pentamidine

CHEBI:45081 ·resolve ·ANTIFUNGAL ·EXACT REVIEWED

A diether consisting of pentane-1,5-diol in which both hydroxyl hydrogens have been replaced by 4-amidinophenyl groups. A trypanocidal drug that is used for treatment of cutaneous leishmaniasis and Chagas disease. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:35359
• Label unavailable CHEBI:35618
• Label unavailable CHEBI:46786

Chemical structure

SMILES

N=C(N)c1ccc(OCCCCCOc2ccc(C(=N)N)cc2)cc1

InChI

InChI=1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23)

Also called

• 4,4'-[pentane-1,5-diylbis(oxy)]dibenzenecarboximidamide (EXACT_SYNONYM)— chebi
• 1,5-bis(4-amidinophenoxy)pentane (EXACT_SYNONYM)— chebi
• 4,4'-(1,5-pentanediylbis(oxy))bis-benzenecarboximidamide (EXACT_SYNONYM)— chebi
• 4,4'-(pentamethylenedioxy)dibenzamidine (EXACT_SYNONYM)— chebi
• 4,4'-Diamidinodiphenoxypentane (EXACT_SYNONYM)— chebi
• Pentamidine (EXACT_SYNONYM)— chebi
• p,p'-(pentamethylenedioxy)dibenzamidine (EXACT_SYNONYM)— chebi
• pentamidin (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

• beilstein:3159790
• cas:100-33-4
• hmdb:HMDB0014876
• kegg.compound:C07420
• lincs.smallmolecule:LSM-4540
• pdb-ccd:PNT
• reaxys:3159790

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

• drugbank:DB00738
• drugcentral:2090
• kegg.drug:D08333

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

• patent:EP975608
• patent:GB507565
• patent:US2006235001
• patent:US2008167296
• patent:US2008214569
• patent:US2394003
• patent:US7115665
• wikipedia.en:Pentamidine

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• antifungal agent CHEBI:35718
• trypanocidal drug CHEBI:36335

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

mitochondrial translation BIOLOGICAL_PROCESS DOWNSTREAM_AFFECTED_PROCESS

Yeast mitochondrial labeling and intron-configuration experiments linked translation inhibition to respiratory growth and in-vivo splicing effects; the molecular target remained unresolved. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2000-07 (retrieved 2026-09-02).

Saccharomyces cerevisiae NCBITaxon:4932

• PMID:10917591 (Primary S. cerevisiae mitochondrial translation and intron-splicing study (DOI:10.1017/S1355838200991726).)

Mechanism summary

Mode of action

PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:10917591 found that pentamidine inhibits mitochondrial, but not cytoplasmic, translation in Saccharomyces cerevisiae at concentrations that also inhibit mitochondrial intron splicing and respiratory growth. The study observed direct RNA-splicing effects in vitro but inferred a different, unresolved target for most in-vivo effects.

Record-level evidence

• PMID:10917591 (Primary pentamidine yeast mitochondrial translation and RNA-splicing study.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. REVIEWED 2026-09-02 · codex · LLM-assisted

   Verified exact ChEBI identity, structure, antifungal/trypanocidal roles, and antifungal filing class; added the mitochondrial protein-synthesis mechanism while preserving the source's unresolved in-vivo molecular-target limitation.

5. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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