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Carfilzomib

CAT#: H200630

CAS#: 868540-17-4

Description: Carfilzomib, also known as PR-171, is a tetrapeptide epoxyketone and an epoxomicin derivate with potential antineoplastic activity. Carfilzomib irreversibly binds to and inhibits the chymotrypsin-like activity of the 20S proteasome, an enzyme responsible for degrading a large variety of cellular proteins. Inhibition of proteasome-mediated proteolysis results in an accumulation of polyubiquinated proteins, which may lead to cell cycle arrest, induction of apoptosis, and inhibition of tumor growth. Carfilzomib was approved by the FDA for use in patients with relapsed and refractory multiple myeloma on 20 July 2012.

Synthetic Routes

Carfilzomib - Synthetic Route 1

Synthetic reference

Screen, Michael; Britton, Matthew; Downey, Sondra L.; Verdoes, Martijn; Voges, Mathias J.; Blom, Annet E. M.; Geurink, Paul P.; Risseeuw, Martijn D. P.; Florea, Bogdan I.; van der Linden, Wouter A.; Pletnev, Alexandre A.; Overkleeft, Herman S.; Kisselev, Alexei F. Nature of Pharmacophore Influences Active Site Specificity of Proteasome Inhibitors. Journal of Biological Chemistry. Volume 285. Issue 51. Pages 40125-40134. Journal. (2010).

Carfilzomib - Synthetic Route 2

Synthetic reference

Anon. Process for the preparation of carfilzomib. IP.com Journal. Volume 14. Issue 12B. Pages 1-19. Journal; Patent. (2014).

Carfilzomib - Synthetic Route 3

Synthetic reference

Chava, Satyanarayana; Gorantla, Seeta Rama Anjaneyulu; Indukuri, Venkata Sunil Kumar; Dehury, Sanjay Kumar; Mekala, Nagaraju; Buddepu, Srinivasa Rao. An improved processes for the preparation of carfilzomib and their pharmaceutically acceptable salts. Assignee Laurus Labs Private Ltd., India. IN 2015CH02543. (2016).

Carfilzomib - Synthetic Route 4

Synthetic reference

Pullagurla, Manik Reddy; Rangisetty, Jagadeesh Babu; Kumar, Mecheril Valsan Nanda; Pendyala, Surya Bala Subrahmanyam; Pitta, Bhaskar Reddy. Process for the preparation of (S)-4-methyl-N-[(S)-1-[[(S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]-2-[[(S)-2-(2-morpholinoacetamido)-4-phenylbutanoyl]amino]pentanamide. Assignee Biophore India Pharmaceutials Pvt. Ltd., India. IN 2014CH04670. (2016).

Carfilzomib - Synthetic Route 5

Synthetic reference

Thirumalai Rajan, Srinivasan; Eswaraiah, Sajja; Reddy, Ghojala Venkat; Reddy, Katta Laxmi. Process for the preparation of (2S)-N-[(S)-1-[[(S)-4-methyl-1-((R)-2-methyloxiran-2-yl)-1-oxopentan-2-yl]carbamoyl]-2-phenylethyl]-2-[[(S)-2-(2-morpholinoacetamido)-4-phenylbutanoyl]amino]-4-methylpentanamide and its novel intermediates. Assignee MSN Laboratories Private Limited, India. WO 2016170544. (2016).

Carfilzomib - Synthetic Route 6

Synthetic reference

Kovi, Ravishanker; Kannapan, Jayaraman; Ramu, Vasanthakumar G.; Prasad, Alaparthi Lakshmi; Chowdary, Talluri Bhushaiah; Kulkarni, Gaurav; Ahmed, Saiyed Akeel Ahmed Shakeel; Bobbili, Veerabhadra Rao; Dusanapudi, N. V. Raghavalu; Mantri, Anand V. Active ester intermediates for the preparation of carfilzomib using fragment condensation. Assignee Apicore US LLC, USA. US 20160115198. (2016).