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Pidolic acid | CAS No: 98-79-3 | GMP-certified suppliers
A medication that is primarily utilized as an amino acid derivative in cosmetic formulations for skin and hair conditioning due to its moisturizing humectant properties.
Therapeutic categories
Alimentary Tract and MetabolismAmino AcidsAmino Acids, AcidicAmino Acids, CyclicAmino Acids, Peptides, and ProteinsGlutamates
Generic name
Pidolic acid
Molecule type
small molecule
CAS number
98-79-3
DrugBank ID
DB03088
Approval status
Approved drug, Investigational drug
ATC code
A12CC08
Primary indications
- There is currently no clinically approved and/or marketed medicine that relies upon pidolic acid as an active ingredient for any formal therapeutic indication
- Although pidolic acid may be sold in a variety of non-prescription, over-the-counter dietary supplement products for cognitive or memory enhancement, there are many studies that suggest that such products or such supplementation do not elicit any kind of cognitive benefit to users [A32981, A32982]
- In fact, the general suggestion for any such pidolic acid product is to exercise caution in their recommendation as much more research is necessary
- Pidolic acid and sodium pidolic acid are, however, used to some extent in skin and hair conditioning agents owing to their humectant characteristics
Product Snapshot
- Pidolic acid is available in multiple formulations including oral tablets, effervescent powders, and topical solutions, gels, and lotions
- It is primarily used in non-prescription products as a dietary supplement and in skin and hair conditioning agents due to its humectant properties, with no formal therapeutic indications approved
- The compound is approved and investigational in regulatory markets including the US and Canada
Clinical Overview
Pidolic acid (CAS number 98-79-3) is a naturally occurring amino acid derivative classified within the alpha amino acids and derivatives group. It is characterized by a lactam structure formed via cyclization of the free amino group of glutamic acid or glutamine. Endogenously, pidolic acid functions as a biological intermediate in various metabolic pathways, notably within the glutathione cycle. It is present predominantly in bound form in brain tissue and other tissues such as skin.
Clinically, pidolic acid does not have any approved therapeutic indications. It is sometimes included in over-the-counter dietary supplements aimed at cognitive or memory enhancement; however, current scientific evidence does not support efficacy for these uses, and caution is advised regarding their recommendation.
Pharmacodynamically, pidolic acid is involved in glutathione metabolism and can accumulate under metabolic dysfunction. Elevated blood levels of pidolic acid are linked to multiple inborn errors of metabolism, including 5-oxoprolinuria, glutathione synthetase deficiency, and propionic acidemia, conditions that lead to organic acidemias characterized by metabolic acidosis. Clinical manifestations of acidosis vary by age and severity, potentially resulting in neurological and systemic complications. High pidolic acid concentrations have also been observed in cases of acetaminophen overdose, contributing to high anion gap metabolic acidosis.
Mechanistically, pidolic acid is formed enzymatically or spontaneously through cyclization reactions of glutamate or glutamine residues. It is converted back to glutamate by the enzyme 5-oxoprolinase. Its presence as a pyroglutamate N-terminal modification can interfere with protein sequencing techniques but can be reversed by pyroglutamate aminopeptidase. Beyond its endogenous roles, salts of pidolic acid (e.g., calcium, magnesium, potassium pidolates) are used in cosmetic formulations for skin and hair conditioning due to their humectant properties, which promote moisture retention through hydrogen bonding with water molecules.
From an ADME perspective, detailed pharmacokinetic data on pidolic acid are limited. Its endogenous origin and metabolic interconversions suggest rapid integration into amino acid and glutathione metabolic cycles.
Quality and sourcing considerations for pidolic acid API procurement include ensuring identity, purity, and absence of contaminants, given its role in metabolic pathways and potential toxicity at elevated levels. Manufacturers should comply with relevant pharmacopeial standards or equivalent quality guidelines. Special attention should be paid to the control of residual solvents and endotoxin levels, especially if used in formulations for cosmetic or nutritional applications. Due to the limited clinical use, regulatory requirements may vary, and suppliers must provide comprehensive analytical documentation to support consistent quality and safety.
Clinically, pidolic acid does not have any approved therapeutic indications. It is sometimes included in over-the-counter dietary supplements aimed at cognitive or memory enhancement; however, current scientific evidence does not support efficacy for these uses, and caution is advised regarding their recommendation.
Pharmacodynamically, pidolic acid is involved in glutathione metabolism and can accumulate under metabolic dysfunction. Elevated blood levels of pidolic acid are linked to multiple inborn errors of metabolism, including 5-oxoprolinuria, glutathione synthetase deficiency, and propionic acidemia, conditions that lead to organic acidemias characterized by metabolic acidosis. Clinical manifestations of acidosis vary by age and severity, potentially resulting in neurological and systemic complications. High pidolic acid concentrations have also been observed in cases of acetaminophen overdose, contributing to high anion gap metabolic acidosis.
Mechanistically, pidolic acid is formed enzymatically or spontaneously through cyclization reactions of glutamate or glutamine residues. It is converted back to glutamate by the enzyme 5-oxoprolinase. Its presence as a pyroglutamate N-terminal modification can interfere with protein sequencing techniques but can be reversed by pyroglutamate aminopeptidase. Beyond its endogenous roles, salts of pidolic acid (e.g., calcium, magnesium, potassium pidolates) are used in cosmetic formulations for skin and hair conditioning due to their humectant properties, which promote moisture retention through hydrogen bonding with water molecules.
From an ADME perspective, detailed pharmacokinetic data on pidolic acid are limited. Its endogenous origin and metabolic interconversions suggest rapid integration into amino acid and glutathione metabolic cycles.
Quality and sourcing considerations for pidolic acid API procurement include ensuring identity, purity, and absence of contaminants, given its role in metabolic pathways and potential toxicity at elevated levels. Manufacturers should comply with relevant pharmacopeial standards or equivalent quality guidelines. Special attention should be paid to the control of residual solvents and endotoxin levels, especially if used in formulations for cosmetic or nutritional applications. Due to the limited clinical use, regulatory requirements may vary, and suppliers must provide comprehensive analytical documentation to support consistent quality and safety.
Identification & chemistry
| Generic name | Pidolic acid |
|---|---|
| Molecule type | Small molecule |
| CAS | 98-79-3 |
| UNII | SZB83O1W42 |
| DrugBank ID | DB03088 |
Pharmacology
| Summary | Pidolic acid is an endogenous amino acid derivative involved as a metabolic intermediate in glutathione and glutamine pathways, primarily converted to glutamate via 5-oxoprolinase. It is found in high concentrations in brain and skin tissues, and elevated levels are associated with metabolic acidosis and several inborn errors of metabolism. Additionally, certain pidolic acid salts are utilized externally for their humectant properties in skin and hair formulations. |
|---|---|
| Mechanism of action | Pidolic acid is an endogenous amino acid derivative where the free amino group of glutamic acid or glutamine cyclizes to generate a lactam [A32991, L2729]. Subsequently it is also a metabolite in the glutathione cycle that is converted to glutamate by the enzyme 5-oxoprolinase [A32991, L2729]. Moreover, N-terminal glutamic acid and glutamine residues can either spontaneously cyclize to become pidolic acid, or be enzymatically transformed by glutaminyl cyclases [A32991, L2729]. In particular, this is ultimately a form of N-termini that is a challenge for N-terminal sequencing using Edman chemistry, which necessitates a free primary amino group that is not present in pidolic acid [A32991, L2729]. Pyroglutamate aminopeptidase can restore a free N-terminus by cleaving off the pyroglutamate residue, however [A32991, L2729]. Additionally, pidolic acid and certain pidolic acid salts like calcium, magnesium, and potassium pidolic acid are sometimes used as skin or hair conditioning agents because of their humectant effects . In such humectant formulations, hydrophilic amine, hydroxyl, or even carboxyl groups possess high affinities for forming hydrogen bonds with molecules of water, allowing the hygroscopic formulations to attract and retain moisture in the air nearby through absorption, therefore drawing the water vapor into the formulation. |
| Pharmacodynamics | Pidolic acid is a naturally occurring but little-studied amino acid derivative that can be formed enzymatically or non-enzymatically and participates as a biological intermediate in various chemical pathways [A32991, L2729]. Elevations of the acid in blood levels may be associated with problems of glutamine or glutathione metabolism . Pidolic acid, in general, is found in large quantities in brain tissue and other tissues in bound form, like skin . Moreover, pidolic acid in high enough levels can act as an acidogen capable of inducing acidosis and a metabotoxin that can result in adverse health effects . Chronically elevated levels of pidolic acid are associated with at least five inborn errors of metabolism including 5-oxoprolinuria (where 5-oxoproline is otherwise known as pidolic acid), 5-oxoprolinase deficiency, glutathione synthetase deficiency, hawkinsinuria, and propionic acidemia . In particular, abnormally high levels of organic acids like pidolic acid in the blood, urine, brain, and/or other tissues results in general metabolic acidosis . Such acidosis generally occurs when arterial pH falls below 7.35 . In infants, the initial symptoms of acidosis consist of poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy . Eventually, acidosis and the symptoms of acidosis can lead to heart, liver, and kidney abnormalities, seizures, coma, and possibly even death . Many children who are afflicted with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures . High levels of pidolic acid in the blood have also been demonstrated following acetaminophen overdose, causing an increased level of acidity called a high anion gap metabolic acidosis . |
Targets
| Target | Organism | Actions |
|---|---|---|
| Alpha-amylase 2B | Humans | |
| Vascular endothelial growth factor A | Humans | |
| Pancreatic alpha-amylase | Humans |
ADME / PK
| Absorption | In skin conditioning agents, it has been observed that the percutaneous absorption of 5, 10, and 20% sodium pidolic acid through human skin was 5.97, 6.78, and 5.89%, respectively . |
|---|---|
| Half-life | Some studies have determined that the specific half-life of the N-terminal glutamic acid is about 9 months in a pH 4.1 buffer at 45 degrees Celsius . |
| Protein binding | Readily available data regarding the protein binding of pidolic acid is not available. |
| Metabolism | In living cells, various metabolic pathways involving pidolic acid exist: (a) glutamyl/glutaminyl (amino acid) n is converted to pyroglutamyl- (amino acid) n by glutaminyl cyclase, pyroglutamyl- (amino acid) n is then metabolised to pyroglutamic acid (pidolic acid) by pyroglutamyl peptidase; (b) via the gamma-Glutamyl cycle, gamma-Glutamyl transpeptidase generates gamma-Glutamyl amino acid which is metabolised to pyroglutamic acid via gamma-Glutamyl cyclotransferase; (c) glutamate via gamma-Glutamylcysteine synthetase or Glutamine synthetase or Glutamate 5-kinase metabolism generates gamma-Glutamyl phosphate which itself can be converted to pyroglutamic acid; and (d) glutamate or glutamine can be non-enzymatically converted to pyroglutamic acid . Finally, pyroglutamic acid (or pidolic acid) itself is metabolized to glutamate via the 5-Oxoprolinase enzyme . |
| Route of elimination | In the dog animal model, it was determined that 30% of an absorbed oral administration of pidolic acid was excreted unchanged in the urine and the remainder converted to urea . |
| Volume of distribution | Readily available data regarding the volume of distribution of pidolic acid is not available. |
| Clearance | Readily available data regarding the clearance of pidolic acid is not available. |
Formulation & handling
- Pidolic acid is a small molecule alpha amino acid derivative suitable for oral and topical formulations. Its high water solubility facilitates formulating various oral dosage forms, including solutions and effervescent tablets. Stability handling should consider standard practices for amino acid derivatives, with no specific indications of sensitivity to food or temperature.
Regulatory status
| Lifecycle | The API's primary patents have expired in both the US and Canada, allowing for generic competition and established market availability. Consequently, the product is positioned in a mature phase across these regions. |
|---|
| Markets | US, Canada |
|---|
Supply Chain
| Supply chain summary | The manufacturing and supply landscape for Pidolic acid includes several originator companies producing multiple branded products primarily available in the US and Canadian markets. The presence of branded formulations such as facial cleansers and acne treatment gels indicates an established market. Patent expiry status is not specified, so the potential for existing or upcoming generic competition cannot be determined from the provided data. |
|---|
Safety
| Toxicity | High levels of pidolic acid in the blood can lead to 5-Oxoprolinuria, which can ultimately result in severe metabolic acidosis, hemolytic anaemia, or even central nervous system dysfunction . |
|---|
High Level Warnings:
- 1
- Exposure to high concentrations of pidolic acid can induce 5-Oxoprolinuria, potentially causing severe metabolic acidosis, hemolytic anemia, and central nervous system impairment
- 2
Pidolic acid is a type of Other substances
The pharmaceutical industry encompasses a diverse range of active pharmaceutical ingredients (APIs) that are used in the production of various medications. One category of APIs is known as other substances. This category includes substances that do not fall under the conventional classifications such as antibiotics, analgesics, or antihypertensives.
Other substances in pharmaceutical APIs consist of a broad array of chemical compounds with unique properties and applications. These substances play a crucial role in the formulation and development of specialized medications, catering to specific therapeutic needs. The category encompasses various substances like excipients, solvents, stabilizers, and pH adjusters.
Excipients are inert substances that aid in the manufacturing process and enhance the stability, bioavailability, and patient acceptability of pharmaceutical formulations. Solvents are used to dissolve other ingredients and facilitate their incorporation into the final product. Stabilizers ensure the integrity and shelf life of medications by preventing degradation or chemical changes. pH adjusters help maintain the desired pH level of a formulation, which can influence the drug's efficacy and stability.
Pharmaceutical manufacturers carefully select and incorporate specific other substances into their formulations, adhering to regulatory guidelines and quality standards. These substances undergo rigorous testing and evaluation to ensure their safety, efficacy, and compatibility with the desired pharmaceutical product. By employing other substances in API formulations, pharmaceutical companies can optimize drug delivery, improve patient compliance, and enhance therapeutic outcomes.
In summary, the other substances category of pharmaceutical APIs comprises a diverse range of chemicals, including excipients, solvents, stabilizers, and pH adjusters. These substances contribute to the formulation, stability, and performance of medications, enabling pharmaceutical manufacturers to develop specialized products that meet specific therapeutic requirements.
