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Nevirapine

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Category Human immunodeficiency Virus (HIV)
CAS 129618-40-2
Description Nevirapine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS.
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Product Information

Synonyms BI-RG-587; BIRG 0587; BIRG587; HSDB 7164; Nevirapine; NSC 641530; NVP; Brand name: Viramune Viramune XR.
IUPAC Name 2-cyclopropyl-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
Molecular Weight 266.3
Molecular Formula C15H14N4O
Canonical SMILES CC1=C2C(=NC=C1)N(C3=C(C=CC=N3)C(=O)N2)C4CC4
InChI 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)
InChIKey NQDJXKOVJZTUJA-UHFFFAOYSA-N
Boiling Point 415.4±45.0 °C at 760 mmHg
Melting Point 239-249 °C
Flash Point 205.0±28.7 °C
Purity >98%
Density 1.4±0.1 g/cm3
Solubility In Vitro:
DMSO: 14.29 mg/mL (53.66 mM; Need ultrasonic)
In Vivo:
1.Add each solvent one by one: 10% DMSO >> 90% corn oil
Solubility: ≥ 1.43 mg/mL (5.37 mM); Clear solution
2.Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline
Solubility: ≥ 1.43 mg/mL (5.37 mM); Clear solution
Appearance White to Pale Yellow Solid
Storage Powder:
-20°C: 3 years
4°C: 2 years
In solvent:
-80°C: 6 months
-20°C: 1 month
Animal Admin Nevirapine are dissolved together in absolute ethanol and methylene chloride (1:1, v/v) with mild heating. The concentration of drug in suspension is 2 mg/mL for oral dosing to rats and 6.7 mg/mL for intraduodenal administration to rats before bile collection. The i.v. dose is administered to rats as a solution in 20% ethanol/80% saline. Mice: Nevirapine and Nevirapine are dissolved together in absolute ethanol and methylene chloride (1:1, v/v) with mild heating. The concentration of drug in suspension is 2 mg/mL with a specific activity of 5.55 μCi/mg for oral dosing to mice.
Complexity 397
Exact Mass 266.11676108
Index Of Refraction 1.672
In Vitro Nevirapine itself is an inhibitor of only CYP3A4 at concentrations that are well above those of therapeutic relevance (Ki=270 μM). At all doses (100, 200, 350, 500 μM) tested, nevirapine significantly inhibits cell proliferation after 48 h treatment. At high dose (500 μM), nevirapine significantly increases the percentage of apoptotic cells compared with control. Nevirapine is a potent and selective inhibitor (IC50=10-100 nM) of the replication of a wide variety of HIV-1 strains in several cellular assays.
In Vivo Nevirapine is available for use in combination with nucleoside HIV-1 reverse transcriptase inhibitors (e.g., zidovudine, didanosine, etc.). Nevirapine has been used in combination with HIV-1 protease inhibitors (e.g., saquinavir, ritonavir, indinavir, etc.). Nevirapine is completely absorbed in both sexes of mouse, rat, rabbit, monkey, and chimpanzee. Nevirapine is extensively metabolized in both sexes of all animal species studied. Nevirapine (9 mg/kg, 18 mg/kg and 36 mg/kg) shows significant reduction in ulcer severity score and ulcer index as compared to the control.
PSA 63.57000
Target HIV; Reverse Transcriptase
Vapor Pressure 0.0±1.0 mmHg at 25°C
XLogP3-AA 2

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