Zalcitabine

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

What is the Zalcitabine?

The molecule Zalcitabine presents a molecular formula of C₉H₁₃N₃O₃ and its IUPAC name is 4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one.

Zalcitabine (dideoxycytidine) is a nucleoside reverse transcriptase inhibitor (NRTI) used as an antiretroviral drug in the treatment of HIV infection and AIDS. Zalcitabine was the third antiretroviral drug approved for use in the United States, after AZT (zidovudine, Retrovir) and ddI (didanosine, Videx). Zalcitabine is no longer manufactured or marketed..

Zalcitabine was first synthesized in the early 1980s. In vitro studies showed that zalcitabine was a potent inhibitor of HIV-1 replication. Zalcitabine was initially tested in humans in 1986. The first large clinical trial of zalcitabine was conducted in 1988. This trial showed that zalcitabine was effective in reducing HIV-1 viral load and increasing CD4+ T cell counts in people with HIV infection..

Zalcitabine was approved for use in the United States in 1992. The recommended dose of zalcitabine was 3 mg twice daily. In 1995, the dose was increased to 3 mg three times daily..

Zalcitabine was generally well-tolerated. The most common side effects were nausea, vomiting, diarrhea, and abdominal pain. Zalcitabine also caused a distinctive rash that was usually mild and resolved with continued use of the drug..

In 1996, the results of two large clinical trials, DDC-002 and DDC-HIV-007, were published. These trials showed that zalcitabine, in combination with other antiretroviral drugs, was associated with an increased risk of death. As a result of these findings, zalcitabine was no longer recommended for use in combination with other antiretroviral drugs..

In 1998, the manufacturer of zalcitabine, Hoffmann-La Roche, announced that it was discontinuing production of the drug. Zalcitabine was no longer available in the United States after December 31, 1998..

3D structure

Cartesian coordinates

Geometry of Zalcitabine 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.