Atazanavir - CAS 198904-31-3
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Not Intended for Therapeutic Use. For research use only.
Atazanavir is a novel and potent azapeptide protease inhibitor that specifically inhibits the human immunodeficiency virus type 1 (HIV-1) protease enzyme with inhibition constant Ki of 66 nmol/L and also inhibits the viral replication of HIV-1 with 50% effective concentration EC50 ranging from 2.6 to 5.3 nmol/L. Atazanavir binds to HIV-1 protease preventing the cleavage of gag and gag-pol polyproteins, which results in the formation of immature virions in HIV-1-infected cells. Atazanavir has a different C-2 symmetric chemical structure and a generally greater antiretroviral potency in various HIV strains compared to other protease inhibitors, including indinavir, nelfinavir, ritonavir, saquinavir and amprenavir.
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Atazanavir ; Reyataz ; Atazanavir sulfate ; CGP75136 ; CGP75176 ; CGP75355 ; BMS232632 ; CGP 73547 ; CGP 75136 ; CGP 75176 ; CGP 75355 ; CGP-73547 ; CGP-75136 ; CGP-75176 ; CGP-75355 ; BMS 232632 ; BMS-232632 ; BMS-232632-05 ; C413408
1. Variations of the P2 group in HIV-1 protease inhibitors containing a tertiary alcohol in the transition-state mimicking scaffold
Jenny K. Ekegren, Johan Gising, Hans Wallberg, Mats Larhed, Bertil Samuelsson and Anders Hallberg*. Org. Biomol. Chem., 2006, 4, 3040–3043
Several of the approved HIV-1 protease inhibitors comprise relatively small, cyclic P2 structural elements. This is the case for example with amprenavir, containing tetrahydrofuran as the P2 group and for nelfinavir with a phenol-related structure in this position. On the other hand, the most recently launched inhibitor atazanavir, carries N-derivatized amino acid residues in the P2/P3 and P2’/P3’positions. Wewere encouraged to evaluate structural units representing both these types of substituents as potential P2 groups in our new inhibitors. The HIV-1 protease inhibition data summarized in Table 1 suggest that the size and polarity of the P2 substituent are crucial to allow proper accommodation in the S2 sub-site. Small P2 groups, unable to reach the enzyme S3 pocket, furnish poor to moderate inhibitory potencies. Furthermore, the distance between the transition-state mimicking tertiary hydroxyl group and P2 aromatic ring structures in 10, 12 and 13 proved to be of importance. A methylene spacer between the amide bond and the P2 aryl group as in compound 10 afforded a 5 to 13 times more potent inhibitor than 12 and 13 (Table 1). The amino acid-derived P2 substituents in compounds 14–18 have the potential of reaching both the enzyme S2 and S3 pockets, which could be beneficial for efficient binding. However, the bulkiness of the P2 side chain strongly affected inhibition and only the iso-propyl group present in compounds 14 and 15 provided highly potent inhibitors (Table 1).
2. HIV-1 protease inhibitors with a tertiary alcohol containing transition-state mimic and various P2 and P1'substituents
Per Ohrngren, Xiongyu Wu, Mats Larhed*. Med. Chem. Commun., 2011, 2, 701
With this background, we were interested in developing a straightforward synthetic approach for the incorporation of new amino acid derived P2–P3 groups into compound C, since amino acid derivated P2–P3 substituents have been successful in the case of the approved inhibitor Atazanavir (Atz) (Fig. 2). Furthermore, we aimed at optimising the most potent derivative in the P2–P3 series by creating a small library of compounds with various aromatic P1’ substituents using microwave accelerated, palladium-catalysed Suzuki–Miyaura and Sonogashira reactions. Within this article we present the synthetic protocols and the inhibitory potency on enzyme and in cell based assay of the final products, together with X-ray evaluation of two of the inhibitors.
3. Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space
Alexander Alex, David S. Millan,* Manuel Perez, Florian Wakenhut and Gavin A. Whitlock. Med. Chem. Commun., 2011, 2, 669
In line with the above thoughts and observations, atazanavir has high intrinsic cell permeability in an MDCK cell line suggesting the apparent polarity of the compound is lower than would be expected given its calculated physicochemistry. Rat pharmacokinetics also suggests the compound is well absorbed, but has low bioavailability due to high first pass clearance (Table 3). These data support the notion that atazanavir does indeed form an IHB stabilised conformation that hides its polarity and enables passive membrane permeation and therefore intestinal absorption to occur in rats and in human.
4. Discovery of GS-8374, a potent human immunodeficiency virus type 1 protease inhibitor with a superior resistance profile
Gong-Xing He, Zheng-Yu Yang, Lianhong Xu*. Med. Chem. Commun., 2011, 2, 1093
Boosting of PIs with low-dose RTV is now widely used to achieve desirable drug plasma concentrations, which lead to improved viral suppression while decreasing both the dosing frequency and pill burden. Current HIV treatment guidelines recommend ritonavir-boosted atazanavir (ATV) or darunavir (DRV) as a third agent of choice for first line antiretroviral therapy. Although there are nine PIs currently licensed for the treatment of HIV-1, and new generation PIs show better pharmacological properties than the earlier agents, profiles of most of the currently approved PIs can be further improved. The clinical benefit of this class of anti-retrovirals in general is still limited by several factors including resistance and long-term safety and tolerability. Among these, the emergence of drug-resistant HIV-1 variants continues to be a major cause of treatment failure and presents a major challenge to the control of HIV infection. In addition, with the exception of ATV, other PIs require high dose and/or frequent dosing regimens, limiting their use in fixed dose combination regimens. Therefore, the design of novel PIs with more favorable resistance profiles and convenient dosing regimens remains a consistent interest in the scientific community. This communication describes the discovery and characteristics of GS-8374 (compound 1, Fig. 1), a potent and orally bioavailable PI with a superior resistance profile against a spectrum of patient-derived HIV-1 variants highly resistant to multiple PIs. Because of its favorable pharmacological profile, GS-8374 (compound 1) has been further explored as a potential candidate for clinical development.
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CAS 198904-31-3 Atazanavir

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