Pyrazinamide
- CAS No.
- 98-96-4
- Chemical Name:
- Pyrazinamide
- Synonyms
- PYRAZINE-2-CARBOXAMIDE;PZA;Aldinamid;2-Carbamylpyrazine;PYRAZINECARBOXAMIDE;mk56;PZAD;MK 56;T 165;Eprazin
- CBNumber:
- CB7429387
- Molecular Formula:
- C5H5N3O
- Molecular Weight:
- 123.11
- MOL File:
- 98-96-4.mol
- Modify Date:
- 2023/6/8 9:02:53
| Melting point | 189-191 °C (lit.) |
|---|---|
| Boiling point | 229.19°C (rough estimate) |
| Density | 1.3260 (rough estimate) |
| refractive index | 1.5900 (estimate) |
| Flash point | >110°(230°F) |
| storage temp. | 2-8°C |
| solubility | H2O: soluble50mg/mL |
| form | Crystalline Powder or Needles |
| pka | 0.5(at 25℃) |
| color | White |
| PH | 7 (H2O) |
| Water Solubility | 15 mg/mL |
| Merck | 14,7956 |
| BRN | 112306 |
| BCS Class | 1,3 |
| LogP | -0.600 |
| CAS DataBase Reference | 98-96-4(CAS DataBase Reference) |
| NIST Chemistry Reference | Pyrazine carboxamide(98-96-4) |
| EPA Substance Registry System | Pyrazinamide (98-96-4) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P271-P280 | |||||||||
| Hazard Codes | F,C | |||||||||
| Risk Statements | 11-34 | |||||||||
| Safety Statements | 22-24/25-45-36/37/39-26-16 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | UQ2275000 | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 29339990 | |||||||||
| Toxicity | LD50 intraperitoneal in mouse: 1680mg/kg | |||||||||
| NFPA 704 |
|
Pyrazinamide price More Price(6)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | P7136 | Pyrazinecarboxamide | 98-96-4 | 10G | ₹5600 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | P7136 | Pyrazinecarboxamide | 98-96-4 | 25G | ₹7980 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1576 | Pyrazinamide Pharmaceutical Secondary Standard; Certified Reference Material | 98-96-4 | 500MG | ₹9103.83 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | P7136 | Pyrazinecarboxamide | 98-96-4 | 100G | ₹16237.5 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.21050 | 2-Pyrazinecarboxamide for synthesis | 98-96-4 | 25G | ₹5070 | 2022-06-14 | Buy |
Pyrazinamide Chemical Properties,Uses,Production
Description
Pyrazinamide was synthesized in 1952, and it is the nitrogen-analog of nicotinamide. It exhibits hepatotoxicity. Synonyms of this drug are dexambutol, miambutol, esnbutol, ebutol, and others.
Chemical Properties
Crystalline Solid
Uses
Pyrazinamide is used therapeutically as an antitubercular agent. Pyrazinamide is used to form polymeric copper complexes, create pyrazine carboxamide scaffolds useful as FXs inhibitors, and as a component of mycobacteria identification kits. It is used to study liver toxicity prevention and mechanisms of resistance .
Indications
Pyrazinamide is a synthetic analogue of nicotinamide. Its exact mechanism of action is not known, although its target appears to be the mycobacterial fatty acid synthetase involved in mycolic acid biosynthesis. Pyrazinamide requires an acidic environment, such as that found in the phagolysosomes, to express its tuberculocidal activity. Thus, pyrazinamide is highly effective on intracellular mycobacteria. The mycobacterial enzyme pyrazinamidase converts pyrazinamide to pyrazinoic acid, the active form of the drug.A mutation in the gene (pncA) that encodes pyrazinamidase is responsible for drug resistance; resistance can be delayed through the use of drug combination therapy.
Antimicrobial activity
It is principally active against actively metabolizing intracellular bacilli and those in acidic, anoxic inflammatory lesions. Activity against M. tuberculosis is highly pH dependent: at pH 5.6 the MIC is 8–16 mg/L, but it is almost inactive at neutral pH. Other mycobacterial species, including M. bovis, are resistant. Activity requires conversion to pyrazinoic acid by the mycobacterial enzyme pyrazinamidase, encoded for by the pncA gene, which is present in M. tuberculosis but not M. bovis. A few resistant strains lack mutations in pncA, indicating alternative mechanisms for resistance, including defects in transportation of the agent into the bacterial cell.
Acquired resistance
Drug resistance is uncommon and cross-resistance to other antituberculosis agents does not occur. Susceptibility testing is technically demanding as it requires very careful control of the pH of the medium, but molecular methods for detection of resistance-conferring mutations are available.
General Description
Pyrazinecarboxamide (PZA) occurs as a white crystalline powder that is sparingly soluble in water and slightly soluble in polar organic solvents. Its antitubercular properties were discovered as a result of an investigation of heterocyclic analogs of nicotinic acid, with which it is isosteric. Pyrazinamide has recently been elevated to first-line status in short-term tuberculosis treatment regimens because of its tuberculocidal activity and comparatively low short-term toxicity. Since pyrazinamide is not active against metabolically inactive tubercle bacilli, it is not considered suitable for long-term therapy. Potential hepatotoxicity also obviates long-term use of the drug. Pyrazinamide is maximally effective in the low pH environment that exists in macrophages (monocytes). Evidence suggests bioactivation of pyrazinamide to pyrazinoic acid by an amidase present in mycobacteria.
Air & Water Reactions
Water soluble.
Reactivity Profile
Pyrazinamide is a carbamate ester. Incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. May react with active metals or nitrides to produce flammable gaseous hydrogen. Incompatible with strongly oxidizing acids, peroxides, and hydroperoxides.
Pharmaceutical Applications
Like isoniazid, pyrazinamide is a synthetic nicotinamide analog, although its mode of action is quite distinct.
Pharmacology
Pyrazinamide is well absorbed from the GI tract and is widely distributed throughout the body. It penetrates tissues, macrophages, and tuberculous cavities and has excellent activity on the intracellular organisms; its plasma half-life is 9 to 10 hours in patients with normal renal function. The drug and its metabolites are excreted primarily by renal glomerular filtration.
Pharmacokinetics
Oral absorption: >90%
Cmax 20–22 mg/kg oral: 10–50 mg/L after 2 h
Plasma half-life: c. 9 h
Plasma protein binding: c. 50%
It readily crosses the blood–brain barrier, achieving CSF
concentrations similar to plasma levels. It is metabolized to
pyrazinoic acid in the liver and oxidized to inactive metabolites,
which are excreted in the urine, although about 70% of
an oral dose is excreted unchanged.
Clinical Use
Pyrazinamide is an essential component of the multidrug short-term therapy of tuberculosis. In combination with isoniazid and rifampin, it is active against the intracellular organisms that may cause relapse.
Side effects
Hepatotoxicity is the major concern in 15% of pyrazinamide recipients. It also can inhibit excretion of urates, resulting in hyperuricemia. Nearly all patients taking pyrazinamide develop hyperuricemia and possibly acute gouty arthritis. Other adverse effects include nausea, vomiting, anorexia, drug fever, and malaise. Pyrazinamide is not recommended for use during pregnancy.
Purification Methods
The amide crystallises from water, EtOH or 1:1 hexane/EtOH in four modifications viz -form, -form, -form and form. [R. & S.rum Acta Cryst 28B 1677 1972, Beilstein 25 III/IV 772.]
Pyrazinamide Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| GLR Innovations | +91 9891111994 | New Delhi, India | 4542 | 58 | Inquiry |
| BIOCHEMICAL & SYNTHETIC PRODUCTS PVT. LT., | +91-91-8421973722 +91-9869455944 | Telangana, India | 31 | 58 | Inquiry |
| SNECOFRi Pvt Ltd | +91-9032850129 +91-9032850129 | Telangana, India | 404 | 58 | Inquiry |
| Murli Krishna Exports Pvt Ltd | +91-2225631595 +91-2225631594 | New Delhi, India | 185 | 58 | Inquiry |
| Anuh Pharma Ltd (SK GROUP) | +912266227575 | Maharashtra, India | 38 | 58 | Inquiry |
| Calyx Chemicals and Pharmaceuticals Ltd | +919819317220 | Mumbai, India | 15 | 58 | Inquiry |
| Ralington Pharma | +91-7948911722 +91-9687771722 | Gujarat, India | 1350 | 58 | Inquiry |
| Amsal Chem Private Limited | +91-2222050500 +91-2222050500 | Maharashtra, India | 15 | 58 | Inquiry |
| Alfa Omega Pharma | +91-8050045945 +91-9972665399 | Maharashtra, India | 126 | 58 | Inquiry |
| Macleods Pharmaceuticals Limited | +91-2266762800 +91-2266762800 | Maharashtra, India | 116 | 58 | Inquiry |
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