Valrubicin

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Cat Number

API56124620

CAS Number

56124-62-0

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Product Detail Description Scientific Support Customer Q&A

CAS Number

56124-62-0

EINECS

680-664-1

Storage

Store at 2-8℃

Synonyms

Valtaxin; AD 32; Valstar Preservative Free; Valrubicina; Valrubicine; DTXSID9046497; 2C6NUM6878; Adriamycin, trifluoroacetyl-, 14-valerate; N-Trifluoroacetyladriamycin-14-valerate

Molecular Formula

C34H36F3NO13

Molecular Weight

723.6

Smiles

CCCCC(=O)OCC(=O)[C@]1(C[C@@H](C2=C(C1)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4OC)O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)NC(=O)C(F)(F)F)O

Appearance

Orange to red powder

Melting Point

116-117℃

General Description

Valrubicin is a semisynthetic anthracycline analogue of doxorubicin, formulated for intravesical instillation in the treatment of bladder cancer. It is a lipophilic prodrug that penetrates rapidly into urothelial cells, where it is converted to active metabolites. This agent was specifically developed for local therapy of bacillus Calmette-Guérin (BCG)-refractory carcinoma in situ of the bladder.

Mechanism of Action

Following cellular uptake, valrubicin is metabolized to multiple active anthracycline derivatives, including N-trifluoroacetyladriamycin and its 14-hemiester. These metabolites intercalate into DNA, inhibiting topoisomerase II and disrupting DNA replication and transcription. The result is cell cycle arrest and apoptosis. Because the drug is administered intravesically, high local concentrations are achieved with minimal systemic absorption, reducing typical anthracycline toxicities such as cardiotoxicity.

Application

It is indicated for intravesical therapy of BCG-refractory carcinoma in situ of the urinary bladder in patients who cannot undergo immediate cystectomy. It is administered weekly for six weeks via a urinary catheter. Common local adverse effects include bladder irritation, dysuria, hematuria, and urinary frequency. Systemic absorption is minimal, but patients should be monitored for bone marrow suppression. Valrubicin is not used for invasive bladder cancer.

Using UV‑Vis spectrophotometry and cyclic voltammetry, the interaction between the anticancer drug valrubicin and fish sperm DNA was characterized in phosphate buffer (pH 7.4). The binding constant (k_b) was 1.75×10³ L/mol. Competitive displacement with methylene blue confirmed intercalation. The non‑electrostatic binding constant remained nearly constant across different ionic strengths, while the electrostatic contribution increased from 4.5% to 23.8%, indicating mixed binding modes (intercalation and electrostatic). Cyclic voltammetry showed a redox pair at 0.45 V and 0.36 V; peak currents decreased and peak potentials shifted positively upon DNA addition, consistent with intercalation. Thermodynamic parameters (ΔH⁰, ΔS⁰, ΔG⁰) suggested a spontaneous, entropy‑driven process.

Fig. 1 Absorption spectra of MB in the present of DNA at different concentrations. (Hajian R, et al., 2017)

References

Hajian R, et al. DNA-binding studies of valrubicin as a chemotherapy drug using spectroscopy and electrochemical techniques. J Pharm Anal. 2017; 7(3):176-180.

Does Valrubicin require refrigerated storage as an anthracycline analog?

Yes, it must be stored at 2-8°C. It is thermally labile and degrades rapidly at room temperature, forming aglycone and other degradation products.

Is Valrubicin sensitive to light during long-term storage?

Yes, it is highly photosensitive. Store in light-resistant containers, preferably amber glass, and protect from direct UV light at all times.

What is the stability of Valrubicin in intravesical solution formulations?

Reconstituted solutions should be used within a few hours under protection from light.

How is the impurity valrubicinol (the 14-hydroxy metabolite) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains below qualification thresholds throughout shelf life.