24280-93-1 Usage
Description
Mycophenolic acid, also known as mycophenolate, is a compound derived from Penicillium stoloniferum and related species. It is an immunosuppressive antibiotic that 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. It was initially marketed as the prodrug mycophenolate mofetil (MMF) to improve oral bioavailability, and more recently, the salt mycophenolate sodium has also been introduced. Mycophenolate mofetil is marketed under the trade name CellCept, and mycophenolate sodium as Myfortic.
Uses
1. Used in Organ Transplant Industry:
Mycophenolic acid is used as an immunosuppressant for preventing tissue rejection following organ transplants. Its potent immunosuppressant activity led to its commercial development to prevent kidney transplant rejection.
2. Used in Autoimmune Disease Treatment:
Mycophenolic acid is used as a treatment for certain autoimmune diseases, such as rheumatoid arthritis and psoriasis, due to its immunosuppressive properties.
3. Used in Antineoplastic Therapy:
Mycophenolic acid is used as an antineoplastic agent, displaying broad antitumor, antiviral, antifungal, and antiprotozoan activities.
4. Used in Antibacterial Applications:
Mycophenolic acid is used as an antibiotic, produced by Penicillium brevi-compactum, P. stoloniferum, and related species, and is active against several strains of bacteria, such as Staphylococcus aureus.
5. Used in Antiviral and Antifungal Applications:
Mycophenolic acid is used for its antiviral and antifungal properties, making it a broad-spectrum acting drug.
6. Used in Progestin Therapy:
Mycophenolic acid is also used as a progestin, contributing to its diverse range of applications in the medical field.
Biosynthesis
The antibiotic, mycophenolic acid, biosynthesised by Penicillium brevicompactum, is unusual in that it is derived from a Cs polyketide chain and three dimethylallyl pyrophosphate molecules as shown in Figure 1.
Mycophenolic acid has useful antitumour properties and efforts have been made to prepare derivatives with enhanced or modified activity. It is of inte rest ,therefore, that cultures of P. brevicompactum can convert halogenated phthalides (4.58; R = Cl or Br) into the corresponding mycophenolic acid derivatives.
References
1. https://pubchem.ncbi.nlm.nih.gov/compound/mycophenolic_acid#section=Top
2. https://www.scbt.com/scbt/product/mycophenolic-acid-24280-93-1
3. http://www.enzolifesciences.com/BML-A249/mycophenolic-acid/
4. http://www.emedicinehealth.com/drug-mycophenolic_acid/article_em.htm
5. https://pubchem.ncbi.nlm.nih.gov/compound/mycophenolic_acid#section=Top
6. http://www.selleckchem.com/products/Mycophenolic-acid(Mycophenolate).html
7. https://www.drugbank.ca/drugs/DB01024
References
References/Citations
1) Eugui et al. (1991), Lymphocyte-selective cyostatic and immunosuppressive effects of mycophenolic acid in vitro: role of deoxyguanosine nucleotide depletion; Scand. J. Immunol., 33 161
2) Jonsson et al. (2002), Mycophenolic acid inhibits inosine 5′-monophosphate dehydrogenase and suppresses production of pro-inflammatory cytokines, nitric oxide and LDH in macrophages; Cell. Immunol., 216 93
3) Allison et al. (1993), Mechanisms of action of mycophenolic acid; Ann. NY Acad. Sci., 696 63
4) Quemeneur et al. (2002), Mycophenolic acid inhibits IL-2-dependent T cell proliferation, but not IL-2-dependent survival and sensitization to apoptosis; J. Immunol., 169 2747
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 24280-93-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,2,8 and 0 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 24280-93:
(7*2)+(6*4)+(5*2)+(4*8)+(3*0)+(2*9)+(1*3)=101
101 % 10 = 1
So 24280-93-1 is a valid CAS Registry Number.
InChI:InChI=1/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/p-1/b9-4+
24280-93-1Relevant articles and documents
A convergent synthesis of mycophenolic acid
Ple, Patrick A.,Hamon, Annie,Jones, Geraint
, p. 3395 - 3400 (1997)
A new method for the synthesis of Mycophenolic acid using a convergent approach has been developed where the key step is a palladium mediated allyl-aryl tin coupling.
Total synthesis of mycophenolic acid by a palladium-catalyzed decarboxylative allylation and biomimetic aromatization sequence
Brookes, Paul A.,Cordes, Jens,White, Andrew J. P.,Barrett, Anthony G. M.
, p. 7313 - 7319 (2013)
This paper describes the total synthesis of the fungal natural product mycophenolic acid through palladium-catalyzed allylation, biomimetic cyclization, and aromatization. Methyl (4E)-6-hydroxy-4-methylhex-4-enoate, which was converted in four steps into the key diketo ester dioxinone via two selective C-acylation reactions, was transformed into a resorcylate. Subsequent phenol methylation, lactonization, iodo-ether formation, and halogenation gave a tricyclic intermediate. Palladium-catalyzed cross-coupling with DABCO-(AlMe3)2 and saponification gave mycophenolic acid. An alternative approach with early stage arene methyl incorporation unexpectedly resulted in the formation of a γ-pyrone. A total synthesis of mycophenolic acid was developed. In a one-pot reaction, a diketo ester dioxinone was transformed into a resorcylate by Pd-catalyzed decarboxylative allylation and biomimetic cyclization and aromatization. Methylation, lactonization, iodo-ether formation, and halogenation led to a tricyclic intermediate. Pd-catalyzed cross-coupling and ester hydrolysis completed the synthesis. Copyright
Method of Synthesis for Mycophenolic Acid and Its Phenylsulfenyl and Phenylseleny Analogues
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, (2020/10/10)
The present invention relates to: a method for synthesizing mycophenolic acid and phenylsulfenyl and phenylselenyl derivatives thereof; and novel phenylsulfenyl and phenylselenyl derivative compounds of mycophenolic acid synthesized by the synthesis method. The novel synthesis method of mycophenolic acid of the present invention does not use a protecting group compared to a conventional synthesis method, has a simple reaction step, and has a high yield. Therefore, the synthesis method of the present invention can usefully use mycophenolic acid in a high-yield mass production method.
Pharmaceutical composition against influenza virus containing s. officinalis l.
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Page/Page column 18, (2018/02/27)
The present invention relates to a pharmaceutical composition against influenza virus. The pharmaceutical composition comprises a therapeutically effective amount of the extract of S. officinalis L., or active compounds obtained from the extract of S. officinalis L., hydrolyzed compounds or pharmaceutically acceptable salts thereof.