tipifarnib

Also 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 Å²
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

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