Vemurafenib
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MedKoo CAT#: 202271

CAS#: 918504-65-1

Description: Vemurafenib, also known as PLX4032, RG7204 or RO5185426, is an orally bioavailable, ATP-competitive, small-molecule inhibitor of BRAF(V600E) kinase with potential antineoplastic activity. Vemurafenib received FDA approval for the treatment of late-stage melanoma on August 17, 2011. Vemurafenib selectively binds to the ATP-binding site of BRAF(V600E) kinase and inhibits its activity, which may result in an inhibition of an over-activated MAPK signaling pathway downstream in BRAF(V600E) kinase-expressing tumor cells and a reduction in tumor cell proliferation.


Chemical Structure

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Vemurafenib
CAS# 918504-65-1

Theoretical Analysis

MedKoo Cat#: 202271
Name: Vemurafenib
CAS#: 918504-65-1
Chemical Formula: C23H18ClF2N3O3S
Exact Mass: 489.07255
Molecular Weight: 489.92
Elemental Analysis: C, 56.39; H, 3.70; Cl, 7.24; F, 7.76; N, 8.58; O, 9.80; S, 6.54

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500.0mg USD 150.0 Ready to ship
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10.0g USD 1250.0 Ready to ship
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Related CAS #: 918505-61-0 (analog)   918504-65-1    

Synonym: PLX4032; PLX 4032; PLX-4032; RG7204 ; RG7204 ; RG 7204 ; RO5185426; RO 5185426 RO5185426 Vemurafenib; Brand name: Zelboraf

IUPAC/Chemical Name: N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide

InChi Key: GPXBXXGIAQBQNI-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H18ClF2N3O3S/c1-2-9-33(31,32)29-19-8-7-18(25)20(21(19)26)22(30)17-12-28-23-16(17)10-14(11-27-23)13-3-5-15(24)6-4-13/h3-8,10-12,29H,2,9H2,1H3,(H,27,28)

SMILES Code: CCCS(=O)(NC1=CC=C(F)C(C(C2=CNC3=NC=C(C4=CC=C(Cl)C=C4)C=C32)=O)=C1F)=O

Appearance: White to off-white crystalline solid

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 80.0 163.29
Ethanol 0.0 0.0
Water 0.0 0.0

Preparing Stock Solutions

The following data is based on the product molecular weight 489.92 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Pellowska M, Merk D, Schubert-Zsilavecz M. Advances in personalized medicine - medicinal chemistry and pharmacology of vemurafenib and ivacaftor. Pharmazie. 2013 Jul;68(7):484-91. Review. PubMed PMID: 23923627.

2: Banaszynski M, Kolesar JM. Vemurafenib and ipilimumab: new agents for metastatic melanoma. Am J Health Syst Pharm. 2013 Jul 15;70(14):1205-10. doi: 10.2146/ajhp120260. Review. PubMed PMID: 23820456.

3: Liszkay G. [Vemurafenib (Zelboraf) in the therapy of melanoma]. Magy Onkol. 2013 Jun;57(2):110-3. doi: MagyOnkol.2013.57.2.110. Epub 2013 May 14. Review. Hungarian. PubMed PMID: 23795356.

4: Shaw HM, Nathan PD. Vemurafenib in melanoma. Expert Rev Anticancer Ther. 2013 May;13(5):513-22. doi: 10.1586/era.13.24. Review. PubMed PMID: 23617343.

5: Gonzalez D, Fearfield L, Nathan P, Tanière P, Wallace A, Brown E, Harwood C, Marsden J, Whittaker S. BRAF mutation testing algorithm for vemurafenib treatment in melanoma: recommendations from an expert panel. Br J Dermatol. 2013 Apr;168(4):700-7. doi: 10.1111/bjd.12248. Review. PubMed PMID: 23360189.

6: Sharma A, Shah SR, Illum H, Dowell J. Vemurafenib: targeted inhibition of mutated BRAF for treatment of advanced melanoma and its potential in other malignancies. Drugs. 2012 Dec 3;72(17):2207-22. doi: 10.2165/11640870-000000000-00000. Review. PubMed PMID: 23116250.

7: Jordan EJ, Kelly CM. Vemurafenib for the treatment of melanoma. Expert Opin Pharmacother. 2012 Dec;13(17):2533-43. doi: 10.1517/14656566.2012.737780. Epub 2012 Oct 24. Review. PubMed PMID: 23094782.

8: Bollag G, Tsai J, Zhang J, Zhang C, Ibrahim P, Nolop K, Hirth P. Vemurafenib: the first drug approved for BRAF-mutant cancer. Nat Rev Drug Discov. 2012 Nov;11(11):873-86. doi: 10.1038/nrd3847. Epub 2012 Oct 12. Review. PubMed PMID: 23060265.

9: Keating GM. Vemurafenib: in unresectable or metastatic melanoma. BioDrugs. 2012 Oct 1;26(5):325-34. doi: 10.2165/11209860-000000000-00000. Review. PubMed PMID: 22946753.

10: Boyd KP, Vincent B, Andea A, Conry RM, Hughey LC. Nonmalignant cutaneous findings associated with vemurafenib use in patients with metastatic melanoma. J Am Acad Dermatol. 2012 Dec;67(6):1375-9. doi: 10.1016/j.jaad.2012.06.045. Epub 2012 Aug 30. Review. PubMed PMID: 22940405.



Additional Information

Vemurafenib is developed by Plexxikon (now part of the Daiichi Sankyo group) and Hoffmann–La Roche for the treatment of late-stage melanoma. Vemurafenib received FDA approval for the treatment of late-stage melanoma on August 17, 2011. 
   
Drug information
ZELBORAF (vemurafenib) is a kinase inhibitor available as 240 mg tablets for oral use. Vemurafenib has the chemical name propane-1-sulfonic acid {3-[5-(4-chlorophenyl)-lH-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl}-amide. It has the molecular formula C23H18ClF2N3O3S and a molecular weight of 489.9. Vemurafenib is a white to off-white crystalline solid. It is practically insoluble in aqueous media. Tablets of ZELBORAF are for oral administration. Each tablet contains 240 mg of vemurafenib. The inactive ingredients of ZELBORAF are: Tablet Core: hypromellose acetate succinate, croscarmellose sodium, colloidal silicon dioxide, magnesium stearate, and hydroxypropyl cellulose. Coating: pinkish white: poly(vinyl alcohol), titanium dioxide, polyethylene glycol 3350, talc, and iron oxide red.  Indication: ZELBORAF™ is indicated for the treatment of patients with unresectable or metastatic melanoma with BRAFV600E mutation as detected by an FDA-approved test. Limitation of Use: ZELBORAF is not recommended for use in patients with wild-type BRAF melanoma.
   
Mechanism of Action:
Vemurafenib is a low molecular weight, orally available, inhibitor of some mutated forms of BRAF serine-threonine kinase, including BRAFV600E. Vemurafenib also inhibits other kinases in vitro such as CRAF, ARAF, wild-type BRAF, SRMS, ACK1, MAP4K5 and FOR at similar concentrations. Some mutations in the BRAF gene including V600E result in constitutively activated BRAF proteins, which can cause cell proliferation in the absence of growth factors that would normally be required for proliferation. Vemurafenib has anti-tumor effects in cellular and animal models of melanomas with mutated BRAFV600E.  Pharmacokinetics: The pharmacokinetics of vemurafenib were determined in patients with BRAF mutation-positive metastatic melanoma following 15 days of dosing at 960 mg twice daily with dosing approximately 12 hours apart. The population pharmacokinetic analysis pooled data from 458 patients. A one-compartment disposition model with first-order absorption and first-order elimination adequately describes the vemurafenib concentration-time profile. At steady state, vemurafenib exhibits linear pharmacokinetics within the 240 mg to 960 mg dose range.