Mycophenolate mofetil

Identification

Summary

Mycophenolate mofetil is an inosine monophosphate dehydrogenase inhibitor used to prevent the rejection of kidney, heart, or liver transplants.

Brand Names

Cellcept, Myfenax

Generic Name

Mycophenolate mofetil

DrugBank Accession Number

DB00688

Background

Mycophenolate mofetil, also known as MMF or CellCept, is a prodrug of mycophenolic acid, and classified as a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH).³ This drug is an immunosuppressant combined with drugs such as Cyclosporine and corticosteroids to prevent organ rejection after hepatic, renal, and cardiac transplants.¹³ It is marketed by Roche Pharmaceuticals and was granted FDA approval for the prophylaxis of transplant rejection in 1995.⁶ In addition to the above uses, mycophenolate mofetil has also been studied for the treatment of nephritis and other complications of autoimmune diseases. Unlike another immunosuppressant class, the calcineurin inhibitors, MMF generally does not cause nephrotoxicity or fibrosis.^2,3

Previously, mycophenolic acid (MPA) was administered to individuals with autoimmune diseases beginning in the 1970s, but was discontinued due to gastrointestinal effects and concerns over carcinogenicity.⁶ The new semi-synthetic 2-morpholinoethyl ester of MPA was synthesized to avoid the gastrointestinal effects associated with the administration of MPA. It demonstrates an increased bioavailability, a higher efficacy, and reduced gastrointestinal effects when compared to MPA.⁶

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Mycophenolate mofetil (DB00688)

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Weight

Average: 433.4947
Monoisotopic: 433.210052351

Chemical Formula

C₂₃H₃₁NO₇

Synonyms

• 2-morpholinoethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate
• Mycophenolate mofetil
• Mycophenolic acid morpholinoethyl ester

External IDs

• 168396
• RS 61443
• RS-61443

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Pharmacology

Indication

Mycophenolate mofetil is indicated in combination with other immunosuppressants to prevent the rejection of kidney, heart, or liver transplants in adult and pediatric patients ≥3 months old.¹⁵ Mycophenolate mofetil may also be used off-label as a second-line treatment for autoimmune hepatitis that has not responded adequately to first-line therapy.⁴ Other off-label uses of this drug include lupus-associated nephritis and dermatitis in children.⁵

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Adjunct therapy in prevention of	Transplanted organ rejection		••••••••••••	•••••• •••••••••		•••••••• •••••••••• ••••••••••• ••••••
Adjunct therapy in prevention of	Transplanted organ rejection		••••••••••••	•••••• •••••••••		•••••••• •••••••••• ••••••••••• ••••••
Adjunct therapy in prevention of	Transplanted organ rejection		••••••••••••	•••••• •••••••••		•••••••• •••••••••• ••••••••••• ••••••

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Pharmacodynamics

Mycophenolate mofetil is a prodrug of mycophenolic acid (MPA). The active form of mycophenolate, MPA, prevents the proliferation of immune cells and the formation of antibodies that cause transplant rejection.³ The above effects lead to higher rates of successful transplantation, avoiding the devastating effects of graft rejection.

Mechanism of action

The active metabolite of mycophenolate, mycophenolic acid, prevents T-cell and B-cell proliferation and the production of cytotoxic T-cells and antibodies. Lymphocyte and monocyte adhesion to endothelial cells of blood vessels that normally part of inflammation is prevented via the glycosylation of cell adhesion molecules by MPA.⁹ MPA inhibits de novo purine biosynthesis (that promotes immune cell proliferation) by inhibiting inosine 5’-monophosphate dehydrogenase enzyme (IMPDH), with a preferential inhibition of IMPDH II.⁶ IMPDH normally transforms inosine monophosphate (IMP) to xanthine monophosphate (XMP), a metabolite contributing to the production of guanosine triphosphate (GTP).^2,3,5 GTP is an important molecule for the synthesis of ribonucleic acid (RNA), deoxyribonucleic acid (DNA), and protein. As a result of the above cascade of effects, mycophenolate mofetil reduces de-novo production of guanosine nucleotides, interfering with the synthesis of DNA, RNA, and protein required for immune cell production.⁶ Further contributing to the above anti-inflammatory effects, MMF depletes tetrahydrobiopterin, causing the decreased function of inducible nitric oxide synthase enzyme, in turn decreasing the production of peroxynitrite, a molecule that promotes inflammation.¹²

Target	Actions	Organism
AInosine-5'-monophosphate dehydrogenase 1	inhibitor inducer	Humans
AInosine-5'-monophosphate dehydrogenase 2	inhibitor	Humans
U6-pyruvoyl tetrahydrobiopterin synthase	inhibitor	Humans

Absorption

Mycophenolate mofetil is rapidly absorbed in the small intestine.^13,10 The maximum concentration of its active metabolite, MPA, is attained 60 to 90 minutes following an oral dose.⁶ The average bioavailability of orally administered mycophenolate mofetil in a pharmacokinetic study of 12 healthy patients was 94%. In healthy volunteers, the Cmax of mycophenolate mofetil was 24.5 (±9.5)μg/mL.¹³ In renal transplant patients 5 days post-transplant, Cmax was 12.0 (±3.82) μg/mL, increasing to 24.1 (±12.1)μg/mL 3 months after transplantation. AUC values were 63.9 (±16.2) μg•h/mL in healthy volunteers after one dose, and 40.8 (±11.4) μg•h/mL, and 65.3 (±35.4)μg•h/mL 5 days and 3 months after a renal transplant, respectively.¹³ The absorption of mycophenolate mofetil is not affected by food.⁶

Volume of distribution

The volume of distribution of mycophenolate mofetil is 3.6 (±1.5) to 4.0 (±1.2) L/kg.¹³

Protein binding

The protein binding of mycophenolic acid, the metabolite of mycophenolate mofetil, is 97%¹³ and it is mainly bound to albumin.⁶ MPAG, the inactive metabolite, is 82% bound to plasma albumin at normal therapeutic concentrations. At elevated MPAG concentrations due to various reasons, including renal impairment, the binding of MPA may be decreased due to competition for binding.¹³

Metabolism

After both oral and intravenous administration mycophenolate mofetil is entirely metabolized by liver carboxylesterases 1 and 2 to mycophenolic acid (MPA), the active parent drug. It is then metabolized by the enzyme glucuronyl transferase, producing the inactive phenolic glucuronide of MPA (MPAG).¹³ The glucuronide metabolite is important, as it is then converted to MPA through enterohepatic recirculation. Mycophenolate mofetil that escapes metabolism in the intestine enters the liver via the portal vein and is transformed to pharmacologically active MPA in the liver cells.¹⁰N-(2-carboxymethyl)-morpholine, N-(2-hydroxyethyl)-morpholine, and the N-oxide portion of N-(2-hydroxyethyl)-morpholine are additional metabolites of MMF occurring in the intestine as a result of liver carboxylesterase 2 activity.^10,13 UGT1A9 and UGT2B7 in the liver are the major enzymes contributing to the metabolism of MPA in addition to other UGT enzymes, which also play a role in MPA metabolism. The four major metabolites of MPA are 7-O-MPA-β-glucuronide (MPAG, inactive), MPA acyl-glucuronide (AcMPAG), produced by uridine 5ʹ-diphosphate glucuronosyltransferases (UGT) activities, 7-O-MPA glucoside produced via UGT, and small amounts 6-O-des-methyl-MPA (DM-MPA) via CYP3A4/5 and CYP2C8 enzymes.⁶

Hover over products below to view reaction partners

• Mycophenolate mofetil
  • Mycophenolic acid
    • 7-O-MPA glucoside
    • 6-O-desmethyl-MPA (DM-MPA)
  • Mycophenolic acid glucuronide + Mycophenolic acyl-glucuronide (AcMPAG)
  • N-(2-carboxymethyl)-morpholine
  • N-(2-hydroxyethyl)-morpholine
  • N-(2-hydroxyethyl)-morpholine N-oxide

Route of elimination

A small amount of drug is excreted as MPA in the urine (less than 1%). When mycophenolate mofetil was given orally in a pharmacokinetic study, it was found to be 93% excreted in urine and 6% excreted in feces. Approximately 87% of the entire administered dose is found to be excreted in the urine as MPAG, an inactive metabolite.^6,13

Half-life

The average apparent half-life of mycophenolate mofetil is 17.9 (±6.5) hours after oral administration and 16.6 (±5.8) hours after intravenous administration.¹³

Clearance

Plasma clearance of mycophenolate mofetil is 193 mL/min after an oral dose and 177 (±31) mL/min after an intravenous dose.¹³

Adverse Effects

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Toxicity

LD50

The LD50 of oral mycophenolate mofetil in rats is 250 mg/kg and >4000 mg/kg in mice.¹⁴

Overdose information

Possible signs and symptoms of acute overdose may consist of hematological abnormalities including leukopenia and neutropenia, and gastrointestinal symptoms.^6,7,8

Pathways

Pathway	Category
Mycophenolic Acid Metabolism Pathway	Drug metabolism

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Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Mycophenolate mofetil may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abametapir	The serum concentration of Mycophenolate mofetil can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Mycophenolate mofetil can be increased when combined with Abatacept.
Abemaciclib	Abemaciclib may decrease the excretion rate of Mycophenolate mofetil which could result in a higher serum level.
Abiraterone	The metabolism of Mycophenolate mofetil can be decreased when combined with Abiraterone.

Food Interactions

• Avoid multivalent ions. Take multivalent ions such as calcium, iron, or magnesium at least 2 hours after taking this medication.
• Take on an empty stomach. Take at least 1 hour before or 2 hours after meals.

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Mycophenolate mofetil hydrochloride	UXH81S8ZVB	116680-01-4	OWLCGJBUTJXNOF-HDNKIUSMSA-N

Active Moieties

Name	Kind	UNII	CAS	InChI Key
Mycophenolic acid	prodrug	HU9DX48N0T	24280-93-1	HPNSFSBZBAHARI-RUDMXATFSA-N

Product Images

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International/Other Brands

CellCept Oral Suspension (Genentech USA, Inc.) / CellCept Intravenous (Genentech USA, Inc.)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
CellCept	Tablet, film coated	500 mg/1	Oral	Genentech, Inc.	1997-06-19	Not applicable
CellCept	Tablet, film coated	500 mg/1	Oral	F. Hoffmann-La Roche Ltd	1997-06-19	2010-06-20
Cellcept	Capsule	250 mg	Oral	Roche Registration Gmb H	2020-12-16	Not applicable
Cellcept	Powder, for suspension	1 g/5ml	Oral	Roche Registration Gmb H	2016-09-08	Not applicable
CellCept	Powder, for suspension	200 mg / mL	Oral	Hoffmann La Roche	2002-08-27	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Accel-mycophenolate Mofetil Capsules	Capsule	250 mg	Oral	Accel Pharma Inc	Not applicable	Not applicable
Accel-mycophenolate Mofetil Tablets	Tablet	500 mg	Oral	Accel Pharma Inc	Not applicable	Not applicable
Ach-mycophenolate	Capsule	250 mg	Oral	Accord Healthcare Inc	2012-05-01	Not applicable
Ach-mycophenolate	Tablet	500 mg	Oral	Accord Healthcare Inc	2012-02-16	Not applicable
Ach-mycophenolate	Powder, for suspension	200 mg / mL	Oral	Accord Healthcare Inc	Not applicable	Not applicable

Categories

Drug Categories

• Agents Causing Muscle Toxicity
• Anti-Bacterial Agents
• Anti-Infective Agents
• Antibiotics, Antineoplastic
• Antibiotics, Antitubercular
• Antimetabolite Immunosuppressant
• BCRP/ABCG2 Substrates
• Cytochrome P-450 CYP2C8 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 CYP3A5 Substrates
• Cytochrome P-450 Substrates
• Drugs that are Mainly Renally Excreted
• Fatty Acids
• Immunologic Factors
• Immunosuppressive Agents
• IMP Dehydrogenase, antagonists & inhibitors
• Lipids
• Mycophenolic Acid and Prodrugs
• OATP1B1/SLCO1B1 Substrates
• OATP1B3 substrates
• P-glycoprotein substrates
• UGT1A1 Substrates
• UGT1A6 substrate
• UGT1A9 Substrates
• UGT2B7 substrates

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as phthalides. These are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Isobenzofuranones

Direct Parent

Phthalides

Alternative Parents

Anisoles / Alkyl aryl ethers / Fatty acid esters / Morpholines / Dicarboxylic acids and derivatives / Vinylogous acids / Trialkylamines / Amino acids and derivatives / Lactones / Carboxylic acid esters / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds / Carbonyl compounds / Hydrocarbon derivatives / Organic oxides / Organopnictogen compounds

show 7 more

Substituents

Alkyl aryl ether / Amine / Amino acid or derivatives / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Dicarboxylic acid or derivatives / Ether / Fatty acid ester / Fatty acyl / Hydrocarbon derivative / Lactone / Morpholine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Oxacycle / Oxazinane / Phthalide / Tertiary aliphatic amine / Tertiary amine / Vinylogous acid

show 20 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound, carboxylic ester, phenols, ether, gamma-lactone (CHEBI:8764)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

9242ECW6R0

CAS number

128794-94-5

InChI Key

RTGDFNSFWBGLEC-SYZQJQIISA-N

InChI

InChI=1S/C23H31NO7/c1-15(5-7-19(25)30-13-10-24-8-11-29-12-9-24)4-6-17-21(26)20-18(14-31-23(20)27)16(2)22(17)28-3/h4,26H,5-14H2,1-3H3/b15-4+

IUPAC Name

2-(morpholin-4-yl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate

SMILES

COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C

References

Synthesis Reference

Roger C. Fu, De-Mei Leung, Jeffrey S. Fleitman, Michele C. Rizzolio, Andrew R. Miksztal, "Process for preparing pharmaceutical compositions containing crystalline anhydrous mycophenolate mofetil salts." U.S. Patent US5545637, issued November, 1988.

US5545637

General References

1. Picard N, Cresteil T, Premaud A, Marquet P: Characterization of a phase 1 metabolite of mycophenolic acid produced by CYP3A4/5. Ther Drug Monit. 2004 Dec;26(6):600-8. [Article]
2. Villarroel MC, Hidalgo M, Jimeno A: Mycophenolate mofetil: An update. Drugs Today (Barc). 2009 Jul;45(7):521-32. doi: 10.1358/dot.2009.45.7.1384878. [Article]
3. Allison AC: Mechanisms of action of mycophenolate mofetil. Lupus. 2005;14 Suppl 1:s2-8. [Article]
4. Santiago P, Schwartz I, Tamariz L, Levy C: Systematic review with meta-analysis: mycophenolate mofetil as a second-line therapy for autoimmune hepatitis. Aliment Pharmacol Ther. 2019 Apr;49(7):830-839. doi: 10.1111/apt.15157. Epub 2019 Feb 13. [Article]
5. Sagcal-Gironella AC, Fukuda T, Wiers K, Cox S, Nelson S, Dina B, Sherwin CM, Klein-Gitelman MS, Vinks AA, Brunner HI: Pharmacokinetics and pharmacodynamics of mycophenolic acid and their relation to response to therapy of childhood-onset systemic lupus erythematosus. Semin Arthritis Rheum. 2011 Feb;40(4):307-13. doi: 10.1016/j.semarthrit.2010.05.007. Epub 2010 Jul 23. [Article]
6. Park H: The emergence of mycophenolate mofetilin dermatology: from its roots in the world of organ transplantation to its versatile role in the dermatology treatment room. J Clin Aesthet Dermatol. 2011 Jan;4(1):18-27. [Article]
7. Alex R, Mathew M, Arul S, Kundavaram A: Overdose of mycophenolate mofetil managed in a secondary care hospital in South India. Indian J Pharmacol. 2014 May-Jun;46(3):337-8. doi: 10.4103/0253-7613.132191. [Article]
8. Parfitt JR, Jayakumar S, Driman DK: Mycophenolate mofetil-related gastrointestinal mucosal injury: variable injury patterns, including graft-versus-host disease-like changes. Am J Surg Pathol. 2008 Sep;32(9):1367-72. [Article]
9. Allison AC, Eugui EM: Purine metabolism and immunosuppressive effects of mycophenolate mofetil (MMF). Clin Transplant. 1996 Feb;10(1 Pt 2):77-84. [Article]
10. Lamba V, Sangkuhl K, Sanghavi K, Fish A, Altman RB, Klein TE: PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9. doi: 10.1097/FPC.0000000000000010. [Article]
11. Sherwin CM, Fukuda T, Brunner HI, Goebel J, Vinks AA: The evolution of population pharmacokinetic models to describe the enterohepatic recycling of mycophenolic acid in solid organ transplantation and autoimmune disease. Clin Pharmacokinet. 2011 Jan;50(1):1-24. doi: 10.2165/11536640-000000000-00000. [Article]
12. Srinivas TR, Kaplan B, Meier-Kriesche HU: Mycophenolate mofetil in solid-organ transplantation. Expert Opin Pharmacother. 2003 Dec;4(12):2325-45. doi: 10.1517/14656566.4.12.2325 . [Article]
13. FDA label, Mycophenolate mofetil [Link]
14. MSDS, Mycophenolate mofetil [Link]
15. FDA Approved Drug Products: Cellcept (mycophenolate mofetil) for oral or intravenous administration [Link]

External Links

Human Metabolome Database

HMDB0014826

KEGG Drug

D00752

KEGG Compound

C07908

PubChem Compound

5281078

PubChem Substance

46505626

ChemSpider

4444535

BindingDB

50248299

RxNav

68149

ChEBI

8764

ChEMBL

CHEMBL1456

ZINC

ZINC000021297660

Therapeutic Targets Database

DNC000397

PharmGKB

PA450566

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Mycophenolic_acid

FDA label

Download (200 KB)

MSDS

Download (82.3 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Basic Science	Immunosuppression / Transplanted Kidney Complication	1
4	Active Not Recruiting	Health Services Research	Liver Transplantation	1
4	Active Not Recruiting	Treatment	Autoimmune Hepatitis	1
4	Active Not Recruiting	Treatment	Elderly Patients / Immunosuppression / Renal Transplant Recipient Patients	1
4	Active Not Recruiting	Treatment	Hepatocellular Carcinoma	1

Pharmacoeconomics

Manufacturers

• Roche palo alto llc
• Accord healthcare inc usa
• Apotex corp
• Endo pharmaceuticals inc
• Mylan pharmaceuticals inc
• Roxane laboratories inc
• Sandoz inc
• Strides arcolab ltd
• Teva pharmaceuticals usa
• Zydus pharmaceuticals usa inc
• Accord healthcare inc
• Apotex inc

Packagers

• Accord Healthcare
• Amerisource Health Services Corp.
• Apotex Inc.
• Cadila Healthcare Ltd.
• Cardinal Health
• Chunghwa Chemical Synthesis and Biotech Co. Ltd.
• Endo Pharmaceuticals Inc.
• F Hoffmann La Roche Ltd.
• F Hoffmann-La Roche Ltd.
• Intas Pharmaceuticals Ltd.
• JHP Pharmaceuticals LLC
• Kaiser Foundation Hospital
• Lake Erie Medical and Surgical Supply
• Legacy Pharmaceuticals Packaging LLC
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Poli Industria Chimica SPA
• Rebel Distributors Corp.
• Roxane Labs
• Sandoz
• Syntex SA
• Teva Pharmaceutical Industries Ltd.
• UDL Laboratories
• Zydus Pharmaceuticals

Dosage Forms

Form	Route	Strength
Solution	Intravenous	500.00 mg
Tablet	Oral	500.00 mg
Tablet	Oral	250.00 mg
Capsule	Oral	250 mg/1
Injection, powder, lyophilized, for solution	Intravenous	500 mg/20mL
Powder, for suspension	Oral	1 g/5ml
Powder, for suspension	Oral	200 mg / mL
Tablet	Oral	500 mg
Tablet, film coated	Oral	500 mg/1
Tablet, coated	Oral	500 mg
Injection, solution	Intravenous	500 mg
Injection, powder, for solution	Intravenous	500 mg
Powder, for solution	Intravenous	500 mg / vial
Tablet	Oral	500.000 mg
Tablet, delayed release	Oral
Tablet	Oral	500.0 mg
Capsule	Oral	250 mg
Capsule	Oral
Tablet	Oral
Tablet, film coated	Oral	250 mg
Capsule, gelatin coated	Oral	250 mg
Powder, for suspension	Oral	200 mg/1mL
Tablet	Oral	500 mg/1
Tablet, coated	Oral	500 mg/1
Tablet, film coated	Oral	500 mg
Injection, powder, for solution	Parenteral	500 mg
Tablet, delayed release	Oral	180 MG
Tablet, delayed release	Oral	360 MG
Tablet, film coated	Oral
Capsule	Oral	250.000 mg
Injection, powder, lyophilized, for solution	Intravenous	500 mg/1vial

Prices

Unit description	Cost	Unit
CellCept 200 mg/ml Suspension 175ml Bottle	875.84USD	bottle
Cellcept 500 mg vial	65.03USD	vial
Cellcept 500 mg tablet	10.43USD	tablet
Mycophenolate Mofetil 500 mg tablet	8.25USD	tablet
Mycophenolate 500 mg tablet	7.93USD	tablet
CellCept 250 mg capsule	5.21USD	capsule
Mycophenolate Mofetil 250 mg capsule	4.13USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5688529	No	1997-11-18	2014-11-18
US5543408	No	1996-08-06	2013-09-15
CA2172506	No	2007-07-17	2014-09-27
CA1333285	No	1994-11-29	2011-11-29

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	93-94	https://pubchem.ncbi.nlm.nih.gov/compound/Mycophenolate-mofetil#section=Experimental-Properties
boiling point (°C)	637.6±55.0	http://www.chemspider.com/Chemical-Structure.4444535.html
water solubility	43 μg/mL	https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050722s021,050723s019,050758s019,050759s024lbl.pdf
logP	2.5	http://www.hmdb.ca/metabolites/HMDB0014826
pKa	5.6 for the morpholino group and 8.5 for the phenolic group	https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050722s021,050723s019,050758s019,050759s024lbl.pdf

Predicted Properties

Property	Value	Source
Water Solubility	0.095 mg/mL	ALOGPS
logP	2.17	ALOGPS
logP	3.47	Chemaxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.76	Chemaxon
pKa (Strongest Basic)	6.19	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	94.53 Å2	Chemaxon
Rotatable Bond Count	10	Chemaxon
Refractivity	117.1 m3·mol-1	Chemaxon
Polarizability	45.54 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.8938
Blood Brain Barrier	+	0.8594
Caco-2 permeable	+	0.5904
P-glycoprotein substrate	Substrate	0.8908
P-glycoprotein inhibitor I	Inhibitor	0.8381
P-glycoprotein inhibitor II	Inhibitor	0.8061
Renal organic cation transporter	Inhibitor	0.5379
CYP450 2C9 substrate	Non-substrate	0.8528
CYP450 2D6 substrate	Non-substrate	0.602
CYP450 3A4 substrate	Substrate	0.7646
CYP450 1A2 substrate	Non-inhibitor	0.6878
CYP450 2C9 inhibitor	Non-inhibitor	0.9155
CYP450 2D6 inhibitor	Non-inhibitor	0.7684
CYP450 2C19 inhibitor	Non-inhibitor	0.9122
CYP450 3A4 inhibitor	Non-inhibitor	0.8316
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8664
Ames test	Non AMES toxic	0.6484
Carcinogenicity	Non-carcinogens	0.953
Biodegradation	Not ready biodegradable	0.658
Rat acute toxicity	3.0412 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.771
hERG inhibition (predictor II)	Non-inhibitor	0.7653

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0w4i-2393200000-d549469b4d276b82f0a4
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0019-1741900000-022d7009668cda105e50
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01q9-2311900000-6c9f1f6a9ba2f7c15dcc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-1002900000-32f1fa3e046be77c6761
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a59-1494700000-ce5bc383a8db64c2eb88
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ftb-3298300000-8f9693becb5be4ab8d21
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0mvi-2491400000-2b78d4502011e99f3075
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052b-0090000000-529ada72463c26884e1c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01q9-2311900000-6c9f1f6a9ba2f7c15dcc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-1002900000-32f1fa3e046be77c6761
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a59-1494700000-ce5bc383a8db64c2eb88
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0ftb-3298300000-8f9693becb5be4ab8d21
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0mvi-2491400000-2b78d4502011e99f3075
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052b-0090000000-529ada72463c26884e1c
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	226.078366	predicted	DarkChem Lite v0.1.0
[M-H]-	227.719866	predicted	DarkChem Lite v0.1.0
[M-H]-	198.02019	predicted	DeepCCS 1.0 (2019)
[M-H]-	226.078366	predicted	DarkChem Lite v0.1.0
[M-H]-	227.719866	predicted	DarkChem Lite v0.1.0
[M-H]-	198.02019	predicted	DeepCCS 1.0 (2019)
[M+H]+	224.998766	predicted	DarkChem Lite v0.1.0
[M+H]+	228.515566	predicted	DarkChem Lite v0.1.0
[M+H]+	200.57143	predicted	DeepCCS 1.0 (2019)
[M+H]+	224.998766	predicted	DarkChem Lite v0.1.0
[M+H]+	228.515566	predicted	DarkChem Lite v0.1.0
[M+H]+	200.57143	predicted	DeepCCS 1.0 (2019)
[M+Na]+	225.318466	predicted	DarkChem Lite v0.1.0
[M+Na]+	227.132566	predicted	DarkChem Lite v0.1.0
[M+Na]+	209.12022	predicted	DeepCCS 1.0 (2019)
[M+Na]+	225.318466	predicted	DarkChem Lite v0.1.0
[M+Na]+	227.132566	predicted	DarkChem Lite v0.1.0
[M+Na]+	209.12022	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Inosine-5'-monophosphate dehydrogenase 1

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

Inducer

General Function

Rna binding

Specific Function

Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...

Gene Name

IMPDH1

Uniprot ID

P20839

Uniprot Name

Inosine-5'-monophosphate dehydrogenase 1

Molecular Weight

55405.365 Da

References

1. Bremer S, Rootwelt H, Bergan S: Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. Clin Chem. 2007 Jun;53(6):1023-9. Epub 2007 Apr 26. [Article]
2. Wang J, Yang JW, Zeevi A, Webber SA, Girnita DM, Selby R, Fu J, Shah T, Pravica V, Hutchinson IV, Burckart GJ: IMPDH1 gene polymorphisms and association with acute rejection in renal transplant patients. Clin Pharmacol Ther. 2008 May;83(5):711-7. Epub 2007 Sep 12. [Article]
3. Sanquer S, Maison P, Tomkiewicz C, Macquin-Mavier I, Legendre C, Barouki R, Lang P: Expression of inosine monophosphate dehydrogenase type I and type II after mycophenolate mofetil treatment: a 2-year follow-up in kidney transplantation. Clin Pharmacol Ther. 2008 Feb;83(2):328-35. Epub 2007 Aug 22. [Article]
4. Allison AC: Mechanisms of action of mycophenolate mofetil. Lupus. 2005;14 Suppl 1:s2-8. [Article]

Details2. Inosine-5'-monophosphate dehydrogenase 2

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Rna binding

Specific Function

Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore pl...

Gene Name

IMPDH2

Uniprot ID

P12268

Uniprot Name

Inosine-5'-monophosphate dehydrogenase 2

Molecular Weight

55804.495 Da

References

1. Vannozzi F, Filipponi F, Di Paolo A, Danesi R, Urbani L, Bocci G, Catalano G, De Simone P, Mosca F, Del Tacca M: An exploratory study on pharmacogenetics of inosine-monophosphate dehydrogenase II in peripheral mononuclear cells from liver-transplant recipients. Transplant Proc. 2004 Nov;36(9):2787-90. [Article]
2. Bremer S, Rootwelt H, Bergan S: Real-time PCR determination of IMPDH1 and IMPDH2 expression in blood cells. Clin Chem. 2007 Jun;53(6):1023-9. Epub 2007 Apr 26. [Article]
3. Allison AC: Mechanisms of action of mycophenolate mofetil. Lupus. 2005;14 Suppl 1:s2-8. [Article]

Details3. 6-pyruvoyl tetrahydrobiopterin synthase

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

General Function

Metal ion binding

Specific Function

Involved in the biosynthesis of tetrahydrobiopterin, an essential cofactor of aromatic amino acid hydroxylases. Catalyzes the transformation of 7,8-dihydroneopterin triphosphate into 6-pyruvoyl tet...

Gene Name

PTS

Uniprot ID

Q03393

Uniprot Name

6-pyruvoyl tetrahydrobiopterin synthase

Molecular Weight

16385.63 Da

References

1. Allison AC: Mechanisms of action of mycophenolate mofetil. Lupus. 2005;14 Suppl 1:s2-8. [Article]
2. Allison AC, Eugui EM: Mycophenolate mofetil and its mechanisms of action. Immunopharmacology. 2000 May;47(2-3):85-118. [Article]
3. Srinivas TR, Kaplan B, Meier-Kriesche HU: Mycophenolate mofetil in solid-organ transplantation. Expert Opin Pharmacother. 2003 Dec;4(12):2325-45. doi: 10.1517/14656566.4.12.2325 . [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54