| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
|
||
| 100mg |
|
||
| Other Sizes |
| Targets |
FR179642 targets the synthesis of 1,3-β-D-glucan, an essential component of the fungal cell wall. As an echinocandin-class compound, it inhibits the enzyme β-(1,3)-D-glucan synthase, which is responsible for the polymerization of glucose into β-glucan chains. This enzyme is present in fungal cells but not in mammalian cells, providing selective antifungal activity. The compound also shows activity against matrix metalloproteinases MMP-2 and MMP-9.
|
|---|---|
| ln Vitro |
FR179642 is the deacylated form of FR901379 and does not possess significant antifungal activity on its own, as it is the N-acyl side chain of FR901379 that confers potent antifungal properties. However, as an intermediate, its utility is demonstrated in the synthesis of micafungin, which exhibits potent antifungal activity against Aspergillus and Candida species. The compound's structural features allow for the attachment of various acyl side chains to generate active echinocandin antifungals.
|
| ln Vivo |
FR179642 itself is not used as a therapeutic agent but serves as a crucial intermediate in the production of micafungin, which has demonstrated in vivo efficacy against fungal infections. Micafungin, derived from FR179642, is used clinically to treat invasive candidiasis and aspergillosis. The compound's role in pharmaceutical manufacturing makes it an important research tool for studying echinocandin biosynthesis and development.
|
| Enzyme Assay |
In vitro enzyme assays for FR179642 are not typically performed for the compound itself, as it is an intermediate rather than a pharmacologically active compound. However, assays can be used to monitor the enzymatic hydrolysis of FR901379 to FR179642, using HPLC to quantify the production of FR179642. The compound's identity and purity are confirmed using analytical techniques such as HPLC, NMR, and mass spectrometry.
|
| Cell Assay |
In vitro cellular assays are not applicable to FR179642 as it is a synthetic intermediate, not a bioactive compound for direct cellular testing. The compound is used in chemical synthesis reactions for the production of micafungin, which is subsequently tested for antifungal activity in cell-based assays against Candida and Aspergillus species.
|
| Animal Protocol |
In vivo animal experiments are not applicable to FR179642 as it is a pharmaceutical intermediate, not a therapeutic agent. The compound is not intended for administration to living organisms. Its safety and efficacy are evaluated through the final drug product, micafungin, which undergoes extensive preclinical and clinical testing.
|
| ADME/Pharmacokinetics |
Pharmacokinetic data are not applicable to FR179642 as it is a synthetic intermediate, not a therapeutic agent. The compound is not intended for systemic administration. Its physicochemical properties include a molecular weight of 936.89 and solubility in ethanol, methanol, DMF, and DMSO. It should be stored at -20°C for long-term stability.
|
| Toxicity/Toxicokinetics |
FR179642 is not intended for human therapeutic use, and toxicological data are not applicable as it is a research chemical and pharmaceutical intermediate. However, the final product micafungin has been extensively evaluated for safety in clinical studies. Standard laboratory safety precautions should be followed when handling this compound.
|
| References | |
| Additional Infomation |
FR179642 (CAS#: 168110-44-9) has the molecular formula C35H52N8O20S and a molecular weight of 936.89. It was patented in 1991 by Ueda and colleagues at Fujisawa (now Astellas Pharma). The compound is formed by the selective hydrolysis of FR901379 using a cyclic lipopeptide acylase found in soil microbes. It is an important pharmaceutical intermediate for the production of micafungin.
|
| Molecular Formula |
C35H52N8O20S
|
|---|---|
| Molecular Weight |
936.89
|
| Exact Mass |
936.301
|
| Elemental Analysis |
C, 44.87; H, 5.59; N, 11.96; O, 34.15; S, 3.42
|
| CAS # |
168110-44-9
|
| PubChem CID |
71714631
|
| Appearance |
White to off-white solid powder
|
| Density |
1.8±0.1 g/cm3
|
| Index of Refraction |
1.718
|
| LogP |
-12.95
|
| Hydrogen Bond Donor Count |
16
|
| Hydrogen Bond Acceptor Count |
21
|
| Rotatable Bond Count |
9
|
| Heavy Atom Count |
64
|
| Complexity |
1860
|
| Defined Atom Stereocenter Count |
15
|
| SMILES |
CC(O)C1NC(=O)C(N)CC(O)C(O)NC(=O)C2C(O)C(C)CN2C(=O)C(NC(=O)C(NC(=O)C2CC(O)CN2C1=O)C(O)C(O)c1ccc(O)c(OS(O)(=O)=O)c1)C(O)CC(N)=O
|
| InChi Key |
QCYMOOBOFFUBHZ-CPYYHODSSA-N
|
| InChi Code |
InChI=1S/C35H52N8O20S/c1-11-9-43-25(26(11)50)33(57)41-31(55)19(48)7-15(36)29(53)38-22(12(2)44)34(58)42-10-14(45)6-16(42)30(54)40-24(32(56)39-23(35(43)59)18(47)8-21(37)49)28(52)27(51)13-3-4-17(46)20(5-13)63-64(60,61)62/h3-5,11-12,14-16,18-19,22-28,31,44-48,50-52,55H,6-10,36H2,1-2H3,(H2,37,49)(H,38,53)(H,39,56)(H,40,54)(H,41,57)(H,60,61,62)/t11-,12+,14+,15-,16-,18+,19+,22-,23-,24-,25-,26-,27-,28-,31+/m0/s1
|
| Chemical Name |
5-((1S,2S)-2-((2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-9-amino-20-((R)-3-amino-1-hydroxy-3-oxopropyl)-2,11,12,15-tetrahydroxy-6-((R)-1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-23-yl)-1,2-dihydroxyethyl)-2-hydroxyphenyl hydrogen sulfate
|
| Synonyms |
FR-133303; FR 133303; FR133303; FR-179642; FR 179642; FR179642; Micafungin FR-179642 impurity; Pneumocandin M1
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O : 100 mg/mL (106.74 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (106.74 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0674 mL | 5.3368 mL | 10.6736 mL | |
| 5 mM | 0.2135 mL | 1.0674 mL | 2.1347 mL | |
| 10 mM | 0.1067 mL | 0.5337 mL | 1.0674 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
