Mycophenolic acid
- CAS No.
- 24280-93-1
- Chemical Name:
- Mycophenolic acid
- Synonyms
- Mycophenolic;melbex;nsc-129185;MycophenoL;Mycophenolate Mofetil EP Impurity F;(E)-6-(4-hydroxy-6-Methoxy-7-Methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-Methylhex-4-enoic acid;68618;lilly-68618;Mycophenolinsure;Micophenolic acid
- CBNumber:
- CB8311003
- Molecular Formula:
- C17H20O6
- Molecular Weight:
- 320.34
- MOL File:
- 24280-93-1.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/1/23 15:19:12
| Melting point | 141°C |
|---|---|
| Boiling point | 419.24°C (rough estimate) |
| Density | 1.2300 (rough estimate) |
| vapor pressure | 0Pa at 22℃ |
| refractive index | 1.5200 (estimate) |
| Flash point | 2℃ |
| storage temp. | Sealed in dry,Store in freezer, under -20°C |
| solubility | methanol: 50 mg/mL, clear, colorless to faintly yellow |
| form | powder |
| pka | 4.5(at 25℃) |
| color | white to white with yellow cast |
| Water Solubility | 13mg/L(25 ºC) |
| Merck | 14,6327 |
| BRN | 1295848 |
| BCS Class | 2? |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| LogP | -1.83-2.28 at 25℃ and pH5-9 |
| Dissociation constant | 4.58-8.05 at 22.5-25℃ |
| CAS DataBase Reference | 24280-93-1(CAS DataBase Reference) |
| EPA Substance Registry System | 4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4E)- (24280-93-1) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS07,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H341-H360D-H372-H410 | |||||||||
| Precautionary statements | P201-P202-P260-P273-P301+P312-P308+P313 | |||||||||
| Hazard Codes | Xn,N,T,F | |||||||||
| Risk Statements | 22-61-40-68-50/53-48/25-52/53-36-20/21/22-11 | |||||||||
| Safety Statements | 53-45-36/37-61-22-26-16 | |||||||||
| RIDADR | 2811 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | MP8050000 | |||||||||
| F | 10 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29419090 | |||||||||
| Toxicity | LD50 in mice (mg/kg): >1250 orally; 972.9±77 i.p. (Williams) | |||||||||
| NFPA 704 |
|
Mycophenolic acid price More Price(9)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | M5255 | Mycophenolic acid ≥98% | 24280-93-1 | 50MG | ₹8779.08 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M5255 | Mycophenolic acid ≥98% | 24280-93-1 | 250MG | ₹31738.9 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M3536 | Mycophenolic acid powder, BioReagent, suitable for cell culture | 24280-93-1 | 50MG | ₹10446.13 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M3536 | Mycophenolic acid powder, BioReagent, suitable for cell culture | 24280-93-1 | 250MG | ₹35928.18 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | M-106 | Mycophenolic acid solution 1.0?mg/mL in acetonitrile, ampule of 1?mL, certified reference material, Cerilliant? | 24280-93-1 | 1ML | ₹24019.8 | 2022-06-14 | Buy |
Mycophenolic acid Chemical Properties,Uses,Production
Description
Mycophenolic acid is an immunosuppresive microbial metabolite that has been found in P. brevicompactum. It is also an active metabolite of mycophenolate mofetil that is formed via carboxylesterase 1 (CES1) and CES2. Mycophenolic acid is an inhibitor of IMP dehydrogenase (IMPDH) type I and type II (IC50s = 32 and 11 nM, respectively, in cell-free assays) and inhibits DNA synthesis in L strain mouse fibroblasts when used at concentrations ranging from 0.1 to 10 μg/ml. It is active against several strains of C. albicans, C. parakrusei, C. tropicalis, and C. neoformans (MICs = 3.9-31.25 μg/ml), as well as various strains of S. aureus (MICs = 31.25-125 μg/ml). Mycophenolic acid (150 mg/kg) reduces splenomegaly in a mouse model of Friend virus-induced leukemia. It decreases the number of hemolytic plaque forming cells isolated from the spleen of mice immunized with sheep red blood cells (RBCs) when administered at doses ranging from 60 to 240 mg/kg. Formulations containing mycophenolic acid have been used as immunosuppressive agents in the prevention of organ transplant rejection.
Chemical Properties
White to Off-White Powder
Uses
Mycophenolic acid is a common Penicillium metabolite first reported in the 1930s as a possible mycotoxin. Re-investigation showed mycophenolic acid to display broad antitumour, antiviral, antifungal and antiprotozoan activities. Its potent immunosuppressant activity led to its commercial development to prevent kidney transplant rejection. Mycophenolic acid acts by inhibiting inosine monophosphate dehydrogenase, controlling the rate of de novo purine synthesis in proliferating B and T lymphocytes.
Definition
ChEBI: A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mo etil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.
General Description
Assayed in therapeutic drug monitoring to ensure patients remain within the drug′s therapeutic range, mycophenolic acid is an immunosuppressant drug and the active metabolite of the prodrug mycophenolate mofetil. This analytical standard is suitable for LC-MS/MS applications including therapeutic drug monitoring and other clinical or diagnostic applications.
Biological Activity
Immunosuppressive agent with antiviral and antitumor effects in vitro and in vivo . Potently inhibits inosine monophosphate dehydrogenase, thus inhibiting de novo GTP synthesis leading to decreased RNA and DNA synthesis. Reversibly inhibits proliferation of T and B lymphocytes and antibody formation.
Mechanism of action
Mycophenolic acid (MPA) is a potent inhibitor of inosine monophosphate dehydrogenase (IMPDH) that prevents the ab initio biosynthesis of purine nucleotides. It predominantly affects lymphocytes, leading to inhibition of DNA synthesis in T cells and B cells, thereby suppressing cell-mediated immune responses and antibody formation.MPA also inhibits glycosylation and expression of adhesion molecules, as well as the recruitment of lymphocytes and monocytes to sites of inflammation.MPA depletes tetrahydrobiopterin and reduces nitric oxide production via inducible NO synthase without affecting the activity of constitutive NO synthase[1].
Purification Methods
Purify the acid by dissolving it in the minimum volume of EtOAc, applying onto a silica gel column (0.05-0.2 mesh) and eluting with a mixture of EtOAc/CHCl3/AcOH (45:55:1) followed by recrystallisation from heptane/EtOAc, from aqueous EtOH or from hot H2O and drying in vacuo. It is a weak dibasic acid, moderately soluble in Et2O, CHCl3 and hot H2O but weakly soluble in *C6H6 and toluene. [Birch & Wright Aust J Chem 22 2635 1969, Canonica et al. J Chem Soc, Perkin Trans 1 2639 1972, Birkinshaw et al. Biochem J 50 630 1952, Beilstein 18 II 393, 18 III/IV 6513.]
References
[1] ALLISON A. Mechanisms of action of mycophenolate mofetil[J]. Lupus, 2005, 14 1: 2-8. DOI:10.1177/096120330501400102.
Mycophenolic acid Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| KARPSCHEM LABORATORIES | +91-7249203006 +91-7249203006 | Maharashtra, India | 786 | 58 | Inquiry |
| Sibram Pharmaceutical | +91-8655777550 +91-8655777550 | Maharashtra, India | 244 | 58 | Inquiry |
| Besil Chem LLP | +91-7760252666 +91-9880731835 | Bangalore, India | 163 | 58 | Inquiry |
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| SynZeal Research Pvt Ltd | +1 226-802-2078 | Gujarat, India | 6522 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Biopole Pharmatech Co., Ltd. | +8615151475053 | China | 37 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| KARPSCHEM LABORATORIES | 58 |
| Sibram Pharmaceutical | 58 |
| Besil Chem LLP | 58 |
| CHEMSWORTH | 30 |
| CLEARSYNTH LABS LTD. | 58 |
| A.J Chemicals | 58 |
| Pharmaffiliates Analytics and Synthetics P. Ltd | 58 |
| SynZeal Research Pvt Ltd | 58 |
| TCI Chemicals (India) Pvt. Ltd. | 58 |
| Biopole Pharmatech Co., Ltd. | 58 |
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