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Key Documents

SML1222

Sigma-Aldrich

Lopinavir

≥98% (HPLC)

Synonym(s):

(αS)-N-[(1S,3S,4S)-4-[[(2,6-Dimethylphenoxy)acetyl]amino]-3-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-

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About This Item

Empirical Formula (Hill Notation):
C37H48N4O5
CAS Number:
192725-17-0
Molecular Weight:
628.80
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -20 to -27°, c = 0.4 in methanol

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

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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Application

Lopinavir has been used as a ZMPSTE24 and human immunodeficiency virus protease inhibitor.

Biochem/physiol Actions

Lopinavir is an antiviral HIV Protease Inhibitor. Lopinavir has insufficient bioavailability alone, so it is used in therapy in combination with Ritonavir, a HIV protease inhibitor, which inhibits cytochrome P450-3A4 (CYP3A4), a liver enzyme that normally metabolizes protease inhibitors. Lopinavir also has an ability to inhibit ZMPSTE24 (zinc metallopeptidase STE24).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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K A Sutherland et al.
The Journal of antimicrobial chemotherapy, 70(1), 243-248 (2014-09-18)
PI susceptibility results from a complex interplay between protease and Gag proteins, with Gag showing wide variation across HIV-1 subtypes. We explored the impact of pre-treatment susceptibility on the outcome of lopinavir/ritonavir monotherapy. Treatment-naive individuals who experienced lopinavir/ritonavir monotherapy failure
Translocon Declogger Ste24 Protects against IAPP Oligomer-Induced Proteotoxicity.
Kayatekin C, et al.
Cell, 173(1), 62-73 (2018)
H L Sham et al.
Antimicrobial agents and chemotherapy, 42(12), 3218-3224 (1998-12-03)
The valine at position 82 (Val 82) in the active site of the human immunodeficiency virus (HIV) protease mutates in response to therapy with the protease inhibitor ritonavir. By using the X-ray crystal structure of the complex of HIV protease
Didier K Ekouevi et al.
BMC infectious diseases, 14, 461-461 (2014-08-27)
Few data are available on antiretroviral therapy (ART) response among HIV-2 infected patients. We conducted a systematic review on treatment outcomes among HIV-2 infected patients on ART, focusing on the immunological and virological responses in adults. Data were extracted from
Camille Fraichard et al.
International journal of molecular sciences, 22(2) (2021-01-16)
Protease Inhibitors (PI e.g., ritonavir (RTV) and lopinavir (LPV)) used to treat pregnant mothers infected by HIV induce prematurity and endocrine dysfunctions. The maintenance of pregnancy relies on placental hormone production (human Chorionic Gonadotrophin (hCG) and progesterone (P4)). Those functions
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