Mycophenolic acid

Base Information

• Chemical Name: Mycophenolic acid
• CAS No.: 24280-93-1
• Molecular Formula: C17H20O6
• Molecular Weight: 320.342
• Hs Code.: 29419090
• European Community (EC) Number: 246-119-3,207-595-8
• NSC Number: 757424,129185
• UNII: HU9DX48N0T
• DSSTox Substance ID: DTXSID4041070
• Nikkaji Number: J49.437B,J2.768E
• Wikipedia: Mycophenolic_acid
• Wikidata: Q420553
• NCI Thesaurus Code: C673
• RXCUI: 7145
• Pharos Ligand ID: KV1WMZTSUMNK
• Metabolomics Workbench ID: 43267
• ChEMBL ID: CHEMBL866
• Mol file: 24280-93-1.mol

Synonyms:Cellcept;Mofetil Hydrochloride, Mycophenolate;Mofetil, Mycophenolate;mycophenolate mofetil;mycophenolate mofetil hydrochloride;Mycophenolate Sodium;Mycophenolate, Sodium;Mycophenolic Acid;mycophenolic acid morpholinoethyl ester;myfortic;RS 61443;RS-61443;RS61443;Sodium Mycophenolate

Chemical Property of Mycophenolic acid

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 8.18E-16mmHg at 25°C
• Melting Point: 141 °C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 611.6 °C at 760 mmHg
• PKA: 4.5(at 25℃)
• Flash Point: 225.8 °C
• PSA: 93.06000
• Density: 1.29 g/cm³
• LogP: 2.73320
• Storage Temp.: 2-8°C
• Solubility.: methanol: 50 mg/mL, clear, colorless to faintly yellow
• Water Solubility.: 13mg/L(25 oC)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 320.12598835
• Heavy Atom Count: 23
• Complexity: 486

Purity/Quality:

99%MIN ^*data from raw suppliers

Mycophenolic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N,T,F
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Transplant Agents
• Canonical SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)O)O
• Isomeric SMILES: CC1=C2COC(=O)C2=C(C(=C1OC)C/C=C(\C)/CCC(=O)O)O
• Recent ClinicalTrials: Evaluating the Safety of Myfortic (Mycophenolate Sodium) in Patients With Lupus Nephritis
• Recent EU Clinical Trials: A prospective, randomized, controlled trial assessing the effect of conversion from Tacrolimus-antimetabolite to Tacrolimus-mTor-inhibitors based immunosuppression to booster SARS-CoV-2-specific seroconversion after a fourth dose of SARS-CoV-2 mRNA vaccine in unresponsive Solid Organ Transplant recipients
• Description: Mycophenolic acid, less accurately called mycophenolate, is a compound derived from Penicillium stoloniferum and related species. It can reversibly inhibit inosine monophosphate dehydrogenase (IMPDH), the enzyme that controls the rate of synthesis of guanine monophosphate in the de novo pathway of purine synthesis used in the proliferation of B and T lymphocytes. Mycophenolic acid also has antibacterial, anticancer, antifungal, and antiviral activities. These powerful properties have been exploited in studies on organ transplant survival, anti-proliferative, rheumatoid arthritis, and psoriasis. It was initially marketed as the prodrug mycophenolate mofetil (MMF) to improve oral bioavailability. More recently, the salt mycophenolate sodium has also been introduced. Mycophenolate mofetil is marketed under the trade name CellCept and mycophenolate sodium as Myfortic. Discovered by an Italian medical scientist Bartolomeo Gosio in 1893, mycophenolic acid was the first antibiotic to be synthesised in pure and crystalline form. But its medical application was forgotten until two American scientists C.L. Alsberg and O.M. Black resynthesised it in 1912, and gave its chemical name. It was eventually found to be a broad-spectrum acting drug having antiviral, antifungal, antibacterial, anticancer, and antipsoriasis properties. The clinically usable drug Cellcept was developed by South African geneticist Anthony Allison and his wife Elsie M. Eugui. It was first approved by the US Food and Drug Administration on 3 May 1995 for use in kidney transplantation. 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.
• Uses: An antibiotic produced by Penicillium brevi-compactum, P. Stoloniferum and related spp. A selective inhibitor of lymphocyte proliferation by blocking inosine monophosphate dehydrogenase, an enzyme involved in the de novo synthesis of purine nucleotides. antineoplastic, progestin 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.

Technology Process of Mycophenolic acid

There total 65 articles about Mycophenolic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

ethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methylhex-4-enoate (32483-51-5,13312-25-9) → mycophenolic acid (24280-93-1)

Guidance literature:

With lithium hydroxide; In methanol; for 12h;

DOI:10.1139/v97-078

Reference yield: 96.0%

methyl mycophenolate (31858-66-9) → mycophenolic acid (24280-93-1)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 25 ℃; for 24h;

DOI:10.1021/acs.orglett.8b01327

Reference yield: 61.0%

7-hydroxy-6-[(E)-6-hydroxy-3-methylhex-2-enyl]-5-methoxy-4-methyl-3H-2-benzofuran-1-one (31327-49-8) → mycophenolic acid (24280-93-1)

Guidance literature:

With jones reagent; In acetone; at -30 ℃; for 5h;

DOI:10.1021/ja00264a038

upstream raw materials:

7-hydroxy-6-[(E)-6-hydroxy-3-methylhex-2-enyl]-5-methoxy-4-methyl-3H-2-benzofuran-1-one

ethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-isobenzofuran-5-yl)-4-methylhex-4-enoate

D-glucose

methyl mycophenolate

Downstream raw materials:

MPAG

7-hydroxy-5-methoxy-4-methyl-6-(2-(2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)isobenzofuran-1(3H)-one

Refernces

• 1、 Plunk, Michael A.,Quintana, Jeremy M.,Darden, Carly M.,Lawrence, Michael C.,Naziruddin, Bashoo,Kane, Robert R.. "Design and Catalyzed Activation of Mycophenolic Acid Prodrugs". . p. 812 - 816. Retrieved 2021.
• 2、 Schmeda-Hirschmann, Guillermo,Aranda, Carlos,Kurina, Marcela,Rodriguez, Jaime A.,Theoduloz, Cristina. "Biotransformations of imbricatolic acid by Aspergillus niger and Rhizopus nigricans cultures". . p. 1092 - 1100. Retrieved 2007.
• 3、 Halle, Mahesh B.,Yudhistira, Tesla,Lee, Woo-Hyun,Mulay, Sandip V.,Churchill, David G.. "Diels-Alder and Stille Coupling Approach for the Short Protecting-Group-Free Synthesis of Mycophenolic Acid, Its Phenylsulfenyl and Phenylselenyl Analogues, and Reactive Oxygen Species (ROS) Probing Capacity in Water". supporting information. p. 3557 - 3561. Retrieved 2018/06/26.