Article · Wikipedia archive · Last revised Jun 30, 2026

Plitidepsin

Plitidepsin, also known as dehydrodidemnin B and sold under the brand name Aplidin, is a chemical compound extracted from the ascidian Aplidium albicans.

Last revised
Jun 30, 2026
Read time
≈ 3 min
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586 w
Citations
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Source
Wikipedia ↗

Plitidepsin
source ↗
Names
Systematic IUPAC name
(2S)-N-[(1R)-1-({(3S,6R,7S,10R,11S,15S,17S,20S,25aS)-10-[(2S)-Butan-2-yl]-11-hydroxy-3-[(4-methoxyphenyl)methyl]-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,8,13,16,18,21-heptaoxo-15-(propan-2-yl)docosahydro-15H-pyrrolo[2,1-d][10,19,1,4,7,14]dioxatetraazacyclotricosin-7-yl}carbamoyl)-3-methylbutyl]-N-methyl-1-(2-oxopropanoyl)pyrrolidine-2-carboxamide
Other names
Aplidine; Aplidin, dehydrodidemnin B; Aplidin; N-[1-(1,2-Dioxopropyl)-L-prolyl]didemnin A
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
  • InChI=1S/C59H91N7O14/c1-15-35(8)50-47(69)30-49(71)80-53(34(6)7)52(72)37(10)54(73)60-41(26-32(2)3)58(77)65-24-16-18-42(65)48(70)31-63(12)44(29-39-20-22-40(79-14)23-21-39)46(68)28-36(9)51(56(75)61-50)62-55(74)45(27-33(4)5)64(13)59(78)43-19-17-25-66(43)57(76)38(11)67/h20-23,32-37,41-45,47,50-51,53,69H,15-19,24-31H2,1-14H3,(H,60,73)(H,61,75)(H,62,74)/t35-,36-,37-,41-,42-,43-,44-,45+,47-,50+,51-,53-/m0/s1
    Key: RZFJKZZAZSUBCF-VETSTYKFSA-N
  • O=C([C@@H](NC([C@@H](C)C([C@@H](OC(C[C@H](O)[C@H](NC([C@@H](NC([C@H](N(C([C@H]1N(C(C(C)=O)=O)CCC1)=O)C)CC(C)C)=O)[C@@H](C)OC([C@H](CC2=CC=C(OC)C=C2)N3C)=O)=O)[C@@H](C)CC)=O)C(C)C)=O)=O)CC(C)C)N4[C@H](C3=O)CCC4
Properties
C57H87N7O15
Molar mass 1110.357 g·mol−1
Pharmacology
L01XX57 (WHO)
Legal status
  • AU: S4 (Prescription only)12
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Plitidepsin, also known as dehydrodidemnin B and sold under the brand name Aplidin, is a chemical compound extracted from the ascidian Aplidium albicans.3

Medical uses

In Australia, plitidepsin, in combination with dexamethasone, is indicated for the treatment of people with relapsed and refractory multiple myeloma.124

Pharmacological activity

Plitidepsin exhibits antitumor, antiviral and immunosuppressive activities. It shows promise in shrinking tumors in pancreatic, stomach, bladder, and prostate cancers.56

Plitidepsin inhibits the human protein eEF1A which has potential interactions with multiple coronavirus proteins. Plitidepsin possesses antiviral activity against SARS-CoV-2 in vitro and in an in vivo mouse model.7

Society and culture

In July 2003, plitidepsin was granted orphan drug status by the European Medicines Agency (EMA) for treating acute lymphoblastic leukemia.8 In December 2017, the EMA's Committee for Medicinal Products for Human Use (CHMP) adopted a negative opinion, recommending the refusal of the marketing authorization for the treatment of multiple myeloma.9 After a re-examination of the opinion, the refusal of the marketing authorization was confirmed in March 2018.9 The CHMP is of the opinion that the benefits of Aplidin do not outweigh its risks.9 In October 2020, the General Court upheld PharmaMar's appeal and annulled the decision refusing marketing authorization for Aplidin, and the European Commission then returned the application for Aplidin to the EMA.910 In July 2025, PharmaMar withdrew its application for a marketing authorization of Aplidin for the treatment of multiple myeloma.9

Plitidepsin was approved for medical used in Australia in December 2018.2

References

References

  1. "TGA eBS - Product and Consumer Medicine Information Licence". www.ebs.tga.gov.au. Retrieved 28 August 2025.
  2. "AusPAR: Plitidepsin". Therapeutic Goods Administration (TGA). 8 July 2019.
  3. Newman DJ, Cragg GM (August 2004). "Marine natural products and related compounds in clinical and advanced preclinical trials". Journal of Natural Products. 67 (8): 1216–38. doi:10.1021/np040031y. PMID 15332835.
  4. "Aplidin (Specialised Therapeutics Pharma Pty Ltd)". Therapeutic Goods Administration (TGA). 24 July 2025. Retrieved 27 July 2025.
  5. Garrison T (2002). Oceanography: An Invitation to Marine Science (4th ed.). United States: Brooks/Cole. p. 98.
  6. Adrio J, Cuevas C, Manzanares I, Joullié MM (July 2007). "Total synthesis and biological evaluation of tamandarin B analogues". The Journal of Organic Chemistry. 72 (14): 5129–38. doi:10.1021/jo070412r. PMID 17555353.
  7. White KM, Rosales R, Yildiz S, Kehrer T, Miorin L, Moreno E, et al. (January 2021). "Plitidepsin has potent preclinical efficacy against SARS-CoV-2 by targeting the host protein eEF1A". Science. 371 (6532): 926–931. Bibcode:2021Sci...371..926W. doi:10.1126/science.abf4058. PMC 7963220. PMID 33495306.
  8. "Public Summary of Positive Opinion for Orphan Designation of Aplidine for the Treatment of Acute Lymphoblastic Leukaemia" (PDF). European Medicines Agency (EMA). 1 September 2011.
  9. "Aplidin EPAR". European Medicines Agency (EMA).
  10. "Aplidin". European Medicines Agency. 28 October 2020. Retrieved 11 July 2024.
Further reading

Further reading

Delgado-Calle J, Kurihara N, Atkinson EG, Nelson J, Miyagawa K, Galmarini CM, et al. (April 2019). "Aplidin (plitidepsin) is a novel anti-myeloma agent with potent anti-resorptive activity mediated by direct effects on osteoclasts". Oncotarget. 10 (28): 2709–2721. doi:10.18632/oncotarget.26831. PMC 6505631. PMID 31105871.