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CAS 24280-93-1

Chemistry

Chemistry

Also known as: 24280-93-1, Mycophenolate, Myfortic, Melbex, Mycophenolsaeure, 483-60-3

Molecular Formula

C₁₇H₂₀O₆

Molecular Weight

320.3 g/mol

InChI Key

HPNSFSBZBAHARI-RUDMXATFSA-N

FDA UNII

HU9DX48N0T

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.

Mycophenolic acid is an Antimetabolite Immunosuppressant.

1 2D Structure

CAS 24280-93-1

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid

2.1.2 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+

2.1.3 InChI Key

HPNSFSBZBAHARI-RUDMXATFSA-N

2.1.4 Canonical SMILES

CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)O)O

2.1.5 Isomeric SMILES

CC1=C2COC(=O)C2=C(C(=C1OC)C/C=C(\C)/CCC(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

HU9DX48N0T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cellcept

2. Mofetil Hydrochloride, Mycophenolate

3. Mofetil, Mycophenolate

4. Mycophenolate Mofetil

5. Mycophenolate Mofetil Hydrochloride

6. Mycophenolate Sodium

7. Mycophenolate, Sodium

8. Mycophenolic Acid Morpholinoethyl Ester

9. Myfortic

10. Rs 61443

11. Rs-61443

12. Rs61443

13. Sodium Mycophenolate

2.3.2 Depositor-Supplied Synonyms

1. 24280-93-1

2. Mycophenolate

3. Myfortic

4. Melbex

5. Mycophenolsaeure

6. 483-60-3

7. Lilly-68618

8. 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic Acid

9. Nsc-129185

10. Acido Micofenolico

11. Micofenolico Acido

12. Acide Mycophenolique

13. Acidum Mycophenolicum

14. (4e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic Acid

15. Ccris 5565

16. Nsc 129185

17. Ly 68618

18. (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic Acid

19. (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic Acid

20. (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1h-2-benzofuran-5-yl)-4-methylhex-4-enoic Acid

21. Mfcd00036814

22. Lilly 68618

23. 4-hexenoic Acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (e)-

24. Chembl866

25. Hu9dx48n0t

26. 6-(1,3-dihydro-7-hydroxy-5-methoxy-4-methyl-1-oxoisobenzofuran-6-yl)-4-methyl-4-hexanoic Acid

27. Chebi:168396

28. Tnp00198

29. Rs-61443 [as Mofetil]

30. Nsc129185

31. 4-hexenoic Acid, 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-, (e)-

32. 4-methyl-5-methoxy-7-hydroxy-6-(5-carboxy-3-methylpent-2-en-1-yl)-phthalide (e)-

33. 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methylhex-4-enoic Acid

34. 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic Acid (e)-

35. 4-hexenoic Acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4e)-

36. Ncgc00016786-01

37. Cas-24280-93-1

38. Mycophenolic Acid 100 Microg/ml In Acetonitrile

39. Dsstox_cid_21070

40. Dsstox_rid_79619

41. Dsstox_gsid_41070

42. Mycophenolic Acid-d3 Solution

43. Mycophenoic Acid

44. 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1h-isobenzofuran-5-yl)-4-methyl-4-hexenoic Acid

45. Micofenolico Acido [spanish]

46. (4e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic Acid (mycophenolic Acid)

47. (e)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid

48. 4-hexenoic Acid,6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4e)-

49. 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid

50. 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic Acid

51. Moa

52. Smr000471887

53. Acido Micofenolico [inn-spanish]

54. Acide Mycophenolique [inn-french]

55. Acidum Mycophenolicum [inn-latin]

56. Sr-01000597602

57. Einecs 246-119-3

58. Unii-hu9dx48n0t

59. Mycophenolic-acid

60. Prestwick_817

61. Einecs 207-595-8

62. Mycophenolic Acid [usan:inn:ban]

63. Tocris-1505

64. (z)-mycophenolic Acid

65. 1jr1

66. Starbld0040186

67. Mycophenolic Acid (tn)

68. Prestwick2_000556

69. Prestwick3_000556

70. Spectrum5_001654

71. Mycophenolic Acid (mpa)

72. Mycophenolic Acid Solution

73. Upcmld-dp028

74. 4-hexenoic Acid, (e)-

75. Ec 246-119-3

76. Mycophenolate;rs-61443

77. Schembl4549

78. Mycophenolic (mycophenolate)

79. Mycophenolic Acid, >=98%

80. Bspbio_000631

81. Bspbio_002534

82. Mycophenolate [vandf]

83. Mls001074701

84. Mls002222265

85. Mls002695945

86. Bidd:gt0456

87. Spectrum1500674

88. Mycophenolic Acid [mi]

89. Bpbio1_000695

90. Gtpl6832

91. Megxm0_000120

92. Mycophenolic Acid (usan/inn)

93. Myfortic (mycophenolate Sodium)

94. Schembl2514376

95. Zinc1758

96. Mycophenolic Acid [inn]

97. Dtxsid4041070

98. Mycophenolic Acid [usan]

99. Upcmld-dp028:001

100. Acon0_000960

101. Acon1_000496

102. Bdbm19264

103. Chebi:92545

104. Hms500h08

105. Ex-a975

106. Mycophenolic Acid [vandf]

107. Mycophenolic Acid [mart.]

108. Hms1569p13

109. Hms1921a18

110. Hms2089a17

111. Hms2092g22

112. Hms2096p13

113. Hms2268h22

114. Hms3403p09

115. Hms3412f09

116. Hms3676f09

117. Pharmakon1600-01500674

118. Mycophenolic Acid [who-dd]

119. Act02623

120. Amy40494

121. Bcp05321

122. Hy-b0421

123. Tox21_110610

124. Bbl034696

125. Ccg-39914

126. Nsc757424

127. S2487

128. Stl419986

129. Mycophenolic Acid, Analytical Standard

130. Akos015888214

131. Tox21_110610_1

132. Ac-4491

133. Bcp9000970

134. Db01024

135. Ds-1638

136. Mycophenolic Acid [orange Book]

137. Nsc-757424

138. Sdccgmls-0066618.p001

139. (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1h-isobenzofuran-5-yl)-4-methyl-hex-4-enoic Acid

140. Idi1_000146

141. Ncgc00016786-02

142. Ncgc00016786-03

143. Ncgc00016786-04

144. Ncgc00016786-05

145. Ncgc00016786-06

146. Ncgc00016786-07

147. Ncgc00016786-08

148. Ncgc00016786-09

149. Ncgc00016786-10

150. Ncgc00016786-11

151. Ncgc00016786-12

152. Ncgc00016786-15

153. Ncgc00025190-01

154. Ncgc00025190-02

155. Ncgc00025190-03

156. Ncgc00025190-04

157. Ncgc00025190-05

158. Ncgc00025190-07

159. Ncgc00025190-08

160. Ncgc00025190-09

161. Ncgc00025190-10

162. (4e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxohydroisobenzofuran-5-yl)-4-methylhex -4-enoic Acid

163. Bm164624

164. Mycophenolic Acid - Cas 24280-93-1

165. Sbi-0051945.p003

166. A-249

167. M2216

168. Sw196951-2

169. C20380

170. D05096

171. M 5255

172. M02087

173. Ab00052466-13

174. Ab00052466-14

175. Ab00052466_15

176. Ab00052466_16

177. 280m931

178. A817192

179. Mycophenolate Mofetil Impurity, Mycophenolic Acid-

180. Q420553

181. Sr-01000597602-1

182. Sr-01000597602-3

183. Sr-01000597602-4

184. Brd-k63750851-001-06-6

185. Brd-k63750851-001-13-2

186. Mycophenolate Mofetil Impurity F [ep Impurity]

187. Mycophenolate Mofetil Impurity, Mycophenolic Acid- [usp Impurity]

188. Mycophenolic Acid, Powder, Bioreagent, Suitable For Cell Culture, >=98%

189. 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic Acid;nsc 129185

190. 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthanlanyl)-4-methyl-4-hexanoic Acid

191. (e)-6-(1,3-dihydro-4-hydroxy-6- Methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic Acid

192. (e)-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic Acid

193. 1162256-90-7

194. 4-hexenoic Acid, 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-, (4e)- (9ci)

195. 4-hexenoic Acid, 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-, (e)- (8ci)

196. 4-hexenoic Acid,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5- Isobenzofuranyl)-4-methyl-, (e)-

197. 4-methyl-6-[3-oxo-7-methyl-4-hydroxy-6-methoxy-1,3-dihydroisobenzofuran-5-yl]-4-hexenoic Acid

198. E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic Acid

199. Mycophenolic Acid Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₂₀O₆
Molecular Weight	320.3 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	320.12598835 g/mol
Monoisotopic Mass	320.12598835 g/mol
Topological Polar Surface Area	93.1 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	486
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the prophylaxis of organ rejection in patients receiving allogeneic renal transplants, administered in combination with cyclosporine and corticosteroids.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Mycophenolic acid is an antibiotic substance derived from Penicillium stoloniferum. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase. Mycophenolic acid is important because of its selective effects on the immune system. It prevents the proliferation of T-cells, lymphocytes, and the formation of antibodies from B-cells. It also may inhibit recruitment of leukocytes to inflammatory sites.

5.2 MeSH Pharmacological Classification

Antibiotics, Antitubercular

Substances obtained from various species of microorganisms that are, alone or in combination with other agents, of use in treating various forms of tuberculosis; most of these agents are merely bacteriostatic, induce resistance in the organisms, and may be toxic. (See all compounds classified as Antibiotics, Antitubercular.)

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

MYCOPHENOLIC ACID

5.3.2 FDA UNII

HU9DX48N0T

5.3.3 Pharmacological Classes

Antimetabolite Immunosuppressant [EPC]

5.4 ATC Code

L - Antineoplastic and immunomodulating agents

L04 - Immunosuppressants

L04A - Immunosuppressants

L04AA - Selective immunosuppressants

L04AA06 - Mycophenolic acid

5.5 Absorption, Distribution and Excretion

Absorption

Bioavailability following oral administration of Myfortic delayed-release tablet ranges from 70-95%

Volume of Distribution

54 25 L

Clearance

140 +/- 30 mL/min [Stable renal transplant patients]

5.6 Metabolism/Metabolites

Mycophenolic acid is metabolized mainly by glucuronyl transferase to glucuronidated metabolites, predominantly the phenolic glucuronide, mycophenolic acid glucuronide (MPAG). MPAG does not manifest pharmacological activity. The acyl glucuronide minor metabolite has pharmacological activity similar to mycophenolic acid. The AUC ratio of Mycophenolic acid:MPAG:acyl glucuronide is approximately 1:24:0.28 at steady state.

Mycophenolic acid has known human metabolites that include 6-O-desmethyl-MPA (DM-MPA) and Mycophenolic acid glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.7 Biological Half-Life

The mean elimination half-life for mycophenolic acid ranges from 8-16 hours, while that of the MPAG metabolite ranges from 13-17 hours.

5.8 Mechanism of Action

Mycophenolic acid is a potent, selective, uncompetitive, and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), and therefore inhibits the de novo pathway of guanosine nucleotide synthesis without incorporation into DNA. Because T- and B-lymphocytes are critically dependent for their proliferation on de novo synthesis of purines, whereas other cell types can utilize salvage pathways, mycophenolic acid has potent cytostatic effects on lymphocytes. Mycophenolic acid inhibits proliferative responses of T- and B-lymphocytes to both mitogenic and allospecific stimulation. Addition of guanosine or deoxyguanosine reverses the cytostatic effects of mycophenolic acid on lymphocytes. Mycophenolic acid also suppresses antibody formation by B-lymphocytes. Mycophenolic acid prevents the glycosylation of lymphocyte and monocyte glycoproteins that are involved in intercellular adhesion to endothelial cells and may inhibit recruitment of leukocytes into sites of inflammation and graft rejection.