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SML0097

Sigma-Aldrich

Nevirapine

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Synonym(s):
11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one
Empirical Formula (Hill Notation):
C15H14N4O
CAS Number:
129618-40-2
Molecular Weight:
266.30
MDL number:
MFCD00866928
PubChem Substance ID:
329825155
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

100

form

powder

color

white to tan

solubility

DMSO: ≥22 mg/mL

storage temp.

room temp

SMILES string

CC1=CC=NC2=C1NC(C(C=CC=N3)=C3N2C4CC4)=O

InChI

1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)

InChI key

NQDJXKOVJZTUJA-UHFFFAOYSA-N

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Application

Nevirapine has been used as non-nucleoside reverse transcriptase inhibitor in in vitro porcine endogenous retrovirus replication, primary hepatocytes and bone marrow dendritic cells (BMDCs).

Biochem/physiol Actions

Nevirapine interacts with glycine 190 residue of human immuno deficiency virus (HIV-2) reverse transcriptase. It is an antiretroviral drug which increases bile synthesis and activates electron transport chain. Use of nevirapine leads to liver toxicity and is associated with Nevirapine hypersensitivity syndrome.
Nevirapine is an allosteric, non-nucleoside inhibitor of HIV reverse transcriptase (NNRTI). The Ki for inhibition of wild-type RT by Nevirapine is 200 nM.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Etienne Audureau et al.
BMC public health, 13, 286-286 (2013-04-04)
Uptake of prevention of mother-to-child HIV transmission (PMTCT) programs remains challenging in sub-Saharan Africa because of multiple barriers operating at the individual or health facility levels. Less is known regarding the influence of program-level and contextual determinants. In this study
The N-terminal domain of cGAS determines preferential association with centromeric DNA and innate immune activation in the nucleus
Gentili M, et al.
Testing, 26(9), 2377-2393 (2019)
Douglas Ward et al.
Journal of the International Association of Providers of AIDS Care, 12(3), 154-156 (2013-03-02)
Nevirapine (NVP) was the first nonnucleoside reverse transcriptase inhibitor (NNRTI) approved for the treatment of HIV infection. NVP can provide safe and efficacious viral suppression for treatment-naive patients and for virologically controlled patients "switching" from other NNRTI or protease inhibitor-based
Transcriptional profiling suggests that Nevirapine and Ritonavir cause drug induced liver injury through distinct mechanisms in primary human hepatocytes
Terelius Y, et al.
Chemico-Biological Interactions, 255, 31-44 (2016)
Charlotte V Hobbs et al.
The Journal of infectious diseases, 208(1), 139-148 (2013-03-30)
Millions of individuals being treated for human immunodeficiency virus (HIV) live in malaria-endemic areas, but the effects of these treatments on malaria transmission are unknown. While drugs like HIV protease inhibitors (PIs) and trimethoprim-sulfamethoxazole (TMP-SMX) have known activity against parasites
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