U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of POSACONAZOLE

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

HIDE SMILES / InChI
Molecular Formula C37H42F2N8O4
Molecular Weight 700.7774
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Originator

Approval Year

2006
178
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 25.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
NOXAFIL

Approved Use

Noxafil 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 Date

2006
Preventing
Approved
8429
NOXAFIL

Approved Use

Noxafil 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 Date

2006
Curative
Approved
8429
NOXAFIL

Approved Use

Noxafil 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 Date

2006
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2764 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
2840 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
3280 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9093 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
51618 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
26200 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
46400 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
36100 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
31.7 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
31 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
24.6 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
2%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
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
Doses

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/28961714
Page: p.3
unhealthy, 51.55
n = 237
Health Status: unhealthy
Condition: Invasive fungal infections
Age Group: 51.55
Sex: M+F
Population Size: 237
Sources:
https://pubmed.ncbi.nlm.nih.gov/28961714
Page: p.3
Disc. AE: Rash...
AEs leading to
discontinuation/dose reduction:
Rash (0.84%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28961714
Page: p.3
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:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
unhealthy
n = 3
Health Status: unhealthy
Condition: Invasive fungal infections
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
Disc. AE: Hepatic enzyme increased...
Other AEs: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Hepatic enzyme increased (67%)
Other AEs:
Nausea (67%)
Vomiting (67%)
Diarrhea (67%)
Somnolence (67%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
unhealthy
n = 605
Health Status: unhealthy
Condition: Aspergillus infections|Candida infections
Population Size: 605
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
Disc. AE: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea (2%)
Vomiting (2%)
Hepatic enzymes increased (2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Aspergillus infections|Candida infections
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
Disc. AE: Arrhythmia, Electrocardiogram QTc interval prolonged...
AEs leading to
discontinuation/dose reduction:
Arrhythmia
Electrocardiogram QTc interval prolonged
Hepatotoxicity
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.13
unhealthy
n = 557
Health Status: unhealthy
Condition: Oropharyngeal Candidiasis
Population Size: 557
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.13
Disc. AE: Pneumonia...
AEs leading to
discontinuation/dose reduction:
Pneumonia (1%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.13
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.14
unhealthy
n = 239
Health Status: unhealthy
Condition: Oropharyngeal Candidiasis
Population Size: 239
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.14
Disc. AE: Pulmonary function impairment, AIDS...
AEs leading to
discontinuation/dose reduction:
Pulmonary function impairment (3%)
AIDS (7%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.14
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/28961714
Page: p.3
unhealthy, 51.55
n = 237
Health Status: unhealthy
Condition: Invasive fungal infections
Age Group: 51.55
Sex: M+F
Population Size: 237
Sources:
https://pubmed.ncbi.nlm.nih.gov/28961714
Page: p.3
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:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
unhealthy
n = 3
Health Status: unhealthy
Condition: Invasive fungal infections
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
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:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
unhealthy
n = 3
Health Status: unhealthy
Condition: Invasive fungal infections
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
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:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
unhealthy
n = 3
Health Status: unhealthy
Condition: Invasive fungal infections
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
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:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
unhealthy
n = 3
Health Status: unhealthy
Condition: Invasive fungal infections
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
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:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
unhealthy
n = 3
Health Status: unhealthy
Condition: Invasive fungal infections
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/21189337
Page: p.1310
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
unhealthy
n = 605
Health Status: unhealthy
Condition: Aspergillus infections|Candida infections
Population Size: 605
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
unhealthy
n = 605
Health Status: unhealthy
Condition: Aspergillus infections|Candida infections
Population Size: 605
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
unhealthy
n = 605
Health Status: unhealthy
Condition: Aspergillus infections|Candida infections
Population Size: 605
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.12
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Aspergillus infections|Candida infections
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Aspergillus infections|Candida infections
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Aspergillus infections|Candida infections
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.1
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.13
unhealthy
n = 557
Health Status: unhealthy
Condition: Oropharyngeal Candidiasis
Population Size: 557
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.13
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.14
unhealthy
n = 239
Health Status: unhealthy
Condition: Oropharyngeal Candidiasis
Population Size: 239
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.14
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.14
unhealthy
n = 239
Health Status: unhealthy
Condition: Oropharyngeal Candidiasis
Population Size: 239
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf
Page: p.14
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767

OverviewOther

Other InhibitorOther SubstrateOther Inducer
MDR3
8

BSEP
402

P-gp
1461

CYP1A2
1524

CYP2C19
1478

BCRP
699

CYP51
2
P-gp
1537

UGT
192
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
BSEP
403
 no
CYP1A2
1692
 no
CYP2C19
1553
 no
CYP2C9
1819
 no
P-gp
1650
 yes [IC50 3 uM]
BCRP
773
 yes [IC50 6 uM]
CYP51
2
 yes
MDR3
9
 yes
CYP3A4
1925
 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

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
1537
 yes
UGT
192
 yes
yes (co-administration study)
Comment: rifabutin decreases posaconazole plasma concentrations
Page: 16, 17, 27
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:64355
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64355
ChemicalBook
CB9946972
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9946972
MolPort
MolPort-006-666-426
https://www.molport.com/shop/molecule-link/MolPort-006-666-426
Selleck Chemicals
Posaconazole
http://www.selleckchem.com/products/Posaconazole.html
ZINC
ZINC000003938482
http://zinc15.docking.org/substances/ZINC000003938482
eMolecules
32176544
https://www.emolecules.com/cgi-bin/more?vid=32176544
eMolecules
36367154
https://www.emolecules.com/cgi-bin/more?vid=36367154
PubMed

PubMed

TitleDatePubMed
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
Current and emerging azole antifungal agents.
1999 Jan
[New antifungal drugs. Present and future].
1999 Sep
In vitro and in vivo activities of SCH 56592 (posaconazole), a new triazole antifungal agent, against Aspergillus and Candida.
2000 Aug
Activity of the new antifungal triazole, posaconazole, against Cryptococcus neoformans.
2001 Dec
Antifungals: what's in the pipeline.
2001 Oct
Activities of caspofungin, itraconazole, posaconazole, ravuconazole, voriconazole, and amphotericin B against 448 recent clinical isolates of filamentous fungi.
2003 Aug
Reversible dilated cardiomyopathy related to amphotericin B therapy.
2004 Jan
Posaconazole: a broad-spectrum triazole antifungal.
2005 Dec
In vitro activities of posaconazole, fluconazole, itraconazole, voriconazole, and amphotericin B against a large collection of clinically important molds and yeasts.
2006 Jun
Potential synergistic activity of antimycotic substances in combination with human platelets against Aspergillus fumigatus.
2010 Jun
Therapeutic efficacy of posaconazole against Candida glabrata in a murine model of vaginitis.
2011 Mar
Antifungal susceptibilities of Aspergillus fumigatus clinical isolates obtained in Nagasaki, Japan.
2012 Jan
In vitro activities of new triazole antifungal agents, posaconazole and voriconazole, against oral Candida isolates from patients suffering from denture stomatitis.
2012 Jan
Posaconazole exhibits in vitro and in vivo synergistic antifungal activity with caspofungin or FK506 against Candida albicans.
2013
In vitro antifungal susceptibility of clinically relevant species belonging to Aspergillus section Flavi.
2013 Apr
Patents

Patents

20040019211
1
20040063628
7

Sample Use Guides

In Vivo Use Guide
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:37:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:37:24 GMT 2023
Record UNII
6TK1G07BHZ
Record Status Validated (UNII)
Record Version
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Name Type Language
POSACONAZOLE
EMA EPAR   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
2,5-Anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[4-[4-[4-[1-[(1S,2S)-1-ethyl-2-hydroxypropyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-D-threo-pentitol
Systematic Name English
Posaconazole [WHO-DD]
Common Name English
4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-ylmethyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2S,3S)-2-hydroxypentan-3-yl]-1,2,4-triazol-3-one
Systematic Name English
3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[5-(2,4-difluorophenyl)tetrahydro-5-(1H-1,2,4-triazol-1-ylmethyl)-3-furanyl]methoxy]phenyl]-1-piperazinyl]phenyl]-2-(1-ethyl-2-hydroxypropyl)-2,4-dihydro-, [3R-[3α(1S*,2S*),5α]]-
Systematic Name English
POSACONAZOLE [MI]
Common Name English
POSACONAZOLE [HSDB]
Common Name English
POSACONAZOLE [EMA EPAR]
Common Name English
POSACONAZOLE [VANDF]
Common Name English
posaconazole [INN]
Common Name English
POSACONAZOLE [ORANGE BOOK]
Common Name English
POSACONAZOLE [USAN]
Common Name English
D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-[[4-[4-[4-[1-[(1S,2S)-1-ethyl-2-hydroxypropyl]-1,5-dihydro-5-oxo-4H-1,2,4-triazol-4-yl]phenyl]-1-piperazinyl]phenoxy]methyl]-1-(1H-1,2,4-triazol-1-yl)-
Systematic Name English
SCH-56592
Code English
(-)-POSACONAZOLE
Common Name English
POSACONAZOLE [MART.]
Common Name English
NOXAFIL
Brand Name English
POSACONAZOLE [JAN]
Common Name English
POSACONAZOLE [GREEN BOOK]
Common Name English
Classification Tree Code System Code
NDF-RT N0000008217
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
WHO-ATC J02AC04
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
WHO-VATC QJ02AC04
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
NDF-RT N0000175487
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
CFR 21 CFR 524.1610
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
FDA ORPHAN DRUG 850521
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
FDA ORPHAN DRUG 187604
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
FDA ORPHAN DRUG 539016
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
LIVERTOX NBK548934
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
Code System Code Type Description
DAILYMED
6TK1G07BHZ
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
NCI_THESAURUS
C61500
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
USAN
JJ-48
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
RXCUI
282446
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY RxNorm
EVMPD
SUB20322
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
SMS_ID
100000089529
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
CAS
171228-49-2
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
MERCK INDEX
m8993
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY Merck Index
CHEBI
64355
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
HSDB
7421
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL1397
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
WIKIPEDIA
POSACONAZOLE
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
DRUG CENTRAL
3483
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
INN
7713
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
FDA UNII
6TK1G07BHZ
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
PUBCHEM
468595
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID6049066
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
DRUG BANK
DB01263
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
MESH
C101425
Created by admin on Fri Dec 15 15:37:24 GMT 2023 , Edited by admin on Fri Dec 15 15:37:24 GMT 2023
PRIMARY
Related Record Type Details
ASPERGILLUS TERREUS
TARGET ORGANISM->INHIBITOR
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Structure of POSACONAZOLE
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
Structure of POSACONAZOLE
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
ASPERGILLUS VERSICOLOR
TARGET ORGANISM->INHIBITOR
CANDIDA TROPICALIS
TARGET ORGANISM->INHIBITOR
CANDIDA ALBICANS
TARGET ORGANISM->INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
ISSATCHENKIA ORIENTALIS WHOLE
TARGET ORGANISM->INHIBITOR
ASPERGILLUS FLAVUS
TARGET ORGANISM->INHIBITOR
ASPERGILLUS FUMIGATUS
TARGET ORGANISM->INHIBITOR
ASPERGILLUS NIGER VAR. NIGER
TARGET ORGANISM->INHIBITOR
CANDIDA PARAPSILOSIS
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of 2-((2S,3S)-2-HYDROXYPENTAN-3-YL)-4-(4-(PIPERAZIN-1-YL)PHENYL)-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE
METABOLITE -> PARENT
MINOR
FECAL; URINE
Structure of POSACONAZOLE N-GLUCURONIDE
METABOLITE -> PARENT
MINOR
PLASMA; URINE
Structure of N-(4-(1-((2S,3S)-2-HYDROXYPENTAN-3-YL)-5-OXO-1,5-DIHYDRO-4H-1,2,4-TRIAZOL-4-YL)PHENYL)ACETAMIDE
METABOLITE -> PARENT
URINE
Structure of POSACONAZOLE-GLUCURONIDE
METABOLITE -> PARENT
up to 28% in plasma, 1.4% urine; major posaconazole-​glucuronide produced from human liver microsomes was mediated via UGT1A4 (In vitro, Drug Metabolism and Disposition, Volume 32, Issue 2, Pages 267-271, Journal 2004)
MAJOR
PLASMA; URINE
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
METABOLITE -> PARENT
MINOR
FECAL; PLASMA; URINE
Related Record Type Details
Structure of POSACONAZOLE SUCCINYL ESTER
IMPURITY -> PARENT
Structure of DESETHYLENE POSACONAZOLE N,N'-DIFORMYL
IMPURITY -> PARENT
Structure of METHYL LACTATE, (-)-
IMPURITY -> PARENT
process impurity Raw material used for prodcution of starting material SPOE
Related Record Type Details
Structure of POSACONAZOLE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC Injection
PHARMACOKINETIC
Oral
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Elimination
PHARMACOKINETIC
Tmax PHARMACOKINETIC
NIH
NCATS
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DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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