Grundinformationen
- Standard-SMILES
On1ccccc1=S- InChIKey
YBBJKCMMCRQZMA-UHFFFAOYSA-N- Summenformel
- C5H5NOS
- Durchschnittliche Molmasse
- 127,17 g/mol
- Monoisotopische Masse
- 127,00918496
Namen und Bezeichner
- Bevorzugter Name
- Pyrithione
- IUPAC
- 1-hydroxypyridine-2-thione
- Lokaler Name
- Pyridin-2-thiol-N-oxid
- Englischer Name
- 2-Pyridinethiol 1-oxide
- Summenformel
- C5H5NOS
- Molmasse
- 127.16
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,5
- Polarare Oberfläche (TPSA)
- 55,6 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 162
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 69 · 69-72 °C (lit.)
- Siedepunkt
- 350.2 · 350.2±15.0 °C(Predicted)
- Dichte
- 1.255 · 1.255 (estimate)
- Brechungsindex
- 1.548 · 1.5480 (estimate)
- storage temp.
- Refrigerator
- Löslichkeit
- Soluble in tris-hydrochloric acid.
- Aggregatzustand
- Powder, Crystals, and/or Chunks
- pka
- 5.4 · 5.40±0.50(Predicted)
- Farbe
- Off-white to beige or yellow to yellow-greenish or grayish-green
- Merck
- 14 · 14,7994
- BRN
- 906983 · 906983
- Stabilität
- Stable. Incompatible with strong bases, strong oxidizing agents.
- InChI
- 1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H
- InChIKey
- FGVVTMRZYROCTH-UHFFFAOYSA-N
- SMILES
- [O-][n+]1ccccc1S
- CAS Datenbank
- 1121 · 1121-31-9(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · 2-Mercaptopyridine-n-oxide(1121-31-9)
- EPA chemische Informationen
- 2 · 2-Pyridinethiol, 1-oxide (1121-31-9)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
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
Toxikologische Informationen
Regulatorische Informationen
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
Sicherheitsdaten
- F
- 8-10-13-23
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- 2811
- hs_code
- 29333990
- RTECS-Nr.
- UT8999000
- risk_code
- 36/37/38-22-63-20/21/22
- hazard_code
- Xi,Xn
- safety_code
- 26-36-24/25-36/37-22
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
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]
Anwendungen
Verwenden2-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.
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