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AB285414

Posaconazole

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MW 700.8 Da, Purity >98%. Posaconazole is a broad-spectrum, second-generation triazole compound that displays antifungal activity. Posaconazole inhibits the growth of fungi by inhibiting the lanosterol 14α-demethylase enzyme (IC50s range from 7-200 nM), which results in a disruption the synthesis of ergosterol, a key sterol necessary for fungal cell membrane integrity and for the function of certain membrane-bound proteins.

View Alternative Names

7-alpha-hydroxy-4-cholesten-3-one 12-alpha-hydroxylase, 7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase, Albendazole monooxygenase, Albendazole sulfoxidase, CP3A4_HUMAN, CP51, CP51A_HUMAN, CP8B, CP8B1_HUMAN, CYP12, CYP3A4, CYP51, CYP51A1, CYPIIIA3, CYPIIIA4, CYPL1, CYPLI, CYPVIIIB1, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 51, Cytochrome P450 51A1, Cytochrome P450 8B1, Cytochrome P450 HLp, Cytochrome P450 NF-25, Cytochrome P450 family 51 subfamily A member 1, Cytochrome P450 family 51 subfamily A polypeptide 1, Cytochrome P450 subfamily VIIIB (sterol 12 alpha hydroxylase) polypeptide 1, Cytochrome P450, 51 (lanosterol 14 alpha demethylase), Cytochrome P450, family 8, subfamily B, polypeptide 1, Cytochrome P450-14DM, Cytochrome P450-PCN1, Cytochrome P450LI, LDM, Lanosterol 14-alpha demethylase, Nifedipine oxidase, P450 14DM, P450L1, Quinine 3-monooxygenase, Sterol 12-alpha-hydroxylase, Sterol 14-alpha demethylase, Taurochenodeoxycholate 6-alpha-hydroxylase

Key facts

CAS number

171228-49-2

Purity

>98%

Form

Solid

form

Molecular weight

700.8 Da

Molecular formula

C<sub>3</sub><sub>7</sub>H<sub>4</sub><sub>2</sub>F<sub>2</sub>N<sub>8</sub>O<sub>4</sub>

PubChem

468595

Nature

Synthetic

Solubility

Soluble in DMSO to 0.5 mg/ml

Biochemical name

Posaconazole

Biological description

Posaconazole is a broad-spectrum, second-generation triazole compound that displays antifungal activity. Posaconazole inhibits the growth of fungi by inhibiting the lanosterol 14α-demethylase enzyme (IC50s range from 7-200 nM), which results in a disruption the synthesis of ergosterol, a key sterol necessary for fungal cell membrane integrity and for the function of certain membrane-bound proteins.

Canonical smiles

CCC(C(C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5CC(OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F

Isomeric smiles

CC[C@@H]([C@H](C)O)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OC[C@H]5C[C@](OC5)(CN6C=NC=N6)C7=C(C=C(C=C7)F)F

InChi

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

InChiKey

RAGOYPUPXAKGKH-XAKZXMRKSA-N

IUPAC 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

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Product details

This product is manufactured by BioVision, an Abcam company and was previously called 9526 Posaconazole. 9526-10 is the same size as the 10 mg size of ab285414.
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Properties and storage information

Shipped at conditions
Blue Ice
Appropriate long-term storage conditions
-20°C
Storage information
Store in the dark|This product is air and light sensitive and impurities can occur as a result of air oxidation or due to metabolism by microbes
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

CYP8B1 Cytochrome P450 3A4/3A5 and CYP51A1/CYP51 are all members of the cytochrome P450 superfamily involved in the metabolism of various substances. CYP8B1 is primarily associated with the synthesis of bile acids influencing the ratio of bile acid components. Cytochrome P450 3A4 and 3A5 (often referred to as CYP3A4 and CYP3A5) are well-known for their role in the metabolism of drugs including substances like posaconazole. CYP3A4 is widely expressed in the liver and intestines and has a molecular mass of approximately 57 kDa. CYP51A1 also identified as lanosterol 14-alpha demethylase plays an important role in sterol biosynthesis and is universally expressed with its mass approximately 53 kDa.
Biological function summary

These enzymes are so important because they facilitate oxidation reactions that aid in the metabolism and elimination of compounds. CYP3A4 exists in a large enzymatic complex in the endoplasmic reticulum contributing to its broad substrate specificity. CYP51 is involved in the demethylation of lanosterol a step in cholesterol synthesis important for cell membrane integrity. CYP8B1 regulates the synthesis of chenodeoxycholic acid impacting bile acid composition. These activities are critical for maintaining metabolic balance and influencing physiological processes.

Pathways

CYP3A4 and CYP3A5 are major players in the drug metabolism pathway affecting the pharmacokinetics of over half of all processed medications including posaconazole. They work closely with drug transporters and other enzymes in the phase I and II metabolic phases. CYP51A1 functions in the cholesterol biosynthesis pathway working alongside proteins like HMG-CoA reductase. CYP8B1 is involved in the primary bile acid biosynthesis pathway which is important for lipid digestion and absorption.

Alterations in these enzymes' functions can lead to significant health impacts. CYP3A4 and CYP3A5 aberrations influence drug toxicity and treatment efficacy particularly in cancer therapies. They interact with proteins involved in detoxification pathways which can modulate therapeutic outcomes. CYP51A1 is targeted by inhibitors like posaconazole which is used in treating fungal infections due to its role in disrupting ergosterol synthesis in fungi. CYP8B1 has links to liver disorders such as cholestasis where imbalance in bile acid synthesis can occur impacting liver function.
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Product protocols

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