoroacetic anhydride (407-25-0) → valrubicin (56124-62-0)

Guidance literature:

In dichloromethane; at -2 - 2 ℃; for 4h;

Reference yield:

N-Trifluoroacetyladriamycin (26295-56-7) + vinyl valerate (5873-43-8) → valrubicin (56124-62-0)

Guidance literature:

With candida antarctic lipase B; In acetonitrile; at 50 ℃; for 8h; Solvent; Reagent/catalyst; Enzymatic reaction;

DOI:10.1039/c3ra44879g

Reference yield:

14-bromo-13-dimethylketal-daunorubicin (106401-68-7) → valrubicin (56124-62-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen bromide / acetone; water / 6 h / 15 - 20 °C / pH 3

2: acetone / 15 - 20 °C / Inert atmosphere

3: dichloromethane / 4 h / -2 - 2 °C

With hydrogen bromide; In dichloromethane; water; acetone;

upstream raw materials:

N-Trifluoroacetyladriamycin

vinyl valerate

adriamycin 14-valerate

trifluoroacetic anhydride

Downstream raw materials:

9,10-anhydro-N-(trifluoroacetyl)adriamycin 14-valerate

Refernces

• 1、 Zhang, Yifei,Dai, Yang,Hou, Miao,Li, Tian,Ge, Jun,Liu, Zheng. "Chemo-enzymatic synthesis of valrubicin using Pluronic conjugated lipase with temperature responsiveness in organic media". . p. 22963 - 22966. Retrieved 2013/11/19.
• 2、 -. "Crystalline forms of valrubicin and processes for their preparation". Page/Page column 6. . Retrieved 2008/12/06.