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[ CAS No. 36791-04-5 ] {[proInfo.proName]}

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Chemical Structure| 36791-04-5
Chemical Structure| 36791-04-5
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Kupke, Paul ; Adenugba, Akinbami ; Schemmerer, Mathias , et al. DOI: PubMed ID:

Abstract: Hepatitis E virus (HEV) is a major cause of acute hepatitis globally. Chronic and fulminant courses are observed especially in immunocompromised transplant recipients since administration of ribavirin (RBV) does not always lead to a sustained virol. response. By in vitro stimulation of NK cells through hepatoma cell lines inoculated with a full-length HEV and treatment with RBV, we analyzed the viral replication and cell response to further elucidate the mechanism of action of RBV on immune cells, especially NK cells, in the context of HEV infection. Co-culture of HEV-infected hepatoma cells with PBMCs and treatment with RBV both resulted in a decrease in viral replication, which in combination showed an additive effect. An anal. of NK cell functions after stimulation revealed evidence of reduced cytotoxicity by decreased TRAIL and CD107a degranulation. Simultaneously, IFN-γ production was significantly increased through the IL-12R pathway. Although there was no direct effect on the IL-12R subunits, downstream events starting with TYK-2 and subsequently pSTAT4 were upregulated. In conclusion, we showed that RBV has an immunomodulatory effect on the IL-12R pathway of NK cells via TYK-2. This subsequently leads to an enhanced IFN-γ response and thus, to an additive antiviral effect in the context of an in vitro HEV infection.

Keywords: ribavirin ; hepatitis E virus ; transplantation ; immunosuppression ; NK cells

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Product Details of [ 36791-04-5 ]

CAS No. :36791-04-5 MDL No. :
Formula : C8H12N4O5 Boiling Point : -
Linear Structure Formula :- InChI Key :IWUCXVSUMQZMFG-AFCXAGJDSA-N
M.W : 244.20 Pubchem ID :37542
Synonyms :
Ribasphere;NSC 163039;Ribavirin, Copegus, Rebetol, Virazole, ICN-1229;Tribavirin;RTCA;ICN-1229
Chemical Name :1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboxamide

Calculated chemistry of [ 36791-04-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.62
Num. rotatable bonds : 3
Num. H-bond acceptors : 7.0
Num. H-bond donors : 4.0
Molar Refractivity : 51.06
TPSA : 143.72 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.35
Log Po/w (XLOGP3) : -1.85
Log Po/w (WLOGP) : -3.34
Log Po/w (MLOGP) : -2.94
Log Po/w (SILICOS-IT) : -2.9
Consensus Log Po/w : -2.14

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.21
Solubility : 151.0 mg/ml ; 0.619 mol/l
Class : Very soluble
Log S (Ali) : -0.65
Solubility : 54.7 mg/ml ; 0.224 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 1.76
Solubility : 14000.0 mg/ml ; 57.3 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.89

Safety of [ 36791-04-5 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P201-P202-P280-P312-P405-P501 UN#:N/A
Hazard Statements:H302-H341-H360 Packing Group:N/A
GHS Pictogram:
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Reason: Stable Isotope

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