MedKoo Cat#: 318554 | Name: Posaconazole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Posaconazole is a triazole antifungal drug marketed in the United States by Schering-Plough under the trade name Noxafil. Posaconazole is a broad-spectrum, second generation, triazole compound with antifungal activity. Posaconazole strongly inhibits 14-alpha demethylase, a cytochrome P450-dependent enzyme. Inhibition of 14-alpha-demethylase prevents the conversion of lanosterol to ergosterol, an important component of the fungal cell wall. Compared to other azole antifungals, posaconazole is a significantly more potent inhibitor of sterol 14-alpha demethylase.

Chemical Structure

Posaconazole
Posaconazole
CAS#171228-49-2

Theoretical Analysis

MedKoo Cat#: 318554

Name: Posaconazole

CAS#: 171228-49-2

Chemical Formula: C37H42F2N8O4

Exact Mass: 700.3297

Molecular Weight: 700.79

Elemental Analysis: C, 63.41; H, 6.04; F, 5.42; N, 15.99; O, 9.13

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
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Synonym
Posaconazole; Noxafil; SCH-56592; Schering 56592; Sch 56592; Schering 56592;
IUPAC/Chemical Name
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
InChi Key
RAGOYPUPXAKGKH-XAKZXMRKSA-N
InChi Code
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
SMILES Code
O=C1N([C@@H](CC)[C@@H](O)C)N=CN1C2=CC=C(N3CCN(C4=CC=C(OC[C@@H]5CO[C@@](CN6N=CN=C6)(C7=CC=C(F)C=C7F)C5)C=C4)CC3)C=C2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Posaconazole is a broad-spectrum, second generation, triazole compound with antifungal activity.
In vitro activity:
Posaconazole was active against isolates of Candida and Aspergillus spp. that exhibit resistance to fluconazole, voriconazole, and amphotericin B and was much more active than the other triazoles against zygomycetes. Posaconazole exhibited potent antifungal activity against a wide variety of clinically important fungal pathogens and was frequently more active than other azoles and amphotericin B. Reference: Antimicrob Agents Chemother. 2006 Jun;50(6):2009-15. https://pubmed.ncbi.nlm.nih.gov/16723559/
In vivo activity:
The in vivo activities of posaconazole, itraconazole, and amphotericin B in neutropenic mice with zygomycosis were compared. The in vitro MICs of posaconazole and itraconazole for the strains of Mucor spp. used in this study ranged from 0.125 to 8 microg/ml and 0.25 to 8 microg/ml, respectively. The in vitro MIC range for amphotericin B is 0.125 to 0.25 microg/ml. At twice-daily doses of >or=15 mg/kg of body weight, posaconazole prolonged the survival of the mice and reduced tissue burden. Reference: Antimicrob Agents Chemother. 2002 Jul;46(7):2310-2. https://pubmed.ncbi.nlm.nih.gov/12069997/
Solvent mg/mL mM comments
Solubility
DMF 0.5 0.71
DMSO 39.8 56.72
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 700.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Varghese FS, Meutiawati F, Teppor M, Jacobs S, de Keyzer C, Taşköprü E, van Woudenbergh E, Overheul GJ, Bouma E, Smit JM, Delang L, Merits A, van Rij RP. Posaconazole inhibits multiple steps of the alphavirus replication cycle. Antiviral Res. 2022 Jan;197:105223. doi: 10.1016/j.antiviral.2021.105223. Epub 2021 Nov 29. PMID: 34856248. 2. Sabatelli F, Patel R, Mann PA, Mendrick CA, Norris CC, Hare R, Loebenberg D, Black TA, McNicholas PM. In vitro activities of posaconazole, fluconazole, itraconazole, voriconazole, and amphotericin B against a large collection of clinically important molds and yeasts. Antimicrob Agents Chemother. 2006 Jun;50(6):2009-15. doi: 10.1128/AAC.00163-06. PMID: 16723559; PMCID: PMC1479149. 3. Wang H, Tan Y, Jia H, Liu D, Liu R. Posaconazole inhibits the stemness of cancer stem-like cells by inducing autophagy and suppressing the Wnt/β-catenin/survivin signaling pathway in glioblastoma. Front Pharmacol. 2022 Aug 11;13:905082. doi: 10.3389/fphar.2022.905082. PMID: 36034873; PMCID: PMC9403519. 4. Sun QN, Najvar LK, Bocanegra R, Loebenberg D, Graybill JR. In vivo activity of posaconazole against Mucor spp. in an immunosuppressed-mouse model. Antimicrob Agents Chemother. 2002 Jul;46(7):2310-2. doi: 10.1128/AAC.46.7.2310-2312.2002. PMID: 12069997; PMCID: PMC127310.
In vitro protocol:
1. Varghese FS, Meutiawati F, Teppor M, Jacobs S, de Keyzer C, Taşköprü E, van Woudenbergh E, Overheul GJ, Bouma E, Smit JM, Delang L, Merits A, van Rij RP. Posaconazole inhibits multiple steps of the alphavirus replication cycle. Antiviral Res. 2022 Jan;197:105223. doi: 10.1016/j.antiviral.2021.105223. Epub 2021 Nov 29. PMID: 34856248. 2. Sabatelli F, Patel R, Mann PA, Mendrick CA, Norris CC, Hare R, Loebenberg D, Black TA, McNicholas PM. In vitro activities of posaconazole, fluconazole, itraconazole, voriconazole, and amphotericin B against a large collection of clinically important molds and yeasts. Antimicrob Agents Chemother. 2006 Jun;50(6):2009-15. doi: 10.1128/AAC.00163-06. PMID: 16723559; PMCID: PMC1479149.
In vivo protocol:
1. Wang H, Tan Y, Jia H, Liu D, Liu R. Posaconazole inhibits the stemness of cancer stem-like cells by inducing autophagy and suppressing the Wnt/β-catenin/survivin signaling pathway in glioblastoma. Front Pharmacol. 2022 Aug 11;13:905082. doi: 10.3389/fphar.2022.905082. PMID: 36034873; PMCID: PMC9403519. 2. Sun QN, Najvar LK, Bocanegra R, Loebenberg D, Graybill JR. In vivo activity of posaconazole against Mucor spp. in an immunosuppressed-mouse model. Antimicrob Agents Chemother. 2002 Jul;46(7):2310-2. doi: 10.1128/AAC.46.7.2310-2312.2002. PMID: 12069997; PMCID: PMC127310.
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Risk Factors and Outcomes of Mucorales Infection in a Modern Cohort of Solid Organ Transplant, Hematopoietic Cell Transplant, and Chimeric Antigen Receptor T-cell Therapy Recipients. Transplant Proc. 2024 Aug 21:S0041-1345(24)00433-0. doi: 10.1016/j.transproceed.2024.07.005. Epub ahead of print. PMID: 39174391. 5: Ali W, Agarwal M, Jamal S, Gangwar R, Sharma R, Mubarak MM, Wani ZA, Ahmad Z, Khan A, Sheikh JA, Grover A, Bhaskar A, Dwivedi VP, Grover S. Revitalizing antimicrobial strategies: paromomycin and dicoumarol repurposed as potent inhibitors of M.tb's replication machinery via targeting the vital protein DnaN. Int J Biol Macromol. 2024 Aug 22;278(Pt 3):134652. doi: 10.1016/j.ijbiomac.2024.134652. Epub ahead of print. PMID: 39173789. 6: Ngo D, Tinajero J, Zhang J, Stein A, Marcucci G, Salhotra A, Pullarkat V, Sandhu KS, Ball BJ, Pourhassan H, Koller P. Concurrent versus sequential or no triazole anti-fungal therapy in patients undergoing 7 + 3 plus midostaurin induction for FLT-3 acute myelogenous leukemia. J Oncol Pharm Pract. 2024 Aug 16:10781552241276547. doi: 10.1177/10781552241276547. Epub ahead of print. PMID: 39150342. 7: Lai CC, Hsueh PR. Chronic pulmonary aspergillosis in Taiwan: Disease burden, diagnosis, treatment, and outcomes. J Microbiol Immunol Infect. 2024 Aug 2:S1684-1182(24)00124-5. doi: 10.1016/j.jmii.2024.07.013. Epub ahead of print. PMID: 39142908. 8: Allen S. Recurrent Mucor indicus central venous catheter infection in a five year old child on long term parenteral nutrition for short gut syndrome: could gut translocation be responsible? Med Mycol Case Rep. 2024 Jul 14;45:100661. doi: 10.1016/j.mmcr.2024.100661. PMID: 39139261; PMCID: PMC11321366. 9: Zhumatayev S, Celen SS, Kara M, Selcuk AA, Bozkurt B, Demir MK, Yalcın K. Successful Treatment of Severe Aplastic Anemia with Hematopoietic Stem Cell Transplantation in the Setting of Active Mucormycosis. Indian J Otolaryngol Head Neck Surg. 2024 Aug;76(4):3552-3555. doi: 10.1007/s12070-024-04610-1. Epub 2024 Apr 4. PMID: 39130341; PMCID: PMC11306456. 10: Yun J, Wang Z, Liu W. Voriconazole-induced central nervous system toxicity: a pharmacovigilance study based on FDA adverse event reporting system (FAERS) database. Expert Opin Drug Saf. 2024 Aug 19:1-8. doi: 10.1080/14740338.2024.2391492. Epub ahead of print. PMID: 39129467. 11: Gupta AK, Wang T, Mann A, Polla Ravi S, Talukder M, Lincoln SA, Foreman HC, Kaplan B, Galili E, Piguet V, Shemer A, Bakotic WL. Antifungal resistance in dermatophytes - review of the epidemiology, diagnostic challenges and treatment strategies for managing Trichophyton indotineae infections. Expert Rev Anti Infect Ther. 2024 Aug 18:1-13. doi: 10.1080/14787210.2024.2390629. Epub ahead of print. PMID: 39114868. 12: Cabanilla MG, Shald EA, Hlavacek NL, Bernauer ML, Sosa NR. Breaking the mold: Insights into the clinical management and outcomes of rhinocerebral mucormycosis in adults. IDCases. 2024 Jul 3;37:e02024. doi: 10.1016/j.idcr.2024.e02024. PMID: 39114643; PMCID: PMC11305272. 13: Halliday CL, Tay E, Green W, Law D, Lopez R, Faris S, Meehan L, Harvey E, Birch M, Chen SCA. In vitro activity of olorofim against 507 filamentous fungi including antifungal drug-resistant strains at a tertiary laboratory in Australia: 2020-2023. J Antimicrob Chemother. 2024 Aug 6:dkae267. doi: 10.1093/jac/dkae267. Epub ahead of print. PMID: 39105545. 14: Wang J, Liu L, Li J, Feng X, Yi H, Jiang E, Zheng Y, Zhang F, Zhu X, Mi Y, Han M, Wang J, Feng S. Clinical Characteristics, Prognosis Factors and Metagenomic Next-Generation Sequencing Diagnosis of Mucormycosis in patients With Hematologic Diseases. Mycopathologia. 2024 Aug 1;189(4):71. doi: 10.1007/s11046-024-00875-w. PMID: 39088077. 15: Kondori N, Jaén-Luchoro D, Karlsson R, Abedzaedeh B, Hammarström H, Jönsson B. Exophiala species in household environments and their antifungal resistance profile. Sci Rep. 2024 Jul 31;14(1):17622. doi: 10.1038/s41598-024-68166-4. PMID: 39085337; PMCID: PMC11291800. 16: Cao J, Pan P, Feng D, Wang M, Zheng Y, Yang N, Chen X, Zhai W, Zhang R, Ma Q, Wei J, Yang D, He Y, Wang X, Feng S, Han M, Jiang E, Pang A. Posaconazole gastro-resistant tablets for preventing invasive fungal disease after haematopoietic stem cell transplantation: a propensity-matched cohort study. Clin Microbiol Infect. 2024 Jul 26:S1198-743X(24)00351-3. doi: 10.1016/j.cmi.2024.07.019. Epub ahead of print. PMID: 39067514. 17: Mehta P, Ngo D, Tinajero J. Concomitant use of calcitonin gene-related peptide (CGRP) antagonists with azole antifungals in patients with hematological malignancies. J Oncol Pharm Pract. 2024 Jul 25:10781552241265884. doi: 10.1177/10781552241265884. Epub ahead of print. PMID: 39052976. 18: Kim U, Perzia B, Kulkarni P, Rajiniganth M, Sundar B, Robin AL, Garg Shukla A, Maeng MM. COVID-19-associated rhino-orbito-cerebral mucormycosis: a single center prospective study of 264 patients. Orbit. 2024 Jul 25:1-10. doi: 10.1080/01676830.2024.2377249. Epub ahead of print. PMID: 39051497. 19: Rathee A, Solanki P, Emad NA, Zai I, Ahmad S, Alam S, Alqahtani AS, Noman OM, Kohli K, Sultana Y. Posaconazole-hemp seed oil loaded nanomicelles for invasive fungal disease. Sci Rep. 2024 Jul 18;14(1):16588. doi: 10.1038/s41598-024-66074-1. PMID: 39025925; PMCID: PMC11258229. 20: Borchardt-Setter KA, Yu J, Stelzer T, Yu L. Surface Enrichment and Depletion of Components in a Ternary Drug-Surfactant-Polymer Amorphous Solid Dispersion. Mol Pharm. 2024 Aug 5;21(8):4074-4081. doi: 10.1021/acs.molpharmaceut.4c00444. Epub 2024 Jul 15. PMID: 39008633.