CHEBI:63637 - vemurafenib

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name vemurafenib
ChEBI ID CHEBI:63637
Definition A pyrrolopyridine that is 1H-pyrrolo[2,3-b]pyridine which is substituted at position 5 by a p-chlorophenyl group and at positions 3 by a 3-amino-2,6-difluorobenzoyl group, the amino group of which has undergone formal condensation with propane-1-sulfonic acid to give the corresponding sulfonamide. An inhibitor of BRAF and other kinases.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Kalpana P
Secondary ChEBI IDs CHEBI:194457
Supplier Information ChemicalBook:CB02550000, ChemicalBook:CB22515128, eMolecules:32176418, Selleckchem:PLX-4032, ZINC000052509366
Download Molfile XML SDF
more structures >>
Wikipedia License
Vemurafenib (INN), sold under the brand name Zelboraf, is a medication used for the treatment of late-stage melanoma. It is an inhibitor of the B-Raf enzyme and was developed by Plexxikon.
Read full article at Wikipedia
Formula C23H18ClF2N3O3S
Net Charge 0
Average Mass 489.920
Monoisotopic Mass 489.07255
InChI 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)
InChIKey GPXBXXGIAQBQNI-UHFFFAOYSA-N
SMILES CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C2=CNC3=C2C=C(C=N3)C2=CC=C(Cl)C=C2)=C1F
Roles Classification
Biological Role(s): B-Raf inhibitor
A serine/threonine kinase inhibitor that specifically inhibits human mutant serine/threonine kinase (B-Raf)
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing vemurafenib (CHEBI:63637) has role antineoplastic agent (CHEBI:35610)
vemurafenib (CHEBI:63637) has role B-Raf inhibitor (CHEBI:75047)
vemurafenib (CHEBI:63637) is a aromatic ketone (CHEBI:76224)
vemurafenib (CHEBI:63637) is a difluorobenzene (CHEBI:38582)
vemurafenib (CHEBI:63637) is a monochlorobenzenes (CHEBI:83403)
vemurafenib (CHEBI:63637) is a pyrrolopyridine (CHEBI:46771)
vemurafenib (CHEBI:63637) is a sulfonamide (CHEBI:35358)
IUPAC Name
N-(3-{[5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl}-2,4-difluorophenyl)propane-1-sulfonamide
INNs Sources
vemurafenib WHO MedNet
vemurafenib WHO MedNet
vémurafénib WHO MedNet
vemurafenibum WHO MedNet
Synonyms Sources
PLX 4032 ChEBI
PLX-4032 DrugBank
PLX4032 DrugBank
RG 7204 ChEBI
RG-7204 DrugBank
RG7204 DrugBank
Ro 51-85426 DrugCentral
RO 5185426 DrugCentral
RO-51-85426 DrugBank
RO-5185426 DrugBank
RO5185426 DrugBank
Brand Name Source
Zelboraf KEGG DRUG
Manual Xrefs Databases
032 PDBeChem
4185 DrugCentral
D09996 KEGG DRUG
DB08881 DrugBank
LSM-1068 LINCS
Vemurafenib Wikipedia
WO2010114928 Patent
View more database links
Registry Numbers Types Sources
12833468 Reaxys Registry Number Reaxys
918504-65-1 CAS Registry Number ChemIDplus
Citations
Dugauquier A, Awada AH, Motulsky E, Kisma N (2024)
INTRAVITREAL METHOTREXATE IN VEMURAFENIB-INDUCED UVEITIS.
Retinal cases & brief reports 18, 455-458 [PubMed:36977328]
[show Abstract]
Pérez CN, Falcón CR, Mons JD, Orlandi FC, Sangiacomo M, Fernandez-Muñoz JM, Guerrero M, Benito PG, Colombo MI, Zoppino FCM, Alvarez SE (2023)
Melanoma cells with acquired resistance to vemurafenib have decreased autophagic flux and display enhanced ability to transfer resistance.
Biochimica et biophysica acta. Molecular basis of disease 1869, 166801 [PubMed:37419396]
[show Abstract]
Car I, Dittmann A, Klobučar M, Grbčić P, Kraljević Pavelić S, Sedić M (2023)
Secretome Screening of BRAFV600E-Mutated Colon Cancer Cells Resistant to Vemurafenib.
Biology 12, 608 [PubMed:37106808]
[show Abstract]
Evseev D, Osipova D, Kalinina I, Raykina E, Ignatova A, Lyudovskikh E, Baidildina D, Popov A, Zhogov V, Semchenkova A, Litvin E, Kotskaya N, Cherniak E, Voronin K, Burtsev E, Bronin G, Vlasova I, Purbueva B, Fink O, Pristanskova E, Dzhukaeva I, Erega E, Novichkova G, Maschan A, Maschan M (2023)
Vemurafenib combined with cladribine and cytarabine results in durable remission of pediatric BRAF V600E-positive LCH.
Blood advances 7, 5246-5257 [PubMed:37216396]
[show Abstract]
Madej E, Brożyna AA, Adamczyk A, Wronski N, Harazin-Lechowska A, Muzyk A, Makuch K, Markiewicz M, Rys J, Wolnicka-Glubisz A (2023)
Vemurafenib and Dabrafenib Downregulates RIPK4 Level.
Cancers 15, 918 [PubMed:36765875]
[show Abstract]
Oliveira-Santos A, Dagda M, Wittmann J, Smalley R, Burkin DJ (2023)
Vemurafenib improves muscle histopathology in a mouse model of LAMA2-related congenital muscular dystrophy.
Disease models & mechanisms 16, dmm049916 [PubMed:37021539]
[show Abstract]
Dummer R, Flaherty KT, Robert C, Arance A, B de Groot JW, Garbe C, Gogas HJ, Gutzmer R, Krajsová I, Liszkay G, Loquai C, Mandalà M, Schadendorf D, Yamazaki N, Pietro AD, Cantey-Kiser J, Edwards M, Ascierto PA (2023)
COLUMBUS 5-year update: a randomized, open-label, phase III trial of encorafenib plus binimetinib versus vemurafenib or encorafenib in patients with BRAF.
Future oncology (London, England) 19, 1091-1098 [PubMed:37309702]
[show Abstract]
Peng J, Lin Z, Chen W, Ruan J, Deng F, Yao L, Rao M, Xiong X, Xu S, Zhang X, Liu X, Sun X (2023)
Vemurafenib induces a noncanonical senescence-associated secretory phenotype in melanoma cells which promotes vemurafenib resistance.
Heliyon 9, e17714 [PubMed:37456058]
[show Abstract]
Hu HF, Gao GB, He X, Li YY, Li YJ, Li B, Pan Y, Wang Y, He QY (2023)
Targeting ARF1-IQGAP1 interaction to suppress colorectal cancer metastasis and vemurafenib resistance.
Journal of advanced research 51, 135-147 [PubMed:36396045]
[show Abstract]
Ma W, Tian M, Hu L, Ruan X, Zhang W, Zheng X, Gao M (2023)
Early Combined SHP2 Targeting Reverses the Therapeutic Resistance of Vemurafenib in Thyroid Cancer.
Journal of Cancer 14, 1592-1604 [PubMed:37325052]
[show Abstract]
Wang X, Cheng Q (2023)
Suppression of exosomal hsa_circ_0001005 eliminates the Vemurafenib resistance of melanoma.
Journal of cancer research and clinical oncology 149, 5921-5936 [PubMed:36598578]
[show Abstract]
Laajala M, Zwaagstra M, Martikainen M, Nekoua MP, Benkahla M, Sane F, Gervais E, Campagnola G, Honkimaa A, Sioofy-Khojine AB, Hyöty H, Ojha R, Bailliot M, Balistreri G, Peersen O, Hober D, Van Kuppeveld F, Marjomäki V (2023)
Vemurafenib Inhibits Acute and Chronic Enterovirus Infection by Affecting Cellular Kinase Phosphatidylinositol 4-Kinase Type IIIβ.
Microbiology spectrum 11, e0055223 [PubMed:37436162]
[show Abstract]
Żołek T, Mazurek A, Grudzinski IP (2023)
In Silico Studies of Novel Vemurafenib Derivatives as BRAF Kinase Inhibitors.
Molecules (Basel, Switzerland) 28, 5273 [PubMed:37446932]
[show Abstract]
Zhou H, Li XF, Chen MJ, Cai LL (2023)
Severe cumulative skin toxicity during toripalimab combined with vemurafenib following toripalimab alone.
Open life sciences 18, 20220606 [PubMed:37215493]
Piejko K, Cybulska-Stopa B, Ziętek M, Dziura R, Galus Ł, Kempa-Kamińska N, Ziółkowska B, Rutkowska E, Kopciński T, Kubiatowski T, Bal W, Suwiński R, Mackiewicz J, Kamińska-Winciorek G, Czarnecka AM, Rutkowski P (2023)
Long-Term Real-World Outcomes and Safety of Vemurafenib and Vemurafenib + Cobimetinib Therapy in Patients with BRAF-Mutated Melanoma.
Targeted oncology 18, 235-245 [PubMed:36906728]
[show Abstract]
Editors of The Lancet Oncology (2023)
Retraction and republication-Atezolizumab, vemurafenib, and cobimetinib in patients with melanoma with CNS metastases (TRICOTEL): a multicentre, open-label, single-arm, phase 2 study.
The Lancet. Oncology 24, 832 [PubMed:37459870]
Dummer R, Queirolo P, Gerard Duhard P, Hu Y, Wang D, de Azevedo SJ, Robert C, Ascierto PA, Chiarion-Sileni V, Pronzato P, Spagnolo F, Mujika Eizmendi K, Liszkay G, de la Cruz Merino L, Tawbi H (2023)
Atezolizumab, vemurafenib, and cobimetinib in patients with melanoma with CNS metastases (TRICOTEL): a multicentre, open-label, single-arm, phase 2 study.
The Lancet. Oncology 24, e461-e471 [PubMed:37459873]
[show Abstract]
Lang M, Longerich T, Anamaterou C (2023)
Targeted therapy with vemurafenib in BRAF(V600E)-mutated anaplastic thyroid cancer.
Thyroid research 16, 5 [PubMed:36855200]
[show Abstract]
Furfaro AL, Loi G, Ivaldo C, Passalacqua M, Pietra G, Mann GE, Nitti M (2022)
HO-1 Limits the Efficacy of Vemurafenib/PLX4032 in BRAFV600E Mutated Melanoma Cells Adapted to Physiological Normoxia or Hypoxia.
Antioxidants (Basel, Switzerland) 11, 1171 [PubMed:35740068]
[show Abstract]
Garutti M, Bergnach M, Polesel J, Palmero L, Pizzichetta MA, Puglisi F (2022)
BRAF and MEK Inhibitors and Their Toxicities: A Meta-Analysis.
Cancers 15, 141 [PubMed:36612138]
[show Abstract]
Johnson AE, Raju AR, Jacob A, Hildebrandt GC (2022)
Case report: A case of classic hairy cell leukemia with CNS involvement treated with vemurafenib.
Frontiers in oncology 12, 1100577 [PubMed:36713531]
[show Abstract]
Tabolacci C, Giordano D, Rossi S, Cordella M, D'Arcangelo D, Moschella F, D'Atri S, Biffoni M, Facchiano A, Facchiano F (2022)
Identification of Dihydrolipoamide Dehydrogenase as Potential Target of Vemurafenib-Resistant Melanoma Cells.
Molecules (Basel, Switzerland) 27, 7800 [PubMed:36431901]
[show Abstract]
Rossman P, Zabka TS, Ruple A, Tuerck D, Ramos-Vara JA, Liu L, Mohallem R, Merchant M, Franco J, Fulkerson CM, Bhide KP, Breen M, Aryal UK, Murray E, Dybdal N, Utturkar SM, Fourez LM, Enstrom AW, Dhawan D, Knapp DW (2021)
Phase I/II Trial of Vemurafenib in Dogs with Naturally Occurring, BRAF-mutated Urothelial Carcinoma.
Molecular cancer therapeutics 20, 2177-2188 [PubMed:34433660]
[show Abstract]
Shirkavand A, Mohajerani E, Farivar S, Ataie-Fashtami L, Ghazimoradi MH (2021)
Monitoring the Response of Skin Melanoma Cell Line (A375) to Treatment with Vemurafenib: A Pilot In Vitro Optical Spectroscopic Study.
Photobiomodulation, photomedicine, and laser surgery 39, 164-177 [PubMed:33595357]
[show Abstract]
Ko CJ, McNiff JM, Iftner A, Iftner T, Choi JN (2013)
Vemurafenib (PLX-4032)-induced keratoses: verrucous but not verrucae.
Journal of the American Academy of Dermatology 69, e95-6 [PubMed:23866896]
Yang H, Higgins B, Kolinsky K, Packman K, Bradley WD, Lee RJ, Schostack K, Simcox ME, Kopetz S, Heimbrook D, Lestini B, Bollag G, Su F (2012)
Antitumor activity of BRAF inhibitor vemurafenib in preclinical models of BRAF-mutant colorectal cancer.
Cancer research 72, 779-789 [PubMed:22180495]
[show Abstract]
Luke JJ, Hodi FS (2012)
Vemurafenib and BRAF inhibition: a new class of treatment for metastatic melanoma.
Clinical cancer research : an official journal of the American Association for Cancer Research 18, 9-14 [PubMed:22083257]
[show Abstract]
Niehr F, von Euw E, Attar N, Guo D, Matsunaga D, Sazegar H, Ng C, Glaspy JA, Recio JA, Lo RS, Mischel PS, Comin-Anduix B, Ribas A (2011)
Combination therapy with vemurafenib (PLX4032/RG7204) and metformin in melanoma cell lines with distinct driver mutations.
Journal of translational medicine 9, 76 [PubMed:21609436]
[show Abstract]
Flaherty KT, Yasothan U, Kirkpatrick P (2011)
Vemurafenib.
Nature reviews. Drug discovery 10, 811-812 [PubMed:22037033]
[show Abstract]
Heakal Y, Kester M, Savage S (2011)
Vemurafenib (PLX4032): an orally available inhibitor of mutated BRAF for the treatment of metastatic melanoma.
The Annals of pharmacotherapy 45, 1399-1405 [PubMed:22028422]
[show Abstract]
Chapman PB, Hauschild A, Robert C, Haanen JB, Ascierto P, Larkin J, Dummer R, Garbe C, Testori A, Maio M, Hogg D, Lorigan P, Lebbe C, Jouary T, Schadendorf D, Ribas A, O'Day SJ, Sosman JA, Kirkwood JM, Eggermont AM, Dreno B, Nolop K, Li J, Nelson B, Hou J, Lee RJ, Flaherty KT, McArthur GA, BRIM-3 Study Group (2011)
Improved survival with vemurafenib in melanoma with BRAF V600E mutation.
The New England journal of medicine 364, 2507-2516 [PubMed:21639808]
[show Abstract]
Last Modified
20 July 2023