Mycophenolic acid

Mycophenolic acid
Clinical data
Pronunciation	/ˌmaɪkoʊfɪˈnɒlɪk/
Trade names	Cellcept, Myfortic, others
Other names	MPA, Mycophenolate sodium, Mycophenolate mofetil (AAN AU), Mycophenolate mofetil (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a601081
License data	EU EMA: by INN; US DailyMed: Mycophenolate_mofetil;
Pregnancy; category	AU: D;
Routes of; administration	By mouth, intravenous
ATC code	L04AA06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	72% (sodium),; 94% (mofetil)
Protein binding	82–97%
Metabolism	Liver
Elimination half-life	17.9±6.5 hours
Excretion	Urine (93%),; faeces (6%)
Identifiers
	IUPAC name (4E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid;
CAS Number	24280-93-1 ;
PubChem CID	446541;
IUPHAR/BPS	6832;
DrugBank	DB01024 ;
ChemSpider	393865 ;
UNII	HU9DX48N0T;
KEGG	D05096 ;
ChEBI	CHEBI:168396 ;
ChEMBL	ChEMBL866 ;
CompTox Dashboard (EPA)	DTXSID4041070 ;
ECHA InfoCard	100.041.912
Chemical and physical data
Formula	C17H20O6
Molar mass	320.341 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1OCc2c1c(O)c(c(OC)c2C)C\C=C(/C)CCC(=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+ ; Key:HPNSFSBZBAHARI-RUDMXATFSA-N ;
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Mycophenolic acid is an immunosuppressant medication used to prevent rejection following organ transplantation and to treat autoimmune conditions such as Crohn's disease and lupus. Specifically it is used following kidney, heart, and liver transplantation. It can be given by mouth or by injection into a vein. It comes as mycophenolate sodium and mycophenolate mofetil.

Common side effects include nausea, infections, and diarrhea. Other serious side effects include an increased risk of cancer, progressive multifocal leukoencephalopathy, anemia, and gastrointestinal bleeding. Use during pregnancy may harm the baby. It works by blocking inosine monophosphate dehydrogenase (IMPDH), which is needed by lymphocytes to make guanosine.

Mycophenolic acid was initially discovered by Italian Bartolomeo Gosio in 1893. It was rediscovered in 1945 and 1968. It was approved for medical use in the United States in 1995 following the discovery of its immunosuppressive properties in the 1990s. It is available as a generic medication. In 2020, it was the 313th most commonly prescribed medication in the United States, with more than 900 thousand prescriptions.

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