Pyrazinamide
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-04531 |
| CAS | 98-96-4 |
| Molecular Weight | 123.11 |
| Molecular Formula | C5H5N3O |
| Purity | >98% |
Online Inquiry
Description
Pyrazinamide is a pyrazine that is used therapeutically as an antitubercular agent. It is a prodrug that stops the growth of Mycobacterium tuberculosis. It is thought to inhibit the enzyme fatty acid synthase (FAS) I, which is required by the bacterium to synthesise fatty acids although this has been discounted. It binds to the ribosomal protein S1 (RpsA) and inhibits trans-translation.
Specification
| Synonyms | Pyrazinecarboxamide; Pyrazinoic acid amide; 2-Pyrazinecarboxamide; Zinamide; Aldinamide; Tebrazid; Pirazinamid; Unipyranamide; Farmizina; Eprazin; Novamid |
| Storage | Store at -20°C |
| IUPAC Name | pyrazine-2-carboxamide |
| Canonical SMILES | C1=CN=C(C=N1)C(=O)N |
| InChI | InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9) |
| InChI Key | IPEHBUMCGVEMRF-UHFFFAOYSA-N |
| Source | Synthetic |
Properties
| Appearance | White to Off-white Solid |
| Antibiotic Activity Spectrum | Mycobacteria |
| Boiling Point | 357.4°C at 760 mmHg |
| Melting Point | 189-191°C |
| Density | 1.301 g/cm3 |
| Solubility | Slightly soluble in DMSO, Methanol |
Reference Reading
1.Inhibitory Interaction Potential of 22 Antituberculosis Drugs on Organic Anion and Cation Transporters of the SLC22A Family.
Parvez MM;Kaisar N;Shin HJ;Jung JA;Shin JG Antimicrob Agents Chemother. 2016 Oct 21;60(11):6558-6567. doi: 10.1128/AAC.01151-16. Print 2016 Nov.
Twenty-two currently marketed antituberculosis drugs were comprehensively evaluated for their inhibitory effect on organic anionic transporter (OAT)- and organic cation transporter (OCT)-mediated uptake using stably transfected HEK293 cells in vitro We observed moderate to strong inhibitory effects on OAT1- and OAT3-mediated para-aminohippurate (PAH) uptake and OCT1- and OCT2-mediated N-methyl-4-phenylpylidinium acetate (MPP;+;) uptake. Ciprofloxacin, linezolid, para-aminosalicylic acid (PAS), and rifampin were observed to have strong inhibitory effects, with the concentrations for a 50% inhibitory effect (IC;50;s) being 35.1, 31.1, 37.6, and 48.1 μM, respectively, for OAT1 and >100, 21.9, 24.6, and 30.2 μM, respectively, for OAT3. Similarly, pyrazinamide, rifabutin, and levofloxacin were observed to have inhibitory effects, with IC;50; values being 36.5, 42.7, and 30.3 μM, respectively, for OCT1 and with the IC;50; value for PAS being 94.2 μM for OCT2. In addition, we used zidovudine and metformin as clinically prescribed substrates of OATs and OCTs, respectively, and zidovudine and metformin uptake was also strongly inhibited by the antituberculosis drugs. Among the tested drugs, the highest drug-drug interaction (DDI) indexes were found for PAS, which were 9.
2.Naïve-pooled pharmacokinetic analysis of pyrazinamide, isoniazid and rifampicin in plasma and cerebrospinal fluid of Vietnamese children with tuberculous meningitis.
Pouplin T;Bang ND;Toi PV;Phuong PN;Dung NH;Duong TN;Caws M;Thwaites GE;Tarning J;Day JN BMC Infect Dis. 2016 Apr 2;16:144. doi: 10.1186/s12879-016-1470-x.
BACKGROUND: ;Among the various forms of TB, tuberculous meningitis (TBM) is the most severe, with about 30% mortality and 50% of survivors left with neurological sequelae. Children suffer more frequently from TBM than adults and outcomes are often poor due to difficulties in making the diagnosis and uncertainty regarding the best anti-tuberculosis drug regimen. The aim of this prospective study was to describe the pharmacokinetics of pyrazinamide, isoniazid and rifampicin in plasma and cerebrospinal fluid of children with tuberculous meningitis treated with the standard TBM regimen.;METHODS: ;We performed a prospective observational study of 100 consecutively treated children (≤ 15 years of age) with tuberculous meningitis in Ho Chi Minh City, Vietnam. Children were treated according to the 2006 WHO recommended pediatric treatment regimen consisting of isoniazid (5 mg/kg), rifampicin (10 mg/kg) and ethambutol (15 mg/kg) for 8 months, with the addition of pyrazinamide (25 mg/kg) for the first 3 months and streptomycin (15 mg/kg) for the first 2 months. Pyrazinamide, isoniazid and rifampicin concentrations were measured in plasma at day 14 and in cerebrospinal fluid (CSF) at 1 month by HPLC-UV.
3.Clofazimine shortens the duration of the first-line treatment regimen for experimental chemotherapy of tuberculosis.
Tyagi S;Ammerman NC;Li SY;Adamson J;Converse PJ;Swanson RV;Almeida DV;Grosset JH Proc Natl Acad Sci U S A. 2015 Jan 20;112(3):869-74. doi: 10.1073/pnas.1416951112. Epub 2015 Jan 5.
A key drug for the treatment of leprosy, clofazimine has recently been associated with highly effective and significantly shortened regimens for the treatment of multidrug-resistant tuberculosis (TB). Consequently, we hypothesized that clofazimine may also shorten the duration of treatment for drug-susceptible TB. We conducted a controlled trial in the mouse model of TB chemotherapy comparing the activity of the 6-mo standard regimen for TB treatment, i.e., 2 mo of daily rifampin, isoniazid, pyrazinamide, and ethambutol followed by 4 mo of rifampin and isoniazid, with a 4-mo clofazimine-containing regimen: 2 mo of daily rifampin, isoniazid, pyrazinamide, and clofazimine followed by 2 mo of rifampin, isoniazid, and clofazimine. Treatment efficacy was assessed on the basis of Mycobacterium tuberculosis colony counts in the lungs and spleens during treatment and on the proportion of mice with culture-positive relapse 6 mo after treatment cessation. No additive effect of clofazimine was observed after the first week of treatment, but, by the second week of treatment, the colony counts were significantly lower in the clofazimine-treated mice than in the mice receiving the standard regimen.
Recommended Products
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-02614 | Nystatin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
