MOA

MYCOPHENOLIC ACID

Created: 2001-08-10
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count0
Bond Count44
Aromatic Bond Count6
2D diagram of MOA

Chemical Component Summary

NameMYCOPHENOLIC ACID
Synonyms6-(1,3-DIHYDRO-7-HYDROXY-5-METHOXY-4-METHYL-1-OXOISOBENZOFURAN-6-YL)-4-METHYL-4-HEXANOIC ACID
Systematic Name (OpenEye OEToolkits)(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methyl-hex-4-enoic acid
FormulaC17 H20 O6
Molecular Weight320.337
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C1OCc2c1c(O)c(c(OC)c2C)C\C=C(/C)CCC(=O)O
SMILESCACTVS3.341COc1c(C)c2COC(=O)c2c(O)c1CC=C(C)CCC(O)=O
SMILESOpenEye OEToolkits1.5.0Cc1c2c(c(c(c1OC)CC=C(C)CCC(=O)O)O)C(=O)OC2
Canonical SMILESCACTVS3.341 COc1c(C)c2COC(=O)c2c(O)c1C\C=C(C)\CCC(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 Cc1c2c(c(c(c1OC)C\C=C(/C)\CCC(=O)O)O)C(=O)OC2
InChIInChI1.03 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+
InChIKeyInChI1.03 HPNSFSBZBAHARI-RUDMXATFSA-N

Drug Info: DrugBank

DrugBank IDDB01024 
NameMycophenolic acid
Groups
  • approved
  • investigational
DescriptionMycophenolic acid is a potent immunosuppressant agent that inhibits _de novo_ purine biosynthesis.[L42165] It was derived from _Penicillium stoloniferum_, and has also shown antibacterial, antifungal and antiviral properties.[A249170]. Mycophenolic acid is used in immunosuppressive regimens as part of a triple therapy that includes a calcineurin inhibitor (ciclosporin or tacrolimus) and prednisolone.[A249175] This regimen can be used in place of the older anti-proliferative [azathioprine] due to its stronger immunosuppressive potency.[A249180] However, mycophenolic acid treatment is more expensive and requires therapeutic drug monitoring to optimize efficacy and minimize toxicity.[A249180,A249185] Mycophenolic acid is available as enteric-coated tablets of delayed-release, in an effort to improve upper gastrointestinal adverse events by delaying mycophenolic acid release until it reaches the small intestine.[A249190] [Mycophenolate mofetil], a prodrug of mycophenolic acid, is also prescribed to transplant recipients to prevent organ rejection.[L42020]
Synonyms
  • Acide mycophenolique
  • Acidum mycophenolicum
  • (e)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid
  • Micofenolico acido
  • Mycophenolic acid
Brand Names
  • Sandoz Mycophenolic Acid
  • Myfortic
  • Apo-mycophenolic Acid
  • Mycophenolic Acid
  • Mar-mycophenolic Acid
IndicationMycophenolic acid is an antimetabolite immunosuppressant indicated for prophylaxis of organ rejection in adult patients receiving kidney transplants and in pediatric patients at least 5 years of age and older who are at least 6 months post kidney transplant. Mycophenolic acid is used in combination with cyclosporine and corticosteroids.[L42165]
Categories
  • Acids, Acyclic
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics, Antineoplastic
  • Antimetabolite Immunosuppressant
ATC-CodeL04AA06
CAS number24280-93-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Inosine-5'-monophosphate dehydrogenase 2MADYLISGGTSYVPDDGLTAQQLFNCGDGLTYNDFLILPGYIDFTADQVD...unknowninhibitor
Inosine-5'-monophosphate dehydrogenase 1MADYLISGGTGYVPEDGLTAQQLFASADGLTYNDFLILPGFIDFIADEVD...unknowninhibitor
UDP-glucuronosyltransferase 2B7MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...unknownsubstrate
UDP-glucuronosyltransferase 1-8MARTGWTSPIPLCVSLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...unknownsubstrate
UDP-glucuronosyltransferase 1-9MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL866
PubChem 446541
ChEMBL CHEMBL866
ChEBI CHEBI:92545, CHEBI:168396
CCDC/CSD XAVTEW, MYCPHA02