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Key Documents

SML0097

Sigma-Aldrich

Nevirapine

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:
Molecular Weight:
266.30
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (HPLC)

Quality Level

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

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 Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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
Complications of long-term antiretroviral therapy in HIV-infected children.
Andrew J Prendergast
Archives of disease in childhood, 98(4), 245-246 (2013-02-16)
Structure of HIV-2 reverse transcriptase at 2.35-AA
Ren J, et al.
Proceedings of the National Academy of Sciences of the USA, 99(22), 14410-14415 (2002)
E H Decloedt et al.
The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease, 17(3), 333-335 (2013-02-15)
Isoniazid preventive therapy (IPT) is recommended in patients on antiretroviral treatment. Isoniazid (INH) inhibits CYP3A4, which metabolises nevirapine (NVP). Administration of INH may cause higher NVP concentrations and toxicity. We studied the effect of INH on NVP concentrations in 21
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)

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