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ピラジンアミド

ピラジンアミド 化学構造式
98-96-4
CAS番号.
98-96-4
化学名:
ピラジンアミド
别名:
ピラジンアミド;PZA【ピラジナミド】;ピラルジナ;2-ピラジンカルボキサミド;アルジンアミド;ピラジミダ;ピラジナミド;ツベルサン;ジナミド;テブラジド;ウニピランアミド;ピラジンカルボアミド;ノバミド;ピラジン酸アミド;エプラジン;ピラファト;ピラジン-2-カルボアミド;ピラマイド;チサミド;ファルミジナ
英語化学名:
Pyrazinamide
英語别名:
PZA;mk56;PZAD;MK 56;T 165;Novamid;Eprazin;Pyrafat;Tisamid;Tebrazid
CBNumber:
CB7429387
化学式:
C5H5N3O
分子量:
123.11
MOL File:
98-96-4.mol

ピラジンアミド 物理性質

融点 :
189-191 °C (lit.)
沸点 :
229.19°C (rough estimate)
比重(密度) :
1.3260 (rough estimate)
屈折率 :
1.5900 (estimate)
闪点 :
>110°(230°F)
貯蔵温度 :
2-8°C
溶解性:
H2O: soluble50mg/mL
外見 :
Crystalline Powder or Needles
酸解離定数(Pka):
0.5(at 25℃)
色:
White
PH:
7 (H2O)
水溶解度 :
15 mg/mL
Merck :
14,7956
BRN :
112306
CAS データベース:
98-96-4(CAS DataBase Reference)
NISTの化学物質情報:
Pyrazine carboxamide(98-96-4)
EPAの化学物質情報:
Pyrazinamide (98-96-4)

安全性情報

主な危険性  F,C
Rフレーズ  11-34
Sフレーズ  22-24/25-45-36/37/39-26-16
WGK Germany  3
RTECS 番号 UQ2275000
TSCA  Yes
HSコード  29339990
有毒物質データの 98-96-4(Hazardous Substances Data)
毒性 LD50 intraperitoneal in mouse: 1680mg/kg

ピラジンアミド 価格 もっと(35)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBOR-0062 ピラジンアミド
Pyrazinamide
98-96-4 5g ¥3600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBOR-0062
Pyrazinamide
98-96-4 1kg ¥115200 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01COBOR-0062 ピラジンアミド
Pyrazinamide
98-96-4 1g ¥11300 2020-09-21 購入
東京化成工業 P0633 ピラジンアミド >98.0%(HPLC)(N)
Pyrazinamide >98.0%(HPLC)(N)
98-96-4 25g ¥5200 2021-03-23 購入
関東化学株式会社(KANTO) 15764-2A ピラジンアミド 99%
Pyrazinamide 99%
98-96-4 10g ¥7200 2021-03-23 購入

ピラジンアミド MSDS


Pyrazinecarboxamide

ピラジンアミド 化学特性,用途語,生産方法

外観

白色~ほとんど白色粉末~結晶

解説

pirazinoic acid amide.C5H5N3O(123.11).ピラジンカルボン酸メチルのアンモニア分解で得られる."白色の結晶.融点188~193 ℃.λmax 269 nm.pKa 0.5.水,メタノールに難溶.肺結核治療薬として,イソニコチン酸ヒドラジドと併用して使用される.[CAS 98-96-4]
森北出版「化学辞典(第2版)

効能

抗結核薬

商品名

ピラマイド (アルフレッサファーマ)

説明

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.

化学的特性

Crystalline Solid

使用

Antibacterial (tuberculostatic)

使用

An antibacterial agent used to study liver toxicity prevention

使用

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 .

適応症

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.

抗菌性

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.

獲得抵抗性

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.

一般的な説明

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.

一般的な説明

White powder. Sublimes from 318°F.

空気と水の反応

Water soluble.

反応プロフィール

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.

応用例(製薬)

Like isoniazid, pyrazinamide is a synthetic nicotinamide analog, although its mode of action is quite distinct.

Biochem/physiol Actions

The active moiety of pyrazinamide is pyrazinoic acid (POA). POA is thought to disrupt membrane energetics and inhibit membrane transport function at acid pH in Mycobacterium tuberculosis. Iron enhances the antituberculous activity of pyrazinamide . Pyrazinamide and its analogs have been shown to inhibit the activity of purified FAS I.

薬理学

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.

薬物動態学

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.

臨床応用

Tuberculosis (a component of the early, intensive phase of short-course therapy)

臨床応用

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.

副作用

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.

副作用

It is usually well tolerated. Moderate elevations of serum transaminases occur early in treatment. Severe hepatotoxicity is uncommon with standard dosage, except in patients with pre-existing liver disease.
Its principal metabolite, pyrazinoic acid, inhibits renal excretion of uric acid, but gout is extremely rare. An unrelated arthralgia, notably of the shoulders and responsive to analgesics, also occurs.
Other side effects include anorexia, nausea, mild flushing of the skin and photosensitization.

Chemical Synthesis

Pyrazinamide, pyrazincarboxamide (34.1.11), is synthesized from quinoxaline (34.1.7) by reacting o-phenylendiamine with glyoxal. Oxidation of this compound with sodium permanganate gives pyrazin-2,3-dicarboxylic acid (34.1.8). Decarboxylation of the resulting product by heating gives pyrazin-2-carboxylic acid (34.1.9). Esterifying the resulting acid with methanol in the presence of hydrogen chloride and further reaction of this ester (34.1.10) with ammonia gives pyrazinamide.


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.

純化方法

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.]

ピラジンアミド 上流と下流の製品情報

原材料

準備製品


ピラジンアミド 生産企業

Global( 397)Suppliers
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98-96-4(ピラジンアミド)キーワード:


  • 98-96-4
  • 2-Carbamylpyrazine
  • Aldinamid
  • Aldinamide
  • Eprazin
  • Farmizina
  • MK 56
  • mk56
  • NCI-C01785
  • Novamid
  • Pirazimida
  • Pirazinamid
  • Pyrafat
  • Pyrazinamid
  • Pyrazine Carboxylamide
  • Pyrazine-2-carboxamide(δ-modification)
  • Pyrazineamide
  • pyrazinecarboxylamide
  • Pyrazinecarboxylic acid amide
  • PZA
  • T 165
  • Tebrazid
  • Unipyranamide
  • Zinamide
  • Pyrazinamide, Pyrazinoic acid amide
  • Tisamid
  • Pyrazinamide (200 mg)
  • 2-Carbamoylpyrazine
  • PyrazinaMide, 99% 25GR
  • PyrazinecarboxaMide, 97+%
  • PyrazinaMide 0
  • ピラジンアミド
  • PZA【ピラジナミド】
  • ピラルジナ
  • 2-ピラジンカルボキサミド
  • アルジンアミド
  • ピラジミダ
  • ピラジナミド
  • ツベルサン
  • ジナミド
  • テブラジド
  • ウニピランアミド
  • ピラジンカルボアミド
  • ノバミド
  • ピラジン酸アミド
  • エプラジン
  • ピラファト
  • ピラジン-2-カルボアミド
  • ピラマイド
  • チサミド
  • ファルミジナ
  • 2-ピラジンカルボアミド
  • イソピラトシン
  • ジアジンアミド
  • ピラジンカルボキサミド
  • ピラジンカルボキシアミド
  • ピラジナミド (JP17)
  • 構造分類
  • クロロピラジン他
  • ピラジン
  • 抗結核薬
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