mycophenolic acid
mycophenolic acid
CAS: 24280-93-1
Molecular Formula: C17H20O6
mycophenolic acid - Names and Identifiers
mycophenolic acid - Physico-chemical Properties
| Molecular Formula | C17H20O6 |
| Molar Mass | 320.34 |
| Density | 1.2300 (rough estimate) |
| Melting Point | 141°C |
| Boling Point | 419.24°C (rough estimate) |
| Flash Point | 2℃ |
| Water Solubility | 13mg/L(25 ºC) |
| Solubility | Soluble in methanol. |
| Vapor Presure | 0Pa at 22℃ |
| Appearance | White to off-white powder |
| Color | white to white with yellow cast |
| Merck | 14,6327 |
| BRN | 1295848 |
| pKa | 4.5(at 25℃) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| 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. |
| Refractive Index | 1.5200 (estimate) |
| MDL | MFCD00036814 |
mycophenolic acid - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R61 - May cause harm to the unborn child R40 - Limited evidence of a carcinogenic effect R68 - Possible risk of irreversible effects R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R48/25 - R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S16 - Keep away from sources of ignition. |
| UN IDs | 2811 |
| WGK Germany | 3 |
| RTECS | MP8050000 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29419090 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in mice (mg/kg): >1250 orally; 972.9±77 i.p. (Williams) |
mycophenolic acid - Reference
| Reference Show more | 1. [IF=5.81] Zhao Jing et al."Intra-Herb Interactions: Primary Metabolites in Coptidis Rhizoma Extract Improved the Pharmacokinetics of Oral Berberine Hydrochloride in Mice."Front Pharmacol. 2021 Jun;0:1426 2. [IF=3.765] Chen Xun et al."Clock gene Bmal1 controls diurnal rhythms in expression and activity of intestinal carboxylesterase 1."J Pharm Pharmacol. 2021 Mar;73(1):52-59 |
mycophenolic acid - Introduction
Mycophenolic acid is a biologically active compound with low molecular weight. It has biological activity against gram-positive bacteria, dermatophytes and viruses, and has selective immunosuppressive effect. This mechanism is related to the selective inhibition of nucleotide synthesis by mycophenolic acid. This product can block the synthesis of purine nucleotides in vivo by inhibiting the action of hypoxanthate (purine nucleus) glycoside dehydrogenase. Prevent the division of T cells, lymphocytes and the formation of antibodies in B cells as an immunosuppressive factor. It is used in molecular biology to screen cells containing the xanthine guanine phosphoribosyltransferase gene of Escherichia coli.
Last Update：2022-10-16 17:15:12
mycophenolic acid - Reference Information
| LogP | -1.83-2.28 at 25℃ and pH5-9 |
| dissociation constant | 4.58-8.05 at 22.5-25 ℃ |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Overview | Mycophenolic acid (mycophenolic acid,MPA) is also known as mycophenolic acid, and its chemical name is E-4-methyl -6-(1, 3-dihydro-7-methyl-hydroxy-6-methoxy-3-oxo-5-isobenzo furyl)-4-hexenoic acid; it is mycophenolate acid (mycophenolate mofetil,MMF) is the active ingredient after metabolism in the body, and is a potent non-competitive hypoxanthine nucleotide dehydrogenase (IMPDH) inhibitor, which can selectively inhibit lymphocyte proliferation and inhibit T and B lymphocytes The proliferation caused by the stimulation of mitogens and allogeneic antigens can also inhibit the production of antibodies by B lymphocytes. In addition, MPA can also block the migration of lymphocytes and monocytes to rejection sites and inflammatory sites by inhibiting the glycosylation of adhesion molecules on the surface of lymphocytes and monocytes related to endothelial cell adhesion; therefore, MPA has Good antiviral, antifungal, antibacterial, anti-tumor and immunosuppressive activities; it is often used in the treatment of heart and kidney transplant rejection and immune diseases such as lupus nephritis and vasculitis. |
| preparation method | 1. solvent extraction process (1) sample treatment appropriate amount of mycophenolic acid standard is prepared into a standard solution with a concentration of 500ug/mL, the tested samples are diluted with absolute ethanol by a certain multiple, then filtered with microporous filter membrane, and tested by HPLC. According to the peak area, the sample titer is calculated by multiplying the dilution multiple according to the external standard method. (2) fig. 1 is the experimental step diagram (3) extraction method ① pretreatment of fermentation broth is added with diatomite according to 5-7% of the volume of fermentation broth, pH 3.0-3.5 is adjusted with hydrochloric acid, stirred for 30min, then filtered into the plate frame, the filtrate is discarded, and wet hyphae are obtained. (2) air flow drying wet hyphae is dried by air flow at about 120 ℃ to make hyphae moisture less than 30% to obtain dry hyphae. (3) soak, wash dry hyphae with 5-7 times (v/w) of ethyl acetate stir soak, filter, get soaking liquid. The soaking solution is stirred and washed with 1/5 volume of 0.1mol/L NaOH solution, left to stand and layered, and then washed once with 1/5 volume of drinking water to obtain washing solution. (4) concentration and crystallization: concentrate the washing liquid to 100,000 ug/ml under the conditions of 50-60 ℃ and vacuum ≤-0.08Mpa, cool to 0-10 ℃, crystallize, and filter to obtain crude mycophenolic acid. ⑤ Dissolve, decolorize and crystallize crude mycophenolic acid with 4-6 times (v/w) acetone, heat to 50 ℃ to dissolve completely, add 10% 767 activated carbon, keep heat and decolorize for 1 hour, and filter decolorization solution. The decolorizing solution is concentrated to 100,000 ug/ml under the conditions of 50-60 ℃ and vacuum degree ≤-0.08Mpa, 1/2 volume of purified water is added, and the primary refined product is cooled and crystallized and filtered. ⑥ Refining and drying The primary refined product is dissolved completely with 4-6 times (v/w) anhydrous ethanol, heated to 60 ℃, filtered with a filter membrane, cooled to 0-10 ℃, crystallized and filtered to obtain wet finished product. The wet finished product is dried for 8 hours under the conditions of about 70 ℃ and vacuum ≤-0.09Mpa to obtain mycophenolic acid finished product. 2. Membrane separation process (1) Figure 2 is a flow chart of membrane separation process Figure 3 is a membrane treatment device diagram of membrane separation process (2) Extraction method ① Pretreatment of fermentation broth The fermentation broth is pH10-11 with NaOH and stirred for 30min. (2) Ceramic membrane filtration The pretreated fermentation broth is filtered into the ceramic membrane, and the pH10-11 alkaline water is continuously added until the titer of the permeate is less than or 10% the titer of the fermentation broth, the filtration is stopped to obtain the ceramic membrane filtrate. (3) ultrafiltration membrane filtration ceramic membrane filtrate into ultrafiltration membrane filtration, the remaining small amount of concentrated solution, continue to add drinking water, until the titer of the permeate ≤ 100ug/ml, stop filtration, ultrafiltration membrane filtrate. (4) concentration, crystallization will ultrafiltrate into nanofiltration membrane concentration, through the discharge, until the volume of concentrated liquid is about 1/2 of the volume of fermentation broth, stop concentration, adjust pH2.0-3.0 with hydrochloric acid, crystallization, filtration to obtain crude mycophenolic acid. ⑤ Dissolve, decolorize and crystallize the crude mycophenolic acid product with 4-6 times (v/w) ethanol, heat to 50 ℃ to dissolve completely, add 5% 767 activated carbon, keep the temperature and decolorize for 1 hour, and filter the decolorization solution. Add 1/2 volume of purified water to the decolorization solution, stir, cool and crystallize, and filter a refined product. ⑥ Refining and Drying Use 4-6 times (v/w) absolute ethanol for primary refined products, heat to 60 ℃ to dissolve completely, filter with a filter membrane, add 1/2 volume of purified water to the filtrate, cool to 0-10 ℃, crystallize and filter to obtain wet finished products, and dry the wet finished products at about 70 ℃ with a vacuum degree ≤-0.09Mpa for 8 hours to obtain mycophenolic acid finished products. |
| pharmacological effects | mycophenolic acid has antiviral, antifungal, antibacterial, antitumor and immunosuppressive activities. The immune response depends on the ability of lymphocytes to proliferate. Biological somatic cells proliferate through mitosis. Purine nucleotides and pyrimidine nucleotides are required to synthesize DNA during mitosis. The synthesis of purine nucleotides is accomplished through two pathways, namely the "de novo synthesis" pathway and the remedial synthesis pathway. The "de novo synthesis" pathway uses some small molecules such as carbon dioxide, formate, glutamine, aspartic acid and glycine as precursors for the synthesis of purine cyclic acid, and finally synthesizes nucleotides after a series of enzymatic reactions. The "remedial synthesis" pathway uses pre-formed bases and nucleosides to synthesize nucleotides. The reason why mycophenolic acid has broad-spectrum biological activity is that mycophenolic acid is an efficient, selective, non-competitive and reversible hypoxanthine single nucleotide dehydrogenase (IMPDH) inhibitor, which can inhibit the initial synthesis pathway of guanine nucleotides, exhaust guanine nucleotides, and block DNA synthesis. Mycophenolic acid selectively acts on T and B lymphocytes to inhibit their proliferation. The MPA concentration required to inhibit lymphocyte proliferation has no inhibitory effect on most lymphocytes. Mycophenolic acid can also inhibit the formation of antibodies by directly inhibiting the proliferation of B cells. The therapeutic amount of mycophenolic acid does not inhibit the production of interleukin-I by polysaccharide-activated human peripheral blood lymphocytes, nor does it inhibit the synthesis of interleukin-II and its receptor expression by mitogen-activated peripheral lymphocytes, which is also different from CsA and FK-506. In addition, mycophenolic acid-mediated depletion of in vitro lymphocyte guanosine triphosphate inhibits the conversion of mannose and fucose into glycoproteins. Through this mechanism, mycophenolic acid can reduce the aggregation of lymphocytes and monocytes in chronic inflammatory sites. |
| pharmacokinetics | mycophenolate mofetil (MMF) is completely absorbed by oral administration, and is quickly metabolized into the active ingredient MPA after entering the body. the 99.99% MPA is distributed in plasma, and the plasma protein binding rate of MPA is 97% ~ 99%. it is mainly covered by guanosine diphosphate-glucuronidase (uridine diphosphategluconosyltran- sferases) in intestine, liver and kidney, UGTs) is metabolized to mycophenolic acid glucuronide (mycophenolic acid glucuronide,MPAG), and a small amount is metabolized to 7-O-glucoside-mycophenolic acid and mycophenolic acid acyl glucuronide (mycophenolic acid acylglucuronide,Ac MPAG). Recently Picard et al. [6] discovered a phase I metabolite of MPA-O-desmethyl-mycophenolic acid. MPAG is an inactive metabolite, and the plasma protein binding rate is about 82%. It can compete with MPA for the binding of plasma proteins, so the increase of MPAG in plasma will lead to the increase of free MPA. UGT1A9 and UGT2B7 are the main metabolic enzymes of MPA. UGT1A9 contributes 55%, 75% and 50% to the production of MPAG in liver, kidney and intestinal mucosa respectively. In addition, UGT1A7, UGT1A8 and UGT1A10 can also metabolize MPA into MPAG outside the liver. UGT2B7 mainly metabolizes MPA to Ac MPAG. In vitro studies have found that Ac MPAG has the activity of inhibiting IMPDH, which is believed to be related to the gastrointestinal and hematological toxicity of MPA. MPA has hepatoenteric circulation in the body. Its metabolites are transported into bile through multi-drug resistance-related protein 2(multi-drug resistance protein 2,MRP-2) in the liver. After being discharged into the intestine with bile, it is decomposed into MPA by bacteria and enters the liver again through blood circulation. Therefore, the second peak concentration of MPA appears 4~12h after medication, which increases the exposure of MPA by nearly 40%. Finally, about 93% MPA is excreted in urine, of which 87% is excreted in the form of MPAG and a small amount is excreted in feces (about 6%). |
| monitoring method | there are usually two analytical tools for the analysis of MPA plasma concentration: high-performance liquid chromatography (HPLC) and enzyme-enhanced immunoassay (the corresponding enzyme-multiplied immunoassay technique,EMIT). EMIT cannot determine the concentration of the active metabolite Ac MPAG, because Ac MPAG has cross-reaction with the antibody of MPA, which makes the concentration of MPA determined by EMIT method higher than HPLC, so EMIT method has lower specificity than HPLC. However, EMIT and HPLC have the same diagnostic value in predicting the risk of acute rejection in children with kidney transplantation. Therefore, HPLC and EMIT are both effective methods to predict the occurrence of rejection during MPA treatment, while HPLC has greater specificity in accurately determining MPA and its metabolites, so it is more commonly used. It is also possible to simultaneously determine MPA and its metabolites MPAG and Ac MPAG by capillary electrophoresis, which is simpler than HPLC. |
| application | is applied to the treatment of heart and kidney transplant rejection and immune diseases such as lupus nephritis and vasculitis. (2015-11-03) |
| Uses | Commonly used to select animal cells that can express the xanthine-guanine phosphoribosyltransferase gene of Escherichia coli. Immunosuppressant, inhibition of cytokine-induced nitric oxide production. In the guanosine monophosphate pathway. Block inosine monophosphate dehydrogenase. |
Last Update：2024-04-09 15:16:49
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