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Identification
NamePosaconazole
Accession NumberDB01263
TypeSmall Molecule
GroupsApproved, Investigational, Vet Approved
Description

Posaconazole is a triazole antifungal drug that is used to treat invasive infections by Candida species and Aspergillus species in severely immunocompromised patients.

Structure
Thumb
SynonymsNot Available
External Identifiers
  • Sch 56592
  • SCH-56592
  • SCH56592
  • Schering 56592
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Noxafilsuspension40 mg/mLoralMerck Sharp & Dohme Corp.2006-09-15Not applicableUs
Noxafilsolution18 mg/mLintravenousMerck Sharp & Dohme Corp.2014-03-13Not applicableUs
Noxafiltablet, coated100 mg/1oralMerck Sharp & Dohme Corp.2013-11-25Not applicableUs
Posanolsolution18 mgintravenousMerck Canada Inc2014-11-24Not applicableCanada
Posanoltablet (delayed-release)100 mgoralMerck Canada Inc2014-05-21Not applicableCanada
Posanolsuspension40 mgoralMerck Canada Inc2007-06-06Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII6TK1G07BHZ
CAS number171228-49-2
WeightAverage: 700.7774
Monoisotopic: 700.329708282
Chemical FormulaC37H42F2N8O4
InChI KeyRAGOYPUPXAKGKH-XAKZXMRKSA-N
InChI
InChI=1S/C37H42F2N8O4/c1-3-35(26(2)48)47-36(49)46(25-42-47)31-7-5-29(6-8-31)43-14-16-44(17-15-43)30-9-11-32(12-10-30)50-20-27-19-37(51-21-27,22-45-24-40-23-41-45)33-13-4-28(38)18-34(33)39/h4-13,18,23-27,35,48H,3,14-17,19-22H2,1-2H3/t26-,27+,35-,37-/m0/s1
IUPAC Name
4-{4-[4-(4-{[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-1-[(2S,3S)-2-hydroxypentan-3-yl]-4,5-dihydro-1H-1,2,4-triazol-5-one
SMILES
[H][C@@](C)(O)[C@]([H])(CC)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@]2([H])CO[C@](CN3C=NC=N3)(C2)C2=C(F)C=C(F)C=C2)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Phenylpiperazine
  • Phenyl-1,3,4-triazole
  • Phenyl-1,2,4-triazole
  • Phenyltriazole
  • Substituted aniline
  • Dialkylarylamine
  • Phenol ether
  • Halobenzene
  • Fluorobenzene
  • Aniline
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Triazole
  • Oxolane
  • Azole
  • Tertiary amine
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor prophylaxis of invasive Aspergillus and Candida infections in patients, 13 years of age and older, who are at high risk of developing these infections due to being severely immunocompromised as a result of procedures such as hematopoietic stem cell transplant (HSCT) recipients with graft-versus-host disease (GVHD), or due to hematologic malignancies with prolonged neutropenia from chemotherapy. Also for the treatment of oropharyngeal candidiasis, including oropharyngeal candidiasis refractory to itraconazole and/or fluconazole. Posaconazole is used as an alternative treatment for invasive aspergillosis, Fusarium infections, and zygomycosis in patients who are intolerant of, or whose disease is refractory to, other antifungals.
PharmacodynamicsPosaconazole is an antifungal agent structurally related to itraconazole. It is a drug derived from itraconzaole through the replacement of the chlorine substituents with flourine in the phenyl ring, as well as hydroxylation of the triazolone side chain. These modifications enhance the potency and spectrum of activity of the drug. Posaconazole can be either fungicial or fungistatic in action.
Mechanism of actionAs a triazole antifungal agent, posaconazole exerts its antifungal activity through blockage of the cytochrome P-450 dependent enzyme, sterol 14α-demethylase, in fungi by binding to the heme cofactor located on the enzyme. This leads to the inhibition of the synthesis of ergosterol, a key component of the fungal cell membrane, and accumulation of methylated sterol precursors. This results in inhibition of fungal cell growth and ultimately, cell death.
Related Articles
AbsorptionPosaconazole is absorbed with a median Tmax of approximately 3 to 5 hours.
Volume of distribution
  • 1774 L
Protein bindingPosaconazole is highly protein bound (>98%), predominantly to albumin.
Metabolism

Posaconazole primarily circulates as the parent compound in plasma. Of the circulating metabolites, the majority are glucuronide conjugates formed via UDP glucuronidation (phase 2 enzymes). Posaconazole does not have any major circulating oxidative (CYP450 mediated) metabolites. The excreted metabolites in urine and feces account for ~17% of the administered radiolabeled dose.

Route of eliminationThe excreted metabolites in urine and feces account for ~17% of the administered radiolabeled dose.
Half lifePosaconazole is eliminated with a mean half-life (t½) of 35 hours (range 20 to 66 hours).
Clearance
  • 32 L/hr
  • 51 L/hr [Single-Dose Suspension Administration of 200 mg, fasted]
  • 21 L/hr [Single-Dose Suspension Administration of 200 mg, nonfat meal]
  • 14 L/hr [Single-Dose Suspension Administration of 200 mg, high fat meal]
  • 91 L/hr [Single-Dose Suspension Administration of 400 mg, fasted]
  • 43 L/hr [Single-Dose Suspension Administration of 400 mg with liquid nutritional supplement (14 g fat)]
ToxicityDuring the clinical trials, some patients received posaconazole up to 1600 mg/day with no adverse events noted that were different from the lower doses. In addition, accidental overdose was noted in one patient who took 1200 mg BID for 3 days. No related adverse events were noted by the investigator.
Affected organisms
  • Aspergillis, Candida and other fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.5499
Caco-2 permeable+0.5332
P-glycoprotein substrateSubstrate0.7822
P-glycoprotein inhibitor IInhibitor0.7338
P-glycoprotein inhibitor IINon-inhibitor0.8895
Renal organic cation transporterNon-inhibitor0.7323
CYP450 2C9 substrateNon-substrate0.8131
CYP450 2D6 substrateNon-substrate0.8354
CYP450 3A4 substrateSubstrate0.6683
CYP450 1A2 substrateNon-inhibitor0.8484
CYP450 2C9 inhibitorInhibitor0.5281
CYP450 2D6 inhibitorNon-inhibitor0.8667
CYP450 2C19 inhibitorNon-inhibitor0.6409
CYP450 3A4 inhibitorNon-inhibitor0.5532
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5074
Ames testAMES toxic0.5235
CarcinogenicityNon-carcinogens0.7341
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8919 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5306
hERG inhibition (predictor II)Inhibitor0.6661
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutionintravenous18 mg/mL
Suspensionoral40 mg/mL
Tablet, coatedoral100 mg/1
Solutionintravenous18 mg
Suspensionoral40 mg
Tablet (delayed-release)oral100 mg
Prices
Unit descriptionCostUnit
Noxafil 40 mg/ml suspension7.08USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2179396 No2001-04-172014-12-20Canada
CA2305803 No2009-12-222018-10-05Canada
US5661151 No1999-07-192019-07-19Us
US5703079 No1994-08-262014-08-26Us
US6958337 No1998-10-052018-10-05Us
US8263600 No2002-04-012022-04-01Us
US8410077 No2009-03-132029-03-13Us
US9023790 No2011-07-042031-07-04Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityInsolubleNot Available
logP5.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 mg/mLALOGPS
logP4.71ALOGPS
logP5.41ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)14.83ChemAxon
pKa (Strongest Basic)3.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area111.79 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity200.71 m3·mol-1ChemAxon
Polarizability73.83 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Dominic De Souza, “PREPARATION OF POSACONAZOLE INTERMEDIATES.” U.S. Patent US20130203994, issued August 08, 2013.

US20130203994
General References
  1. Cornely OA, Maertens J, Winston DJ, Perfect J, Ullmann AJ, Walsh TJ, Helfgott D, Holowiecki J, Stockelberg D, Goh YT, Petrini M, Hardalo C, Suresh R, Angulo-Gonzalez D: Posaconazole vs. fluconazole or itraconazole prophylaxis in patients with neutropenia. N Engl J Med. 2007 Jan 25;356(4):348-59. [PubMed:17251531 ]
  2. Ullmann AJ, Lipton JH, Vesole DH, Chandrasekar P, Langston A, Tarantolo SR, Greinix H, Morais de Azevedo W, Reddy V, Boparai N, Pedicone L, Patino H, Durrant S: Posaconazole or fluconazole for prophylaxis in severe graft-versus-host disease. N Engl J Med. 2007 Jan 25;356(4):335-47. [PubMed:17251530 ]
  3. Bhattacharya M, Rajeshwari K, Dhingra B: Posaconazole. J Postgrad Med. 2010 Apr-Jun;56(2):163-7. doi: 10.4103/0022-3859.65281. [PubMed:20622401 ]
  4. Frampton JE, Scott LJ: Posaconazole : a review of its use in the prophylaxis of invasive fungal infections. Drugs. 2008;68(7):993-1016. [PubMed:18457464 ]
  5. Schiller DS, Fung HB: Posaconazole: an extended-spectrum triazole antifungal agent. Clin Ther. 2007 Sep;29(9):1862-86. [PubMed:18035188 ]
  6. Kwon DS, Mylonakis E: Posaconazole: a new broad-spectrum antifungal agent. Expert Opin Pharmacother. 2007 Jun;8(8):1167-78. [PubMed:17516880 ]
  7. Groll AH, Walsh TJ: Posaconazole: clinical pharmacology and potential for management of fungal infections. Expert Rev Anti Infect Ther. 2005 Aug;3(4):467-87. [PubMed:16107193 ]
  8. Rachwalski EJ, Wieczorkiewicz JT, Scheetz MH: Posaconazole: an oral triazole with an extended spectrum of activity. Ann Pharmacother. 2008 Oct;42(10):1429-38. doi: 10.1345/aph.1L005. Epub 2008 Aug 19. [PubMed:18713852 ]
  9. Li Y, Theuretzbacher U, Clancy CJ, Nguyen MH, Derendorf H: Pharmacokinetic/pharmacodynamic profile of posaconazole. Clin Pharmacokinet. 2010 Jun;49(6):379-96. doi: 10.2165/11319340-000000000-00000. [PubMed:20481649 ]
External Links
ATC CodesJ02AC04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (183 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Posaconazole.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Posaconazole.
AlmotriptanThe serum concentration of Almotriptan can be increased when it is combined with Posaconazole.
AlosetronThe serum concentration of Alosetron can be increased when it is combined with Posaconazole.
AmlodipineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Amlodipine.
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Posaconazole.
AmrinoneThe risk or severity of adverse effects can be increased when Posaconazole is combined with Amrinone.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Posaconazole.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Posaconazole.
AstemizoleThe serum concentration of Astemizole can be increased when it is combined with Posaconazole.
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Posaconazole.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Posaconazole.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Posaconazole.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Posaconazole.
BarnidipineThe serum concentration of Barnidipine can be increased when it is combined with Posaconazole.
BedaquilineThe serum concentration of Bedaquiline can be increased when it is combined with Posaconazole.
BepridilThe risk or severity of adverse effects can be increased when Posaconazole is combined with Bepridil.
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Posaconazole.
BortezomibThe serum concentration of Bortezomib can be increased when it is combined with Posaconazole.
BosentanThe serum concentration of Bosentan can be increased when it is combined with Posaconazole.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Posaconazole.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Posaconazole.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Posaconazole.
BrinzolamideThe serum concentration of Brinzolamide can be increased when it is combined with Posaconazole.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Posaconazole.
BuspironeThe metabolism of Buspirone can be decreased when combined with Posaconazole.
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Posaconazole.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Posaconazole.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Posaconazole.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Posaconazole.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Posaconazole.
CimetidineThe serum concentration of Posaconazole can be decreased when it is combined with Cimetidine.
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Posaconazole.
CitalopramPosaconazole may increase the QTc-prolonging activities of Citalopram.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Posaconazole.
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Posaconazole.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Posaconazole.
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Posaconazole.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Posaconazole.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Posaconazole.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Posaconazole.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Posaconazole.
DidanosineDidanosine can cause a decrease in the absorption of Posaconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
DienogestThe serum concentration of Dienogest can be increased when it is combined with Posaconazole.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Posaconazole.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Posaconazole.
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Posaconazole.
DofetilideThe metabolism of Dofetilide can be decreased when combined with Posaconazole.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Posaconazole.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Posaconazole.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Posaconazole.
DronedaroneThe serum concentration of Dronedarone can be increased when it is combined with Posaconazole.
DrospirenoneThe serum concentration of Drospirenone can be increased when it is combined with Posaconazole.
DutasterideThe serum concentration of Dutasteride can be increased when it is combined with Posaconazole.
EfavirenzThe serum concentration of Posaconazole can be decreased when it is combined with Efavirenz.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Posaconazole.
EliglustatThe serum concentration of Eliglustat can be increased when it is combined with Posaconazole.
EnzalutamideThe serum concentration of Enzalutamide can be increased when it is combined with Posaconazole.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Posaconazole.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Posaconazole.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Posaconazole.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Posaconazole.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Posaconazole.
EsomeprazoleThe serum concentration of Posaconazole can be decreased when it is combined with Esomeprazole.
EstazolamThe serum concentration of Estazolam can be increased when it is combined with Posaconazole.
EtizolamThe serum concentration of Etizolam can be increased when it is combined with Posaconazole.
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Posaconazole.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Posaconazole.
FamotidineThe serum concentration of Posaconazole can be decreased when it is combined with Famotidine.
FelodipineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Felodipine.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Posaconazole.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Posaconazole.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Posaconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Posaconazole.
FlunarizineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Flunarizine.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Posaconazole.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Posaconazole.
FosamprenavirThe serum concentration of the active metabolites of Fosamprenavir can be increased when Fosamprenavir is used in combination with Posaconazole.
FosphenytoinThe serum concentration of Posaconazole can be decreased when it is combined with Fosphenytoin.
GabapentinThe risk or severity of adverse effects can be increased when Posaconazole is combined with Gabapentin.
GlipizidePosaconazole may increase the hypoglycemic activities of Glipizide.
GoserelinPosaconazole may increase the QTc-prolonging activities of Goserelin.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Posaconazole.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Posaconazole.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Posaconazole.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Posaconazole.
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Posaconazole.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Posaconazole resulting in a loss in efficacy.
IloperidoneThe serum concentration of the active metabolites of Iloperidone can be increased when Iloperidone is used in combination with Posaconazole.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Posaconazole.
ImidafenacinThe serum concentration of Imidafenacin can be increased when it is combined with Posaconazole.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Posaconazole.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be increased when Isavuconazonium is used in combination with Posaconazole.
IsradipineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Isradipine.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Posaconazole.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Posaconazole.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Posaconazole.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Posaconazole.
LamotrigineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Lamotrigine.
LansoprazoleThe serum concentration of Posaconazole can be decreased when it is combined with Lansoprazole.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Posaconazole.
LercanidipineThe serum concentration of Lercanidipine can be increased when it is combined with Posaconazole.
LeuprolidePosaconazole may increase the QTc-prolonging activities of Leuprolide.
LevobupivacaineThe serum concentration of Levobupivacaine can be increased when it is combined with Posaconazole.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Posaconazole.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Posaconazole.
LosartanThe metabolism of Losartan can be decreased when combined with Posaconazole.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Posaconazole.
LumacaftorThe serum concentration of Posaconazole can be decreased when it is combined with Lumacaftor.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Posaconazole.
MacitentanThe serum concentration of MACITENTAN can be increased when it is combined with Posaconazole.
Magnesium SulfateThe risk or severity of adverse effects can be increased when Posaconazole is combined with Magnesium Sulfate.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Posaconazole.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be increased when it is combined with Posaconazole.
MethadonePosaconazole may increase the QTc-prolonging activities of Methadone.
MethylergometrineThe serum concentration of Methylergometrine can be increased when it is combined with Posaconazole.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Posaconazole.
MetoclopramideThe serum concentration of Posaconazole can be decreased when it is combined with Metoclopramide.
MifepristoneThe serum concentration of Mifepristone can be increased when it is combined with Posaconazole.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Posaconazole.
NicardipineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Nicardipine.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Posaconazole.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Posaconazole.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Posaconazole.
NitrendipineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Nitrendipine.
NizatidineThe serum concentration of Posaconazole can be decreased when it is combined with Nizatidine.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Posaconazole.
OmeprazoleThe serum concentration of Posaconazole can be decreased when it is combined with Omeprazole.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Posaconazole.
OxybutyninThe serum concentration of Oxybutynin can be increased when it is combined with Posaconazole.
OxycodoneThe risk or severity of adverse effects can be increased when Posaconazole is combined with Oxycodone.
PalbociclibThe serum concentration of Palbociclib can be increased when it is combined with Posaconazole.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Posaconazole.
PantoprazoleThe serum concentration of Posaconazole can be decreased when it is combined with Pantoprazole.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Posaconazole.
ParicalcitolThe serum concentration of Paricalcitol can be increased when it is combined with Posaconazole.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Posaconazole.
PerhexilineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Perhexiline.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Posaconazole.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Posaconazole.
PimozidePosaconazole may increase the arrhythmogenic activities of Pimozide.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Posaconazole.
PranlukastThe serum concentration of Pranlukast can be increased when it is combined with Posaconazole.
PrasugrelThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Posaconazole resulting in a loss in efficacy.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Posaconazole.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Posaconazole.
PrenylamineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Prenylamine.
PropafenoneThe serum concentration of Propafenone can be increased when it is combined with Posaconazole.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Posaconazole.
QuinidineThe metabolism of Quinidine can be decreased when combined with Posaconazole.
RabeprazoleThe serum concentration of Posaconazole can be decreased when it is combined with Rabeprazole.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Posaconazole.
RanitidineThe serum concentration of Posaconazole can be decreased when it is combined with Ranitidine.
RanolazineThe metabolism of Ranolazine can be decreased when combined with Posaconazole.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Posaconazole.
RepaglinideThe serum concentration of Repaglinide can be increased when it is combined with Posaconazole.
RetapamulinThe serum concentration of Retapamulin can be increased when it is combined with Posaconazole.
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Posaconazole.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Posaconazole.
RisedronateThe risk or severity of adverse effects can be increased when Posaconazole is combined with Risedronate.
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Posaconazole.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Posaconazole.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Posaconazole.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Posaconazole.
SaxagliptinThe serum concentration of Saxagliptin can be increased when it is combined with Posaconazole.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Posaconazole.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Posaconazole.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Posaconazole.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Posaconazole.
SirolimusThe serum concentration of Sirolimus can be increased when it is combined with Posaconazole.
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Posaconazole.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Posaconazole.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Posaconazole.
SucralfateSucralfate can cause a decrease in the absorption of Posaconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
SunitinibThe metabolism of Sunitinib can be decreased when combined with Posaconazole.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Posaconazole.
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Posaconazole.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Posaconazole.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Posaconazole.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Posaconazole.
TelaprevirThe serum concentration of Posaconazole can be increased when it is combined with Telaprevir.
TemsirolimusThe serum concentration of the active metabolites of Temsirolimus can be increased when Temsirolimus is used in combination with Posaconazole.
TerfenadineThe serum concentration of Terfenadine can be increased when it is combined with Posaconazole.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Posaconazole resulting in a loss in efficacy.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Posaconazole.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Posaconazole.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Posaconazole.
ToremifeneThe risk or severity of adverse effects can be increased when Posaconazole is combined with Toremifene.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Posaconazole.
TramadolThe serum concentration of Tramadol can be increased when it is combined with Posaconazole.
Trastuzumab emtansineThe serum concentration of the active metabolites of ado-trastuzumab emtansine can be increased when ado-trastuzumab emtansine is used in combination with Posaconazole.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Posaconazole.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Posaconazole.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Posaconazole.
VerapamilThe risk or severity of adverse effects can be increased when Posaconazole is combined with Verapamil.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Posaconazole.
VinblastineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Vinblastine.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Posaconazole.
VindesineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Vindesine.
VinorelbineThe risk or severity of adverse effects can be increased when Posaconazole is combined with Vinorelbine.
VorapaxarThe serum concentration of Vorapaxar can be increased when it is combined with Posaconazole.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Posaconazole.
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Posaconazole.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Posaconazole.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be increased when it is combined with Posaconazole.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
yes
Actions
antagonist
General Function:
Sterol 14-demethylase activity
Specific Function:
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
ERG11
Uniprot ID:
P10613
Molecular Weight:
60674.965 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. Chau AS, Mendrick CA, Sabatelli FJ, Loebenberg D, McNicholas PM: Application of real-time quantitative PCR to molecular analysis of Candida albicans strains exhibiting reduced susceptibility to azoles. Antimicrob Agents Chemother. 2004 Jun;48(6):2124-31. [PubMed:15155210 ]
  4. Li X, Brown N, Chau AS, Lopez-Ribot JL, Ruesga MT, Quindos G, Mendrick CA, Hare RS, Loebenberg D, DiDomenico B, McNicholas PM: Changes in susceptibility to posaconazole in clinical isolates of Candida albicans. J Antimicrob Chemother. 2004 Jan;53(1):74-80. Epub 2003 Dec 4. [PubMed:14657086 ]
  5. Bhattacharya M, Rajeshwari K, Dhingra B: Posaconazole. J Postgrad Med. 2010 Apr-Jun;56(2):163-7. doi: 10.4103/0022-3859.65281. [PubMed:20622401 ]
  6. Schiller DS, Fung HB: Posaconazole: an extended-spectrum triazole antifungal agent. Clin Ther. 2007 Sep;29(9):1862-86. [PubMed:18035188 ]
  7. Kwon DS, Mylonakis E: Posaconazole: a new broad-spectrum antifungal agent. Expert Opin Pharmacother. 2007 Jun;8(8):1167-78. [PubMed:17516880 ]
  8. Groll AH, Walsh TJ: Posaconazole: clinical pharmacology and potential for management of fungal infections. Expert Rev Anti Infect Ther. 2005 Aug;3(4):467-87. [PubMed:16107193 ]
  9. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
  10. Warrilow AG, Melo N, Martel CM, Parker JE, Nes WD, Kelly SL, Kelly DE: Expression, purification, and characterization of Aspergillus fumigatus sterol 14-alpha demethylase (CYP51) isoenzymes A and B. Antimicrob Agents Chemother. 2010 Oct;54(10):4225-34. doi: 10.1128/AAC.00316-10. Epub 2010 Jul 26. [PubMed:20660663 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Nagappan V, Deresinski S: Reviews of anti-infective agents: posaconazole: a broad-spectrum triazole antifungal agent. Clin Infect Dis. 2007 Dec 15;45(12):1610-7. doi: 10.1086/523576. [PubMed:18190324 ]
  2. Kharuzhyk SA, Matskevich SA, Filjustin AE, Bogushevich EV, Ugolkova SA: Survey of computed tomography doses and establishment of national diagnostic reference levels in the Republic of Belarus. Radiat Prot Dosimetry. 2010 Apr-May;139(1-3):367-70. doi: 10.1093/rpd/ncq070. Epub 2010 Feb 24. [PubMed:20181649 ]
  3. Kwon DS, Mylonakis E: Posaconazole: a new broad-spectrum antifungal agent. Expert Opin Pharmacother. 2007 Jun;8(8):1167-78. [PubMed:17516880 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Nagappan V, Deresinski S: Reviews of anti-infective agents: posaconazole: a broad-spectrum triazole antifungal agent. Clin Infect Dis. 2007 Dec 15;45(12):1610-7. doi: 10.1086/523576. [PubMed:18190324 ]
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Drug created on May 16, 2007 11:41 / Updated on June 25, 2016 01:52