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Merck

SML0097

Nevirapine

≥98% (HPLC), HIV-1 reverse transcriptase inhibitor, powder

Synonym(s):

11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one

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About This Item

Empirical Formula (Hill Notation):
C15H14N4O
CAS Number:
129618-40-2
Molecular Weight:
266.30
UNSPSC Code:
12352200
PubChem Substance ID:
329825155
NACRES:
NA.77
MDL number:
MFCD00866928

Key Documents

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Product Name

Nevirapine,

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

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥22 mg/mL

storage temp.

room temp

Quality Level

100

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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

NNRTI (non-nucleoside reverse transcriptase inhibitor) of HIV-1
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

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000394208
0000394206
0000394206
0000394208
0000244238

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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)
Amy M Sharma et al.
Chemical research in toxicology, 26(3), 410-421 (2013-02-08)
Nevirapine (NVP) treatment is associated with serious skin rashes that appear to be immune-mediated. We previously developed a rat model of this skin rash that is immune-mediated and is very similar to the rash in humans. Treatment of rats with
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)
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
Dongyue Li et al.
Bioorganic & medicinal chemistry, 21(7), 2128-2134 (2013-02-19)
In continuation of our efforts toward identification and optimization of novel non-nucleoside reverse transcriptase inhibitors (NNRTIs), we have employed a structure-based bioisosterism strategy, with which a new series of diarylpyridazine (DAPD) derivatives were synthesized and evaluated for their anti-HIV-1 (human
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