2-メルカプトピリジン N-オキシド

Pyrithione

HCID 1570CAS 1121-30-8

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

pyrithione1121-30-82-MERCAPTOPYRIDINE-N-OXIDE1-Hydroxy-2-pyridinethioneOmadine2-Pyridinethiol 1-oxide1-hydroxypyridine-2-thione1-hydroxypyridine-2(1H)-thione1-Hydroxy-2(1H)-pyridinethioneN-Hydroxypyridine-2-thioneSQ 2113pyridinethiol n-oxide
名称をさらに表示
2-メルカプトピリジン N-オキシドピリジン-2-チオール1-オキシド2-メルカプトピリジンN-オキシドオマジン2-ピリジンチオール1-オキシド2-メルカプトピリジン1-オキシド2-メルカプトピリジン-N-オキシド2‐メルカプトピリジン‐N‐オキシド2-メルカプトピリジン=N-オキシド2-メルカプトピリジン=N-オキシド, 99%2-MERCAPTOPYRIDINE N-OXIDEN-Hydroxy-2-thiopyridoneCPAMD4FLJ17816FLJ17822Human C5 ProteinPYRIDINETHIOLOXIDEZINE PYRITHIONE 50 %
2(1H)-Pyridinethione, 1-hydroxy-NSC-1797906GK82EC25DCHEBI:36578DTXSID001499082-HPT cpdRefChem:57830DTXCID1072399

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

実験および物理化学的性質

SolubilitySoluble in cold water (Zinc salt)
Boiling Point100

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。

化学的性質

化学的特性off-white powder

安全と法規制

GHS分類

GHS Classification · 5 件

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 件

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

Hazards SummaryAllergic contact dermatitis reported in a metallurgic worker; [Kanerva, p. 1832]
Hazard Classes and CategoriesAcute Tox. 3 (95.7%);Skin Irrit. 2 (100%);Eye Irrit. 2 (100%);STOT SE 3 (97.8%)

毒性情報

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.

法規制情報

Regulatory Information · 2 件

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

化学と産業

薬理情報

Pharmacodynamics · 1 件

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 · 1 件

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.

Metabolism/MetabolitesAfter oral administration in rabbits, rats, monkeys, and dogs, pyrithione zinc is biotransformed into 2-pyridinethiol 1-oxide S-glucuronide and 2-pyridinethiol S-glucuronide.
MeSH Pharmacological ClassificationSubstances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Absorption, Distribution and Excretion · 2 件

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 · 2 件

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]

General Manufacturing Information2-Pyridinethiol, 1-oxide: ACTIVE
応用分野 · 2 件

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.

上流・下流製品情報

下流製品

サプライヤー50 社

韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Suzhou ARTK Medchem Co., Ltd.+86-18168183658 · [email protected]

関連反応

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