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 157.89 32.45 23 1693 219 46684127
Hypomania 111.62 32.45 27 1689 4361 46679985
Jaundice cholestatic 98.04 32.45 25 1691 5004 46679342
Schizophrenia 93.71 32.45 27 1689 8541 46675805
Psychotic disorder 93.33 32.45 34 1682 22587 46661759
Blood bilirubin increased 63.51 32.45 29 1687 34155 46650191
Hepatotoxicity 62.00 32.45 26 1690 24983 46659363
Congenital absence of cranial vault 53.23 32.45 7 1709 28 46684318
Cholelithiasis 51.16 32.45 26 1690 38655 46645691
Neural tube defect 47.97 32.45 8 1708 192 46684154
Hepatic enzyme increased 42.24 32.45 30 1686 81757 46602589
Exposure during pregnancy 38.93 32.45 32 1684 108180 46576166
Dermatitis acneiform 36.46 32.45 11 1705 4059 46680287
Plasmodium falciparum infection 34.26 32.45 5 1711 48 46684298

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 150.21 30.85 22 1079 219 29951158
Plasmodium falciparum infection 52.85 30.85 7 1094 30 29951347
Hallucination 37.56 30.85 23 1078 49036 29902341
Abnormal dreams 32.70 30.85 12 1089 8103 29943274

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
FDA EPC N0000175482 Antimalarial
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
CHEBI has role CHEBI:35820 antiprotozoal agent
CHEBI has role CHEBI:38068 antimalarials
CHEBI has role CHEBI:50683 7,8-dihydrofolate reductase inhibitors

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
4021225 VUID
N0000148669 NUI
D02487 KEGG_DRUG
637-32-1 SECONDARY_CAS_RN
4021225 VANDF
C0008241 UMLSCUI
CHEBI:8455 CHEBI
CHEMBL1377 ChEMBL_ID
CHEMBL1201059 ChEMBL_ID
DB01131 DRUGBANK_ID
D002727 MESH_DESCRIPTOR_UI
6178111 PUBCHEM_CID
9676 IUPHAR_LIGAND_ID
418 INN_ID
S61K3P7B2V UNII
142428 RXNORM
15669 MMSL
d04593 MMSL
002942 NDDF
002943 NDDF
16970001 SNOMEDCT_US
387094004 SNOMEDCT_US
395845004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 0173-0675 TABLET, FILM COATED 100 mg ORAL NDA 24 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 0173-0676 TABLET, FILM COATED 25 mg ORAL NDA 24 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-4160 TABLET, FILM COATED 25 mg ORAL ANDA 27 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-4162 TABLET, FILM COATED 100 mg ORAL ANDA 27 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 10544-909 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 33261-900 TABLET, FILM COATED 100 mg ORAL ANDA 22 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 42254-150 TABLET 100 mg ORAL ANDA 20 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 43063-393 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 43063-522 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 26 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 50090-1302 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 50090-2980 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 27 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 50090-2980 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 27 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 54868-6393 TABLET, FILM COATED 100 mg ORAL ANDA 22 sections
MALARONE HUMAN PRESCRIPTION DRUG LABEL 2 55289-747 TABLET, FILM COATED 100 mg ORAL NDA 24 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 60760-498 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 63187-879 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 63629-5531 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 26 sections
Atovaquone and Proguanil HCl HUMAN PRESCRIPTION DRUG LABEL 2 66993-060 TABLET, FILM COATED 100 mg ORAL NDA authorized generic 26 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68001-245 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68258-1104 TABLET, FILM COATED 100 mg ORAL ANDA 22 sections
Atovaquone and Proguanil Hydrochloride Pediatric HUMAN PRESCRIPTION DRUG LABEL 2 68462-402 TABLET, FILM COATED 25 mg ORAL ANDA 26 sections
Atovaquone and Proguanil Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 68462-404 TABLET, FILM COATED 100 mg ORAL ANDA 26 sections