Mycophenolic acid
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| Category | Antibiotics |
| Catalog number | BBF-02567 |
| CAS | 24280-93-1 |
| Molecular Weight | 320.34 |
| Molecular Formula | C17H20O6 |
| Purity | >98% |
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Description
Mycophenolic acid is a small lactone antibiotic produced by Pen. brevicom pactum and Pen. stoloniferum. Activity against gram-positive bacteria. In animal experiments, it has inhibitory effect on sarcoma-180, Lewis lung cancer, adenocarcinoma Ca-755, Walker tumor 256, Yoshida sarcoma, Freund ascites tumor, etc. Mycophenolic acid is a potent IMPDH inhibitor and the active metabolite of an immunosuppressive drug, used to prevent rejection in organ transplantation. It inhibits an enzyme needed for the growth of T cells and B cells.
Specification
| Synonyms | Mycophenolate; Myfortic; Melbex |
| Storage | -20°C |
| IUPAC Name | (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid |
| Canonical SMILES | CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)O)O |
| InChI | InChI=1S/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)/b9-4+ |
| InChI Key | HPNSFSBZBAHARI-RUDMXATFSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | Colorless Needle Crystal |
| Application | Antibiotics, Antineoplastic |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 611.6°C at 760 mmHg |
| Melting Point | 141°C |
| Density | 1.29 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
| LogP | 2.8 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Mycophenolic acid is a potent, selective, uncompetitive, and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), and therefore inhibits the de novo pathway of guanosine nucleotide synthesis without incorporation into DNA. Because T- and B-lymphocytes are critically dependent for their proliferation on de novo synthesis of purines, whereas other cell types can utilize salvage pathways, mycophenolic acid has potent cytostatic effects on lymphocytes. Mycophenolic acid inhibits proliferative responses of T- and B-lymphocytes to both mitogenic and allospecific stimulation. Addition of guanosine or deoxyguanosine reverses the cytostatic effects of mycophenolic acid on lymphocytes. Mycophenolic acid also suppresses antibody formation by B-lymphocytes. Mycophenolic acid prevents the glycosylation of lymphocyte and monocyte glycoproteins that are involved in intercellular adhesion to endothelial cells and may inhibit recruitment of leukocytes into sites of inflammation and graft rejection. |
| Toxicity | LD50: 352 mg/kg (Oral, Rat); LD50: 1000 mg/kg (Oral, Mouse); LD50: >6000 mg/kg (Oral, Rabbit). |
Reference Reading
1.A Longitudinal Analysis of Outcomes of Lupus Nephritis in an International Inception Cohort Using a Multistate Model Approach.
Hanly JG1, Su L2, Urowitz MB3, Romero-Diaz J4, Gordon C5, Bae SC6, Bernatsky S7, Clarke AE8, Wallace DJ9, Merrill JT10, Isenberg DA11, Rahman A11, Ginzler EM12, Petri M13, Bruce IN14, Dooley MA15, Fortin P16, Gladman DD3, Sanchez-Guerrero J3, Steinsson K1 Arthritis Rheumatol. 2016 Mar 18. doi: 10.1002/art.39674. [Epub ahead of print]
OBJECTIVE: To study bidirectional change and predictors of change in estimated glomerular filtration rate (eGFR) and proteinuria (ePrU) in lupus nephritis (LN) using a multistate modelling approach.
2.Expression of UGT1A Subfamily in Rat Brain.
Sakakibara Y1, Katoh M1, Imai K1, Kondo Y1, Asai Y, Ikushiro SI2, Nadai M1. Biopharm Drug Dispos. 2016 Apr 7. doi: 10.1002/bdd.2012. [Epub ahead of print]
UDP-glucuronosyltransferase (UGT) is an enzyme that catalyzes a major phase II reaction in drug metabolism. Glucuronidation occurs mainly in the liver, but UGTs are also expressed in extrahepatic tissues, where they play an important role in local metabolism. UGT1A isoforms catalyze the glucuronidation of several drugs, neurotransmitters, and neurosteroids that exert pharmacological and physiological effects on the brain. The aim of the current study was to determine UGT1A mRNA expression levels and glucuronidation activity in different regions of the rat brain (namely the cerebellum, frontal cortex, parietal cortex, piriform cortex, hippocampus, medulla oblongata, olfactory bulb, striatum and thalamus). We found that all UGT1A isoforms were expressed in all the nine regions, but their expression levels differed between the regions. The difference between the regions of the brain where the mRNA levels were highest and those where they were lowest ranged between 2.
3.Therapeutic drug monitoring of enteric-coated mycophenolate sodium by limited sampling strategies is associated with a high rate of failure.
Hougardy JM1, Maufort L1, Cotton F2, Coussement J1, Mikhalski D1, Wissing KM3, Le Moine A1, Broeders N1, Abramowicz D4. Clin Kidney J. 2016 Apr;9(2):319-23. doi: 10.1093/ckj/sfw001. Epub 2016 Mar 1.
BACKGROUND: Therapeutic drug monitoring of mycophenolic acid (MPA) is usually performed with a limited sampling strategy (LSS), which relies on a limited number of blood samples and subsequent extrapolation of the global exposure to MPA. LSS is usually performed successfully with mycophenolate mofetil (MMF), but data on enteric-coated mycophenolate sodium (EC-MPS) are scarce. Here, we evaluated the feasibility of 6-h LSS therapeutic drug monitoring with EC-MPS compared with MMF monitoring among kidney transplant recipients.
4.The Value of Monitoring the Serum Concentration of Mycophenolate Mofetil in Children with Steroid-Dependent/Frequent Relapsing Nephrotic Syndrome.
Tong K1, Mao J, Fu H, Shen H, Liu A, Shu Q, Du L. Nephron. 2016 Mar 19. [Epub ahead of print]
BACKGROUND: Mycophenolate mofetil (MMF) is an alternative treatment strategy in children with steroid sensitivity who have frequent relapses or steroid-dependent nephrotic syndrome (FRNS/SDNS).
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H20O6
Molecular Weight (Monoisotopic Mass): 320.126 Da
Molecular Weight (Avergae Mass): 320.3371 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C17H20O6
Molecular Weight (Monoisotopic Mass): 320.126 Da
Molecular Weight (Avergae Mass): 320.3371 Da
LC-MS/MS Spectrum - LC-ESI-ITFT , negative
Experimental Conditions
Instrument Type: LC-ESI-ITFT
Ionization Mode: negative
Ionization Mode: negative
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
