Oglufanide

Oglufanide
Clinical data
Other namesIM-862; Oglufanide disodium; Thymogen
Identifiers
  • (4S)-4-amino-5-[[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-5-oxopentanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H19N3O5
Molar mass333.344 g·mol−1
3D model (JSmol)
  • C1=CC=C2C(=C1)C(=CN2)C[C@@H](C(=O)O)NC(=O)[C@H](CCC(=O)O)N
  • InChI=1S/C16H19N3O5/c17-11(5-6-14(20)21)15(22)19-13(16(23)24)7-9-8-18-12-4-2-1-3-10(9)12/h1-4,8,11,13,18H,5-7,17H2,(H,19,22)(H,20,21)(H,23,24)/t11-,13-/m0/s1
  • Key:LLEUXCDZPQOJMY-AAEUAGOBSA-N

Oglufanide (Glu-Trp, thymogen) is a dipeptide having the sequence L-Glu-L-Trp.[1][2] It is an immunomodulator and has been investigated for the treatment of hepatitis C.[3][4][1] It was originally isolated from calf thymus gland extracts and has been used medicinally in Russia as a component of Thymalin, a mixture of thymus derived peptides and small proteins also containing other components such as thymosins and thymulin.[5][6][7] Synthetic versions of Glu-Trp containing unnatural D-amino acids or with gamma-peptide bond links also have different immunomodulatory effects such as the immunosuppressor thymodepressin (D-Glu-D-Trp).[8][9][2]

References

  1. 1 2 Kaushik NK, Kaushik N, Attri P, Kumar N, Kim CH, Verma AK, et al. (June 2013). "Biomedical importance of indoles". Molecules. 18 (6). Basel, Switzerland: 6620–6662. doi:10.3390/molecules18066620. PMC 6270133. PMID 23743888.
  2. 1 2 Deigin V, Linkova N, Vinogradova J, Vinogradov D, Polyakova V, Medvedev D, et al. (6 May 2024). "The First Reciprocal Activities of Chiral Peptide Pharmaceuticals: Thymogen and Thymodepressin, as Examples". International Journal of Molecular Sciences. 25 (9): 5042. doi:10.3390/ijms25095042. PMC 11084461. PMID 38732260.
  3. ↑ Nesterova IV (December 1999). "Modern Immunotherapy in Clinical Medicine: Present and Future". Russian Journal of Immunology. 4 (4): 322–326. PMID 12687147.
  4. ↑ Hamill P, Brown K, Jenssen H, Hancock RE (1 December 2008). "Novel anti-infectives: is host defence the answer?". Current Opinion in Biotechnology. 19 (6): 628–636. doi:10.1016/j.copbio.2008.10.006. PMID 19000763.
  5. ↑ Anisimov VN, Khavinson VK, Morozov VG (2000). "Immunomodulatory synthetic dipeptide L-Glu-L-Trp slows down aging and inhibits spontaneous carcinogenesis in rats". Biogerontology. 1 (1): 55–59. doi:10.1023/a:1010042008969. PMID 11707921.
  6. ↑ Malinin VV, Durnova AO, Polyakova VO, Kvetnoi IM (May 2015). "Dipeptides Increase Functional Activity of Human Skin Fibroblasts". Bulletin of Experimental Biology and Medicine. 159 (1): 164–167. doi:10.1007/s10517-015-2914-9. PMID 26033609.
  7. ↑ Avolio F, Martinotti S, Khavinson VK, Esposito JE, Giambuzzi G, Marino A, et al. (25 March 2022). "Peptides Regulating Proliferative Activity and Inflammatory Pathways in the Monocyte/Macrophage THP-1 Cell Line". International Journal of Molecular Sciences. 23 (7): 3607. doi:10.3390/ijms23073607. PMC 8999041. PMID 35408963.
  8. ↑ Semina OV, Semenets TN, Zamulaeva IA, Selivanova EI, Malyutina YV, Saenko AS, et al. (February 2006). "Effects of structural and "mixed" isomers of Glu-Trp dipeptide on normal hemopoietic stem cells". Bulletin of Experimental Biology and Medicine. 141 (2): 250–253. doi:10.1007/s10517-006-0141-0. PMID 16984110.
  9. ↑ Deigin VI, Semenets TN, Zamulaeva IA, Maliutina YV, Selivanova EI, Saenko AS, et al. (March 2007). "The effects of the EW dipeptide optical and chemical isomers on the CFU-S population in intact and irradiated mice". International Immunopharmacology. 7 (3): 375–382. doi:10.1016/j.intimp.2006.11.010. PMID 17276896.
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