Mycophenolic acid | CAS#24280-93-1

MedKoo Cat#: 318293 | Name: Mycophenolic acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mycophenolic acid is an immunosuppressant drug used to prevent rejection in organ transplantation. It inhibits an enzyme needed for the growth of T cells and B cells. It was initially marketed as the prodrug mycophenolate mofetil (MMF) to improve oral bioavailability.

Chemical Structure

Mycophenolic acid

CAS#24280-93-1 (free acid)

Theoretical Analysis

MedKoo Cat#: 318293

Name: Mycophenolic acid

CAS#: 24280-93-1 (free acid)

Chemical Formula: C17H20O6

Exact Mass: 320.1300

Molecular Weight: 320.34

Elemental Analysis: C, 63.74; H, 6.29; O, 29.97

Price and Availability

Size	Price	Availability
2g	USD 250.00	2 Weeks
5g	USD 450.00	2 Weeks
10g	USD 750.00	2 Weeks

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Related CAS #

24280-93-1 (free acid) 66341-85-3 (triethylamine) 37415-62-6 (sodium)

Synonym

Mycophenolic acid, MPA, NSC 129185, NSC129185, NSC-129185

IUPAC/Chemical Name

(E)-6-(1,3-Dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid

InChi Key

HPNSFSBZBAHARI-RUDMXATFSA-N

InChi Code

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+

SMILES Code

O=C(O)CC/C(C)=C/CC1=C(O)C2=C(COC2=O)C(C)=C1OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Mycophenolic acid is a potent uncompetitive inosine monophosphate dehydrogenase (IMPDH) inhibitor with an EC50 of 0.24 µM.

In vitro activity:

MPA (mycophenolic acid) suppresses mixed lymphocyte reactions when added 3 days after their initiation. These findings suggest that MPA does not inhibit early responses of T and B lymphocytes to mitogenic or antigenic stimulation but blocks the cells at the time of DNA synthesis. The cytostatic effect of MPA is more potent on lymphocytes than on other cell types, such as fibroblasts and endothelial cells. MPA also inhibits antibody formation by polyclonally activated human B lymphocytes. MPA is an immunosuppressive agent reversibly inhibiting proliferation of T and B lymphocytes and antibody formation, with a profile of activity different from that of other immunosuppressive drugs. Reference: Scand J Immunol. 1991 Feb;33(2):161-73. https://pubmed.ncbi.nlm.nih.gov/1826793/

In vivo activity:

U87 tumor growth was markedly inhibited in vivo in BALB/c nude mice, suggesting that MPA (mycophenolic acid) exerted its antitumor effects via modulation of the tumor microenvironment. Accordingly, microvascular density and pericyte coverage were markedly reduced in MPA-treated tumors in vivo. Reference: Mol Cancer Ther. 2008 Jun;7(6):1656-68. https://pubmed.ncbi.nlm.nih.gov/18566237/

	Solvent	mg/mL	mM
Solubility
	Ethanol	5.0	15.61
	PBS (pH 7.2)	10.0	31.22

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 320.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Senda M, DeLustro B, Eugui E, Natsumeda Y. Mycophenolic acid, an inhibitor of IMP dehydrogenase that is also an immunosuppressive agent, suppresses the cytokine-induced nitric oxide production in mouse and rat vascular endothelial cells. Transplantation. 1995 Nov 27;60(10):1143-8. doi: 10.1097/00007890-199511270-00015. PMID: 7482723. 2. Eugui EM, Almquist SJ, Muller CD, Allison AC. Lymphocyte-selective cytostatic and immunosuppressive effects of mycophenolic acid in vitro: role of deoxyguanosine nucleotide depletion. Scand J Immunol. 1991 Feb;33(2):161-73. doi: 10.1111/j.1365-3083.1991.tb03746.x. PMID: 1826793. 3. Deng Y, Zhang Z, Yang H, Wang J, Feng L, Su Y, Xu D. Mycophenolic Acid Induces the Intestinal Epithelial Barrier Damage through Mitochondrial ROS. Oxid Med Cell Longev. 2022 Jul 5;2022:4195699. doi: 10.1155/2022/4195699. PMID: 35847589; PMCID: PMC9277164. 4. Domhan S, Muschal S, Schwager C, Morath C, Wirkner U, Ansorge W, Maercker C, Zeier M, Huber PE, Abdollahi A. Molecular mechanisms of the antiangiogenic and antitumor effects of mycophenolic acid. Mol Cancer Ther. 2008 Jun;7(6):1656-68. doi: 10.1158/1535-7163.MCT-08-0193. PMID: 18566237.

In vitro protocol:

In vivo protocol:

1. Deng Y, Zhang Z, Yang H, Wang J, Feng L, Su Y, Xu D. Mycophenolic Acid Induces the Intestinal Epithelial Barrier Damage through Mitochondrial ROS. Oxid Med Cell Longev. 2022 Jul 5;2022:4195699. doi: 10.1155/2022/4195699. PMID: 35847589; PMCID: PMC9277164. 2. Domhan S, Muschal S, Schwager C, Morath C, Wirkner U, Ansorge W, Maercker C, Zeier M, Huber PE, Abdollahi A. Molecular mechanisms of the antiangiogenic and antitumor effects of mycophenolic acid. Mol Cancer Ther. 2008 Jun;7(6):1656-68. doi: 10.1158/1535-7163.MCT-08-0193. PMID: 18566237.

1: Berti A, Scotti R, Rizzo N, Sabbadini MG, Tresoldi M. Kaposi's Sarcoma in a Patient with Eosinophilic Granulomatosis with Polyangiitis While Taking Mycophenolate Mofetil. J Allergy Clin Immunol Pract. 2015 May-Jun;3(3):431-2. doi: 10.1016/j.jaip.2014.11.023. Epub 2015 Jan 21. Review. PubMed PMID: 25609339. 2: Walkiewicz-Pielaszek K, Swacha M, Bułło-Piontecka B, Rutkowski B, Olesiñska M. [Mycophenolate mofetil--20 years of experience in treatment of rheumatic diseases]. Postepy Hig Med Dosw (Online). 2015 Feb 6;69:176-87. Review. Polish. PubMed PMID: 25661917. 3: Doukaki S, Platamone A, Alaimo R, Bongiorno MR. Mycophenolate mofetil and enteric-coated mycophenolate sodium in the treatment of pemphigus vulgaris and pemphigus foliaceus. J Dermatolog Treat. 2015 Feb;26(1):67-72. doi: 10.3109/09546634.2014.880395. Epub 2014 Feb 13. Review. PubMed PMID: 24521072. 4: Chen Y, Li Y, Yang S, Li Y, Liang M. Efficacy and safety of mycophenolate mofetil treatment in IgA nephropathy: a systematic review. BMC Nephrol. 2014 Dec 5;15:193. doi: 10.1186/1471-2369-15-193. Review. PubMed PMID: 25475967; PubMed Central PMCID: PMC4267433. 5: Conti F, Ceccarelli F, Perricone C, Massaro L, Cipriano E, Pacucci VA, Truglia S, Miranda F, Morello F, Alessandri C, Spinelli FR, Valesini G. Mycophenolate mofetil in systemic lupus erythematosus: results from a retrospective study in a large monocentric cohort and review of the literature. Immunol Res. 2014 Dec;60(2-3):270-6. doi: 10.1007/s12026-014-8609-x. Review. PubMed PMID: 25468307. 6: Li P, Shuker N, Hesselink DA, van Schaik RH, Zhang X, van Gelder T. Do Asian renal transplant patients need another mycophenolate mofetil dose compared with Caucasian or African American patients? Transpl Int. 2014 Oct;27(10):994-1004. doi: 10.1111/tri.12382. Epub 2014 Aug 22. Review. PubMed PMID: 24963914. 7: Smith MR, Cooper SC. Mycophenolate mofetil therapy in the management of inflammatory bowel disease--a retrospective case series and review. J Crohns Colitis. 2014 Aug;8(8):890-7. doi: 10.1016/j.crohns.2014.01.014. Epub 2014 Feb 4. Review. PubMed PMID: 24507162. 8: Kharfan-Dabaja M, Mhaskar R, Reljic T, Pidala J, Perkins JB, Djulbegovic B, Kumar A. Mycophenolate mofetil versus methotrexate for prevention of graft-versus-host disease in people receiving allogeneic hematopoietic stem cell transplantation. Cochrane Database Syst Rev. 2014 Jul 25;7:CD010280. doi: 10.1002/14651858.CD010280.pub2. Review. PubMed PMID: 25061777. 9: Olejarz W, Bryk D, Zapolska-Downar D. Mycophenolate mofetil--a new atheropreventive drug? Acta Pol Pharm. 2014 May-Jun;71(3):353-61. Review. PubMed PMID: 25265813. 10: Ram R, Yeshurun M, Vidal L, Shpilberg O, Gafter-Gvili A. Mycophenolate mofetil vs. methotrexate for the prevention of graft-versus-host-disease--systematic review and meta-analysis. Leuk Res. 2014 Mar;38(3):352-60. doi: 10.1016/j.leukres.2013.12.012. Epub 2013 Dec 25. Review. PubMed PMID: 24418750. 11: Xiao Y, Huang J, Luo H, Wang J. Mycophenolate mofetil for relapsing-remitting multiple sclerosis. Cochrane Database Syst Rev. 2014 Feb 7;2:CD010242. doi: 10.1002/14651858.CD010242.pub2. Review. PubMed PMID: 24505016. 12: Maripuri S, Kasiske BL. The role of mycophenolate mofetil in kidney transplantation revisited. Transplant Rev (Orlando). 2014 Jan;28(1):26-31. doi: 10.1016/j.trre.2013.10.005. Epub 2013 Oct 25. Review. PubMed PMID: 24321304. 13: Kaltenborn A, Schrem H. Mycophenolate mofetil in liver transplantation: a review. Ann Transplant. 2013 Dec 18;18:685-96. doi: 10.12659/AOT.889299. Review. PubMed PMID: 24346057. 14: Wang X, Qin X, Wang Y, Huang Z, Li X, Zeng Q, Zeng H, Lu Y, Wang L, Lin T. Controlled-dose versus fixed-dose mycophenolate mofetil for kidney transplant recipients: a systematic review and meta-analysis of randomized controlled trials. Transplantation. 2013 Aug 27;96(4):361-7. doi: 10.1097/TP.0b013e31828c6dc7. Review. PubMed PMID: 23558507. 15: Lau EW, Ma PH, Wu X, Chung VC, Wong SY. Mycophenolate mofetil for primary focal segmental glomerulosclerosis: systematic review. Ren Fail. 2013 Jul;35(6):914-29. doi: 10.3109/0886022X.2013.794687. Epub 2013 May 28. Review. PubMed PMID: 23751146. 16: Del Pozo JL, de la Garza RG, de Rada PD, Ornilla E, Yuste JR. Listeria monocytogenes septic arthritis in a patient treated with mycophenolate mofetil for polyarteritis nodosa: a case report and review of the literature. Int J Infect Dis. 2013 Feb;17(2):e132-3. doi: 10.1016/j.ijid.2012.11.005. Epub 2012 Dec 5. Review. PubMed PMID: 23218550. 17: Feng L, Deng J, Huo DM, Wu QY, Liao YH. Mycophenolate mofetil versus azathioprine as maintenance therapy for lupus nephritis: a meta-analysis. Nephrology (Carlton). 2013 Feb;18(2):104-10. doi: 10.1111/nep.12006. Review. PubMed PMID: 23113811. 18: Batko B, Krawiec P, Osieleniec J, Sułowicz W. [Mycophenolate mofetil in the treatment of selected connective tissue diseases]. Przegl Lek. 2013;70(9):724-9. Review. Polish. PubMed PMID: 24455833. 19: Downing HJ, Pirmohamed M, Beresford MW, Smyth RL. Paediatric use of mycophenolate mofetil. Br J Clin Pharmacol. 2013 Jan;75(1):45-59. doi: 10.1111/j.1365-2125.2012.04305.x. Review. PubMed PMID: 22519685; PubMed Central PMCID: PMC3555046. 20: Hogan J, Schwenk MH, Radhakrishnan J. Should mycophenolate mofetil replace cyclophosphamide as first-line therapy for severe lupus nephritis? Kidney Int. 2012 Dec;82(12):1256-60. doi: 10.1038/ki.2012.203. Epub 2012 May 30. Review. PubMed PMID: 22648298.