Pyrazinamide

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

What is the Pyrazinamide?

The molecule Pyrazinamide presents a molecular formula of C5H5N3O and its IUPAC name is pyrazine-2-carboxamide.

Pyrazinamide (PZA) is a medication that is used to treat tuberculosis (TB), a bacterial infection that affects the lungs and other parts of the body. It is often used in combination with other medications, such as isoniazid and rifampin, to treat TB. Pyrazinamide is highly effective against TB, and is particularly useful for treating TB infections that are resistant to other medications..

The pyrazinamide molecule is a small, water-soluble compound with a molecular weight of about 123.1 g/mol. It is a prodrug, which means that it is inactive until it is metabolized in the body. Once it is metabolized, pyrazinamide is converted to the active compound pyrazinoic acid, which inhibits the growth of TB bacteria by inhibiting the synthesis of nucleic acids and proteins..

Pyrazinamide is typically administered orally, with a usual recommended dose of 15-30 mg/kg/day. It is metabolized in the liver, and the metabolites are eliminated through the kidneys. It is important to monitor liver and kidney function during treatment with pyrazinamide, as the drug can cause liver and kidney toxicity in some patients..

Pyrazinamide is generally well-tolerated, with few serious side effects. The most common side effects are nausea, vomiting, and diarrhea. Rarely, pyrazinamide can cause more serious side effects, such as liver and kidney toxicity, hypersensitivity reactions, and pancreatitis. It is important to notify a healthcare provider if any side effects occur during treatment with pyrazinamide..

Summary

From all the above, this molecule pyrazinamide is a valuable medication that is used to treat tuberculosis, a bacterial infection that affects the lungs and other parts of the body. It is highly effective against TB, and is particularly useful for treating TB infections that are resistant to other medications. Pyrazinamide is generally well-tolerated, with few serious side effects. However, it is important to monitor liver and kidney function during treatment and to notify a healthcare provider if any side effects occur..

3D structure

Cartesian coordinates

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

2D drawing

 

Pyrazinamide IPEHBUMCGVEMRF-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Pyrazinamide

 

Molecule descriptors

 
IUPAC namepyrazine-2-carboxamide
InChI codeInChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
InChI KeyIPEHBUMCGVEMRF-UHFFFAOYSA-N
SMILESc1cnc(cn1)C(=O)N

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.

  • .alpha.-pyrazinamide
  • 1,2-dihydro-1,2,4-triazol-3-one;Pyrazinamide
  • 2-Carbamylpyrazine
  • 2-Carbamylpyrazine ;Aldinamid ;Aldinamide; Pyrazinoic acid amide
  • 2-Pyrazinecarboxamide
  • 2-pyrazine carboxamide
  • 2KNI5N06TI
  • 98-96-4
  • A845937
  • AB00052083
  • AB00052083-16
  • AB00052083_17
  • AB00052083_18
  • AC-907/25014068
  • ACT01761
  • AMY14180
  • AZT + Pyrazinamide combination
  • Aldinamid
  • Aldinamide
  • B2122
  • BB 0253141
  • BCP30257
  • BDBM228814
  • BIDD:GT0228
  • BPBio1_000515
  • BRN 0112306
  • BSPBio_000467
  • BSPBio_002572
  • C01956
  • C5H5N3O
  • CCG-39243
  • CCRIS 545
  • D-50
  • D00144
  • D70481
  • DB-002866
  • DB00339
  • DRG 0124
  • DSSTox_CID_1215
  • DSSTox_GSID_21215
  • DSSTox_RID_76014
  • DivK1c_000241
  • EU-0101011
  • Eprazin
  • FT-0659757
  • Farmizina
  • GTPL7287
  • HMS1569H09
  • HMS1920N08
  • HMS2092E09
  • HMS2096H09
  • HMS2235G17
  • HMS3259O04
  • HMS3263K03
  • HMS3371G09
  • HMS3655A10
  • HMS3713H09
  • HMS500M03
  • HSDB 3576
  • HY-B0271
  • IDI1_000241
  • Isopas
  • KBio1_000241
  • KBio2_001382
  • KBio2_003950
  • KBio2_006518
  • KBio3_001792
  • KBioGR_001851
  • KBioSS_001382
  • KSC-27-052E
  • KUC109577N
  • LP01011
  • Lopac-P-7136
  • Lopac0_001011
  • MFCD00006132
  • MK 56
  • MLS000069730
  • MLS002222347
  • NC00534
  • NCGC00015833-01
  • NCGC00015833-02
  • NCGC00015833-03
  • NCGC00015833-04
  • NCGC00015833-05
  • NCGC00015833-06
  • NCGC00015833-07
  • NCGC00015833-08
  • NCGC00015833-09
  • NCGC00015833-10
  • NCGC00015833-11
  • NCGC00015833-12
  • NCGC00015833-15
  • NCGC00015833-16
  • NCGC00015833-25
  • NCGC00090695-01
  • NCGC00090695-03
  • NCGC00090695-04
  • NCGC00090695-05
  • NCGC00090695-06
  • NCGC00090695-07
  • NCGC00256336-01
  • NCGC00259608-01
  • NCGC00261696-01
  • NCI-C01785
  • NINDS_000241
  • NSC 14911
  • NSC-14911
  • NSC-757304
  • NSC14911
  • NSC757304
  • Novamid
  • Opera_ID_735
  • P 7136
  • P0633
  • PYRAZINAMIDE COMPONENT OF RIFATER
  • PZA
  • Pezetamid
  • Pharmakon1600-01500518
  • Piraldina
  • Pirazimida
  • Pirazinamid
  • Pirazinamida
  • Pirazinamide
  • Prestwick0_000514
  • Prestwick1_000514
  • Prestwick2_000514
  • Prestwick3_000514
  • Prestwick_811
  • Pyrafat
  • Pyrazide
  • Pyrazinamdie
  • Pyrazinamide
  • Pyrazinamide (JP17/USP/INN)
  • Pyrazinamide (Pyrazinoic acid amide)
  • Pyrazinamide,(S)
  • Pyrazinamidum
  • Pyrazine carboxamide
  • Pyrazine-2-carboxylic acid amide
  • Pyrazine-[d3]-carboxamide-[15N]
  • Pyrazineamide
  • Pyrazinecarboxylic acid amide
  • Pyrazinoic acid amide; pyrazinamide; PZA
  • Pyrizinamide
  • Q417571
  • RIFATER COMPONENT PYRAZINAMIDE
  • Rifafour
  • Rifafour e-200
  • Rozide
  • SBI-0050984.P004
  • SDCCGSBI-0050984.P005
  • SMR000036662
  • SPECTRUM1500518
  • SR-01000076077
  • SR-01000076077-1
  • SR-01000076077-4
  • SR-01000076077-6
  • STK801661
  • SW196945-3
  • SY013550
  • T 165
  • TS-01626
  • Tebrazid
  • Tisamid
  • Unipyranamide
  • W-100059
  • WLN: T6N DNJ BVZ
  • Z33546644
  • Zinamide
  • pyramizade
  • pyrazinamida
  • pyrazinamide
  • pyrazine amide
  • pyrazine carboxylamide
  • pyrazine-2-carboxamide
  • pyrazine-2-carboximidic acid
  • pyrazinecarboxamide
  • pyrazinoic acid amide
  • s1762

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2005
  • CAS-98-96-4
  • CAS- 98-96-4
  • UNII-2KNI5N06TI
  • AKOS000120280
  • DTXSID9021215
  • CHEMBL614
  • CHEBI:45285
  • Tox21_110237
  • Tox21_202059
  • Tox21_302771
  • Tox21_501011
  • Tox21_110237_1
  • EINECS 202-717-6
  • SPBio_001369
  • SPBio_002388
  • SCHEMBL24102
  • Spectrum_000902
  • Spectrum2_001305
  • Spectrum3_001046
  • Spectrum4_001186
  • Spectrum5_001026

Physico-Chemical properties

IUPAC namepyrazine-2-carboxamide
Molecular formulaC5H5N3O
Molecular weight123.11
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity30.1
LogP-0.6
Topological polar surface area68.9

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

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow 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(Kow) (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 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.