Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Mycophenolic acid [USAN:INN:BAN]
RN: 24280-93-1
UNII: HU9DX48N0T
InChIKey: HPNSFSBZBAHARI-RUDMXATFSA-N

Note

  • Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.

Molecular Formula

  • C17-H20-O6

Molecular Weight

  • 320.339
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics, Antineoplastic
  • Antibiotics, Antitubercular
  • Antineoplastic
  • Antineoplastic Agents
  • Antitubercular Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Mutation Data
  • Natural Product
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Mycophenolic acid
  • Mycophenolic acid [USAN:INN:BAN]

MeSH Heading

  • Mycophenolic acid

Synonyms

  • (E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid
  • 4-Methyl-5-methoxy-7-hydroxy-6-(5-carboxy-3-methylpent-2-en-1-yl)-phthalide (E)-
  • 6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid (E)-
  • Acide mycophenolique
  • Acide mycophenolique [INN-French]
  • Acido micofenolico
  • Acido micofenolico [INN-Spanish]
  • Acidum mycophenolicum
  • Acidum mycophenolicum [INN-Latin]
  • CCRIS 5565
  • EC 246-119-3
  • EINECS 246-119-3
  • Lilly-68618
  • Ly 68618
  • Melbex
  • Micofenolico acido
  • Micofenolico acido [Spanish]
  • Mycophenolate
  • Mycophenolic acid
  • Mycophenolsaeure
  • Myfortic
  • NSC 129185
  • NSC-129185
  • RS-61443 [as mofetil]
  • UNII-HU9DX48N0T

Systematic Names

  • 4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (E)-
  • 4-Hexenoic acid, 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-, (E)-
  • Mycophenolic acid

Registry Numbers

CAS Registry Number

  • 24280-93-1

FDA UNII

  • HU9DX48N0T

System Generated Number

  • 0024280931

Structure Descriptors

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+

InChIKey

HPNSFSBZBAHARI-RUDMXATFSA-N

Smiles

c12c(c(c(C\C=C(\CCC(O)=O)C)c(c1C)OC)O)C(=O)OC2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 intraperitoneal 1gm/kg (1000mg/kg)   Agricultural and Biological Chemistry. Vol. 33, Pg. 1594, 1969.
mouse LD50 intraperitoneal 505mg/kg (505mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 29, Pg. 400, 1982.
mouse LD50 oral 1gm/kg (1000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 445, 1981.
mouse LD50 subcutaneous 1175mg/kg (1175mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 29, Pg. 400, 1982.
mouse LDLo intravenous 500mg/kg (500mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 3, Pg. 1740, 1978.
rabbit LD50 oral > 6gm/kg (6000mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 29, Pg. 400, 1982.
rat LD50 intraperitoneal 220mg/kg (220mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 29, Pg. 400, 1982.
rat LD50 intravenous 450mg/kg (450mg/kg)   Progress in Medical Chemistry. Vol. 9, Pg. 1, 1973.
rat LD50 intravenous 450mg/kg (450mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: NORMOCYTIC ANEMIA
Progress in Medical Chemistry. Vol. 9, Pg. 1, 1973.
rat LD50 oral 352mg/kg (352mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE WEAKNESS
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 29, Pg. 400, 1982.
rat LD50 subcutaneous 230mg/kg (230mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 29, Pg. 400, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 141 deg C   EXP
log P (octanol-water) 4.220 (none)   EST
Atmospheric OH Rate Constant 2.93E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.