Structure via PubChem · Public domain (PubChem)
proguanil
Sign in to saveAlso known as N-(4-Chlorophenyl)-n'-(isopropyl)-imidodicarbonimidic diamide, Chlorguanide, 1-(P-Chlorophenyl)-5-isopropylbiguanide, Chloroguanide
Proguanil, also known as chlorguanide and chloroguanide, is a medication used to treat and prevent malaria. It is often used together with chloroquine or atovaquone. When used with chloroquine the combination will treat mild chloroquine resistant malaria. It is taken by mouth.
Chemical data
- Formula
- C11H16ClN5
- Molecular weight
- 253.73 g/mol
- IUPAC name
- (1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine
- SMILES
- CC(C)N=C(N)/N=C(\N)/NC1=CC=C(C=C1)Cl
- InChIKey
- SSOLNOMRVKKSON-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 88.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,803 papers- Atovaquone-proguanil for treating uncomplicated Plasmodium falciparum malaria.The Cochrane database of systematic reviews · 2021
- Atovaquone/proguanil for plasmodium falciparum malaria.The Pediatric infectious disease journal · 2002
- Atovaquone/proguanil for the prophylaxis and treatment of malaria.Expert review of anti-infective therapy · 2005
- Atovaquone-proguanil for prophylaxis and treatment of malaria.The Annals of pharmacotherapy · 2003
- Proguanil.Lancet (London, England) · 1989
via PubMed
Wikidata facts
- Mass
- 253.109423
Show 6 more facts
- chemical formula
- C₁₁H₁₆ClN₅
- canonical SMILES
- CC(C)N=C(N)N=C(N)NC1=CC=C(C=C1)Cl
- isomeric SMILES
- CC(C)N=C(N)/N=C(\N)/NC1=CC=C(C=C1)Cl
- World Health Organisation international non-proprietary name
- proguanil
- Commons category
- Proguanil
- defined daily dose
- 0.2
Sources (7)
via Wikidata · CC0
~4 min read
Article
5 sectionsContents
- History
- Medical uses
- Side effects
- Mechanism
- References
Proguanil, also known as chlorguanide and chloroguanide, is a medication used to treat and prevent malaria. It is often used together with chloroquine or atovaquone. When used with chloroquine the combination will treat mild chloroquine resistant malaria. It is taken by mouth.
Side effects include diarrhea, constipation, skin rashes, hair loss, and itchiness. Because malaria tends to be more severe in pregnancy, the benefit typically outweighs the risk. If used during pregnancy it should be taken with folate. It is likely safe for use during breastfeeding. Proguanil is converted by the liver to its active metabolite, cycloguanil.