proguanil Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2282 500-92-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • proguanil
  • proguanil hydrochloride
  • chloroguanide
  • chloroguanide hydrochloride
  • proguanil HCl
  • chloroguanide HCl
A biguanide compound which metabolizes in the body to form cycloguanil, an anti-malaria agent.
  • Molecular weight: 253.73
  • Formula: C11H16ClN5
  • CLOGP: 2.53
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 5
  • TPSA: 83.79
  • ALOGS: -3.34
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.20 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 9.09 mg/mL Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 60 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
July 14, 2000 FDA GLAXOSMITHKLINE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Malaria 197.99 38.05 24 395 73 2357593
Pyrexia 96.24 38.05 39 380 53669 2303997
Exposure during pregnancy 96.14 38.05 32 387 25187 2332479
Nausea 80.02 38.05 43 376 112146 2245520
Diarrhoea 79.67 38.05 39 380 83525 2274141
Decreased appetite 54.86 38.05 22 397 28869 2328797
Angioedema 54.17 38.05 16 403 8380 2349286
Urticaria 51.37 38.05 20 399 24241 2333425
Abdominal pain 51.17 38.05 22 397 34352 2323314
Fatigue 45.06 38.05 27 392 84846 2272820
Malaise 43.95 38.05 23 396 55562 2302104
Vomiting 43.84 38.05 25 394 71577 2286089
Headache 43.83 38.05 26 393 80153 2277513
Abortion spontaneous 42.87 38.05 15 404 13430 2344236
Hallucination 41.69 38.05 13 406 8135 2349531

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Malaria 154.92 44.79 20 333 76 1746352
Pyrexia 92.93 44.79 40 313 46360 1700068
Hallucination 84.02 44.79 24 329 8146 1738282
Vomiting 60.14 44.79 28 325 38287 1708141
Plasmodium falciparum infection 57.38 44.79 7 346 14 1746414
Transaminases increased 51.53 44.79 14 339 3903 1742525
Diarrhoea 51.10 44.79 28 325 53824 1692604
Anxiety 46.43 44.79 18 335 15509 1730919

Pharmacologic Action:

SourceCodeDescription
ATC P01BB01 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Biguanides
ATC P01BB51 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTIPROTOZOALS
ANTIMALARIALS
Biguanides
FDA MoA N0000000191 Dihydrofolate Reductase Inhibitors
CHEBI has role CHEBI:38068 antimalarial
CHEBI has role CHEBI:35820 antiprotozoal drug
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000963 Antimetabolites
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D009676 Noxae

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Falciparum malaria indication 62676009 DOID:14067
Chloroquine-Resistant Plasmodium Falciparum Malaria Prevention indication
Plasmodium Falciparum Malaria Prevention indication
Vivax malaria off-label use 27052006 DOID:12978
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Hyperglycemia contraindication 80394007 DOID:4195
Anemia due to enzyme deficiency contraindication 111577008
Disease of liver contraindication 235856003 DOID:409
Chronic diarrhea contraindication 236071009
Vomiting contraindication 422400008
Malabsorption States contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.73 Basic
pKa2 2.36 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme INHIBITOR DRUGBANK CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme WOMBAT-PK
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme WOMBAT-PK

External reference:

IDSource
D002727 MESH_DESCRIPTOR_UI
4021225 VUID
N0000148669 NUI
C0008241 UMLSCUI
D02487 KEGG_DRUG
16970001 SNOMEDCT_US
2382 RXNORM
4021225 VANDF
002942 NDDF
387094004 SNOMEDCT_US
d04593 MMSL
CHEBI:8455 CHEBI
CHEMBL1377 ChEMBL_ID
DB01131 DRUGBANK_ID
R71Y86M0WT UNII
637-32-1 SECONDARY_CAS_RN
418 INN_ID
6178111 PUBCHEM_CID
CHEMBL1201059 ChEMBL_ID
9676 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 0173-0675 TABLET, FILM COATED 100 mg ORAL NDA 16 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 0173-0676 TABLET, FILM COATED 25 mg ORAL NDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-4160 TABLET, FILM COATED 25 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-4162 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 10544-909 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 33261-900 TABLET, FILM COATED 100 mg ORAL ANDA 14 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 42254-150 TABLET 100 mg ORAL ANDA 12 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 43063-393 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 43063-522 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 16 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 50090-0687 TABLET, FILM COATED 100 mg ORAL NDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 50090-1302 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 50090-2980 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 17 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 54868-6393 TABLET, FILM COATED 100 mg ORAL ANDA 14 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 55289-747 TABLET, FILM COATED 100 mg ORAL NDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 60760-498 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 63187-879 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 63629-5531 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 16 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 66993-060 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68001-245 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68258-1104 TABLET, FILM COATED 100 mg ORAL ANDA 14 sections
Atovaquone and Proguanil Hydrochloride Pediatric HUMAN PRESCRIPTION DRUG LABEL 2 68462-402 TABLET, FILM COATED 25 mg ORAL ANDA 16 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68462-404 TABLET, FILM COATED 100 mg ORAL ANDA 16 sections