Des(benzylpyridyl) Atazanavir | CAS#1192224-24-0 | Atazanavir metabolite

MedKoo Cat#: 562705 | Name: Des(benzylpyridyl) Atazanavir

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Des(benzylpyridyl) Atazanavir is a metabolite of Atazanavir, a human immunodeficiency virus protease inhibitor.

Chemical Structure

Des(benzylpyridyl) Atazanavir

CAS#1192224-24-0

Theoretical Analysis

MedKoo Cat#: 562705

Name: Des(benzylpyridyl) Atazanavir

CAS#: 1192224-24-0

Chemical Formula: C26H43N5O7

Exact Mass: 537.3162

Molecular Weight: 537.65

Elemental Analysis: C, 58.08; H, 8.06; N, 13.03; O, 20.83

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 285.00	2 Weeks
25mg	USD 550.00	2 Weeks

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Synonym

Des(benzylpyridyl) Atazanavir; FT-0665859; FT 0665859; FT0665859;

IUPAC/Chemical Name

Methyl N-[(2R)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2R)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate

InChi Key

LUAXFCAWZAZCNR-MUGJNUQGSA-N

InChi Code

InChI=1S/C26H43N5O7/c1-25(2,3)19(29-23(35)37-7)21(33)28-17(14-16-12-10-9-11-13-16)18(32)15-27-31-22(34)20(26(4,5)6)30-24(36)38-8/h9-13,17-20,27,32H,14-15H2,1-8H3,(H,28,33)(H,29,35)(H,30,36)(H,31,34)/t17-,18-,19-,20-/m0/s1

SMILES Code

O=C(OC)N[C@H](C(C)(C)C)C(NNC[C@H](O)[C@@H](NC([C@H](NC(OC)=O)C(C)(C)C)=O)CC1=CC=CC=C1)=O

Appearance

Off-White Solid

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

A metabolite of atazanavir.

In vitro activity:

After CoCl2-induced hypoxia, HLF-1 cell proliferation increased compared with the control group (p < 0.01) (fig. 4), but was significantly inhibited in a concentration-dependent manner after atazanavir sulphate treatment at concentrations between 1 and 10 μM compared with the CoCl2 group (p < 0.05). To further characterize this inhibitory effect, atazanavir sulphate treatment was combined with HCQ, a TLR-9 antagonist. However, this study found no further decline in HLF-1 proliferation compared with the HCQ group (p > 0.05) (fig. 4). Reference: Basic Clin Pharmacol Toxicol. 2018 Feb;122(2):199-207. https://pubmed.ncbi.nlm.nih.gov/28816009/

In vivo activity:

This study evaluated the effect of atazanavir on LVSP and ± dp/dtmax of the left ventricle after MI 28 days. Compared with vehicle-treated animals, rats treated with atazanavir had significantly improved LVSP, + dp/dtmax and − dp/dtmax 28 days after MI as shown in Table 2. In addition, this study found no further change in SP, DP and HR compared with the HCQ group (P > 0.05). It is clear that continuous atazanavir treatment 28 days provided long-term benefits for the myocardial function recovery after MI. Reference: Eur J Pharmacol. 2018 Jun 5;828:97-102. https://pubmed.ncbi.nlm.nih.gov/29605419/

	Solvent	mg/mL	mM
Solubility
	DMSO	30.0	55.80
	DMF	30.0	55.80
	Ethanol	30.0	55.80

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 537.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Zhang G, Zhang X, Li D, Tian J, Jiang W. Long-term oral atazanavir attenuates myocardial infarction-induced cardiac fibrosis. Eur J Pharmacol. 2018 Jun 5;828:97-102. doi: 10.1016/j.ejphar.2018.03.041. Epub 2018 Mar 29. PMID: 29605419. 2. Song S, Ji Y, Zhang G, Zhang X, Li B, Li D, Jiang W. Protective Effect of Atazanavir Sulphate Against Pulmonary Fibrosis In Vivo and In Vitro. Basic Clin Pharmacol Toxicol. 2018 Feb;122(2):199-207. doi: 10.1111/bcpt.12871. Epub 2017 Sep 6. PMID: 28816009.

In vitro protocol:

1. Song S, Ji Y, Zhang G, Zhang X, Li B, Li D, Jiang W. Protective Effect of Atazanavir Sulphate Against Pulmonary Fibrosis In Vivo and In Vitro. Basic Clin Pharmacol Toxicol. 2018 Feb;122(2):199-207. doi: 10.1111/bcpt.12871. Epub 2017 Sep 6. PMID: 28816009.

In vivo protocol:

1: ter Heine R, Hillebrand MJ, Rosing H, van Gorp EC, Mulder JW, Beijnen JH, Huitema AD. Identification and profiling of circulating metabolites of atazanavir, a HIV protease inhibitor. Drug Metab Dispos. 2009 Sep;37(9):1826-40. doi: 10.1124/dmd.109.028258. Epub 2009 Jun 22. PubMed PMID: 19546238.