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Regulatory Challenges for Look-Alike and Sound-Alike Non-Biological Complex Drugs: Molecular Fingerprint Discrimination of <i>Ichthammol</i> Formulations

2025· article· en· W4415680159 on OpenAlexaff
Ole Tiemann, Lukas Schwalb, Helly J. Hansen, Martha L. Chacón‐Patiño, Thomas Gröger, Peter Huy, Dirk Michalik, Guido Gayko, Christopher P. Rüger, Ralf Zimmermann

Bibliographic record

VenueMolecular Pharmaceutics · 2025
Typearticle
Languageen
FieldMedicine
TopicPharmaceutical Quality and Counterfeiting
Canadian institutionsIONICS Mass Spectrometry (Canada)
Fundersnot available
KeywordsMass spectrometrySulfuric acidCharacterization (materials science)SulfonateAmmoniumFatty acid

Abstract

fetched live from OpenAlex

Look-alike and sound-alike (LASA) medications are a critical source of medication errors, posing significant risks to patient safety. This issue is particularly relevant for non-biological complex drugs (NBCDs), whose intricate compositions and manufacturing-dependent properties complicate regulatory assessment and comparability of follow-on products. In this study, we employ high-resolution mass spectrometry (HRMS) techniques, including Fourier-transform ion cyclotron resonance mass spectrometry (FT-ICR MS) and comprehensive two-dimensional gas chromatography coupled to high-resolution time-of-flight mass spectrometry (GC×GC-HRToF MS), to differentiate between Ichthammol formulations compliant with different pharmacopeia definitions. Despite similar bulk properties, comprehensive molecular-level characterization reveals substantial compositional differences: European Pharmacopeia (Ph. Eur.) compliant samples, which also largely correspond to the U.S. pharmacopeia (USP), predominantly contain sulfonated thiaarenes derived from shale oil, while samples compliant with the Chinese Pharmacopeia (ChP) consist mainly of sulfurized fatty acids and sulfur-linked fatty acid oligomers derived from vegetable oils. Proposed reaction mechanisms describe a classical aromatic sulfonation by sulfuric acid yielding ammonium sulfonates of thiaarenes and, in smaller quantities, ammonium sulfonate arenes in the Ph. Eur. formulations after neutralization with ammonia. In contrast, ChP formulations likely undergo an initial sulfurization via vulcanization, leading to thiophene-containing fatty acids and sulfur-linked oligomers, followed by sulfonation and neutralization. Our findings provide strong evidence for distinct chemical fingerprints, allowing robust differentiation between these complex LASA drugs. These findings were in accordance with the mechanistic pathways for their respective manufacturing processes proposed in this study. These insights highlight the necessity of molecular-level analysis for regulatory assessment of complex pharmaceuticals and underscore the potential risks of relying solely on bulk parameter equivalence in complex drug approval and substitution.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.157
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.109
GPT teacher head0.404
Teacher spread0.296 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations0
Published2025
Admission routes1
Has abstractyes

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