Mycophenolate mofetil

Mycophenolic acid
Clinical data


Pronunciation	/ˌmaɪkoʊfᵻˈnɒlɪk/
Trade names	CellCept, Myfortic
AHFS/Drugs.com	Multum Consumer Information
MedlinePlus	a601081
License data	EU EMA: Cellcept US FDA: mycophenol
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	Oral, intravenous
ATC code	L04AA06 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	72% (sodium), 94% (mofetil)
Protein binding	82–97%
Metabolism	Hepatic
Biological 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^Y
PubChem (CID)	446541
IUPHAR/BPS	6832
DrugBank	DB01024^Y
ChemSpider	393865^Y
UNII	HU9DX48N0T^N
KEGG	D05096^Y
ChEBI	CHEBI:168396^Y
ChEMBL	CHEMBL866^Y
ECHA InfoCard	100.041.912
Chemical and physical data
Formula	C₁₇H₂₀O₆
Molar mass	320.34 g/mol
3D model (Jmol)	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+^Y Key:HPNSFSBZBAHARI-RUDMXATFSA-N^Y
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Mycophenolate mofetil
Clinical data


Trade names	CellCept
AHFS/Drugs.com	Monograph
License data	EU EMA: CellCept US FDA: Mycophenolate_mofetil
ATC code	L04AA06 (WHO)
Legal status
Legal status	as above
Identifiers
IUPAC name 2-Morpholin-4-ylethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
CAS Number	128794-94-5^Y
PubChem (CID)	5281078
DrugBank	DB00688^Y
ChemSpider	4444535^Y
KEGG	C07908^Y
ChEBI	CHEBI:8764^N
ChEMBL	CHEMBL1456^Y
ECHA InfoCard	100.041.912
Chemical and physical data
Formula	C₂₃H₃₁NO₇
Molar mass	433.49474 g/mol
3D model (Jmol)	Interactive image
SMILES CC1=C(C(=C(C2=C1COC2=O)O)CC=C(C)CCC(=O)OCCN3CCOCC3)OC
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+^Y Key:RTGDFNSFWBGLEC-SYZQJQIISA-N^Y
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Mycophenolic acid, less accurately called mycophenolate, 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. More recently, the salt mycophenolate sodium has also been introduced. Mycophenolate mofetil is marketed under the trade name CellCept and mycophenolate sodium as Myfortic.

Discovered by an Italian medical scientist Bartolomeo Gosio in 1893, mycophenolic acid was the first antibiotic to be synthesised in pure and crystalline form. But its medical application was forgotten until two American scientists C.L. Alsberg and O.M. Black resynthesised it in 1912, and gave its chemical name. It was eventually found to be a broad-spectrum acting drug having antiviral, antifungal, antibacterial, anticancer, and antipsoriasis properties. The clinically usable drug Cellcept was developed by South African geneticist Anthony Allison and his wife Elsie M. Eugui. It was first approved by the US Food and Drug Administration on 3 May 1995 for use in kidney transplantation.

Mycophenolate is used for the prevention of organ transplant rejection. Mycophenolate mofetil is indicated for the prevention of organ transplant rejection in adults and renal transplant rejection in children over 2 years; whereas mycophenolate sodium is indicated for the prevention of renal transplant rejection in adults. Mycophenolate sodium has also been used for the prevention of rejection in liver, heart, and/or lung transplants in children older than two years. It is also used for retroperitoneal fibrosis along with a number of other medications.

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Wikipedia