Vemurafenib

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Cat Number

API918504651

CAS Number

918504-65-1

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Product Detail Description Scientific Support Customer Q&A

CAS Number

918504-65-1

EINECS

850-250-7

Storage

Store at room temperature

Synonyms

Zelboraf; PLX 4032; RG 7204; RO 5185426; vemurafenibum

Molecular Formula

C23H18ClF2N3O3S

Molecular Weight

489.9

Smiles

CCCS(=O)(=O)NC1=C(C(=C(C=C1)F)C(=O)C2=CNC3=C2C=C(C=N3)C4=CC=C(C=C4)Cl)F

Appearance

White to almost white powder

Melting Point

271°C

Relative Density

1.47 (Predicted)

General Description

Vemurafenib is a low molecular weight, oral, small-molecule inhibitor of the BRAF serine-threonine kinase, specifically targeting the V600E mutant form, a sulfonamide derivative with a pyrrolopyridine core. The drug is a white to off-white powder, practically insoluble in water. Vemurafenib is structurally distinct from other kinase inhibitors, with a unique 7-azaindole scaffold.

Mechanism of Action

Vemurafenib selectively binds to the ATP-binding site of the mutated BRAF kinase (V600E), inhibiting its activity and blocking downstream signaling through the mitogen-activated protein kinase (MAPK) pathway. This inhibits the proliferation of tumor cells harboring the BRAF V600E mutation and induces apoptosis. The drug is 100-fold more potent against the mutant form than against wild-type BRAF.

Application

Vemurafenib is indicated for the treatment of unresectable or metastatic melanoma with the BRAF V600E mutation, as detected by an FDA-approved test. It is also used for Erdheim-Chester disease and for BRAF V600E-positive non-small cell lung cancer (NSCLC).

In a single-arm phase 2 study, 30 previously untreated hairy cell leukemia patients received vemurafenib (960 mg twice daily for 4 cycles) plus obinutuzumab (cycles 2–4). Complete remission was achieved in 27 of 30 patients (90%; 95% CI 73–98). Among CR patients, 96% achieved minimal residual disease negativity, and BRAF V600E was undetectable by ddPCR in all evaluable patients. At median 34.9 months follow-up, no relapses occurred. Common adverse events were rash and arthralgia. This time-limited combination is highly active and well tolerated.

Fig. 1 Hematologic and Molecular Parameters in Patients with HCL during Combination Treatment with Vemurafenib and Obinutuzumab. (Park JH, et al., 2023)

References

Park JH, et al. Vemurafenib and Obinutuzumab as Frontline Therapy for Hairy Cell Leukemia. NEJM Evid. 2023;2(10):EVIDoa2300074.

Does Vemurafenib require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation of the sulfonamide group. Store in light-resistant containers, preferably original opaque packaging.

What is the recommended storage temperature for Vemurafenib?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which can soften the powder and accelerate oxidative degradation.

Is Vemurafenib hygroscopic, and how is this managed?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump. Storage in tightly sealed containers with desiccant is recommended.

How is the impurity vemurafenib N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.