MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 534824 | Name: Murabutide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Murabutide is an adjuvant devoid of pyrogenicity.

Chemical Structure

Murabutide
Murabutide
CAS#74817-61-1

Theoretical Analysis

MedKoo Cat#: 534824

Name: Murabutide

CAS#: 74817-61-1

Chemical Formula: C23H40N4O11

Exact Mass: 548.2694

Molecular Weight: 548.59

Elemental Analysis: C, 50.36; H, 7.35; N, 10.21; O, 32.08

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Murabutide
IUPAC/Chemical Name
2-Acetamido-3-O-((R)-1-(((S)-1-(((R)-3-carbamoyl-1-carboxypropyl)carbamoyl)ethyl)carbamoyl)ethyl)-2-deoxy-D-glucopyranose, butyl ester
InChi Key
ZDSXRJABOCTJTD-HUYBTDLASA-N
InChi Code
InChI=1S/C23H40N4O11/c1-5-6-9-36-22(34)14(7-8-16(24)30)27-20(32)11(2)25-21(33)12(3)37-19-17(26-13(4)29)23(35)38-15(10-28)18(19)31/h11-12,14-15,17-19,23,28,31,35H,5-10H2,1-4H3,(H2,24,30)(H,25,33)(H,26,29)(H,27,32)/t11-,12+,14+,15+,17+,18+,19+,23?/m0/s1
SMILES Code
OC1[C@H](NC(C)=O)[C@H]([C@@H]([C@@H](CO)O1)O)O[C@@H](C(N[C@H](C(N[C@@H](C(OCCCC)=O)CCC(N)=O)=O)C)=O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 548.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Jakopin Ž. Murabutide revisited: a review of its pleiotropic biological effects. Curr Med Chem. 2013;20(16):2068-79. doi: 10.2174/0929867311320160002. PMID: 23531213. 2: Liu L, Qu H, Qin H, Yang Y, Liao Z, Cui J, Gao F, Cai J. NOD2 agonist murabutide alleviates radiation-induced injury through DNA damage response pathway mediated by ATR. J Cell Physiol. 2019 Nov;234(11):21294-21306. doi: 10.1002/jcp.28734. Epub 2019 May 3. PMID: 31054162. 3: Kantipakala R, Bonam SR, Vemireddy S, Miryala S, Halmuthur M SK. Squalane- based emulsion vaccine delivery system: composition with murabutide activate Th1 response. Pharm Dev Technol. 2019 Mar;24(3):269-275. doi: 10.1080/10837450.2018.1469150. Epub 2018 Jul 4. PMID: 29688119. 4: Audibert FM, Przewlocki G, Leclerc CD, Jolivet ME, Gras-Masse HS, Tartar AL, Chedid LA. Enhancement by murabutide of the immune response to natural and synthetic hepatitis B surface antigens. Infect Immun. 1984 Jul;45(1):261-6. PMID: 6735468; PMCID: PMC263310. 5: Vidal V, Dewulf J, Bahr GM. Enhanced maturation and functional capacity of monocyte-derived immature dendritic cells by the synthetic immunomodulator Murabutide. Immunology. 2001 Aug;103(4):479-87. doi: 10.1046/j.1365-2567.2001.01269.x. PMID: 11529939; PMCID: PMC1783259. 6: Bahr GM, De La Tribonniere X, Darcissac E, Ajana F, Bocket L, Sissoko D, Yazdanpanah Y, Dewulf J, Amiel C, Mouton Y. Clinical and immunological effects of a 6 week immunotherapy cycle with murabutide in HIV-1 patients with unsuccessful long-term antiretroviral treatment. J Antimicrob Chemother. 2003 Jun;51(6):1377-88. doi: 10.1093/jac/dkg244. Epub 2003 Apr 25. PMID: 12716777. 7: Amiel C, De La Tribonnière X, Vidal V, Darcissac E, Mouton Y, Bahr GM. Clinical tolerance and immunologic effects after single or repeated administrations of the synthetic immunomodulator murabutide in HIV-1-infected patients. J Acquir Immune Defic Syndr. 2002 Jul 1;30(3):294-305. doi: 10.1097/00126334-200207010-00005. PMID: 12131566. 8: Truong MJ, Delsart V, Bahr GM. Differentially expressed genes in HIV-1-infected macrophages following treatment with the virus-suppressive immunomodulator murabutide. Virus Res. 2004 Jan;99(1):25-33. doi: 10.1016/j.virusres.2003.09.011. PMID: 14687943. 9: Feinen B, Petrovsky N, Verma A, Merkel TJ. Advax-adjuvanted recombinant protective antigen provides protection against inhalational anthrax that is further enhanced by addition of murabutide adjuvant. Clin Vaccine Immunol. 2014 Apr;21(4):580-6. doi: 10.1128/CVI.00019-14. Epub 2014 Feb 19. PMID: 24554695; PMCID: PMC3993118. 10: Darcissac EC, Truong MJ, Dewulf J, Mouton Y, Capron A, Bahr GM. The synthetic immunomodulator murabutide controls human immunodeficiency virus type 1 replication at multiple levels in macrophages and dendritic cells. J Virol. 2000 Sep;74(17):7794-802. doi: 10.1128/jvi.74.17.7794-7802.2000. PMID: 10933686; PMCID: PMC112309. 11: Jackson EM, Herbst-Kralovetz MM. Intranasal vaccination with murabutide enhances humoral and mucosal immune responses to a virus-like particle vaccine. PLoS One. 2012;7(7):e41529. doi: 10.1371/journal.pone.0041529. Epub 2012 Jul 25. PMID: 22855691; PMCID: PMC3405106. 12: Bahr GM. Non-specific immunotherapy of HIV-1 infection: potential use of the synthetic immunodulator murabutide. J Antimicrob Chemother. 2003 Jan;51(1):5-8. doi: 10.1093/jac/dkg063. PMID: 12493780. 13: Bahr GM, Darcissac E, Pouillart PR, Chedid LA. Synergistic effects between recombinant interleukin-2 and the synthetic immunomodulator murabutide: selective enhancement of cytokine release and potentiation of antitumor activity. J Interferon Cytokine Res. 1996 Feb;16(2):169-78. doi: 10.1089/jir.1996.16.169. PMID: 8742370. 14: Sridevi K, Khanna N, Chattree V, Pal PC, Haq W, Rao DN. Reversal of T cell anergy in leprosy patients: in vitro presentation with Mycobacterium leprae antigens using murabutide and Trat peptide in liposomal delivery. Int Immunopharmacol. 2003 Nov;3(12):1589-600. doi: 10.1016/S1567-5769(03)00181-4. PMID: 14555284. 15: De La Tribonniere X, Mouton Y, Vidal V, Darcissac E, Sissoko D, Fontier C, Douadi Y, Dewulf Jl, Amiel C, Bahr GM. A phase I study of a six-week cycle of immunotherapy with Murabutide in HIV-1 patients naive to antiretrovirals. Med Sci Monit. 2003 Jun;9(6):PI43-50. PMID: 12824957. 16: Darcissac EC, Bahr GM, Pouillart PR, Riveau GJ, Parant MA. Selective potentiation of cytokine expression in human whole blood by murabutide, a muramyl dipeptide analogue. Cytokine. 1996 Aug;8(8):658-66. doi: 10.1006/cyto.1996.0088. PMID: 8894442. 17: Vidal VF, Castéran N, Riendeau CJ, Kornfeld H, Darcissac EC, Capron A, Bahr GM. Macrophage stimulation with Murabutide, an HIV-suppressive muramyl peptide derivative, selectively activates extracellular signal-regulated kinases 1 and 2, C/EBPbeta and STAT1: role of CD14 and Toll-like receptors 2 and 4. Eur J Immunol. 2001 Jul;31(7):1962-71. doi: 10.1002/1521-4141(200107)31:7<1962::aid- immu1962>3.0.co;2-v. PMID: 11449348. 18: Chattree V, Khanna N, Bisht V, Rao DN. Liposomal delivery of Mycobacterium leprae antigen(s) with murabutide and Trat peptide inhibits Fas-mediated apoptosis of peripheral blood mononuclear cells derived from leprosy patients. Indian J Biochem Biophys. 2007 Oct;44(5):386-93. PMID: 18341215. 19: Audibert F, Przewlocki G, Lefrancier P, Choay J, Chedid L. Renforcement de l'activité d'un vaccin contre l'hépatite virale de type B par association avec le murabutide [Enhancement of the activity of hepatitis B virus vaccine by association with murabutide]. C R Seances Acad Sci III. 1982 Nov 22;295(10):611-4. French. PMID: 6218866. 20: Goasduff T, Darcissac EC, Vidal V, Capron A, Bahr GM. The transcriptional response of human macrophages to murabutide reflects a spectrum of biological effects for the synthetic immunomodulator. Clin Exp Immunol. 2002 Jun;128(3):474-82. doi: 10.1046/j.1365-2249.2002.01872.x. PMID: 12067302; PMCID: PMC1906249.