기본 정보
- 표준 SMILES
On1ccccc1=S- InChIKey
YBBJKCMMCRQZMA-UHFFFAOYSA-N- 분자식
- C5H5NOS
- 평균 분자량
- 127.17 g/mol
- 단동위원소 질량
- 127.00918496
이름 및 식별자
- 우선 이름
- Pyrithione
- IUPAC
- 1-hydroxypyridine-2-thione
- 현지명
- 오마딘
- 영어명
- 2-Pyridinethiol 1-oxide
- 분자식
- C5H5NOS
- 분자량
- 127.16
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
1121-30-8、1121-31-9- PubChem CID
- 1570
- DTXSID
DTXSID00149908- ChEMBL
CHEMBL1356238、CHEMBL1650619- ChEBI
CHEBI:36578- UNII
- 6GK82EC25D
- EC Number
- 214-328-9、214-329-4
- Nikkaji
- J2.517.340F、J39.629J、J7.264H
물성
구조 계산 물성
- XLogP
- 0.5
- 극성 표면적
- 55.6 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 0
- 무거운 원자 수
- 8
- 형식 전하
- 0
- 복잡도
- 162
실험 및 물리화학적 성질
물리화학적 성질
- 녹는점
- 69 · 69-72 °C (lit.)
- 끓는 점
- 350.2 · 350.2±15.0 °C(Predicted)
- 밀도
- 1.255 · 1.255 (estimate)
- 굴절률
- 1.548 · 1.5480 (estimate)
- 저장 조건
- Refrigerator
- 용해도
- 트리스 염산에 용해됩니다.
- 물리적 상태
- 분말, 결정 및/또는 덩어리
- 산도 계수 (pKa)
- 5.4 · 5.40±0.50(Predicted)
- 색상
- 황백색에서 베이지색 또는 노란색에서 황록색 또는 회녹색
- Merck
- 14 · 14,7994
- BRN
- 906983 · 906983
- 안정성
- 안정적인. 강염기, 강산화제와 호환되지 않습니다.
- InChI
- 1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H
- InChIKey
- FGVVTMRZYROCTH-UHFFFAOYSA-N
- SMILES
- [O-][n+]1ccccc1S
- NIST
- 2 · 2-Mercaptopyridine-n-oxide(1121-31-9)
- EPA
- 2 · 2-Pyridinethiol, 1-oxide (1121-31-9)
화학적 성질
off-white powder
안전 및 규제
GHS 분류
GHS Classification
Danger
H301 (95.7%): Toxic if swallowed [Danger Acute toxicity, oral];H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (97.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
Regulatory Information
2(1H)-Pyridinethione, 1-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard
2-Pyridinethiol, 1-oxide: Does not have an individual approval but may be used under an appropriate group standard
독성 정보
규제 정보
Regulatory Information
2(1H)-Pyridinethione, 1-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard
2-Pyridinethiol, 1-oxide: Does not have an individual approval but may be used under an appropriate group standard
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UT8999000
- ridadr
- 2811
- HS 번호
- 29333990
- risk_code
- 36/37/38-22-63-20/21/22
- hazard_code
- Xi,Xn
- safety_code
- 26-36-24/25-36/37-22
- 기존화학 물질
- KE-29947
- F 고인화성물질
- 8-10-13-23
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 함량 및 규제정보
- 물질구분: 유독물질; 혼합물(제품)함량정보: 오마딘 및 이를 1% 이상 함유한 혼합물
- 유해화학물질 필터링
- 97-1-210
화학 및 산업
약리 정보
Pharmacodynamics
Pyrithione zinc has a broad antimicrobial spectrum of activity, including fungi, gram-positive and gram-negative bacteria. Pyrithione zinc is effective against Malassezia and all other fungi, especially the Malassezia species found on scalp. In patients with dandruff, treatment with pyrithione zinc reduced the amount of fungus on the scalp, which reduces the amount of free fatty acids, thereby reducing scalp flaking and itch.
Mechanism of Action
Inhibition of fungal growth by pyrithione zinc is linked to increased copper uptake and cellular levels of copper, which is demonstrated by decreased CTR1-lacZ expression and slightly increased CUP1-lacZ expression in affected microorganisms. The coordination complex of pyrithione zinc dissociates, and pyrithione ligand forms a CuPT complex from available extracellular copper in the target organism. Pyrithione acts as an ionophore, interacting nonspecifically with the plasma membrane to shuttle copper into the cell, and facilitates copper transport across intracellular membranes. Copper may be shuttled into the mitochondria. Copper inactivates iron-sulfur (Fe-S) cluster-containing proteins via a mechanism similar to that described for copper-induced growth inhibition in bacteria. Decreased activity of Fe-S proteins leads to inhibition of fungal metabolism and fungal growth. Pyrithione zinc has been shown to slightly increase the levels of zinc.
Absorption, Distribution and Excretion
Following oral ingestion, only the pyrithione moiety is absorbed. Less than 1% of administered zinc pyrithione is absorbed from the skin. Radioabeled Zn pyrithione administered to rats, rabbits and monkeys, either orally or via intraperitoneal injection were absorbed into circulatin to extent of 80-90%.
The major route of elimination from the body after oral administration in rat was urine, with S-glucuronides of 2-mercaptopyridine-N-oxide being the major metabolites and 2-mercaptopyridine-N-oxide as the minor metabolite. Following oral administration, the majority of zinc is eliminated in the feces. Upon dermal administration, >90% of recovery was obtained from washings of the application site of pigs. Urinary excretion was 3% in animals with intact skin.
용도 및 제조
Uses
The sodium salt of pyrithione is used as a biocide in metalworking fluids; also used in ink, synthetic fiber lubricants, and dandruff shampoo; [Kanerva, p. 1832] Used as a biocide in the aircraft industry; [Kanerva, p. 1259] Used as an anti-fungal agent and disinfectant; [ChemIDplus]
Metal Machining [Category: Heat or Machine];Using Disinfectants or Biocides [Category: Clean]
응용 분야
용도2-Mercaptopyridine N-oxide is used in ratiometric fluorescence imaging of intracellular zinc ions in mammalian cultures. It is used in the radical coupling of benzoyl derivatives of 2-deoxy-D-ribose, with heterocyclic bases to give C-nucleosides. It acts as a ligand and form coordination complexes with palladium chloride. It is a precursor to O-acyl thiohydroxamates. Further, it serves as an antifungal agent. In addition to this, it is used in the preparation of 1-oxa-2-oxo-3-thia-indolizinium chloride by reaction with carbonyl dichloride.
일반 설명2-Mercaptopyridine N-oxide forms complexes on reaction with palladium chloride. It inhibits NADH-fumarate reductase purified from Trypanosoma cruzi. It is precursor to O-acyl thiohydroxamates. It ligates to metals to form biologically active complexes.
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