2-Hydroxynevirapine glucuronide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 2-Hydroxynevirapine glucuronide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 2-Hydroxynevirapine glucuronide?

The molecule 2-Hydroxynevirapine glucuronide presents a molecular formula of C₂₁H₂₂N₄O₈ and its IUPAC name is (2S,3S,4S,5R,6S)-6-[(2-cyclopropyl-7-methyl-10-oxo-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

2-Hydroxynevirapine glucuronide (2HN) is a nevirapine (NVP) metabolite that is formed by the addition of a glucuronic acid moiety to the 2-hydroxy group of NVP. 2HN is a potent inhibitor of the human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) and has been shown to be active against HIV-1 in vitro and in vivo. The inhibitory activity of 2HN against HIV-1 RT is approximately 10-fold greater than that of NVP. 2HN is also a competitive inhibitor of the HIV-1 protease (HIV-1 PR). The 50% inhibitory concentration (IC50) values of 2HN against HIV-1 RT and HIV-1 PR are in the nanomolar range. 2HN is rapidly metabolized to NVP and glucuronide conjugates. The elimination half-life of 2HN is approximately 2 hours. 2HN is excreted in the urine as NVP and 2HN-glucuronide conjugates..

2HN has antiviral activity against HIV-1 in vitro and in vivo. In a Phase I clinical trial, 2HN was well tolerated and demonstrated antiviral activity in HIV-1-infected patients. 2HN is a potent inhibitor of HIV-1 RT and HIV-1 PR and has activity against HIV-1 in vitro and in vivo. 2HN is rapidly metabolized to NVP and glucuronide conjugates and is excreted in the urine. 2HN has the potential to be used as a single agent or in combination with other antiretroviral agents for the treatment of HIV-1 infection..

3D structure

Cartesian coordinates

Geometry of 2-Hydroxynevirapine glucuronide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

Molecule descriptors

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

Reference codes for other databases

• CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
• Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
• ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
• PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
• RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
• ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
• CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.

Physico-Chemical properties

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (K_ow) data is applied in toxicology and drug research. K_ow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(K_ow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Ų are required. Thus, molecules with a polar surface area greater than 140 Ų tend to be poorly permeable to cell membranes.