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193275-84-2,MFCD06795138
Catalog No.:AA00ABHU

193275-84-2 | Lonafarnib

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Purity
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Price(USD)
Quantity
  
1mg
99%
in stock  
$24.00   $17.00
- +
5mg
99%
in stock  
$82.00   $57.00
- +
100mg
98%
in stock  
$1,077.00   $754.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00ABHU
Chemical Name:
Lonafarnib
CAS Number:
193275-84-2
Molecular Formula:
C27H31Br2ClN4O2
Molecular Weight:
638.8216
MDL Number:
MFCD06795138
SMILES:
Clc1cc(Br)c2c(c1)CCc1c([C@@H]2C2CCN(CC2)C(=O)CC2CCN(CC2)C(=O)N)ncc(c1)Br
NSC Number:
719467
Properties
Computed Properties
 
Complexity:
790  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
36  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
4.8  

Upstream Synthesis Route

[1]Patent:WO2004/31153,2004,A2,.Locationinpatent:Page20-22;30

[1]JournalofMedicinalChemistry,1998,vol.41,#24,p.4890-4902

[1]JournalofOrganicChemistry,2003,vol.68,#12,p.4984-4987

[1]JournalofOrganicChemistry,2003,vol.68,#12,p.4984-4987

[2]JournalofMedicinalChemistry,1998,vol.41,#24,p.4890-4902

[1]JournalofOrganicChemistry,2003,vol.68,#12,p.4984-4987

[2]JournalofMedicinalChemistry,1998,vol.41,#24,p.4890-4902

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Title: Hyperleukocytosis complicating lonafarnib treatment in patients with chronic myelomonocytic leukemia.

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Title: Farnesyl protein transferase inhibitors targeting the catalytic zinc for enhanced binding.

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Title: Bridgehead modification of trihalocycloheptabenzopyridine leads to a potent farnesyl protein transferase inhibitor with improved oral metabolic stability.

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Title: Design, synthesis, and activity of 4-quinolone and pyridone compounds as nonthiol-containing farnesyltransferase inhibitors.

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Title: The farnesyltransferase inhibitor Lonafarnib induces growth arrest or apoptosis of human lung cancer cells without downregulation of Akt.

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Title: Clinical activity of farnesyl transferase inhibitors in hematologic malignancies: possible mechanisms of action.

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Title: Farnesyltransferase inhibition: who are the Aktors?

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Title: Effects of insulin-like growth factor binding protein-3 and farnesyltransferase inhibitor SCH66336 on Akt expression and apoptosis in non-small-cell lung cancer cells.

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Title: Solution phase parallel synthesis and evaluation of MAPK inhibitory activities of close structural analogues of a Ras pathway modulator.

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Title: Farnesyltransferase inhibitors as anticancer agents: critical crossroads.

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Title: Protein farnesyltransferase inhibitor (SCH 66336) abolishes NF-kappaB activation induced by various carcinogens and inflammatory stimuli leading to suppression of NF-kappaB-regulated gene expression and up-regulation of apoptosis.

Journal: The Journal of biological chemistry 20040618

Title: Phase I study of the farnesyltransferase inhibitor lonafarnib with paclitaxel in solid tumors.

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Title: Novel agents and incremental advances in the treatment of head and neck cancer.

Journal: Seminars in oncology 20040401

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Title: In vitro study of farnesyltransferase inhibitor SCH 66336, in combination with chemotherapy and radiation, in non-small cell lung cancer cell lines.

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Title: Design, synthesis, and biological activity of 4-[(4-cyano-2-arylbenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitriles as potent and selective farnesyltransferase inhibitors.

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Title: Cancer treatment with kinase inhibitors: what have we learnt from imatinib?

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Title: The farnesyl protein transferase inhibitor lonafarnib (SCH66336) is an inhibitor of multidrug resistance proteins 1 and 2.

Journal: Chemotherapy 20031201

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20031101

Title: Farnesyltransferase inhibitors and their potential in the treatment of breast carcinoma.

Journal: Seminars in oncology 20031001

Title: Implication of protein kinase B/Akt and Bcl-2/Bcl-XL suppression by the farnesyl transferase inhibitor SCH66336 in apoptosis induction in squamous carcinoma cells.

Journal: Cancer research 20030815

Title: Farnesyltransferase inhibitors in acute myeloid leukemia and myelodysplastic syndromes.

Journal: Clinical lymphoma 20030801

Title: High-performance liquid chromatography-atmospheric pressure photoionization/tandem mass spectrometric analysis for small molecules in plasma.

Journal: Analytical chemistry 20030701

Title: A novel enantioselective alkylation and its application to the synthesis of an anticancer agent.

Journal: The Journal of organic chemistry 20030613

Title: Farnesyl transferase inhibitor SCH66336 is cytostatic, pro-apoptotic and enhances chemosensitivity to cisplatin in melanoma cells.

Journal: International journal of cancer 20030610

Title: Farnesyl transferase inhibitors in clinical development.

Journal: Expert opinion on investigational drugs 20030601

Title: Novel and selective imidazole-containing biphenyl inhibitors of protein farnesyltransferase.

Journal: Bioorganic & medicinal chemistry letters 20030407

Title: Preclinical and clinical evaluation of farnesyltransferase inhibitors.

Journal: Current oncology reports 20030301

Title: Apoptotic synergism between STI571 and the farnesyl transferase inhibitor SCH66336 on an imatinib-sensitive cell line.

Journal: Blood 20030301

Title: Farnesyl transferase inhibitors in the treatment of breast cancer.

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Title: Efficacy of SCH66336, a farnesyl transferase inhibitor, in conjunction with imatinib against BCR-ABL-positive cells.

Journal: Molecular cancer therapeutics 20030301

Title: Overcoming resistance to imatinib by combining targeted agents.

Journal: Molecular cancer therapeutics 20030301

Title: Trihalobenzocycloheptapyridine analogues of Sch 66336 as potent inhibitors of farnesyl protein transferase.

Journal: Bioorganic & medicinal chemistry 20030102

Title: Targeting RAS signalling pathways in cancer therapy.

Journal: Nature reviews. Cancer 20030101

Title: Sch-66336 (sarasar) and other benzocycloheptapyridyl farnesyl protein transferase inhibitors: discovery, biology and clinical observations.

Journal: Current topics in medicinal chemistry 20030101

Title: Farnesyltransferase inhibitors--a novel approach in the treatment of advanced pancreatic carcinomas.

Journal: Anticancer research 20030101

Title: Phase I and pharmacological study of the oral farnesyltransferase inhibitor SCH 66336 given once daily to patients with advanced solid tumours.

Journal: European journal of cancer (Oxford, England : 1990) 20021101

Title: Farnesyl transferase inhibitors as anticancer agents.

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Title: Farnesyl transferase inhibitors: a major breakthrough in anticancer therapy? Naples, 12 April 2002.

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Title: Exploring the role of bromine at C(10) of (+)-4-[2-[4-(8-chloro-3,10-dibromo- 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(R)-yl)-1-piperidinyl]-2- oxoethyl]-1-piperidinecarboxamide (Sch-66336): the discovery of indolocycloheptapyridine inhibitors of farnesyl protein transferase.

Journal: Journal of medicinal chemistry 20020829

Title: Overcoming STI571 resistance with the farnesyl transferase inhibitor SCH66336.

Journal: Blood 20020801

Title: A phase II trial of farnesyl protein transferase inhibitor SCH 66336, given by twice-daily oral administration, in patients with metastatic colorectal cancer refractory to 5-fluorouracil and irinotecan.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20020701

Title: Inhibitors of farnesyl protein transferase and MEK1,2 induce apoptosis in fibroblasts transformed with farnesylated but not geranylgeranylated H-Ras.

Journal: Experimental cell research 20020215

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20020101

Title: Agents targeting ras signaling pathway.

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Title: Farnesyltransferase inhibitors in breast cancer therapy.

Journal: Cancer investigation 20020101

Title: An anion-induced regio- and chemoselective acylation and its application to the synthesis of an anticancer agent.

Journal: Organic letters 20011115

Title: Current status of clinical trials of farnesyltransferase inhibitors.

Journal: Current opinion in oncology 20011101

Title: The farnesyl protein transferase inhibitor SCH66336 is a potent inhibitor of MDR1 product P-glycoprotein.

Journal: Cancer research 20011015

Title: Farnesyl protein transferase inhibition: a novel approach to anti-tumor therapy. the discovery and development of SCH 66336.

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Title: Farnesyltransferase inhibitors.

Journal: Seminars in oncology 20011001

Title: Isotype-specific Ras.GTP-levels predict the efficacy of farnesyl transferase inhibitors against human astrocytomas regardless of Ras mutational status.

Journal: Cancer research 20010601

Title: Synergy of the protein farnesyltransferase inhibitor SCH66336 and cisplatin in human cancer cell lines.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20010501

Title: Treatment of Bcr/Abl-positive acute lymphoblastic leukemia in P190 transgenic mice with the farnesyl transferase inhibitor SCH66336.

Journal: Blood 20010301

Title: Activity of the farnesyl protein transferase inhibitor SCH66336 against BCR/ABL-induced murine leukemia and primary cells from patients with chronic myeloid leukemia.

Journal: Blood 20010301

Title: Phase I and pharmacokinetic study of the oral farnesyl transferase inhibitor SCH 66336 given twice daily to patients with advanced solid tumors.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20010215

Title: The farnesyl transferase inhibitor SCH 66336 induces a G(2) --> M or G(1) pause in sensitive human tumor cell lines.

Journal: Experimental cell research 20010101

Title: Antitumor activity of SCH 66336, an orally bioavailable tricyclic inhibitor of farnesyl protein transferase, in human tumor xenograft models and wap-ras transgenic mice.

Journal: Cancer research 19981101

Title: Liu M, et al. Antitumor activity of SCH 66336, an orally bioavailable tricyclic inhibitor of farnesyl protein transferase, in human tumor xenograft models and wap-ras transgenic mice. Cancer Res. 1998 Nov 1;58(21):4947-56.

Title: Chaponis D, et al. Lonafarnib (SCH66336) improves the activity of temozolomide and radiation for orthotopic malignant gliomas. J Neurooncol. 2011 Aug;104(1):179-89.

Title: Koh C,et al. Oral prenylation inhibition with lonafarnib in chronic hepatitis D infection: a proof-of-concept randomised, double-blind, placebo-controlled phase 2A trial. Lancet Infect Dis. 2015 Oct;15(10):1167-1174.

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