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Parachlorophenol | CAS No: 106-48-9 | GMP-certified suppliers

A medication that serves as a local antibacterial agent in root canal therapy and topical antiseptic applications, supporting anti-infective treatment in clinical and pharmaceutical settings.

Therapeutic categories

Anti-Infective AgentsAnti-Infective Agents, LocalBenzene DerivativesChlorobenzenesDrugs that are Mainly Renally ExcretedOATP1B3 substrates
Generic name
Parachlorophenol
Molecule type
small molecule
CAS number
106-48-9
DrugBank ID
DB13154
Approval status
Approved drug

Primary indications

  • Used as an intermediate in organic synthesis of dyes and drugs
  • Local antibacterial agent in root canal therapy, as topical antiseptic in ointments

Product Snapshot

  • Parachlorophenol is supplied as a liquid formulation for topical application
  • It is primarily used as a local antibacterial agent in dental therapies and as a topical antiseptic in ointments
  • The product is approved for use in the Canadian pharmaceutical market

Clinical Overview

Parachlorophenol (CAS Number 106-48-9) is an organic compound classified within the p-chlorophenols, characterized by a chlorine substituent at the para position of the phenol benzene ring. It presents as white crystalline solids with a strong phenol odor and is slightly to moderately soluble in water, varying by isomer. It is denser than water and categorized as noncombustible.

Clinically, parachlorophenol finds application as a local antibacterial agent in root canal therapy and as a topical antiseptic in ointment formulations. It is also utilized as an intermediate in the organic synthesis of dyes and pharmaceutical agents. Its approved status reflects its recognized use within these contexts, particularly in anti-infective formulations.

Pharmacologically, parachlorophenol acts primarily through the uncoupling of oxidative phosphorylation within microbial cells. This disruption impairs ATP synthesis, leading to antimicrobial effects. The potency of this mechanism correlates with the degree and position of chlorination on the phenol ring, with parachlorophenol exhibiting a stronger uncoupling effect compared to other chlorophenol isomers. Although pharmacodynamic parameters are not fully specified, this mechanism underpins its antiseptic properties.

Absorption, distribution, metabolism, and excretion (ADME) data indicate that parachlorophenol is mainly renally excreted and is a substrate of the hepatic transporter OATP1B3. These characteristics suggest the molecule undergoes some degree of hepatic processing but is cleared predominantly through renal pathways.

From a safety and toxicity perspective, chlorophenols, including parachlorophenol, warrant cautious handling due to their cellular toxicity associated with uncoupling mitochondrial oxidative phosphorylation. Exposure risks and potential systemic toxicity mandate controlled usage in pharmaceutical and clinical settings.

Notable usage contexts center around its role as a benzene derivative antiseptic and intermediate compound. Procurement of parachlorophenol APIs requires consideration of purity, isomeric composition, and compliance with relevant pharmacopeial standards to ensure consistent quality and performance in finished formulations. Suppliers should provide comprehensive certificates of analysis confirming chemical identity, assay, and impurity profiles aligned with intended pharmaceutical use.

Identification & chemistry

Generic name Parachlorophenol
Molecule type Small molecule
CAS 106-48-9
UNII 3DLC36A01X
DrugBank ID DB13154

Pharmacology

SummaryChlorophenols primarily act by uncoupling oxidative phosphorylation, with the degree of uncoupling influenced by chlorination patterns. They target the sodium channel protein type 4 subunit alpha, exerting antibacterial effects locally. Chlorophenols are utilized as intermediates in organic synthesis and as topical antiseptics in clinical applications such as root canal therapy.
Mechanism of actionThe major mode of action of chlorophenols appears to be the uncoupling of oxidative phosphorylation. The strength of the uncoupling effect is related to the degree of chlorination: PCP is the strongest inhibitor of oxidative phosphorylation, MCP the weakest. To a lesser extent, inhibition of oxidative phosphorylation is affected by the positions of the chlorine atoms on the molecule.
Targets
TargetOrganismActions
Sodium channel protein type 4 subunit alphaHumans

ADME / PK

Absorptionabsorbed from gastrointestinal tract.
MetabolismP-Chlorophenol yields p-chloroanisole in guinea pigs. P-Chlorophenol yields 4-chlorocatechol p-chloro phenyl-beta-D-glucuronide & p-chlorphenyl sulfate in rabbits. P-Chlorophenol yields p-chlorophenyl sulfate in rats.
Route of elimination87% of 4-chlorophenol was excreted in urine of dogs as sulfate and glucuronide.

Formulation & handling

  • Parachlorophenol is a small molecule solid suitable for dental liquid formulations, not intended for oral systemic or injectable administration.
  • Moderate water solubility and LogP indicate balanced hydrophilicity and lipophilicity, relevant for formulation solvent selection.
  • No peptide or biologic characteristics suggest standard chemical stability and handling procedures apply without special sensitivity to food or enzymatic degradation.

Regulatory status

LifecycleThe active pharmaceutical ingredient is marketed in Canada with primary patents expired, indicating a mature market with availability of generic alternatives. Ongoing regulatory approvals support continued product presence.
MarketsCanada
Supply Chain
Supply chain summaryThe manufacturing landscape for Parachlorophenol includes several originator companies producing branded formulations such as Camphorated Para Chlorophenol Liq and Cresophene Liq, primarily serving the Canadian market. Branded products have a limited global presence, with distribution mainly focused in Canada and minimal activity in the US and EU regions. Patent expirations have allowed generic competition to exist or emerge, facilitating broader availability through multiple suppliers.

Safety

ToxicitySigns and symptoms in human : When undiluted, it whitens & cauterizes the skin & mucous membranes. 4-chlorophenol was shown to permeate the skin. It produces damage at a threshold concentration of 0.75% (w/v). Routes of Entry: Absorbed through skin. Eye contact. Toxicity to Animals: Acute oral toxicity (LD50): 367 mg/kg [Mouse]. Acute dermal toxicity (LD50): 1500 mg/kg [Rat]. Chronic Effects on Humans: CARCINOGENIC EFFECTS: Classified 2B (Possible for human.) by IARC. DEVELOPMENTAL TOXICITY: Classified Reproductive system/toxin/male, Development toxin [POSSIBLE]. May cause damage to the following organs: liver, brain, gastrointestinal tract, upper respiratory tract, central nervous system (CNS). Other Toxic Effects on Humans: Very hazardous in case of skin contact (irritant).
High Level Warnings:
  • Causes severe skin and mucous membrane irritation
  • May whiten and cauterize undiluted contact areas
  • Absorbed through skin and eyes

Parachlorophenol is a type of Anti-infective Agents


Anti-infective agents are a vital category of pharmaceutical active pharmaceutical ingredients (APIs) used in the treatment of various infectious diseases. These agents play a crucial role in combating bacterial, viral, fungal, and parasitic infections. The demand for effective anti-infective APIs has grown significantly due to the increasing prevalence of drug-resistant microorganisms.

Anti-infective APIs encompass a wide range of substances, including antibiotics, antivirals, antifungals, and antiparasitics. Antibiotics are particularly important in fighting bacterial infections and are further categorized into different classes based on their mode of action and target bacteria. Antivirals are designed to inhibit viral replication and are essential in the treatment of viral infections such as influenza and HIV. Antifungals combat fungal infections, while antiparasitics are used to eliminate parasites that cause diseases like malaria and helminthiasis.

The development and production of high-quality anti-infective APIs require stringent manufacturing processes and adherence to regulatory standards. Pharmaceutical companies invest heavily in research and development to discover new and more effective anti-infective agents. Additionally, ensuring the safety, efficacy, and stability of these APIs is of utmost importance.

The global market for anti-infective APIs is driven by factors such as the rising incidence of infectious diseases, the emergence of new and drug-resistant pathogens, and the growing demand for improved healthcare infrastructure. Continuous advancements in pharmaceutical technology and the development of innovative drug delivery systems further contribute to the expansion of this market.

In conclusion, anti-infective agents are a critical category of pharmaceutical APIs that play a pivotal role in treating infectious diseases. Their effectiveness in combating various types of infections makes them essential components in the arsenal of modern medicine.