Identification

Name
Pentamidine
Accession Number
DB00738  (APRD00303, EXPT02625)
Type
Small Molecule
Groups
Approved
Description

Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of pneumocystis pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects. [PubChem]

Structure
Thumb
Synonyms
  • 1,5-Bis(4-amidinophenoxy)pentane
  • 4,4'-(1,5-Pentanediylbis(oxy))bis-benzenecarboximidamide
  • 4,4'-(Pentamethylenedioxy)dibenzamidine
  • 4,4'-Diamidinodiphenoxypentane
  • P,P'-(pentamethylenedioxy)dibenzamidine
  • Pentamidin
  • Pentamidina
  • Pentamidindiisetionat
  • Pentamidine
  • Pentamidinum
External IDs
MB 800 / RP 2512
Product Ingredients
IngredientUNIICASInChI Key
Pentamidine gluconateB0WU872RIR123245-08-9JAVCHNFPSHBZAF-UUPCJSQJSA-N
Pentamidine IsethionateV2P3K60DA2140-64-7YBVNFKZSMZGRAD-UHFFFAOYSA-N
Pentamidine mesylate863QBB4D0A6823-79-6WRXSODAXJSKMAW-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NebuPentInhalant300 mg/6mLRespiratory (inhalation)Fresenius Kabi2011-02-15Not applicableUs
Pentacarinat 300 Inj Pws 300mg/vialPowder, for solution300 mgIntramuscular; Intravenous; Respiratory (inhalation)Aventis Pharma Ltd.1989-12-312005-08-01Canada
Pentam 300Injection, powder, lyophilized, for solution300 mg/3mLIntramuscular; IntravenousAPP Pharmaceuticals, Inc.2001-01-16Not applicableUs
Pentamidine Isethionate Inj 300mg/vial BPPowder, for solution300 mgIntramuscular; IntravenousDavid Bull Laboratories (Pty) Ltd.1990-12-311998-08-13Canada
Pentamidine Isetionate for Injection BPPowder, for solution300 mgIntramuscular; IntravenousPfizer1998-09-10Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Pentamidine IsethionateInjection, powder, lyophilized, for solution300 mg/300mgIntramuscular; IntravenousSeton Pharmaceuticals2013-09-01Not applicableUs
International/Other Brands
Pentacarinat (Sanofi-Aventis) / Pentacrinat (Abbot) / Pentam (Abbot) / Pentamidine isethionate (Abbot) / Pneumopent
Categories
UNII
673LC5J4LQ
CAS number
100-33-4
Weight
Average: 340.4195
Monoisotopic: 340.189926032
Chemical Formula
C19H24N4O2
InChI Key
XDRYMKDFEDOLFX-UHFFFAOYSA-N
InChI
InChI=1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23)
IUPAC Name
4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide
SMILES
NC(=N)C1=CC=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1

Pharmacology

Indication

For the treatment of pneumonia due to Pneumocystis carinii.

Structured Indications
Pharmacodynamics

Pentamidine is an antiprotozoal agent. It is an aromatic diamidine, and is known to have activity against Pneumocystis carinii. The exact nature of its antiprotozoal action is unknown. in vitro studies with mammalian tissues and the protozoan Crithidia oncopelti indicate that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids and proteins. Little is known about the drug's pharmacokinetics. The medication is also useful in Leishmaniasis and in prophylaxis against sleeping sickness caused by Trypanosoma brucei gambiense. Hydration before treatment lessens the incidence and severity of side effects, which include liver or kidney dysfunction, hypertension, hypotension, hypoglycemia, hypocalemia, leukopenia, thrombcytopenia, anemia, and allergic reaction. It is generally well-tolerated.

Mechanism of action

The mode of action of pentamidine is not fully understood. It is thought that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids, and proteins.

TargetActionsOrganism
UDNA
intercalation
Human
UtRNA (cytosine(38)-C(5))-methyltransferase
other
Human
Absorption

Absorbed poorly through the gastrointestinal tract and is usually administered parenterally.

Volume of distribution
Not Available
Protein binding

69%

Metabolism

Hepatic.

Route of elimination
Not Available
Half life

9.1-13.2 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include pain, nausea, anorexia, hypotension, fever, rash, bad taste in mouth, confusion/hallucinations, dizziness, and diarrhea.

Affected organisms
  • Pneumocystis carinii
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Pentamidine can be increased when it is combined with Abiraterone.Approved
AmiodaroneThe metabolism of Pentamidine can be decreased when combined with Amiodarone.Approved, Investigational
AmlodipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Pentamidine.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Pentamidine is combined with Amrinone.Approved
AprepitantThe serum concentration of Pentamidine can be increased when it is combined with Aprepitant.Approved, Investigational
ArmodafinilThe metabolism of Pentamidine can be decreased when combined with Armodafinil.Approved, Investigational
ArtemetherThe metabolism of Pentamidine can be decreased when combined with Artemether.Approved
AtazanavirThe metabolism of Pentamidine can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Pentamidine can be decreased when combined with Atomoxetine.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Azelnidipine.Approved, Investigational
AzimilideThe risk or severity of adverse effects can be increased when Pentamidine is combined with Azimilide.Investigational
AzithromycinThe metabolism of Pentamidine can be decreased when combined with Azithromycin.Approved
BarnidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Barnidipine.Approved
BencyclaneThe risk or severity of adverse effects can be increased when Pentamidine is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Benidipine.Approved, Investigational
BepridilThe risk or severity of adverse effects can be increased when Pentamidine is combined with Bepridil.Approved, Withdrawn
BetaxololThe metabolism of Pentamidine can be decreased when combined with Betaxolol.Approved
BoceprevirThe metabolism of Pentamidine can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Pentamidine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Pentamidine can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe metabolism of Pentamidine can be decreased when combined with Bupropion.Approved
BuspironeThe metabolism of Buspirone can be decreased when combined with Pentamidine.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Pentamidine.Approved, Investigational
CaffeineThe metabolism of Pentamidine can be decreased when combined with Caffeine.Approved
CarbamazepineThe metabolism of Pentamidine can be increased when combined with Carbamazepine.Approved, Investigational
CarboxyamidotriazoleThe risk or severity of adverse effects can be increased when Pentamidine is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Caroverine.Experimental
CelecoxibThe metabolism of Pentamidine can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Pentamidine can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Pentamidine can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineThe metabolism of Pentamidine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Pentamidine can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Pentamidine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CilnidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Cilnidipine.Approved, Investigational
CimetidineThe metabolism of Pentamidine can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Pentamidine can be decreased when combined with Cinacalcet.Approved
CinnarizineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Pentamidine.Approved, Investigational, Withdrawn
CitalopramThe metabolism of Pentamidine can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Pentamidine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Pentamidine can be decreased when combined with Clemastine.Approved
ClevidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Clevidipine.Approved
ClobazamThe metabolism of Pentamidine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Pentamidine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe metabolism of Pentamidine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Pentamidine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Pentamidine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Pentamidine can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Pentamidine.Approved, Investigational
CrisaboroleThe metabolism of Pentamidine can be decreased when combined with Crisaborole.Approved, Investigational
CrizotinibThe metabolism of Pentamidine can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Pentamidine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Pentamidine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Pentamidine can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe metabolism of Pentamidine can be decreased when combined with Darifenacin.Approved, Investigational
DarodipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Darodipine.Experimental
DarunavirThe serum concentration of Pentamidine can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Pentamidine can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Pentamidine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Pentamidine can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Pentamidine can be decreased when combined with Desipramine.Approved
DidanosineDidanosine can cause a decrease in the absorption of Pentamidine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DihydroergotamineThe metabolism of Pentamidine can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Pentamidine is combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Pentamidine can be decreased when combined with Diphenhydramine.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Pentamidine.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Pentamidine.Approved
DosulepinThe metabolism of Pentamidine can be decreased when combined with Dosulepin.Approved
DotarizineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Dotarizine.Investigational
DoxycyclineThe metabolism of Pentamidine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Pentamidine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Pentamidine can be decreased when combined with Duloxetine.Approved
EfavirenzThe metabolism of Pentamidine can be decreased when combined with Efavirenz.Approved, Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Efonidipine.Approved, Investigational
EliglustatThe metabolism of Pentamidine can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Pentamidine can be decreased when it is combined with Enzalutamide.Approved
EperisoneThe risk or severity of adverse effects can be increased when Pentamidine is combined with Eperisone.Approved, Investigational
ErythromycinThe metabolism of Pentamidine can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe metabolism of Pentamidine can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Pentamidine can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Pentamidine.Approved
FelodipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Fendiline.Withdrawn
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Pentamidine.Approved
FluconazoleThe metabolism of Pentamidine can be decreased when combined with Fluconazole.Approved
FlunarizineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Flunarizine.Approved
FluoxetineThe metabolism of Pentamidine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Pentamidine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Pentamidine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Pentamidine can be increased when it is combined with Fosaprepitant.Approved
FoscarnetThe risk or severity of adverse effects can be increased when Pentamidine is combined with Foscarnet.Approved
FosphenytoinThe serum concentration of Pentamidine can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Pentamidine can be increased when it is combined with Fusidic Acid.Approved
GabapentinThe risk or severity of adverse effects can be increased when Pentamidine is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Pentamidine is combined with Gallopamil.Investigational
GemfibrozilThe metabolism of Pentamidine can be decreased when combined with Gemfibrozil.Approved
HaloperidolThe metabolism of Pentamidine can be decreased when combined with Haloperidol.Approved
IdelalisibThe metabolism of Pentamidine can be decreased when combined with Idelalisib.Approved
ImatinibThe metabolism of Pentamidine can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Pentamidine can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Pentamidine can be decreased when combined with Indinavir.Approved
IrbesartanThe metabolism of Pentamidine can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Pentamidine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Pentamidine can be decreased when combined with Isoniazid.Approved
IsradipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Isradipine.Approved
ItraconazoleThe metabolism of Pentamidine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Pentamidine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Pentamidine can be decreased when combined with Ketoconazole.Approved, Investigational
LacidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Lacidipine.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Lamotrigine.Approved, Investigational
LapatinibThe metabolism of Pentamidine can be decreased when combined with Lapatinib.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Lercanidipine.Approved, Investigational
LidocaineThe metabolism of Pentamidine can be decreased when combined with Lidocaine.Approved, Vet Approved
LidoflazineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Lidoflazine.Experimental
LobeglitazoneThe metabolism of Pentamidine can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Pentamidine can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Pentamidine can be decreased when combined with Lorcaserin.Approved
LorpiprazoleThe serum concentration of Pentamidine can be increased when it is combined with Lorpiprazole.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Pentamidine.Approved
LovastatinThe metabolism of Pentamidine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Pentamidine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Pentamidine can be increased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Pentamidine can be decreased when combined with Lumefantrine.Approved
MacimorelinPentamidine may increase the QTc-prolonging activities of Macimorelin.Approved, Investigational
Magnesium SulfateThe risk or severity of adverse effects can be increased when Pentamidine is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Manidipine.Approved, Investigational
MequitazinePentamidine may increase the arrhythmogenic activities of Mequitazine.Approved
MethadoneThe metabolism of Pentamidine can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Pentamidine can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Pentamidine.Approved, Investigational
MexiletineThe metabolism of Pentamidine can be decreased when combined with Mexiletine.Approved
MibefradilThe risk or severity of adverse effects can be increased when Pentamidine is combined with Mibefradil.Investigational, Withdrawn
MidostaurinThe metabolism of Pentamidine can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Pentamidine can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe metabolism of Pentamidine can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Pentamidine can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Pentamidine can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Pentamidine can be decreased when combined with Modafinil.Approved, Investigational
NaftopidilThe risk or severity of adverse effects can be increased when Pentamidine is combined with Naftopidil.Investigational
NefazodoneThe metabolism of Pentamidine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Pentamidine can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Pentamidine can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Pentamidine can be increased when combined with Nevirapine.Approved
NicardipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Niguldipine.Experimental
NilotinibThe metabolism of Pentamidine can be decreased when combined with Nilotinib.Approved, Investigational
NiludipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Nilvadipine.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Pentamidine is combined with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Nitrendipine.Approved, Investigational
OlaparibThe metabolism of Pentamidine can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Pentamidine can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Pentamidine can be increased when it is combined with Osimertinib.Approved
OtiloniumThe risk or severity of adverse effects can be increased when Pentamidine is combined with Otilonium.Experimental, Investigational
PalbociclibThe serum concentration of Pentamidine can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Pentamidine can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Pentamidine can be decreased when combined with Pantoprazole.Approved
ParoxetineThe metabolism of Pentamidine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Pentamidine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Pentamidine can be increased when combined with Pentobarbital.Approved, Vet Approved
PerhexilineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Perhexiline.Approved, Investigational
PhenobarbitalThe metabolism of Pentamidine can be increased when combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Pentamidine.Approved, Vet Approved
PinaveriumThe risk or severity of adverse effects can be increased when Pentamidine is combined with Pinaverium.Approved
PioglitazoneThe metabolism of Pentamidine can be decreased when combined with Pioglitazone.Approved, Investigational
PosaconazoleThe metabolism of Pentamidine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PregabalinThe risk or severity of adverse effects can be increased when Pentamidine is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Prenylamine.Withdrawn
PrimidoneThe metabolism of Pentamidine can be increased when combined with Primidone.Approved, Vet Approved
ProgesteroneThe absorption of Progesterone can be decreased when combined with Pentamidine.Approved, Vet Approved
PromazineThe metabolism of Pentamidine can be decreased when combined with Promazine.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Pentamidine.Approved
QuinineThe metabolism of Pentamidine can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Pentamidine can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Pentamidine.Approved, Investigational
RanolazineThe metabolism of Pentamidine can be decreased when combined with Ranolazine.Approved, Investigational
RibociclibThe risk or severity of QTc prolongation can be increased when Ribociclib is combined with Pentamidine.Approved
RifabutinThe metabolism of Pentamidine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Pentamidine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Pentamidine can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Pentamidine.Approved, Investigational
RisedronateThe risk or severity of adverse effects can be increased when Pentamidine is combined with Risedronate.Approved, Investigational
RitonavirThe metabolism of Pentamidine can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Pentamidine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Pentamidine can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneThe metabolism of Pentamidine can be decreased when combined with Rosiglitazone.Approved, Investigational
RucaparibThe metabolism of Pentamidine can be decreased when combined with Rucaparib.Approved, Investigational
SaquinavirThe metabolism of Pentamidine can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Pentamidine can be decreased when used in combination with Sarilumab.Approved
SecobarbitalThe metabolism of Pentamidine can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Pentamidine can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Pentamidine can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Pentamidine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Pentamidine can be increased when it is combined with Simeprevir.Approved
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Pentamidine.Approved
St. John's WortThe serum concentration of Pentamidine can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Pentamidine can be increased when it is combined with Stiripentol.Approved
SucralfateSucralfate can cause a decrease in the absorption of Pentamidine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SulfamethoxazoleThe metabolism of Pentamidine can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Pentamidine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Pentamidine.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Pentamidine.Approved, Investigational
TamoxifenThe metabolism of Pentamidine can be decreased when combined with Tamoxifen.Approved
TelaprevirThe metabolism of Pentamidine can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Pentamidine can be decreased when combined with Telithromycin.Approved
Tenofovir disoproxilThe metabolism of Pentamidine can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TerbinafineThe metabolism of Pentamidine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TeriflunomideThe serum concentration of Pentamidine can be decreased when it is combined with Teriflunomide.Approved
TerodilineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Tetrahydropalmatine.Investigational
TheophyllineThe metabolism of Pentamidine can be decreased when combined with Theophylline.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Pentamidine.Approved, Withdrawn
TiclopidineThe metabolism of Pentamidine can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Pentamidine can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Pentamidine can be decreased when it is combined with Tocilizumab.Approved
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Pentamidine is combined with Tolfenamic Acid.Approved
TopiramateThe metabolism of Pentamidine can be decreased when combined with Topiramate.Approved
TopiroxostatThe metabolism of Pentamidine can be decreased when combined with Topiroxostat.Approved, Investigational
TranilastThe risk or severity of adverse effects can be increased when Pentamidine is combined with Tranilast.Approved, Investigational
TranylcypromineThe metabolism of Pentamidine can be decreased when combined with Tranylcypromine.Approved
TrimethoprimThe metabolism of Pentamidine can be decreased when combined with Trimethoprim.Approved, Vet Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Pentamidine.Approved
VenlafaxineThe metabolism of Pentamidine can be decreased when combined with Venlafaxine.Approved
VerapamilThe risk or severity of adverse effects can be increased when Pentamidine is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Vinpocetine.Investigational
VoriconazoleThe metabolism of Pentamidine can be decreased when combined with Voriconazole.Approved, Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Pentamidine is combined with Ziconotide.Approved
ZiprasidoneThe metabolism of Pentamidine can be decreased when combined with Ziprasidone.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Pentamidine.Approved
ZucapsaicinThe metabolism of Pentamidine can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not Available

References

General References
  1. Nguewa PA, Fuertes MA, Cepeda V, Iborra S, Carrion J, Valladares B, Alonso C, Perez JM: Pentamidine is an antiparasitic and apoptotic drug that selectively modifies ubiquitin. Chem Biodivers. 2005 Oct;2(10):1387-400. [PubMed:17191940]
External Links
Human Metabolome Database
HMDB0014876
KEGG Compound
C07420
PubChem Compound
4735
PubChem Substance
46508562
ChemSpider
4573
BindingDB
45440
ChEBI
45081
ChEMBL
CHEMBL55
Therapeutic Targets Database
DAP000764
PharmGKB
PA450850
HET
PNT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pentamidine
ATC Codes
P01CX01 — Pentamidine isethionate
AHFS Codes
  • 08:30.92 — Miscellaneous Antiprotozoals
PDB Entries
1d64 / 1rkw / 3cr4 / 3cr5 / 3ey0 / 3gy3 / 3hii
MSDS
Download (50.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHepatocellular,Carcinoma1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii2
1RecruitingTreatmentHepatic Steatosis1
1, 2CompletedTreatmentColorectal Cancers1
1, 2CompletedTreatmentKidney Diseases / Transplantation, Kidney1
1, 2CompletedTreatmentMalignant Neoplasm of Pancreas1
2CompletedNot AvailableMalignancies, Hematologic1
2CompletedTreatmentDiabetes Mellitus, Insulin-Dependent1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii1
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentMelanoma (Skin)1
2CompletedTreatmentTrypanosoma brucei gambiense infection1
3CompletedPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS) / Visceral Leishmaniosis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii6
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii1
4WithdrawnTreatmentPneumonia, Pneumocystis Carinii1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii10

Pharmacoeconomics

Manufacturers
  • App pharmaceuticals llc
  • Armour pharmaceutical co
  • Baxter healthcare corp anesthesia and critical care
  • Hospira inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
InhalantRespiratory (inhalation)300 mg/6mL
Powder, for solutionIntramuscular; Intravenous; Respiratory (inhalation)300 mg
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous300 mg/3mL
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous300 mg/300mg
Powder, for solutionIntramuscular; Intravenous300 mg
Prices
Unit descriptionCostUnit
Nebupent 300 mg inhal powder122.84USD each
Pentam 300 vial94.8USD vial
Pentamidine 300 mg vial45.31USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)186.0 °C (decomposes)Not Available
water solubilityCompleteNot Available
logP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0236 mg/mLALOGPS
logP1.32ALOGPS
logP2.32ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)12.13ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.2 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity120.53 m3·mol-1ChemAxon
Polarizability38.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9416
Blood Brain Barrier+0.9133
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.5352
P-glycoprotein inhibitor INon-inhibitor0.8571
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterInhibitor0.6653
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.7339
CYP450 1A2 substrateNon-inhibitor0.5272
CYP450 2C9 inhibitorNon-inhibitor0.7439
CYP450 2D6 inhibitorNon-inhibitor0.7676
CYP450 2C19 inhibitorNon-inhibitor0.6581
CYP450 3A4 inhibitorNon-inhibitor0.8661
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5621
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8395
BiodegradationNot ready biodegradable0.9818
Rat acute toxicity2.2925 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7428
hERG inhibition (predictor II)Non-inhibitor0.7711
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0009000000-e30f537a55b02f867429
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0009000000-18ffa88d8e83e0c224b3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0309000000-22a206e2fffa6ce5cf2f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dr-0900000000-d135e9c44dbf5da10735
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-d01e29cdf614c3660180
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0009000000-1499530d0d768e480fd7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0009000000-3c60569ced478a95001f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0209000000-58a168dde59140860009
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dr-0901000000-7cd36861b140e4e5a6a2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-60dfcd75868e869bcbf7
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0009000000-6677c6c06aa266d05ff1

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Alkyl aryl ethers / Carboximidamides / Carboxamidines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Carboximidamide / Ether / Carboxylic acid amidine / Amidine / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
carboxamidine, diether (CHEBI:45081)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Unknown
Actions
Intercalation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Shankar SM, Nania JJ: Management of Pneumocystis jiroveci pneumonia in children receiving chemotherapy. Paediatr Drugs. 2007;9(5):301-9. [PubMed:17927302]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Other
General Function
Trna methyltransferase activity
Specific Function
Specifically methylates cytosine 38 in the anticodon loop of tRNA(Asp).
Gene Name
TRDMT1
Uniprot ID
O14717
Uniprot Name
tRNA (cytosine(38)-C(5))-methyltransferase
Molecular Weight
44596.17 Da
References
  1. Sun T, Zhang Y: Pentamidine binds to tRNA through non-specific hydrophobic interactions and inhibits aminoacylation and translation. Nucleic Acids Res. 2008 Mar;36(5):1654-64. doi: 10.1093/nar/gkm1180. Epub 2008 Feb 7. [PubMed:18263620]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Afrin LB, Afrin JB: Value of preemptive CYP2C19 genotyping in allogeneic stem cell transplant patients considered for pentamidine administration. Clin Transplant. 2011 May-Jun;25(3):E271-5. doi: 10.1111/j.1399-0012.2011.01399.x. Epub 2011 Feb 7. [PubMed:21299635]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [PubMed:12920490]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [PubMed:12920490]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [PubMed:12920490]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Leukotriene-b4 20-monooxygenase activity
Specific Function
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 2...
Gene Name
CYP4A11
Uniprot ID
Q02928
Uniprot Name
Cytochrome P450 4A11
Molecular Weight
59347.31 Da
References
  1. Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [PubMed:12920490]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on January 19, 2018 10:50