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Oglufanide

From Wikipedia, the free encyclopedia

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

[edit]
  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.