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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:53662
Label unavailable 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

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.

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.

Patents and articles

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

wikipedia.en:Proguanil

Activity roles

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

antiprotozoal drug CHEBI:35820
antimalarial 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

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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).

Explore across X-Mech: MediaIngredientMech (proguanil) · CultureMech · NaturalProductMech · PathwayMech · TraitMech