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Details

Stereochemistry ACHIRAL
Molecular Formula C17H20O6
Molecular Weight 320.3371
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MYCOPHENOLIC ACID

SMILES

COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(O)=O

InChI

InChIKey=HPNSFSBZBAHARI-RUDMXATFSA-N
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+

HIDE SMILES / InChI

Molecular Formula C17H20O6
Molecular Weight 320.3371
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Mycophenolic acid (MPA) possesses antibacterial, antifungal, antiviral, immunosuppressive and anticancer properties. Mycophenolic acid (MPA) is a fungal metabolite that was initially discovered by Bartolomeo Gosio in 1893 as an antibiotic against anthrax bacillus, Bacillus anthracis. It is an uncompetitive and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), and therefore inhibits the de novo pathway of guanosine nucleotide synthesis without incorporation to DNA. It was approved under the brand name Myfortic for the prophylaxis of organ rejection in adult patients receiving a kidney transplant and is indicated for the prophylaxis of organ rejection in pediatric patients 5 years of age and older who are at least 6 months post kidney transplant. Myfortic is to be used in combination with cyclosporine and corticosteroids.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
MYFORTIC

Cmax

ValueDoseCo-administeredAnalytePopulation
18.9 μg/mL
720 mg 2 times / day multiple, oral
MYCOPHENOLIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
57.4 μg × h/mL
720 mg 2 times / day multiple, oral
MYCOPHENOLIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11.7 h
720 mg 2 times / day multiple, oral
MYCOPHENOLIC ACID plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Dosage in Adult Kidney Transplant Patients: the recommended dose of Myfortic is 720 mg administered twice daily (1440 mg total daily dose). Dosage in Pediatric Kidney Transplant Patients: the recommended dose of Myfortic in conversion (at least 6 months post-transplant) pediatric patients age 5 years and older is 400 mg/m2 body surface area (BSA) administered twice daily (up to a maximum dose of 720 mg administered twice daily. Administration Myfortic tablets should be taken on an empty stomach, 1 hour before or 2 hours after food intake
Route of Administration: Oral
In Vitro Use Guide
It was investigated the antiviral activity and mechanism of action of mycophenolic acid (MPA) against contemporary clinical isolates of influenza A and B viruses. The 50 % cellular cytotoxicity (CC50) of MPA in Madin Darby canine kidney cell line was over 50 µM. MPA prevented influenza virus-induced cell death in the cell-protection assay, with significantly lower IC50 for influenza B virus B/411 than that of influenza A(H1N1)pdm09 virus H1/415 (0.208 vs 1.510 µM, P=0.0001). For H1/415, MPA interfered with the early stage of viral replication before protein synthesis. For B/411, MPA may also act at a later stage since MPA was active against B/411 even when added 12 h post-infection. Virus-yield reduction assay showed that the replication of B/411 was completely inhibited by MPA at concentrations ≥0.78 µM, while there was a dose-dependent reduction of viral titer for H1/415. The antiviral effect of MPA was completely reverted by guanosine supplementation. Plaque reduction assay showed that MPA had antiviral activity against eight different clinical isolates of A(H1N1), A(H3N2), A(H7N9) and influenza B viruses (IC50 <1 µM).
Substance Class Chemical
Record UNII
HU9DX48N0T
Record Status Validated (UNII)
Record Version