Basic information
- CAS
1121-30-8- Standard SMILES
On1ccccc1=S- InChIKey
YBBJKCMMCRQZMA-UHFFFAOYSA-N- Molecular formula
- C5H5NOS
- Average molar mass
- 127.17 g/mol
- Monoisotopic mass
- 127.00918496
Names & identifiers
- Preferred name
- Pyrithione
- IUPAC
- 1-hydroxypyridine-2-thione
- English name
- 2-Pyridinethiol 1-oxide
- Molecular formula
- C5H5NOS
- Molecular weight
- 127.16
Names & synonyms
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
Show more names
2-MERCAPTOPYRIDINE N-OXIDEN-Hydroxy-2-thiopyridoneCPAMD4FLJ17816FLJ17822Human C5 ProteinPYRIDINETHIOLOXIDEZINE PYRITHIONE 50 %
2(1H)-Pyridinethione, 1-hydroxy-NSC-1797906GK82EC25DCHEBI:36578DTXSID001499082-HPT cpdRefChem:57830DTXCID1072399
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 55.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 162
Experimental & physicochemical properties
SolubilitySoluble in cold water (Zinc salt)
Boiling Point100
Physicochemical properties
- Melting point
- 69 · 69-72 °C (lit.)
- Boiling point
- 350.2 · 350.2±15.0 °C(Predicted)
- Density
- 1.255 · 1.255 (estimate)
- refractive index
- 1.548 · 1.5480 (estimate)
- storage temp.
- Refrigerator
- solubility
- Soluble in tris-hydrochloric acid.
- form
- Powder, Crystals, and/or Chunks
- pka
- 5.4 · 5.40±0.50(Predicted)
- color
- Off-white to beige or yellow to yellow-greenish or grayish-green
- Sensitive
- Air & Light Sensitive
- Merck
- 14 · 14,7994
- BRN
- 906983 · 906983
Safety & regulation
GHS classification
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.
Hazard information
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
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%)
Toxicology
Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Chemistry & industry
Pharmacology
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.
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
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%.
Related reactions
8 records
Compound notes
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