Celgosivir free base | CAS#121104-96-9 | α-glucosidase inhibitor

MedKoo Cat#: 529538 | Name: Celgosivir free base

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Description:

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

Celgosivir is an α-glucosidase I inhibitor. Celgosivir was derived from Castanospermum australe seeds, has demonstrated antiviral activity against various viruses, including all four serotypes of dengue virus (DENV). In vitro studies have reported that celgosivir inhibits DENV2 replication with an EC50 value of 1.6 μM. Celgosivir is well absorbed in vitro and in vivo, and is rapidly converted to castanospermine. Celgosivir has a novel mechanism of action (preventing the glycosylation of viral proteins by the host), and demonstrates broad antiviral activity in vitro.

Chemical Structure

Celgosivir free base

CAS#121104-96-9 (free base)

Theoretical Analysis

MedKoo Cat#: 529538

Name: Celgosivir free base

CAS#: 121104-96-9 (free base)

Chemical Formula: C12H21NO5

Exact Mass: 259.1420

Molecular Weight: 259.30

Elemental Analysis: C, 55.58; H, 8.16; N, 5.40; O, 30.85

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks

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Related CAS #

141117-12-6 (HCl) 121104-96-9 (free base)

Synonym

Celgosivir (free base); 60-P-001; MBI-3253; MDL-28574; MX-3253; VIR-222; 60P001; MBI3253; MDL28574; MX3253; VIR222; 60 P 001; MBI 3253; MDL 28574; MX 3253; VIR 222

IUPAC/Chemical Name

(1R,6R,7R,8S,8aS)-1,7,8-trihydroxyoctahydroindolizin-6-yl butyrate

InChi Key

HTJGLYIJVSDQAE-PPJKGSGRSA-N

InChi Code

InChI=1S/C12H21NO5/c1-2-3-9(15)18-8-6-13-5-4-7(14)10(13)12(17)11(8)16/h7-8,10-12,14,16-17H,2-6H2,1H3/t7-,8-,10+,11+,12+/m1/s1

SMILES Code

CCCC(O[C@@H]1CN2CC[C@@H](O)[C@@]2([H])[C@H](O)[C@H]1O)=O

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

>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:

Celgosivir (MBI 3253; MDL 28574; MX3253) is an α-glucosidase I inhibitor; inhibits bovine viral diarrhoea virus (BVDV) with an IC50 of 1.27 μM in in vitro assay.

In vitro activity:

Celgosivir, a prodrug of castanospermine, is an alpha-glucosidase I inhibitor that impedes the processing of N-linked oligosaccharides on viral envelope glycoproteins, thereby hindering viral maturation. EN.WIKIPEDIA.ORG In Vitro Antiviral Activity: Dengue Virus (DENV): In primary human macrophages infected with DENV serotype 2, celgosivir exhibited an EC₅₀ of 5 μM, indicating its potency in reducing viral secretion. PUBMED CENTRAL Hepatitis C Virus (HCV): Celgosivir has demonstrated broad antiviral activity in vitro against HCV. RESEARCHGATE.NET Bovine Viral Diarrhea Virus (BVDV): Studies have explored celgosivir's efficacy in combination with other agents to inhibit BVDV replication. SAGE JOURNALS These findings underscore celgosivir's potential as a broad-spectrum antiviral agent targeting host glycoprotein processing pathways.

In vivo activity:

Celgosivir, an alpha-glucosidase I inhibitor, has undergone various in vivo studies to assess its antiviral efficacy: Dengue Virus (DENV): Mouse Models: In AG129 mice infected with DENV serotype 2 (strain TSV01), celgosivir treatment significantly reduced viremia levels. MEDKOO.COM Clinical Trials: The CELADEN phase 1b trial, a randomized, double-blind, placebo-controlled study involving 50 patients with confirmed dengue fever, evaluated celgosivir's efficacy and safety. Participants received a 400 mg loading dose followed by 200 mg twice daily for five days. The study found that, while celgosivir was generally safe and well-tolerated, it did not significantly reduce viral load or fever burden compared to placebo. PUBMED.NCBI.NLM.NIH.GOV Hepatitis C Virus (HCV): Clinical Trials: Celgosivir has been investigated as a monotherapy and in combination with standard treatments for HCV. As a monotherapy, it did not demonstrate significant efficacy. However, when combined with pegylated interferon alfa-2b and ribavirin, celgosivir showed a synergistic effect, enhancing antiviral activity in vitro and in phase II clinical trials lasting up to one year in patients with chronic HCV infection. EN.WIKIPEDIA.ORG Bovine Viral Diarrhea Virus (BVDV): In Vivo Studies: Celgosivir has demonstrated antiviral activity against BVDV, a model for HCV, in vivo. Specifically, in AG129 mice infected with a clinical strain of DENV2 (TSV01), celgosivir treatment significantly reduced viremia levels. MEDKOO.COM These studies highlight celgosivir's potential as a broad-spectrum antiviral agent. However, its clinical efficacy varies across different viruses, emphasizing the need for further research to optimize its therapeutic applications.

Preparing Stock Solutions

The following data is based on the product molecular weight 259.30 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:

In vitro protocol:

In vivo protocol:

1. Rathore AP, Paradkar PN, Watanabe S, Tan KH, Sung C, Connolly JE, Low J, Ooi EE, Vasudevan SG. Celgosivir treatment misfolds dengue virus NS1 protein, induces cellular pro-survival genes and protects against lethal challenge mouse model. Antiviral Res. 2011 Dec;92(3):453-60. doi: 10.1016/j.antiviral.2011.10.002. Epub 2011 Oct 12. PMID: 22020302. 2. Watanabe S, Rathore AP, Sung C, Lu F, Khoo YM, Connolly J, Low J, Ooi EE, Lee HS, Vasudevan SG. Dose- and schedule-dependent protective efficacy of celgosivir in a lethal mouse model for dengue virus infection informs dosing regimen for a proof of concept clinical trial. Antiviral Res. 2012 Oct;96(1):32-5. doi: 10.1016/j.antiviral.2012.07.008. Epub 2012 Jul 31. PMID: 22867971.

1: Hanson G, Adams J, Kepgang DIB, Zondagh LS, Tem Bueh L, Asante A, Shirolkar SA, Kisaakye M, Bondarwad H, Awe OI. Machine learning and molecular docking prediction of potential inhibitors against dengue virus. Front Chem. 2024 Dec 24;12:1510029. doi: 10.3389/fchem.2024.1510029. PMID: 39776767; PMCID: PMC11703810. 2: Pfarr KM, Krome AK, Al-Obaidi I, Batchelor H, Vaillant M, Hoerauf A, Opoku NO, Kuesel AC. The pipeline for drugs for control and elimination of neglected tropical diseases: 2. Oral anti-infective drugs and drug combinations for off- label use. Parasit Vectors. 2023 Oct 31;16(1):394. doi: 10.1186/s13071-023-05909-8. PMID: 37907954; PMCID: PMC10619278. 3: Thangaraju P, Narasimhan G, Ramamurthy VA, Gurunthalingam MP, Yella SST, Venkatesan S, Thangaraju E. Molecular Docking Analysis of Adhatoda vasica with Thromboxane A2 Receptor (TXA2R) (6IIU) and Antiviral Molecules for Possible Dengue Complications. Infect Disord Drug Targets. 2023;23(1):e180722206836. doi: 10.2174/1871526522666220718101544. PMID: 35850647. 4: Byrne AB, García CC, Damonte EB, Talarico LB. Murine models of dengue virus infection for novel drug discovery. Expert Opin Drug Discov. 2022 Apr;17(4):397-412. doi: 10.1080/17460441.2022.2033205. Epub 2022 Jan 31. PMID: 35098849. 5: Santos-Beneit F, Raškevičius V, Skeberdis VA, Bordel S. A metabolic modeling approach reveals promising therapeutic targets and antiviral drugs to combat COVID-19. Sci Rep. 2021 Jun 7;11(1):11982. doi: 10.1038/s41598-021-91526-3. PMID: 34099831; PMCID: PMC8184994. 6: Rajasekharan S, Milan Bonotto R, Nascimento Alves L, Kazungu Y, Poggianella M, Martinez-Orellana P, Skoko N, Polez S, Marcello A. Inhibitors of Protein Glycosylation Are Active against the Coronavirus Severe Acute Respiratory Syndrome Coronavirus SARS-CoV-2. Viruses. 2021 Apr 30;13(5):808. doi: 10.3390/v13050808. PMID: 33946304; PMCID: PMC8144969. 7: Clarke EC, Nofchissey RA, Ye C, Bradfute SB. The iminosugars celgosivir, castanospermine and UV-4 inhibit SARS-CoV-2 replication. Glycobiology. 2021 May 3;31(4):378-384. doi: 10.1093/glycob/cwaa091. PMID: 32985653; PMCID: PMC7543591. 8: Li LH, Kaptein SJF, Schmid MA, Zmurko J, Leyssen P, Neyts J, Dallmeier K. A dengue type 2 reporter virus assay amenable to high-throughput screening. Antiviral Res. 2020 Nov;183:104929. doi: 10.1016/j.antiviral.2020.104929. Epub 2020 Sep 6. PMID: 32898584. 9: Dos Santos Nascimento IJ, de Aquino TM, da Silva-Júnior EF. Drug Repurposing: A Strategy for Discovering Inhibitors against Emerging Viral Infections. Curr Med Chem. 2021;28(15):2887-2942. doi: 10.2174/0929867327666200812215852. PMID: 32787752. 10: Williams SJ, Goddard-Borger ED. α-glucosidase inhibitors as host-directed antiviral agents with potential for the treatment of COVID-19. Biochem Soc Trans. 2020 Jun 30;48(3):1287-1295. doi: 10.1042/BST20200505. PMID: 32510142. 11: Bhushan G, Lim L, Bird I, Chothe SK, Nissly RH, Kuchipudi SV. Iminosugars With Endoplasmic Reticulum α-Glucosidase Inhibitor Activity Inhibit ZIKV Replication and Reverse Cytopathogenicity in vitro. Front Microbiol. 2020 Apr 7;11:531. doi: 10.3389/fmicb.2020.00531. PMID: 32373079; PMCID: PMC7179685. 12: Vicenti I, Dragoni F, Giannini A, Giammarino F, Spinicci M, Saladini F, Boccuto A, Zazzi M. Development of a Cell-Based Immunodetection Assay for Simultaneous Screening of Antiviral Compounds Inhibiting Zika and Dengue Virus Replication. SLAS Discov. 2020 Jun;25(5):506-514. doi: 10.1177/2472555220911456. Epub 2020 Mar 18. PMID: 32186426. 13: Watanabe S, Low JG, Vasudevan SG. Preclinical Antiviral Testing for Dengue Virus Infection in Mouse Models and Its Association with Clinical Studies. ACS Infect Dis. 2018 Jul 13;4(7):1048-1057. doi: 10.1021/acsinfecdis.8b00054. Epub 2018 Jun 1. PMID: 29756760. 14: Budigi Y, Ong EZ, Robinson LN, Ong LC, Rowley KJ, Winnett A, Tan HC, Hobbie S, Shriver Z, Babcock GJ, Alonso S, Ooi EE. Neutralization of antibody-enhanced dengue infection by VIS513, a pan serotype reactive monoclonal antibody targeting domain III of the dengue E protein. PLoS Negl Trop Dis. 2018 Feb 9;12(2):e0006209. doi: 10.1371/journal.pntd.0006209. PMID: 29425203; PMCID: PMC5823465. 15: Dowall SD, Bewley K, Watson RJ, Vasan SS, Ghosh C, Konai MM, Gausdal G, Lorens JB, Long J, Barclay W, Garcia-Dorival I, Hiscox J, Bosworth A, Taylor I, Easterbrook L, Pitman J, Summers S, Chan-Pensley J, Funnell S, Vipond J, Charlton S, Haldar J, Hewson R, Carroll MW. Antiviral Screening of Multiple Compounds against Ebola Virus. Viruses. 2016 Oct 27;8(11):277. doi: 10.3390/v8110277. PMID: 27801778; PMCID: PMC5127007. 16: Kaptein SJ, Neyts J. Towards antiviral therapies for treating dengue virus infections. Curr Opin Pharmacol. 2016 Oct;30:1-7. doi: 10.1016/j.coph.2016.06.002. Epub 2016 Jun 28. PMID: 27367615. 17: Sung C, Wei Y, Watanabe S, Lee HS, Khoo YM, Fan L, Rathore AP, Chan KW, Choy MM, Kamaraj US, Sessions OM, Aw P, de Sessions PF, Lee B, Connolly JE, Hibberd ML, Vijaykrishna D, Wijaya L, Ooi EE, Low JG, Vasudevan SG. Extended Evaluation of Virological, Immunological and Pharmacokinetic Endpoints of CELADEN: A Randomized, Placebo-Controlled Trial of Celgosivir in Dengue Fever Patients. PLoS Negl Trop Dis. 2016 Aug 10;10(8):e0004851. doi: 10.1371/journal.pntd.0004851. PMID: 27509020; PMCID: PMC4980036. 18: Beesetti H, Khanna N, Swaminathan S. Investigational drugs in early development for treating dengue infection. Expert Opin Investig Drugs. 2016 Sep;25(9):1059-69. doi: 10.1080/13543784.2016.1201063. Epub 2016 Jun 24. PMID: 27322111. 19: Sayce AC, Alonzi DS, Killingbeck SS, Tyrrell BE, Hill ML, Caputo AT, Iwaki R, Kinami K, Ide D, Kiappes JL, Beatty PR, Kato A, Harris E, Dwek RA, Miller JL, Zitzmann N. Iminosugars Inhibit Dengue Virus Production via Inhibition of ER Alpha-Glucosidases--Not Glycolipid Processing Enzymes. PLoS Negl Trop Dis. 2016 Mar 14;10(3):e0004524. doi: 10.1371/journal.pntd.0004524. PMID: 26974655; PMCID: PMC4790851. 20: Watanabe S, Chan KW, Dow G, Ooi EE, Low JG, Vasudevan SG. Optimizing celgosivir therapy in mouse models of dengue virus infection of serotypes 1 and 2: The search for a window for potential therapeutic efficacy. Antiviral Res. 2016 Mar;127:10-9. doi: 10.1016/j.antiviral.2015.12.008. Epub 2016 Jan 13. PMID: 26794905.

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