Iproniazid

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

What is the Iproniazid?

The molecule Iproniazid presents a molecular formula of C₉H₁₃N₃O and its IUPAC name is N'-propan-2-ylpyridine-4-carbohydrazide.

Iproniazid (INN) is a medication used to treat tuberculosis.[1] It is an isonicotinic acid hydrazide, specifically a prodrug of isonicotinic acid, and acts as an inhibitor of mycolic acid synthesis.[2][3] Iproniazid was the first antituberculosis medication,[4] and was introduced in 1952.[5].

Iproniazid is generally well-tolerated, with the most common side effects being gastrointestinal upset and rashes.[1][6] More serious side effects include liver damage, which can be fatal, and neuropathy.[1][6] Iproniazid lies as a pregnancy category C drug, meaning it may be harmful to a developing fetus.[7].

Iproniazid is a prodrug of isonicotinic acid, which is thought to be the active ingredient.[2][3] It is a competitive inhibitor of mycolic acid synthesis, which is required for the Mycobacterium tuberculosis to build its cell wall.[2][3] Iproniazid is also a monoamine oxidase inhibitor (MAOI),[8] although this is not thought to be the mechanism by which it kills mycobacteria.[2].

Iproniazid was the first antituberculosis medication,[4] and was introduced in 1952.[5] It was initially used as an MAOI for the treatment of depression,[5] but was found to have activity against M. tuberculosis.[5] Iproniazid was used extensively to treat tuberculosis in the 1950s and 1960s before the introduction of other antituberculosis medications.[9].

Iproniazid is generally well-tolerated, with the most common side effects being gastrointestinal upset and rashes.[1][6] More serious side effects include liver damage, which can be fatal, and neuropathy.[1][6] Iproniazid lies as a pregnancy category C drug, meaning it may be harmful to a developing fetus.[7].

Iproniazid is no longer used as a first-line treatment for tuberculosis due to the development of resistance and the availability of more effective and less toxic drugs.[1] However, it is still used in the treatment of latent tuberculosis infection (LTBI).[1].

3D structure

Cartesian coordinates

Geometry of Iproniazid 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.