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MedKoo Cat#: 461884 | Name: Glycovir
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Description:

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

Glycovir, also known as SC-49483, is an anti-HIV prodrug. Glycovir is an alpha-glucosidase-1 inhibitor, and a candidate anti-HIV agent targeted against viral glycoprotein processing in host cell endoplasmic reticulum.

Chemical Structure

Glycovir
Glycovir
CAS#131262-82-3 (free base)

Theoretical Analysis

MedKoo Cat#: 461884

Name: Glycovir

CAS#: 131262-82-3 (free base)

Chemical Formula: C26H45NO8

Exact Mass: 499.3145

Molecular Weight: 499.64

Elemental Analysis: C, 62.50; H, 9.08; N, 2.80; O, 25.62

Price and Availability

Size Price Availability Quantity
1mg USD 90.00 Ready to ship
5mg USD 250.00 Ready to ship
10mg USD 450.00 Ready to ship
25mg USD 950.00 Ready to ship
50mg USD 1,650.00 Ready to ship
100mg USD 2,650.00 Ready to ship
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Related CAS #
131262-82-3 (free base) 238075-09-7 (free base)
Synonym
Glycovir; SC 49483; SC-49483; SC49483; p-N-butyl-DNJ; Perbutylated-N-butyl-1-deoxynojiromycin;
IUPAC/Chemical Name
(2R,3R,4R,5S)-1-butyl-2-((butyryloxy)methyl)piperidine-3,4,5-triyl tributyrate
InChi Key
MKGDNVHZSCXBKR-KYVQNOJUSA-N
InChi Code
InChI=1S/C26H45NO8/c1-6-11-16-27-17-20(33-22(29)13-8-3)26(35-24(31)15-10-5)25(34-23(30)14-9-4)19(27)18-32-21(28)12-7-2/h19-20,25-26H,6-18H2,1-5H3/t19-,20+,25-,26-/m1/s1
SMILES Code
CCCC(OC[C@H]1N(CCCC)C[C@H](OC(CCC)=O)[C@@H](OC(CCC)=O)[C@@H]1OC(CCC)=O)=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
>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
2934.99.03.00
More Info
Biological target:
Glycovir is an alpha-glucosidase-1 inhibitor, and a candidate anti-HIV agent targeted against viral glycoprotein processing in host cell endoplasmic reticulum.
In vitro activity:
TBD
In vivo activity:
The potential toxicity of perbutylated-N-butyl-1-deoxynojiromycin (p-N-butyl-DNJ, SC-49483), was evaluated in Sprague-Dawley rats after 4, 13, or 26 wk of oral administration at doses ranging from 300 to 3,670 mg/kg/day. In these studies, the target organs of p-N-butyl-DNJ effects were thyroid gland, salivary gland, stomach, and pancreas. The most prominent histologic change in these organs was the presence of clear or lightly eosinophilic vacuoles in the cytoplasm of thyroid follicular cells, gastric chief cells, salivary gland acinar cells, and exocrine pancreatic acinar cells. Ultrastructurally, these vacuoles were consistent with dilated rough endoplasmic reticulum, which sometimes contained homogeneously stained, moderately electron-dense material. The vacuoles in thyroid follicular cells contained pale eosinophilic colloidlike material consistent with accumulated thyroglobulin, as shown by immunohistochemical staining methods. The biological functions of these organs were not adversely affected as evidenced by the absence of clinical signs and the results of selected hormonal analyses. The morphologic changes were completely reversed after a 4-wk recovery period. It is believed that morphologic changes in thyroid follicular cells, salivary gland acinar cells, pancreatic acinar cells, and gastric chief cells were the result of nonspecific inhibition of host alpha-glucosidase(s) by p-N-butyl-DNJ, causing clinically silent perturbation in host cell glycoprotein processing and/or glycoprotein transport. Reference: Toxicol Pathol. Sep-Oct 1996;24(5):531-8. https://pubmed.ncbi.nlm.nih.gov/8923673/
Solvent mg/mL mM
Solubility
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 499.64 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.

Recalculate based on batch purity %
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. Khan KN, Snook SS, Semler DE, Baron DA, Alden CL. Pathology of perbutylated-N-butyl-1-deoxynojiromycin (an alpha-glucosidase-1 inhibitor) in Sprague-Dawley rats. Toxicol Pathol. 1996 Sep-Oct;24(5):531-8. doi: 10.1177/019262339602400501. PMID: 8923673.
In vitro protocol:
TBD
In vivo protocol:
The potential toxicity of perbutylated-N-butyl-1-deoxynojiromycin (p-N-butyl-DNJ, SC-49483), was evaluated in Sprague-Dawley rats after 4, 13, or 26 wk of oral administration at doses ranging from 300 to 3,670 mg/kg/day. In these studies, the target organs of p-N-butyl-DNJ effects were thyroid gland, salivary gland, stomach, and pancreas. The most prominent histologic change in these organs was the presence of clear or lightly eosinophilic vacuoles in the cytoplasm of thyroid follicular cells, gastric chief cells, salivary gland acinar cells, and exocrine pancreatic acinar cells. Ultrastructurally, these vacuoles were consistent with dilated rough endoplasmic reticulum, which sometimes contained homogeneously stained, moderately electron-dense material. The vacuoles in thyroid follicular cells contained pale eosinophilic colloidlike material consistent with accumulated thyroglobulin, as shown by immunohistochemical staining methods. The biological functions of these organs were not adversely affected as evidenced by the absence of clinical signs and the results of selected hormonal analyses. The morphologic changes were completely reversed after a 4-wk recovery period. It is believed that morphologic changes in thyroid follicular cells, salivary gland acinar cells, pancreatic acinar cells, and gastric chief cells were the result of nonspecific inhibition of host alpha-glucosidase(s) by p-N-butyl-DNJ, causing clinically silent perturbation in host cell glycoprotein processing and/or glycoprotein transport. Reference: Toxicol Pathol. Sep-Oct 1996;24(5):531-8. https://pubmed.ncbi.nlm.nih.gov/8923673/
1: Khan KN, Snook SS, Semler DE, Baron DA, Alden CL. Pathology of perbutylated- N-butyl-1-deoxynojiromycin (an alpha-glucosidase-1 inhibitor) in Sprague-Dawley rats. Toxicol Pathol. 1996 Sep-Oct;24(5):531-8. doi: 10.1177/019262339602400501. PMID: 8923673. 2: Cook CS, Karabatsos PJ, Schoenhard GL, Karim A. Species dependent esterase activities for hydrolysis of an anti-HIV prodrug glycovir and bioavailability of active SC-48334. Pharm Res. 1995 Aug;12(8):1158-64. doi: 10.1023/a:1016259826037. PMID: 7494828.

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