POSACONAZOLE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H42F2N8O4
Molecular Weight	700.7788
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@]([H])([C@]([H])(C)O)n1c(=O)n(cn1)-c2ccc(cc2)N3CCN(CC3)c4ccc(cc4)OC[C@@]5([H])C[C@](Cn6cncn6)(c7ccc(cc7F)F)OC5

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 51 20 Target ID: CHEMBL1780 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16107193	Inhibitor 3315		25.0 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Candida infections 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022003s021,205053s005,205596s004lbl.pdf	Preventing	Approved 4033	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 1.15827841E12
Aspergillus infections 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022003s021,205053s005,205596s004lbl.pdf	Preventing	Approved 4033	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 1.15827841E12
Oropharyngeal candidiasis 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022003s021,205053s005,205596s004lbl.pdf	Curative	Approved 4033	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 1.15827841E12

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

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: 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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 753	inhibitor 825

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MDR3 4 BSEP 185 P-gp 666 CYP1A2 725 CYP2C19 700 BCRP 303 CYP51 1	P-gp 724 UGT 90

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BSEP 186	inhibitor 1612 Sources: https://pubmed.ncbi.nlm.nih.gov/27112167/	no
CYP1A2 805	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205596Orig1s000MedR.pdf Page: 15.0	no
CYP2C19 738	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205596Orig1s000MedR.pdf Page: 15.0	no
CYP2C9 851	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205596Orig1s000MedR.pdf Page: 15.0	no
P-gp 754	inhibitor 1612 Sources: https://pubmed.ncbi.nlm.nih.gov/27001813/	yes [IC50 3 uM]
BCRP 346	inhibitor 1612 Sources: https://pubmed.ncbi.nlm.nih.gov/27001813/	yes [IC50 6 uM]
CYP51 1	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/022003s000_Noxafil_ClinPharmR.pdf Page: 3.0	yes
MDR3 4	inhibitor 1612 Sources: https://pubmed.ncbi.nlm.nih.gov/27112167/	yes
CYP3A4 920	inhibitor 1612 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022003Orig1s026,205053Orig1s010,205596Orig1s010lbl.pdf Page: 17.0	yes	yes (co-administration study) Comment: concommitant administration of psconazole with midazolam increases midazolam plasma concentritons by 5-fold Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022003Orig1s026,205053Orig1s010,205596Orig1s010lbl.pdf Page: 17.0

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 724	substrate 1689 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022003Orig1s026,205053Orig1s010,205596Orig1s010lbl.pdf Page: 27.0	yes
UGT 90	substrate 1689 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022003Orig1s026,205053Orig1s010,205596Orig1s010lbl.pdf Page: 16, 17, 27	yes		yes (co-administration study) Comment: rifabutin decreases posaconazole plasma concentrations Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022003Orig1s026,205053Orig1s010,205596Orig1s010lbl.pdf Page: 16, 17, 27

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
		252160250
In vitro and in vivo efficacies of the azole SCH56592 against Cryptococcus neoformans.	1996 Aug	8843302
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	9021172
In vitro studies of activities of the antifungal triazoles SCH56592 and itraconazole against Candida albicans, Cryptococcus neoformans, and other pathogenic yeasts.	1997 Jan	8980776
Activity of SCH 56592 compared with those of fluconazole and itraconazole against Candida spp.	1997 Oct	9333073
In vitro activity of a new triazole antifungal agent, Sch 56592, against clinical isolates of filamentous fungi.	1998	9750338
In vitro susceptibilities of Candida bloodstream isolates to the new triazole antifungal agents BMS-207147, Sch 56592, and voriconazole.	1998 Dec	9835520
SCH56592 treatment of murine invasive aspergillosis.	1998 Oct	9818757
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	9738049
In-vitro and in-vivo activities of SCH56592 against Cryptococcus neoformans.	1999 Dec	10590286
Current and emerging azole antifungal agents.	1999 Jan	9880474
[New antifungal drugs. Present and future].	1999 Sep	10878508
In vitro and in vivo activities of SCH 56592 (posaconazole), a new triazole antifungal agent, against Aspergillus and Candida.	2000 Aug	10898669
In vitro activities of the new antifungal triazole SCH 56592 against common and emerging yeast pathogens.	2000 Jan	10602757
In vitro antifungal activity of posaconazole against various pathogenic fungi.	2001 Aug	11516940
Activity of the new antifungal triazole, posaconazole, against Cryptococcus neoformans.	2001 Dec	11733459
Antifungals: what's in the pipeline.	2001 Oct	11587930
In vitro activities of posaconazole (Sch 56592) compared with those of itraconazole and fluconazole against 3,685 clinical isolates of Candida spp. and Cryptococcus neoformans.	2001 Oct	11557481
Treatment of Scedosporium apiospermum brain abscesses with posaconazole.	2002 Jun 15	12032903
Activities of caspofungin, itraconazole, posaconazole, ravuconazole, voriconazole, and amphotericin B against 448 recent clinical isolates of filamentous fungi.	2003 Aug	12904365
Reversible dilated cardiomyopathy related to amphotericin B therapy.	2004 Jan	14657095
Posaconazole: a broad-spectrum triazole antifungal.	2005 Dec	16310149
In vitro activities of posaconazole, fluconazole, itraconazole, voriconazole, and amphotericin B against a large collection of clinically important molds and yeasts.	2006 Jun	16723559
Possible increase of the neurotoxicity of vincristine by the concurrent use of posaconazole in a young adult with leukemia.	2007 Feb	17279013
Adverse drug events complicate antifungal therapy for pulmonary aspergilloma.	2008 Oct	19032016
Posaconazole-increased vincristine neurotoxicity in a child: a case report.	2009 Apr	19346885
Activity of MGCD290, a Hos2 histone deacetylase inhibitor, in combination with azole antifungals against opportunistic fungal pathogens.	2009 Dec	19794038
Potential synergistic activity of antimycotic substances in combination with human platelets against Aspergillus fumigatus.	2010 Jun	20378674
Isavuconazole: a comprehensive review of spectrum of activity of a new triazole.	2010 Nov	20524153
Multilaboratory testing of two-drug combinations of antifungals against Candida albicans, Candida glabrata, and Candida parapsilosis.	2011 Apr	21282457
In vitro activity of isavuconazole against 208 Aspergillus flavus isolates in comparison with 7 other antifungal agents: assessment according to the methodology of the European Committee on Antimicrobial Susceptibility Testing.	2011 Dec	21937186
Therapeutic efficacy of posaconazole against Candida glabrata in a murine model of vaginitis.	2011 Mar	19811615
Triazole and echinocandin MIC distributions with epidemiological cutoff values for differentiation of wild-type strains from non-wild-type strains of six uncommon species of Candida.	2011 Nov	21900519
In vitro activity of a novel broad-spectrum antifungal, E1210, tested against Candida spp. as determined by CLSI broth microdilution method.	2011 Oct	21696907
Antifungal susceptibilities of Aspergillus fumigatus clinical isolates obtained in Nagasaki, Japan.	2012 Jan	22024829
In vitro activities of new triazole antifungal agents, posaconazole and voriconazole, against oral Candida isolates from patients suffering from denture stomatitis.	2012 Jan	21842426
Effect of pH on in vitro susceptibility of Candida glabrata and Candida albicans to 11 antifungal agents and implications for clinical use.	2012 Mar	22232293
Posaconazole exhibits in vitro and in vivo synergistic antifungal activity with caspofungin or FK506 against Candida albicans.	2013	23472097
In vitro antifungal susceptibility of clinically relevant species belonging to Aspergillus section Flavi.	2013 Apr	23335742
Epidemiological cutoff values for fluconazole, itraconazole, posaconazole, and voriconazole for six Candida species as determined by the colorimetric Sensititre YeastOne method.	2013 Aug	23761155
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013 Nov	23956101

Patents

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

Unknown

Name

Type

Language

POSACONAZOLE

Official 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-(3.ALPHA.(1S*,2S*),5.ALPHA.))-

Common Name

English

POSACONAZOLE [MI]

Common Name

English

POSACONAZOLE [HSDB]

Common Name

English

POSACONAZOLE [WHO-DD]

Common Name

English

POSACONAZOLE [EMA EPAR]

Common Name

English

POSACONAZOLE [VANDF]

Common Name

English

SCH 56592

Code

English

POSACONAZOLE [INN]

Common Name

English

POSACONAZOLE [ORANGE BOOK]

Common Name

English

POSACONAZOLE [USAN]

Common Name

English

SCH-56592

Code

English

POSACONAZOLE [MART.]

Common Name

English

4-(P-(4-(P-(((3R,5R)-5-(2,4-DIFLUOROPHENYL)TETRAHYDRO-5-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-3-FURYL)METHOXY)PHENYL)-1-PIPERAZINYL)PHENYL)-1-((1S,2S)-1-ETHYL-2-HYDROXYPROPYL)-.DELTA.(SUP 2)-1,2,4-TRIAZOLIN-5-ONE

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