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Mycophenolic acid

Names

[ CAS No. ]:
24280-93-1

[ Name ]:
Mycophenolic acid

[Synonym ]:
Mycophenolic acid
melbex
6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
EINECS 246-119-3
micofenolicoacido
4-Hexenoic acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-
6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methyl-4-hexenoic acid
Micophenolic acid
Mycophenolinsure
Mycophenolic
mycophenolate
MFCD00036814
6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid
Mycophenolate Mofetil Impurity 6

Biological Activity

[Description]:

Mycophenolic acid is an an immunosuppresant drug and has potent anti-proliferative activity.Target: OthersMycophenolic acid(MPA) 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. MPA did not block the initial phase of viral translation but did interfere with viral protein synthesis in the amplification phase. Quantitative RT-PCR demonstrated that MPA prevented the accumulation of viral positive- and negative-strand RNA as the infection proceeded. MPA inhibits flavivirus infection by preventing synthesis and accumulation of viral RNA [1]. The effects of mycophenolic acid (MPA) on DEN replication in monkey kidney (LLC-MK2) cells were examined. MPA (IC(50)=0.4+/-0.3 microM) inhibited DEN2 replication. Quantitative real-time RT-PCR of viral RNA and plaque assays of virions from DEN2-infected and MPA (10 microM) -treated cells showed a fivefold increase in defective viral RNA production by cells treated with each drug. suggesting that one mode of antiviral action of MPA is by inhibition of inosine monophosphate dehydrogenase and thereby depletion of the intracellular GTP pool [2].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Inflammation/Immunology

[References]

[1]. Diamond, M.S., M. Zachariah, and E. Harris, Mycophenolic acid inhibits dengue virus infection by preventing replication of viral RNA. Virology, 2002. 304(2): p. 211-21.

[2]. Takhampunya, R., et al., Inhibition of dengue virus replication by mycophenolic acid and ribavirin. J Gen Virol, 2006. 87(Pt 7): p. 1947-52.


[Related Small Molecules]

Captisol | Cyclosporin A | H2DCFDA | 0MPTP hydrochloride | GW4869 | Etomoxir | TD139 | Mitoquinone mesylate | GSK2795039 | JC-1 | BAPTA-AM | AP 20187 | Setanaxib (GKT137831) | D-Luciferin | Crotaline

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
611.6±55.0 °C at 760 mmHg

[ Melting Point ]:
141°C

[ Molecular Formula ]:
C17H20O6

[ Molecular Weight ]:
320.337

[ Flash Point ]:
225.8±25.0 °C

[ Exact Mass ]:
320.125977

[ PSA ]:
93.06000

[ LogP ]:
2.92

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.585

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
methanol: 50 mg/mL, clear, colorless to faintly yellow

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MP8050000
CHEMICAL NAME :
4-Hexenoic acid, 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4 -methyl-, (E)-
CAS REGISTRY NUMBER :
24280-93-1
LAST UPDATED :
199409
DATA ITEMS CITED :
24
MOLECULAR FORMULA :
C17-H20-O6
MOLECULAR WEIGHT :
320.37
WISWESSER LINE NOTATION :
T56 BVO DHJ F1 GO1 H2UY1&2VQ IQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
352 mg/kg
TOXIC EFFECTS :
Behavioral - muscle weakness Behavioral - ataxia Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
220 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
230 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
450 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Blood - normocytic anemia Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
505 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1175 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>6 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
900 mg/kg
SEX/DURATION :
male 30 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
2 umol/L
REFERENCE :
BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 31,1109,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - A1173 No. of Facilities: 33 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 2409 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H341-H360D-H372-H410

[ Precautionary Statements ]:
P201-P273-P281-P308 + P313-P501

[ Target Organs ]:
Immune system

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S53-S45

[ RIDADR ]:
2811

[ WGK Germany ]:
3

[ RTECS ]:
MP8050000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2932209090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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