2-pyridinethiol 1-oxide
2-pyridinethiol 1-oxide Uses, Dosage, Side Effects, Food Interaction and all others data.
2-pyridinethiol 1-oxide zinc, or zinc pyrithione or zinc pyridinethione, is a coordination complex consisted of pyrithione ligands chelated to zinc (2+) ions via oxygen and sulfur centers. In the crystalline state, it exists as a centrosymmetric dimer. Due to its dynamic fungistatic and bacteriostatic properties, pyrithione zinc is used to treat dandruff and seborrheic dermatitis. Dandruff is a common scalp disease affecting >40% of the world's adult population, and may be caused by fungi such as Malassezia globosa and M. restricta .
2-pyridinethiol 1-oxide zinc is commonly found as an active ingredient in OTC antidandruff topical treatments such as shampoos. It mediates its action by increasing the cellular levels of copper, and damaging iron-sulfur clusters of proteins essential for fungal metabolism and growth . Due to low solubility, pyrithione zinc released from the topical formulations is deposited and retained relatively well onto the target skin surfaces . Other uses of pyrithione zinc include additive in antifouling outdoor paints and algaecide. While its use has been approved in the early 1960's by the FDA , safety and effectiveness of pyrithione zinc has been reported for decades. It is not shown to have any significant estrogenic activity according to the in vivo and in vitro assays .
2-pyridinethiol 1-oxide zinc has a broad antimicrobial spectrum of activity, including fungi, gram-positive and gram-negative bacteria . 2-pyridinethiol 1-oxide 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 .
| Trade Name | 2-pyridinethiol 1-oxide |
| Generic | Pyrithione |
| Pyrithione Other Names | 2-pyridinethiol 1-oxide, Omadine, Pyridinethiol N-oxide |
| Type | |
| Formula | C5H5NOS |
| Weight | Average: 127.16 Monoisotopic: 127.009184959 |
| Groups | Approved |
| Therapeutic Class | |
| Manufacturer | |
| Available Country | |
| Last Updated: | September 19, 2023 at 7:00 am |
Uses
2-pyridinethiol 1-oxide is an antimicrobial agent used for the treatment of dandruff and seborrheic dermatitis.
Indicated for the treatment of dandruff and seborrheic dermatitis .
2-pyridinethiol 1-oxide is also used to associated treatment for these conditions: Dandruff, Seborrheic Dermatitis
How 2-pyridinethiol 1-oxide works
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. 2-pyridinethiol 1-oxide 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. 2-pyridinethiol 1-oxide zinc has been shown to slightly increase the levels of zinc .
Toxicity
Acute oral LD50 value is 177 mg/kg in rat and 160 mg/kg in mouse. Acute dermal LD50 was 100 mg/kg in rabbit .
Food Interaction
No interactions found.Elimination Route
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% .
Elimination Route
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 .
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