Posaconazole

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 Search

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
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 28 Target ID: CHEMBL1780 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16107193	Inhibitor 8504		25.0 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Candida infections 20 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022003s021,205053s005,205596s004lbl.pdf	Preventing	Approved 8583	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
Aspergillus infections 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022003s021,205053s005,205596s004lbl.pdf	Preventing	Approved 8583	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
Oropharyngeal candidiasis 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/022003s021,205053s005,205596s004lbl.pdf	Curative	Approved 8583	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

C_max

Value	Dose	Analyte	Population
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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

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 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% 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

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	unhealthy, 51.55 Health Status: unhealthy Age Group: 51.55 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28961714	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (0.84%) Sources: https://pubmed.ncbi.nlm.nih.gov/28961714
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	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/21189337	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
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf	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
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf	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
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf	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
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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/022003s018s020,0205053s002s004,0205596s001s003lbl.pdf	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

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MDR3 8 BSEP 550 P-gp 1741 CYP1A2 2153 CYP2C19 2057 BCRP 910 CYP51 2	P-gp 2052 UGT 219

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27112167/	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205596Orig1s000MedR.pdf Page: 15.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205596Orig1s000MedR.pdf Page: 15.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205596Orig1s000MedR.pdf Page: 15.0	no
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27001813/	yes [IC50 3 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27001813/	yes [IC50 6 uM]
CYP51 2	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/022003s000_Noxafil_ClinPharmR.pdf Page: 3.0	yes
MDR3 9	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27112167/	yes
CYP3A4 2633	inhibitor 4027 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 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/022003Orig1s026,205053Orig1s010,205596Orig1s010lbl.pdf Page: 27.0	yes
UGT 219	substrate 4014 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
eMolecules	32176544	https://www.emolecules.com/cgi-bin/more?vid=32176544
eMolecules	36367154	https://www.emolecules.com/cgi-bin/more?vid=36367154
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

PubMed

Title	Date	PubMed
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013-11	23956101
Epidemiological cutoff values for fluconazole, itraconazole, posaconazole, and voriconazole for six Candida species as determined by the colorimetric Sensititre YeastOne method.	2013-08	23761155
In vitro antifungal susceptibility of clinically relevant species belonging to Aspergillus section Flavi.	2013-04	23335742
Posaconazole exhibits in vitro and in vivo synergistic antifungal activity with caspofungin or FK506 against Candida albicans.	2013	23472097
Effect of pH on in vitro susceptibility of Candida glabrata and Candida albicans to 11 antifungal agents and implications for clinical use.	2012-03	22232293
Antifungal susceptibilities of Aspergillus fumigatus clinical isolates obtained in Nagasaki, Japan.	2012-01	22024829
In vitro activities of new triazole antifungal agents, posaconazole and voriconazole, against oral Candida isolates from patients suffering from denture stomatitis.	2012-01	21842426
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.	2011-12	21937186
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.	2011-11	21900519
In vitro activity of a novel broad-spectrum antifungal, E1210, tested against Candida spp. as determined by CLSI broth microdilution method.	2011-10	21696907
Multilaboratory testing of two-drug combinations of antifungals against Candida albicans, Candida glabrata, and Candida parapsilosis.	2011-04	21282457
Therapeutic efficacy of posaconazole against Candida glabrata in a murine model of vaginitis.	2011-03	19811615
Isavuconazole: a comprehensive review of spectrum of activity of a new triazole.	2010-11	20524153
Potential synergistic activity of antimycotic substances in combination with human platelets against Aspergillus fumigatus.	2010-06	20378674
Activity of MGCD290, a Hos2 histone deacetylase inhibitor, in combination with azole antifungals against opportunistic fungal pathogens.	2009-12	19794038
Posaconazole-increased vincristine neurotoxicity in a child: a case report.	2009-04	19346885
Adverse drug events complicate antifungal therapy for pulmonary aspergilloma.	2008-10	19032016
Possible increase of the neurotoxicity of vincristine by the concurrent use of posaconazole in a young adult with leukemia.	2007-02	17279013
In vitro activities of posaconazole, fluconazole, itraconazole, voriconazole, and amphotericin B against a large collection of clinically important molds and yeasts.	2006-06	16723559
Posaconazole: a broad-spectrum triazole antifungal.	2005-12	16310149
Reversible dilated cardiomyopathy related to amphotericin B therapy.	2004-01	14657095
Activities of caspofungin, itraconazole, posaconazole, ravuconazole, voriconazole, and amphotericin B against 448 recent clinical isolates of filamentous fungi.	2003-08	12904365
Treatment of Scedosporium apiospermum brain abscesses with posaconazole.	2002-06-15	12032903
Activity of the new antifungal triazole, posaconazole, against Cryptococcus neoformans.	2001-12	11733459
Antifungals: what's in the pipeline.	2001-10	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.	2001-10	11557481
In vitro antifungal activity of posaconazole against various pathogenic fungi.	2001-08	11516940
In vitro and in vivo activities of SCH 56592 (posaconazole), a new triazole antifungal agent, against Aspergillus and Candida.	2000-08	10898669
In vitro activities of the new antifungal triazole SCH 56592 against common and emerging yeast pathogens.	2000-01	10602757
In-vitro and in-vivo activities of SCH56592 against Cryptococcus neoformans.	1999-12	10590286
[New antifungal drugs. Present and future].	1999-09	10878508
Current and emerging azole antifungal agents.	1999-01	9880474
In vitro susceptibilities of Candida bloodstream isolates to the new triazole antifungal agents BMS-207147, Sch 56592, and voriconazole.	1998-12	9835520
SCH56592 treatment of murine invasive aspergillosis.	1998-10	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.	1998-10	9738049
In vitro activity of a new triazole antifungal agent, Sch 56592, against clinical isolates of filamentous fungi.	1998	9750338
Activity of SCH 56592 compared with those of fluconazole and itraconazole against Candida spp.	1997-10	9333073
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.	1997-02	9021172
In vitro studies of activities of the antifungal triazoles SCH56592 and itraconazole against Candida albicans, Cryptococcus neoformans, and other pathogenic yeasts.	1997-01	8980776
In vitro and in vivo efficacies of the azole SCH56592 against Cryptococcus neoformans.	1996-08	8843302

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:19 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:19 GMT 2025`
Record UNII	6TK1G07BHZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Posaconazole

Official Name

English

Noxafil

Preferred 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-[3?(1S*,2S*),5?]]-

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

Posaconazole [JAN]

Common Name

English

Posaconazole [GREEN BOOK]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000008217