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피라진아마이드

피라진아마이드
피라진아마이드 구조식 이미지
카스 번호:
98-96-4
한글명:
피라진아마이드
동의어(한글):
피라진아미드;피라진아마이드
상품명:
Pyrazinamide
동의어(영문):
PZA;PZAD;mk56;MK 56;T 165;Eprazin;Novamid;Pyrafat;Tisamid;Tebrazid
CBNumber:
CB7429387
분자식:
C5H5N3O
포뮬러 무게:
123.11
MOL 파일:
98-96-4.mol

피라진아마이드 속성

녹는점
189-191 °C(lit.)
끓는 점
229.19°C (rough estimate)
밀도
1.3260 (rough estimate)
굴절률
1.5900 (estimate)
인화점
>110°(230°F)
저장 조건
-20°C Freezer
용해도
H2O: soluble50mg/mL
물리적 상태
Crystalline Powder or Needles
산도 계수 (pKa)
0.5(at 25℃)
색상
White
수소이온지수(pH)
7 (H2O)
수용성
15 mg/mL
Merck
14,7956
BRN
112306
CAS 데이터베이스
98-96-4(CAS DataBase Reference)
NIST
Pyrazine carboxamide(98-96-4)
EPA
Pyrazinecarboxamide(98-96-4)

안전

위험품 표기 F,C
위험 카페고리 넘버 11-34
안전지침서 22-24/25-45-36/37/39-26-16
WGK 독일 3
RTECS 번호 UQ2275000
TSCA Yes
HS 번호 29339990
유해 물질 데이터 98-96-4(Hazardous Substances Data)

피라진아마이드 MSDS


Pyrazinecarboxamide

피라진아마이드 C화학적 특성, 용도, 생산

화학적 성질

Crystalline Solid

용도

An antibacterial agent used to study liver toxicity prevention

용도

Antibacterial (tuberculostatic)

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.

원료

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.

일반 설명

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.

일반 설명

White powder. Sublimes from 318°F.

공기와 물의 반응

Water soluble.

반응 프로필

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

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

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.

부작용

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.

부작용

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.

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.]

피라진아마이드 준비 용품 및 원자재

원자재

준비 용품


피라진아마이드 공급 업체

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