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Structure via PubChem · Public domain (PubChem)
tipifarnib
Sign in to saveAlso known as Zarnestra
Tipifarnib (INN, proposed trade name Zarnestra) is a farnesyltransferase inhibitor. Farnesyltransferase inhibitors block the activity of the farnesyltransferase enzyme by inhibiting prenylation of the CAAX tail motif, which ultimately prevents Ras from binding to the membrane, rendering it inactive.
In the Vinony graph
Within Vinony's link graph, tipifarnib is referenced by 327 other articles, and connects out to tiazofurin, digital object identifier and chemical formula.
It is catalogued under topics including 2-Quinolones, 3-Chlorophenyl compounds and 4-Chlorophenyl compounds.
Its subject is documented across 4 Wikipedia language editions.
Chemical data
- Formula
- C27H22Cl2N4O
- Molecular weight
- 489.4 g/mol
- IUPAC name
- 6-[(R)-amino-(4-chlorophenyl)-(3-methylimidazol-4-yl)methyl]-4-(3-chlorophenyl)-1-methylquinolin-2-one
- SMILES
- CN1C=NC=C1[C@@](C2=CC=C(C=C2)Cl)(C3=CC4=C(C=C3)N(C(=O)C=C4C5=CC(=CC=C5)Cl)C)N
- InChIKey
- PLHJCIYEEKOWNM-HHHXNRCGSA-N
- XLogP
- 4.1
- Polar surface area
- 64.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- chronic lymphocytic leukemia, melanoma, pancreatic carcinoma, gliosarcoma
via ChEMBL · EBI
Research
480 papers- Tipifarnib Reduces Extracellular Vesicles and Protects From Heart Failure.Circulation research · 2024
- Tipifarnib: farnesyl transferase inhibition at a crossroads.Expert review of anticancer therapy · 2006
- Tipifarnib Inhibits HRAS-Driven Dedifferentiated Thyroid Cancers.Cancer research · 2018
- Tipifarnib in Head and Neck Squamous Cell Carcinoma With HRAS Mutations.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 2021
- Tipifarnib (Janssen Pharmaceutica).Current opinion in investigational drugs (London, England : 2000) · 2002
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 488.117066684
- Has use
- medication
Show 5 more facts
- chemical formula
- C₂₇H₂₂Cl₂N₄O
- canonical SMILES
- CN1C=NC=C1C(C2=CC=C(C=C2)Cl)(C3=CC4=C(C=C3)N(C(=O)C=C4C5=CC(=CC=C5)Cl)C)N
- subject has role
- antineoplastic
- Commons category
- Tipifarnib
- isomeric SMILES
- Cn1cncc1[C@@](N)(c1ccc(Cl)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)cc(=O)n2C
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- History
- Investigations
- Cancer
- Progeria
- References
Tipifarnib (INN, proposed trade name Zarnestra) is a farnesyltransferase inhibitor. Farnesyltransferase inhibitors block the activity of the farnesyltransferase enzyme by inhibiting prenylation of the CAAX tail motif, which ultimately prevents Ras from binding to the membrane, rendering it inactive.
==History== The compound was discovered by Johnson & Johnson Pharmaceutical Research & Development, L.L.C, with registration number R115777.
Excerpted from Wikipedia’s “tipifarnib” article, available under the CC BY-SA 4.0 licence.