Oxocarbazate | CAS#1014405-03-8 | Cathepsin L Inhibitor

MedKoo Cat#: 564753 | Name: Oxocarbazate

Description:

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

Oxocarbazate, also known as CID23631927, is an inhibitor of human cathepsin L. In the cathepsin L inhibition assay, The oxocarbazate caused a time-dependent 17-fold drop in IC50 from 6.9 nM (no preincubation) to 0.4 nM (4-h preincubation). Slowly reversible inhibition was demonstrated in a dilution assay. CID 23631927 is a subnanomolar, slow-binding, reversible inhibitor of human cathepsin L that blocked SARS-CoV and Ebola pseudotype virus entry in human cells. Inhibition of cathepsin L thus holds promise for therapeutic intervention for both SARS-CoV and Ebola virus infection.

Chemical Structure

Oxocarbazate

CAS#1014405-03-8

Theoretical Analysis

MedKoo Cat#: 564753

Name: Oxocarbazate

CAS#: 1014405-03-8

Chemical Formula: C28H33N5O6

Exact Mass: 535.2431

Molecular Weight: 535.60

Elemental Analysis: C, 62.79; H, 6.21; N, 13.08; O, 17.92

Price and Availability

Size	Price	Availability
5mg	USD 150.00	Ready to ship
10mg	USD 250.00	Ready to ship
25mg	USD 450.00	Ready to ship
50mg	USD 750.00	Ready to ship
100mg	USD 1,250.00	Ready to ship
200mg	USD 1,750.00	Ready to ship
500mg	USD 2,950.00	Ready to Ship

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Related CAS #

1014405-03-8 1194047-02-3

Synonym

Oxocarbazate; CID 23631927; CID23631927; CID-23631927;

IUPAC/Chemical Name

N-[(1,1-Dimethylethoxy)carbonyl]-L-tryptophan 2-[[2-(3,4-dihydro-1(2H)-quinolinyl)-2-oxoethoxy]carbonyl]hydrazide

InChi Key

MITOFRSPGLYHSJ-QFIPXVFZSA-N

InChi Code

InChI=1S/C28H33N5O6/c1-28(2,3)39-26(36)30-22(15-19-16-29-21-12-6-5-11-20(19)21)25(35)31-32-27(37)38-17-24(34)33-14-8-10-18-9-4-7-13-23(18)33/h4-7,9,11-13,16,22,29H,8,10,14-15,17H2,1-3H3,(H,30,36)(H,31,35)(H,32,37)/t22-/m0/s1

SMILES Code

O=C(NNC(OCC(N1CCCC2=C1C=CC=C2)=O)=O)[C@@H](NC(OC(C)(C)C)=O)CC3=CNC4=C3C=CC=C4

Appearance

Solid powder

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

>3 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

Inhibition of cathepsin L thus holds promise for therapeutic intervention for both SARS-CoV and Ebola virus infection. With respect to the development of antiviral agents, inhibitors of human cathepsin L are not subject to resistance because of rapid mutations of the viral genome. Cathepsin L is therefore an attractive target for drug development.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#YXM200716

QC Data

View QC data: current batch, Lot#YXM200716

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Oxocarbazate, also known as CID23631927, is an inhibitor of human cathepsin L.

In vitro activity:

CID 23631927 was found to inhibit cathepsin L with an IC50 of 6.9 ± 1.0 nM when assayed immediately after mixing with the target enzyme in HEK 293T cells. Upon preincubation with cathepsin L for a period of 1, 2, or 4 h, the tetrahydroquinoline oxocarbazate demonstrated a time-dependent reduction of IC50 from 2.3 ± 0.1 nM (1 h) to 1.2 ± 0.1 nM (2 h) to 0.4 ± 0.1 nM (4 h) (Fig. 1C), demonstrating a slow on-rate of inhibition. The slow on-rate of inhibition is clearly apparent in Fig. 3C, as product formation rate slowly dropped in the assay. The best fit parameters for CID 23631927 were k1 = 2.27 × 106 M−1 · s−1, k−1 = 0.29 s−1, kcat = 3.78 s−1, kon = 153,000 M−1 · s−1, and koff = 4.40 × 10−5 · s−1. The five parameters, k1, k−1, kcat, and koff do not vary substantially between the thiocarbazate (CID 16725315) and the oxocarbazate (CID 23631927) tests. For the two slow on-rate inhibitors, the fitted kinetic parameter kon for CID 23631927 was rate controlling, displaying a rate almost five times greater than that for CID 16725315, resulting in a calculated inhibition constant for the oxocarbazate of Ki = 0.29 nM. Additionally, the oxocarbazate inhibitor (CID 23631927) caused a 38% reduction in the active intracellular cathepsin L level compared with lane 1. This suggests that inhibition of cathepsin L alone is sufficient to block Ebola pseudotype virus entry in HEK 293T cells without the need to simultaneously block cathepsin B. Reference: Mol Pharmacol. 2010 Aug; 78(2): 319–324. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2917856/

In vivo activity:

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	0.00

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 535.60 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. Shah PP, Wang T, Kaletsky RL, Myers MC, Purvis JE, Jing H, Huryn DM, Greenbaum DC, Smith AB 3rd, Bates P, Diamond SL. A small-molecule oxocarbazate inhibitor of human cathepsin L blocks severe acute respiratory syndrome and ebola pseudotype virus infection into human embryonic kidney 293T cells. Mol Pharmacol. 2010 Aug;78(2):319-24. doi: 10.1124/mol.110.064261. Epub 2010 May 13. PMID: 20466822; PMCID: PMC2917856.

In vitro protocol:

In vivo protocol:

1: Shah PP, Wang T, Kaletsky RL, Myers MC, Purvis JE, Jing H, Huryn DM, Greenbaum DC, Smith AB 3rd, Bates P, Diamond SL. A small-molecule oxocarbazate inhibitor of human cathepsin L blocks severe acute respiratory syndrome and ebola pseudotype virus infection into human embryonic kidney 293T cells. Mol Pharmacol. 2010 Aug;78(2):319-24. doi: 10.1124/mol.110.064261. Epub 2010 May 13. PubMed PMID: 20466822; PubMed Central PMCID: PMC2917856. 2: Utami, J. P., Kurnianingsih, N., & Faisal, M. R. (2022). An in silico study of the Cathepsin L inhibitory activity of bioactive compounds in Stachytarpheta jamaicensis as a COVID-19 drug therapy. Makara Journal of Science, 26(1), 3.