AntibioticMech

proguanil

CHEBI:8455 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A biguanide compound which has isopropyl and p-chlorophenyl substituents on the terminal N atoms. A prophylactic antimalarial drug, it works by inhibiting the enzyme dihydrofolate reductase, which is involved in the reproduction of the malaria parasites Plasmodium falciparum and P. vivax within the red blood cells. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:53662 CHEBI:53662
• CHEBI:83403 CHEBI:83403

Chemical structure

Computed structure properties

Molecular formula	C11H16ClN5
Charge	0
Average mass	253.737 Da
Monoisotopic mass	253.10942 Da
Source	ChEBI
InChIKey	SSOLNOMRVKKSON-UHFFFAOYSA-N

SMILES

CC(C)NC(=N)NC(=N)Nc1ccc(Cl)cc1

InChI

InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)

Also called

• proguanilum (INN)— chebi
• N-(4-chlorophenyl)-N'-(propan-2-yl)imidodicarbonimidic diamide (EXACT_SYNONYM)— chebi
• 1-(p-chlorophenyl)-5-isopropylbiguanide (EXACT_SYNONYM)— chebi
• Chlorguanide (EXACT_SYNONYM)— chebi
• Chloroguanide (EXACT_SYNONYM)— chebi
• N-(4-Chlorophenyl)-N'-(isopropyl)-imidodicarbonimidic diamide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• cas:500-92-5
• drugbank:DB01131
• drugcentral:2282
• hmdb:HMDB0015263
• kegg.compound:C07631
• kegg.drug:D08428
• lincs.smallmolecule:LSM-2618
• reaxys:2811599
• wikipedia.en:Proguanil

Activity roles

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

• CHEBI:35820 CHEBI:35820
• CHEBI:38068 CHEBI:38068

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.

Upstream concepts merged into this record

Source	Native ID	Label	Minted CURIE	Version
CHEBI	CHEBI:8455	proguanil	antibioticmech:chebi-9cfb8eda6a	2026-08-30

Mechanism summary

Mode of action

FOLATE_PATHWAY_INHIBITION host shared target — Assigned from ChEBI role CHEBI:50683 (EC 1.5.1.3 (dihydrofolate reductase) inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

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

Provenance

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