Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C37H42F2N8O4 |
| Molecular Weight | 700.7774 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@@H]([C@H](C)O)N1N=CN(C1=O)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(OC[C@@H]5CO[C@](CN6C=NC=N6)(C5)C7=CC=C(F)C=C7F)C=C4
InChI
InChIKey=RAGOYPUPXAKGKH-XAKZXMRKSA-N
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
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022003s021,205053s005,205596s004lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18035188
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022003s021,205053s005,205596s004lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/18035188
Posaconazole is a triazole antifungal drug that is used to treat invasive infections by Candida species and Aspergillus species in severely immunocompromised patients. It marketed in the United States, the European Union, and in other countries by Schering-Plough under the trade name Noxafil. Noxafil is used for 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 blocks the synthesis of ergosterol, a key component of the fungal cell membrane, through the inhibition of cytochrome P-450 dependent enzyme lanosterol 14α-demethylase responsible for the conversion of lanosterol to ergosterol in the fungal cell membrane. This results in an accumulation of methylated sterol precursors and a depletion of ergosterol within the cell membrane thus weakening the structure and function of the fungal cell membrane. This may be responsible for the antifungal activity of posaconazole. It is absorbed within three to five hours and predominately eliminated through the liver, and has a half-life of about 35 hours. Oral administration of posaconazole taken with a high-fat meal exceeds 90% bioavailability and increases the concentration by four times compared to fasting state.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1780 |
25.0 nM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | NOXAFIL Approved UseNoxafil is an azole antifungal agent indicated for: injection, delayed-release tablets, and oral suspension prophylaxis of invasive Aspergillus and Candida infections in patients who are at high risk of developing these infections due to being severely immunocompromised, such as HSCT recipients with GVHD or those with hematologic malignancies with prolonged neutropenia from chemotherapy. (1.1) Oral suspension treatment of oropharyngeal candidiasis (OPC), including OPC refractory (rOPC) to itraconazole and/or fluconazole. (1.2) 1.1 Prophylaxis of Invasive Aspergillus and Candida Infections Noxafil® injection, delayed-release tablets, and oral suspension are indicated for prophylaxis of invasive Aspergillus and Candida infections in patients who are at high risk of developing these infections due to being severely immunocompromised, such as hematopoietic stem cell transplant (HSCT) recipients with graft-versus-host disease (GVHD) or those with hematologic malignancies with prolonged neutropenia from chemotherapy. Noxafil injection is indicated in patients 18 years of age and older. Noxafil delayed-release tablets and oral suspension are indicated in patients 13 years of age and older. 1.2 Treatment of Oropharyngeal Candidiasis Including Oropharyngeal Candidiasis Refractory to Itraconazole and/or Fluconazole Noxafil oral suspension is indicated for the treatment of oropharyngeal candidiasis, including oropharyngeal candidiasis refractory to itraconazole and/or fluconazole. Launch Date2006 |
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| Preventing | NOXAFIL Approved UseNoxafil is an azole antifungal agent indicated for: injection, delayed-release tablets, and oral suspension prophylaxis of invasive Aspergillus and Candida infections in patients who are at high risk of developing these infections due to being severely immunocompromised, such as HSCT recipients with GVHD or those with hematologic malignancies with prolonged neutropenia from chemotherapy. (1.1) Oral suspension treatment of oropharyngeal candidiasis (OPC), including OPC refractory (rOPC) to itraconazole and/or fluconazole. (1.2) 1.1 Prophylaxis of Invasive Aspergillus and Candida Infections Noxafil® injection, delayed-release tablets, and oral suspension are indicated for prophylaxis of invasive Aspergillus and Candida infections in patients who are at high risk of developing these infections due to being severely immunocompromised, such as hematopoietic stem cell transplant (HSCT) recipients with graft-versus-host disease (GVHD) or those with hematologic malignancies with prolonged neutropenia from chemotherapy. Noxafil injection is indicated in patients 18 years of age and older. Noxafil delayed-release tablets and oral suspension are indicated in patients 13 years of age and older. 1.2 Treatment of Oropharyngeal Candidiasis Including Oropharyngeal Candidiasis Refractory to Itraconazole and/or Fluconazole Noxafil oral suspension is indicated for the treatment of oropharyngeal candidiasis, including oropharyngeal candidiasis refractory to itraconazole and/or fluconazole. Launch Date2006 |
|||
| Curative | NOXAFIL Approved UseNoxafil is an azole antifungal agent indicated for: injection, delayed-release tablets, and oral suspension prophylaxis of invasive Aspergillus and Candida infections in patients who are at high risk of developing these infections due to being severely immunocompromised, such as HSCT recipients with GVHD or those with hematologic malignancies with prolonged neutropenia from chemotherapy. (1.1) Oral suspension treatment of oropharyngeal candidiasis (OPC), including OPC refractory (rOPC) to itraconazole and/or fluconazole. (1.2) 1.1 Prophylaxis of Invasive Aspergillus and Candida Infections Noxafil® injection, delayed-release tablets, and oral suspension are indicated for prophylaxis of invasive Aspergillus and Candida infections in patients who are at high risk of developing these infections due to being severely immunocompromised, such as hematopoietic stem cell transplant (HSCT) recipients with graft-versus-host disease (GVHD) or those with hematologic malignancies with prolonged neutropenia from chemotherapy. Noxafil injection is indicated in patients 18 years of age and older. Noxafil delayed-release tablets and oral suspension are indicated in patients 13 years of age and older. 1.2 Treatment of Oropharyngeal Candidiasis Including Oropharyngeal Candidiasis Refractory to Itraconazole and/or Fluconazole Noxafil oral suspension is indicated for the treatment of oropharyngeal candidiasis, including oropharyngeal candidiasis refractory to itraconazole and/or fluconazole. Launch Date2006 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3280 ng/mL |
300 mg 1 times / day multiple, intravenous dose: 300 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
POSACONAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2840 ng/mL |
300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2764 ng/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
935 ng/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
1060 ng/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
36100 ng × h/mL |
300 mg 1 times / day multiple, intravenous dose: 300 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
POSACONAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
46400 ng × h/mL |
300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
51618 ng × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
9093 ng × h/mL |
400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
26200 ng × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
38400 ng × h/mL |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
24.6 h |
300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
31 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
31.7 h |
400 mg 2 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2% |
300 mg 1 times / day multiple, intravenous dose: 300 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
POSACONAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2% |
300 mg single, intravenous dose: 300 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
[NO STEREO] POSACONAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 mg 2 times / day multiple, intravenous Recommended Dose: 300 mg, 2 times / day Route: intravenous Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, 51.55 |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (0.84%) Sources: |
1600 mg 1 times / day multiple, oral Highest studied dose Dose: 1600 mg, 1 times / day Route: oral Route: multiple Dose: 1600 mg, 1 times / day Sources: |
unhealthy |
Disc. AE: Hepatic enzyme increased... Other AEs: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Hepatic enzyme increased (67%) Other AEs:Nausea (67%) Sources: Vomiting (67%) Diarrhea (67%) Somnolence (67%) |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (2%) Sources: Vomiting (2%) Hepatic enzymes increased (2%) |
300 mg 2 times / day multiple, intravenous Recommended Dose: 300 mg, 2 times / day Route: intravenous Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Arrhythmia, Electrocardiogram QTc interval prolonged... AEs leading to discontinuation/dose reduction: Arrhythmia Sources: Electrocardiogram QTc interval prolonged Hepatotoxicity |
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Pneumonia... AEs leading to discontinuation/dose reduction: Pneumonia (1%) Sources: |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Pulmonary function impairment, AIDS... AEs leading to discontinuation/dose reduction: Pulmonary function impairment (3%) Sources: AIDS (7%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Rash | 0.84% Disc. AE |
300 mg 2 times / day multiple, intravenous Recommended Dose: 300 mg, 2 times / day Route: intravenous Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy, 51.55 |
| Diarrhea | 67% | 1600 mg 1 times / day multiple, oral Highest studied dose Dose: 1600 mg, 1 times / day Route: oral Route: multiple Dose: 1600 mg, 1 times / day Sources: |
unhealthy |
| Nausea | 67% | 1600 mg 1 times / day multiple, oral Highest studied dose Dose: 1600 mg, 1 times / day Route: oral Route: multiple Dose: 1600 mg, 1 times / day Sources: |
unhealthy |
| Somnolence | 67% | 1600 mg 1 times / day multiple, oral Highest studied dose Dose: 1600 mg, 1 times / day Route: oral Route: multiple Dose: 1600 mg, 1 times / day Sources: |
unhealthy |
| Vomiting | 67% | 1600 mg 1 times / day multiple, oral Highest studied dose Dose: 1600 mg, 1 times / day Route: oral Route: multiple Dose: 1600 mg, 1 times / day Sources: |
unhealthy |
| Hepatic enzyme increased | 67% Disc. AE |
1600 mg 1 times / day multiple, oral Highest studied dose Dose: 1600 mg, 1 times / day Route: oral Route: multiple Dose: 1600 mg, 1 times / day Sources: |
unhealthy |
| Hepatic enzymes increased | 2% Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Nausea | 2% Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Vomiting | 2% Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Arrhythmia | Disc. AE | 300 mg 2 times / day multiple, intravenous Recommended Dose: 300 mg, 2 times / day Route: intravenous Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Electrocardiogram QTc interval prolonged | Disc. AE | 300 mg 2 times / day multiple, intravenous Recommended Dose: 300 mg, 2 times / day Route: intravenous Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Hepatotoxicity | Disc. AE | 300 mg 2 times / day multiple, intravenous Recommended Dose: 300 mg, 2 times / day Route: intravenous Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Pneumonia | 1% Disc. AE |
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Pulmonary function impairment | 3% Disc. AE |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| AIDS | 7% Disc. AE |
400 mg 2 times / day multiple, oral Recommended Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [IC50 3 uM] | ||||
| yes [IC50 6 uM] | ||||
| yes | ||||
| yes | ||||
| yes | yes (co-administration study) Comment: concommitant administration of psconazole with midazolam increases midazolam plasma concentritons by 5-fold Page: 17.0 |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | yes (co-administration study) Comment: rifabutin decreases posaconazole plasma concentrations Page: 16, 17, 27 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro and in vivo efficacies of the azole SCH56592 against Cryptococcus neoformans. | 1996 Aug |
|
| Activity of a new triazole, Sch 56592, compared with those of four other antifungal agents tested against clinical isolates of Candida spp. and Saccharomyces cerevisiae. | 1997 Feb |
|
| In vitro studies of activities of the antifungal triazoles SCH56592 and itraconazole against Candida albicans, Cryptococcus neoformans, and other pathogenic yeasts. | 1997 Jan |
|
| Activity of SCH 56592 compared with those of fluconazole and itraconazole against Candida spp. | 1997 Oct |
|
| In vitro activity of a new triazole antifungal agent, Sch 56592, against clinical isolates of filamentous fungi. | 1998 |
|
| In vitro susceptibilities of Candida bloodstream isolates to the new triazole antifungal agents BMS-207147, Sch 56592, and voriconazole. | 1998 Dec |
|
| SCH56592 treatment of murine invasive aspergillosis. | 1998 Oct |
|
| Comparison of In vitro activities of the new triazole SCH56592 and the echinocandins MK-0991 (L-743,872) and LY303366 against opportunistic filamentous and dimorphic fungi and yeasts. | 1998 Oct |
|
| In-vitro and in-vivo activities of SCH56592 against Cryptococcus neoformans. | 1999 Dec |
|
| Current and emerging azole antifungal agents. | 1999 Jan |
|
| Multilaboratory testing of two-drug combinations of antifungals against Candida albicans, Candida glabrata, and Candida parapsilosis. | 2011 Apr |
|
| In vitro activity of a novel broad-spectrum antifungal, E1210, tested against Candida spp. as determined by CLSI broth microdilution method. | 2011 Oct |
Patents
Sample Use Guides
Injection:
Loading dose: 300 mg Noxafil injection intravenously twice a day on the first day. Maintenance dose: 300 mg Noxafil injection intravenously once a day, starting on the second day.
Oral suspension:
Prophylaxis of invasive Aspergillus and Candida infections: 200 mg (5 mL) three times a day.
Oropharyngeal Candidiasis: Loading dose: 100 mg (2.5 mL) twice a day on the first day. Maintenance dose: 100 mg (2.5 mL) once a day for 13 days.
Route of Administration:
Other
In Vitro Use Guide
Curator's Comment: The HL-60 leukemia cell line was differentiated to a neutrophil-like phenotype (dHL-60 cells) then exposed to a range of posaconazole concentrations. The functional capacity and antifungal activity of these cells were assessed in vitro. Posaconazole accumulates to high concentrations in dHL-60 cells, and increases their antifungal activity in vitro and in vivo.
Unknown
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NDF-RT |
N0000008217
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WHO-ATC |
J02AC04
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WHO-VATC |
QJ02AC04
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NCI_THESAURUS |
C514
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NDF-RT |
N0000175487
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CFR |
21 CFR 524.1610
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FDA ORPHAN DRUG |
850521
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FDA ORPHAN DRUG |
187604
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FDA ORPHAN DRUG |
539016
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LIVERTOX |
NBK548934
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6TK1G07BHZ
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C61500
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JJ-48
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282446
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SUB20322
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100000089529
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171228-49-2
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m8993
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64355
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7421
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CHEMBL1397
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POSACONAZOLE
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3483
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7713
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6TK1G07BHZ
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468595
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DTXSID6049066
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DB01263
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C101425
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
![Structure of 2-[(1S,2S)-1-Ethyl-2-hydroxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one](/img/e6b1ab3b-cdfb-4753-a561-b23ed44dd4f7.svg "Structure of 2-[(1S,2S)-1-Ethyl-2-hydroxypropyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one")