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lopinavir

别名	ABT-378, ABT378, Kaletra® (LPV+RTV), Aluviran®, A-157378-0, A-1573780
Compound Class	Synthetic organic
变动原因	Lopinavir is an antiretroviral protease inhibitor. It has subsequently been discovered to exhibit antiviral activity against human papilloma virus (HPV), and to inhibit MERS-CoV replication in vitro . Antiviral activity against SARS-CoV-2 has been explored , however lopinavir/ritonavir therapy provided no benefit in hospitalised COVID-19 patients .
Related Product	Lopinavir

Summary

是否批准为药物？	(FDA (2000), EMA (2001))
IUPAC Name	(2S)-N-[(2S,4S,5S)-5-[[2-(2,6-dimethylphenoxy)acetyl]amino]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide
别名	ABT-378, ABT378, Kaletra® (LPV+RTV), Aluviran®, A-157378-0, A-1573780

数据库链接

PubChem CID	92727
ChEMBL Ligand	CHEMBL729
BindingDB Ligand	50180655
DrugBank Ligand	DB01601
CAS Registry No.	192725-17-0
RCSB PDB Ligand	AB1

生物活性

生物活性评价	Inhibits HIV1 protease with K_i 0.0013 nM in vitro .

临床资料

Summary of Clinical Use	Lopinavir is used in combination with to treat and prevent human immunodeficiency virus (HIV) infection and acquired immunodeficiency syndrome (AIDS).
作用机制与药效学效应	Sulfonamides are structural analogues of 4-aminobenzoic acid (pABA) an intermediate in the de novo synthesis of folate by some prokaryotes, lower eukaryotes and plants . The antibacterial MMOA is competitive inhibition of bacterial dihydropteroate synthase (DHPS) resulting in a block of folate biosynthesis .

参考文献

1. de Wilde AH, Jochmans D, Posthuma CC, Zevenhoven-Dobbe JC, van Nieuwkoop S, Bestebroer TM, van den Hoogen BG, Neyts J, Snijder EJ. (2014) Screening of an FDA-approved compound library identifies four small-molecule inhibitors of Middle East respiratory syndrome coronavirus replication in cell culture.. Antimicrob Agents Chemother, 58 (8): (4875-84). [PMID:24841269]
2. Cao B, Wang Y, Wen D, Liu W, Wang J, Fan G, Ruan L, Song B, Cai Y, Wei M et al.. (2020) A Trial of Lopinavir-Ritonavir in Adults Hospitalized with Severe Covid-19.. N Engl J Med, 382 (19): (1787-1799). [PMID:32187464]
3. Sham HL, Betebenner DA, Herrin T, Kumar G, Saldivar A, Vasavanonda S, Molla A, Kempf DJ, Plattner JJ, Norbeck DW. (2001) Synthesis and antiviral activities of the major metabolites of the HIV protease inhibitor ABT-378 (Lopinavir).. Bioorg Med Chem Lett, 11 (11): (1351-3). [PMID:11378352]
4. B?hm R, Bulin C, Waetzig V, Cascorbi I, Klein HJ, Herdegen T. (2021) Pharmacovigilance-based drug repurposing: The search for inverse signals via OpenVigil identifies putative drugs against viral respiratory infections.. Br J Clin Pharmacol, 71 (13): (1755-70). [PMID:33871897]

结构

Canonical SMILES	O=C(N[C@H]([C@H](C[C@H](Cc1ccccc1)NC(=O)[C@@H](N1CCCNC1=O)C(C)C)O)Cc1ccccc1)COc1c(C)cccc1C
Isomeric SMILES	O=C(N[C@H]([C@H](C[C@H](Cc1ccccc1)NC(=O)[C@@H](N1CCCNC1=O)C(C)C)O)Cc1ccccc1)COc1c(C)cccc1C
InChI	InChI=1S/C37H48N4O5/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43)/t30-,31-,32-,34-/m0/s1
InChI key	KJHKTHWMRKYKJE-SUGCFTRWSA-N

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