基本情報
- 標準SMILES
On1ccccc1=S- InChIKey
YBBJKCMMCRQZMA-UHFFFAOYSA-N- 分子式
- C5H5NOS
- 平均分子量
- 127.17 g/mol
- 単同位体質量
- 127.00918496
名称と識別子
- 優先名称
- Pyrithione
- IUPAC
- 1-hydroxypyridine-2-thione
- 現地名
- 2-メルカプトピリジン N-オキシド
- 英語名
- 2-Pyridinethiol 1-oxide
- 分子式
- C5H5NOS
- 分子量
- 127.16
名称と別名
名称をさらに表示
データベース識別子
- 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
物性
構造計算による物性
- XLogP
- 0.5
- 極性表面積
- 55.6 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 0
- 重原子数
- 8
- 形式電荷
- 0
- 複雑度
- 162
実験および物理化学的性質
物理化学的性質
- 融点
- 69 · 69-72 °C (lit.)
- 沸点
- 350.2 · 350.2±15.0 °C(Predicted)
- 比重(密度)
- 1.255 · 1.255 (estimate)
- 屈折率
- 1.548 · 1.5480 (estimate)
- 貯蔵温度
- Refrigerator
- 溶解性
- トリス塩酸に可溶。
- 外見
- パウダー、クリスタル、および/またはチャンク
- 酸解離定数(Pka)
- 5.4 · 5.40±0.50(Predicted)
- 色
- オフホワイトからベージュまたはイエローから黄緑または灰緑
- Merck
- 14 · 14,7994
- BRN
- 906983 · 906983
- 安定性
- 安定。強塩基、強酸化剤とは相容れない。
- InChI
- 1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H
- InChIKey
- FGVVTMRZYROCTH-UHFFFAOYSA-N
- SMILES
- [O-][n+]1ccccc1S
- CAS データベース
- 1121 · 1121-31-9(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · 2-Mercaptopyridine-n-oxide(1121-31-9)
- EPAの化学物質情報
- 2 · 2-Pyridinethiol, 1-oxide (1121-31-9)
化学的性質
化学的特性off-white powder
安全と法規制
GHS分類
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.
危険有害性情報
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
毒性情報
法規制情報
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
安全データ
- F
- 8-10-13-23
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UT8999000
- ridadr
- 2811
- hs_code
- 29333990
- risk_code
- 36/37/38-22-63-20/21/22
- 化審法
- (5)-752
- hazard_code
- Xi,Xn
- safety_code
- 26-36-24/25-36/37-22
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
化学と産業
薬理情報
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.
用途と製造
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]
応用分野
使用2-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.
一般的な説明2-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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