Diaminopropanol Tetraacetic Acid (DB12362): A Pharmacological and Developmental Review

1. Abstract

Diaminopropanol tetraacetic acid, registered under DrugBank ID DB12362 and CAS number 3148-72-9, is a small molecule identified primarily as a chelating agent. It is also known by synonyms such as Diaminohydroxypropanetetraacetic acid (DHPTA) and DPTA-OH.[1] This compound has reportedly been investigated for therapeutic applications in a range of vascular conditions, including Vascular Disease, Coronary Disease, Myocardial Ischemia, Coronary Restenosis, and Coronary Artery Disease.[1] Chemically, it is classified as a tetracarboxylic acid and an EDTA derivative, possessing multiple functional groups conducive to metal ion chelation.[1] Despite its investigational history in significant cardiovascular pathologies, its current regulatory status is listed as "Approved, Withdrawn".[1] This designation, coupled with a notable scarcity of detailed clinical efficacy, pharmacokinetic, and mechanistic data specific to its vascular applications within publicly accessible databases (as represented by the provided information), presents a complex profile. This report aims to synthesize the available information on Diaminopropanol tetraacetic acid, focusing on its chemical characteristics, investigational background in vascular diseases, potential mechanisms, and the implications of its regulatory status, while critically highlighting the substantial gaps in the existing knowledge base derived from the provided documentation.

2. Introduction to Diaminopropanol Tetraacetic Acid (DB12362)

2.1. Nomenclature and Identifiers

Diaminopropanol tetraacetic acid is a defined chemical entity with several associated names and identifiers. Its primary generic names include Diaminopropanol tetraacetic acid and Diaminohydroxypropanetetraacetic acid.[1] Commonly used abbreviations in literature and databases are DPTA-OH and DHPTA.[2] The compound is uniquely identified by its DrugBank Accession Number DB12362 and CAS Registry Number 3148-72-9.[1] Other external identifiers include UNII 949B9ZMO7M and EC Number 221-575-6.[2] The consistent linkage of these various names and identifiers to the same CAS number and DrugBank ID across multiple sources [1] confirms they refer to the same molecule, although the presence of multiple synonyms necessitates careful attention during literature reviews to ensure comprehensive data retrieval.

2.2. Chemical Classification

Diaminopropanol tetraacetic acid is classified as a small molecule.[1] From a structural perspective, it belongs to the class of organic compounds known as tetracarboxylic acids and derivatives, characterized by the presence of four carboxyl groups.[1] It can also be described by its constituent functional groups as an alpha amino acid derivative, a trialkylamine, a secondary alcohol, and a 1,2-aminoalcohol.[1] Significantly, it is also referred to as an EDTA (ethylenediaminetetraacetic acid) derivative.[3] This classification as an EDTA derivative is particularly pertinent as it immediately suggests strong metal-chelating properties, a characteristic central to many of its investigated and actual uses. The structural similarity to EDTA, a well-established chelating agent, provides a foundational hypothesis for its potential utility in conditions where metal ion dysregulation plays a pathological role, such as certain vascular diseases involving calcification or metal-induced oxidative stress.[6]

3. Physicochemical Properties

The physicochemical properties of Diaminopropanol tetraacetic acid (DB12362) are crucial for understanding its potential behavior in biological systems and its suitability as a therapeutic agent. Its molecular formula is C11​H18​N2​O9​.[1] The average molecular weight is approximately 322.27 g/mol, with a monoisotopic mass of 322.101230168 Da.[1] It typically presents as a white to almost white crystalline powder.[2]

Key computed and experimental properties are summarized in Table 1. The compound exhibits good water solubility (9.18 mg/mL, ALOGPS).[1] LogP values, which indicate lipophilicity, vary depending on the prediction method, with ALOGPS yielding -1.7 and Chemaxon predicting a more hydrophilic -6.8.[1] It possesses multiple acidic and basic centers, with the strongest acidic pKa predicted at 1.79 and the strongest basic pKa at 7.77 (Chemaxon).[1] The polar surface area is substantial at 175.91 A˚2 (Chemaxon), consistent with its hydrophilic nature and multiple polar functional groups.[1] A notable prediction from Chemaxon is a bioavailability of 0.[1] This prediction, if accurate for oral administration, would imply negligible systemic absorption via this route, posing a significant challenge for its development as an oral therapeutic unless specific formulation strategies can overcome this limitation or alternative administration routes are employed. The presence of four carboxylic acid groups and a hydroxyl group, evident from its structure (SMILES: OC(CN(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O) [1], underpins its strong chelating capabilities.

Table 1: Key Physicochemical and Identification Properties of Diaminopropanol Tetraacetic Acid (DB12362)

Property	Value	Source(s)
CAS RN	3148-72-9	1
IUPAC Name	2-({3-[bis(carboxymethyl)amino]-2-hydroxypropyl}(carboxymethyl)amino)acetic acid	1
Common Synonyms	Diaminohydroxypropanetetraacetic acid, DPTA-OH, DHPTA	1
Molecular Formula	C11​H18​N2​O9​	1
Molecular Weight (Average)	322.27 g/mol	1
Molecular Weight (Monoisotopic)	322.101230168 Da	1
Appearance	White to almost white crystalline powder	2
Water Solubility (ALOGPS)	9.18 mg/mL	1
logP (ALOGPS)	-1.7	1
logP (Chemaxon)	-6.8	1
pKa (Strongest Acidic)	1.79 (Chemaxon)	1
pKa (Strongest Basic)	7.77 (Chemaxon)	1
Polar Surface Area (Chemaxon)	175.91 A˚2	1
Bioavailability (Chemaxon)	0	1

4. Investigational Profile in Vascular Diseases

Diaminopropanol tetraacetic acid (DB12362), also referred to as Diaminohydroxypropanetetraacetic acid, is documented in multiple database entries as having been investigated for the treatment of several vascular diseases. These include general "Vascular Disease," "Coronary Disease," "Myocardial Ischemia," "Coronary Restenosis," and "Coronary Artery Disease".[1] This consistent reporting across different sources suggests a period of research focused on its potential utility in these significant cardiovascular conditions.

The rationale for investigating a chelating agent like DB12362 in such diseases likely stems from the known involvement of metal ions in the pathophysiology of atherosclerosis and related vascular disorders. For instance, calcium deposition is a hallmark of atherosclerotic plaque development and vascular calcification.[7] Additionally, certain transition metals can contribute to oxidative stress and inflammation within the vascular wall, processes central to atherogenesis.[6] The hypothesis would be that a chelating agent could interfere with these pathological processes by sequestering these metal ions.

However, despite the repeated assertion of its investigation for these conditions, the provided documentation lacks specific details regarding the nature, phase, or outcomes of such investigations for DB12362. Searches for clinical trials specifically involving DB12362 (or its synonyms like DPTA-OH) for these vascular indications within the scope of the supplied materials did not yield direct results.[1] For example, while snippet [13] discusses clinical trials for cardiovascular disease, the agents mentioned are Olpasiran and Inclisiran, not DB12362. Similarly, [14] details a trial with Ticagrelor. This absence of concrete clinical trial data for DB12362 in the context of its stated vascular investigations represents a significant information gap. The claim that it "has been investigated" is present, but the evidence detailing these investigations (e.g., study design, patient populations, endpoints, results, sponsoring institutions) is not provided in these documents. This raises questions about the extent and success of these past investigational efforts.

5. Putative Mechanism of Action in Vascular Pathologies

The primary characteristic of Diaminopropanol tetraacetic acid relevant to its investigation in vascular diseases is its nature as a chelating agent.[2] As an EDTA derivative, it possesses multiple carboxyl and amine groups capable of forming stable coordinate complexes with various metal ions.[1]

The theoretical basis for using chelating agents in cardiovascular diseases, such as atherosclerosis and its complications, revolves around several hypotheses:

1. Decalcification of Atherosclerotic Plaques: Early theories proposed that chelators like EDTA could remove calcium from established atherosclerotic plaques, potentially reducing plaque burden or altering plaque stability.[6] Vascular calcification is a well-recognized component of advanced atherosclerosis and contributes to arterial stiffness.[7]
2. Removal of Pro-oxidant/Pro-inflammatory Metals: Certain metal ions, such as iron and copper, can catalyze the formation of reactive oxygen species, contributing to oxidative stress and inflammation within the vascular wall—key drivers of atherosclerosis.[6] Chelation of these metals could theoretically mitigate such damage.
3. Removal of Toxic Heavy Metals: Exposure to heavy metals like lead and cadmium has been linked to increased cardiovascular risk. Chelation therapy has been suggested as a means to reduce the body burden of these toxic metals.[6]

Reviews on chelation therapy, primarily focusing on EDTA, for cardiovascular disease indicate that these mechanisms have been explored.[6] For instance, EDTA is known to have a high affinity for divalent cations, including calcium, lead, and cadmium.[6]

However, it is crucial to note that while these are general rationales for investigating chelators in vascular disease, the provided documentation does not contain specific mechanistic studies detailing how Diaminopropanol tetraacetic acid (DB12362) itself interacts with vascular tissues, atherosclerotic plaques, or specific metal ions implicated in vascular pathology in vivo or in relevant preclinical models. The link between its chelating ability and a therapeutic effect in the listed vascular diseases remains largely speculative based on the provided information. Furthermore, the broader field of chelation therapy for atherosclerotic cardiovascular disease has a history of mixed results and controversy, with many studies on EDTA failing to show clear, consistent benefits, particularly in well-controlled trials.[18] The TACT (Trial to Assess Chelation Therapy) showed some potential benefit in a subgroup of patients with diabetes who had a prior myocardial infarction, but overall, the evidence for EDTA remains debated.[6] If the investigation of DB12362 was predicated on similar general chelation principles, the historical skepticism and lack of robust, unequivocal evidence for EDTA itself might have influenced its developmental trajectory. The absence of specific studies demonstrating DB12362's efficacy in reducing vascular calcification or mitigating metal-induced vascular damage in the provided materials is a critical gap.

6. Pharmacokinetics and Pharmacodynamics (PK/PD)

Detailed pharmacokinetic (PK) and pharmacodynamic (PD) data for Diaminopropanol tetraacetic acid (DB12362), particularly in the context of its investigated vascular indications, are largely absent in the provided documentation. The primary DrugBank entries [1] explicitly state that key PK parameters such as Absorption, Volume of distribution, Protein binding, Metabolism, Route of elimination, Half-life, and Clearance are "Not Available."

A significant point from the DrugBank data is the Chemaxon-predicted oral bioavailability of 0 for DB12362.[1] If this computational prediction accurately reflects its in vivo behavior, it would imply that the compound is not absorbed systemically when administered orally, or is completely metabolized before reaching systemic circulation. This would render oral administration ineffective for treating systemic conditions like vascular diseases, unless specialized formulation technologies were employed to enhance absorption, or alternative routes of administration were used. The provided snippets do not contain information about the formulation or route of administration used during its investigation for vascular diseases.

Pharmacodynamic information is similarly sparse. While its chelating nature is established [2], specific studies quantifying its interaction with relevant biological targets in vascular disease (e.g., specific metal ions in plaque, effects on vascular cells) are not present in these documents. One snippet [21] mentions that DPTA-OH (a synonym for DB12362) was efficient in displacing Manganese (Mn) bound to bovine serum proteins in vitro. While this confirms its metal-binding capability, it is an in vitro finding with a specific metal and does not directly inform its in vivo pharmacodynamics in the complex milieu of vascular disease or its affinity for other pathologically relevant metals like calcium, iron, or copper in that context. Another snippet [22], from a patent application concerning lentivirus inhibition, mentions DPTA-OH in relation to pharmacokinetics, drug distribution, and metabolism, but this is for a different therapeutic application and lacks the rigor of a peer-reviewed PK study focused on vascular indications.

The profound lack of specific, peer-reviewed PK/PD data for DB12362 related to its stated vascular investigations is a critical deficiency. Without such data, understanding its dose-exposure-response relationships, optimizing dosing regimens, and assessing its true potential as a systemic therapeutic agent for vascular diseases are not possible based on the available information. This absence is particularly striking given its "Approved, Withdrawn" status, as some level of PK/PD characterization would typically be expected for an approved drug.

7. Safety and Toxicology Profile

The available safety and toxicology information for Diaminopropanol tetraacetic acid (DB12362) within the provided documents primarily relates to its properties as a chemical rather than comprehensive clinical safety data from human trials for vascular indications.

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) classifications reported in PubChem and supplier information, DB12362 is associated with the following hazard statements:

• H315: Causes skin irritation [2]
• H319: Causes serious eye irritation [2]
• H335: May cause respiratory irritation [2]

These classifications suggest that the compound requires careful handling in laboratory or industrial settings to avoid dermal, ocular, and respiratory exposure. Chemical suppliers also note its incompatibility with strong oxidizing agents.[3]

Table 2: Summary of GHS Hazard Classifications for Diaminopropanol Tetraacetic Acid (DB12362)

Hazard Statement	Description	Source(s)
H315	Causes skin irritation	2
H319	Causes serious eye irritation	2
H335	May cause respiratory irritation	2

The DrugBank entries [1] indicate that detailed information on "Adverse Effects," including blackbox warnings, adverse reactions, and precautions, might be available through their subscription services or Clinical API, but this specific data is not directly provided in the free-access snippets. Similarly, specific "Toxicity" data is listed as "Not Available".[1]

The absence of detailed clinical safety data (e.g., common adverse events, serious adverse events, organ-specific toxicities) from human studies where DB12362 was investigated for vascular diseases is a significant gap. For any compound that reached an "Approved" status, a substantial clinical safety database would have been required by regulatory agencies. The subsequent "Withdrawn" status could potentially be linked to safety concerns that emerged post-approval or during further studies, but such information is not contained within these documents. General risks associated with potent chelating agents like EDTA, such as hypocalcemia or kidney damage with prolonged or high-dose use [18], might be relevant considerations by analogy, but specific data for DB12362 are lacking.

8. Regulatory Trajectory and Development History

The regulatory history of Diaminopropanol tetraacetic acid (DB12362) is summarized by its DrugBank classification as "Approved, Withdrawn".[1] This status implies that the drug, at some point, received marketing approval from at least one regulatory agency for a specific indication, but this approval was later rescinded, or the drug was voluntarily removed from the market by its developers.

The term "Withdrawn" in the context of DrugBank can signify that a drug was removed from the market or had its development halted due to safety or efficacy concerns.[26] The provided documents do not offer any specific details regarding:

• Which regulatory authority (e.g., FDA, EMA) granted the approval.
• The specific indication(s) for which DB12362 was approved.
• The date of approval.
• The date of withdrawal.
• The explicit reasons for its withdrawal (e.g., safety issues, lack of efficacy, commercial considerations).

This lack of information is a central and critical gap in understanding the compound's developmental lifecycle. For a drug to achieve approval, particularly for conditions as prevalent and serious as vascular diseases, a considerable dossier of preclinical and clinical data demonstrating safety and efficacy would have been necessary. Its subsequent withdrawal raises significant questions about what new information or circumstances led to this decision. Without these details, it is difficult to ascertain whether the withdrawal was due to issues intrinsic to the drug's profile (e.g., unacceptable adverse effects, insufficient efficacy) or other external factors. The snippets do not clarify if the approval was related to its investigated use in vascular diseases or potentially for a different application, perhaps as a chelating agent in a non-therapeutic or diagnostic context, which might have different regulatory pathways and data requirements.

9. Non-Therapeutic Applications

Beyond its investigational therapeutic uses, Diaminopropanol tetraacetic acid is recognized for its utility as a chelating agent in various non-therapeutic contexts. Its chemical structure, rich in carboxylic acid and amine functional groups, makes it effective at binding metal ions.[1] This property is leveraged in several applications:

• Laboratory Chemical/Synthetic Reagent: It is listed as an EDTA derivative used in chelation and complexation chemistry.[3]
• Analytical Chemistry: Used as a reagent for detecting and quantifying metal ions in samples, which is important for quality control and environmental monitoring.[17]
• Water Treatment: Employed to sequester metal ions, potentially aiding in the removal of heavy metals from wastewater.[17]
• Agriculture: Used in fertilizers to enhance the solubility and bioavailability of essential metal micronutrients for crops.[17] Patent literature also describes the use of chelating agents, including EDTA and related compounds, in herbicidal compositions, though DB12362 is not specifically named as the primary active chelator in the provided patent snippet [41] for this purpose.
• Biochemical Research: Can serve as a buffer in biochemical assays to control metal ion concentrations.[17]
• Cosmetic Applications: Incorporated into skincare products to chelate harmful metals, potentially reducing oxidative stress caused by environmental pollutants.[17]
• Industrial Uses: The EPA TSCA Commercial Activity Status for a related glycine derivative, N,N'-(2-hydroxy-1,3-propanediyl)bis

These established non-therapeutic uses underscore the compound's fundamental chelating properties. This contrasts with the lack of detailed evidence supporting the successful translation of these properties into effective and safe therapeutic interventions for complex human diseases like vascular disorders, as indicated by its "Withdrawn" status and the absence of robust clinical data in the provided materials.

10. Comprehensive Discussion and Conclusions

Diaminopropanol tetraacetic acid (DB12362), also known as Diaminohydroxypropanetetraacetic acid, presents a perplexing profile based on the assembled information. It is a well-characterized small molecule chelating agent, an EDTA derivative, with clearly defined physicochemical properties.[1] Multiple sources state it has been "investigated for the treatment of Vascular Disease, Coronary Disease, Myocardial Ischemia, Coronary Restenosis, and Coronary Artery Disease".[1] This suggests a historical interest in leveraging its metal-binding capabilities for cardiovascular therapy, likely based on theories of decalcification or removal of pro-oxidant metals implicated in atherosclerosis.[6]

However, a significant discrepancy emerges between this stated investigational history and the tangible evidence available within the provided documentation. There is a notable absence of specific preclinical mechanistic studies or detailed clinical trial data (Phase I, II, or III) for DB12362 pertaining to these vascular indications. The predicted oral bioavailability of zero [1] further complicates the picture for any systemic therapeutic intent via oral administration, unless specific unmentioned formulations or routes were used.

The most critical and unresolved aspect is its regulatory status of "Approved, Withdrawn".[1] For a compound to achieve approval, a substantial body of evidence supporting its safety and efficacy for a given indication would typically be required by regulatory authorities. Its subsequent withdrawal implies that significant issues arose post-approval or that its initial approval was perhaps for a niche, non-cardiovascular, or even non-therapeutic application not detailed in these sources. The lack of information regarding the approving agency, the approved indication(s), and, crucially, the reasons for withdrawal, constitutes a major gap in understanding its developmental trajectory and ultimate fate as a therapeutic agent.

The general literature on EDTA chelation therapy for cardiovascular disease, as reflected in the provided reviews [6], is characterized by mixed results, controversy, and a general lack of endorsement by major cardiovascular organizations for routine use. If DB12362's therapeutic rationale was similar to that of general EDTA chelation, the prevailing skepticism and lack of definitive, robust evidence for the broader class could have contributed to its eventual withdrawal or discontinuation of development for these indications.

The available safety data for DB12362 primarily describes it as a chemical irritant [2], with a lack of specific clinical safety profiles from human studies related to its use in vascular diseases. This, too, is inconsistent with a drug that once held an "Approved" status for systemic therapeutic use.

In conclusion, Diaminopropanol tetraacetic acid (DB12362) is a known chelating agent that was explored for serious cardiovascular conditions. However, based solely on the provided documentation, its journey as a therapeutic agent is poorly defined. The "Approved, Withdrawn" status, without further context on the approval specifics or withdrawal reasons, alongside the dearth of supporting clinical and mechanistic data for its purported vascular indications, leaves its therapeutic potential and history largely enigmatic. Any future consideration of this compound for therapeutic use would necessitate a thorough retrieval and critical evaluation of the original data that led to its approval, a clear understanding of the reasons for its withdrawal, and likely, substantial new preclinical and clinical research to address the evident gaps in efficacy, safety, and pharmacokinetic understanding, particularly for complex systemic diseases. The currently available information does not provide a strong basis for a positive future outlook in the investigated vascular indications without significant new data.

11. References

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