Synonym
Butirosin sulfate; CI642; CI 642; CI-642
IUPAC/Chemical Name
4-amino-N-((1R,2S,3R,4R,5S)-5-amino-4-(((2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-2-hydroxycyclohexyl)-2-hydroxybutanamide bis(sulfate) dihydrate
InChi Key
IUQWHBUMCWSQIM-OXNIXSIASA-N
InChi Code
InChI=1S/C21H41N5O12.2H2O4S.2H2O/c22-2-1-8(28)19(34)26-7-3-6(24)17(37-20-11(25)15(32)13(30)9(4-23)35-20)18(12(7)29)38-21-16(33)14(31)10(5-27)36-21;2*1-5(2,3)4;;/h6-18,20-21,27-33H,1-5,22-25H2,(H,26,34);2*(H2,1,2,3,4);2*1H2/t6-,7+,8?,9+,10+,11+,12-,13+,14?,15+,16+,17+,18+,20+,21-;;;;/m0..../s1
SMILES Code
NCCC(C(N[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O)O[C@@H]2O[C@@H](C([C@H]2O)O)CO)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3N)O)O)CN)N)=O)O.OS(=O)(O)=O.OS(=O)(O)=O.O.O
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
>2 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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
787.76
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.
| 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: Ota Y, Tamegai H, Kudo F, Kuriki H, Koike-Takeshita A, Eguchi T, Kakinuma K. Butirosin-biosynthetic gene cluster from Bacillus circulans. J Antibiot (Tokyo). 2000 Oct;53(10):1158-67. doi: 10.7164/antibiotics.53.1158. PMID: 11132962.
2: Takeishi R, Kudo F, Numakura M, Eguchi T. Epimerization at C-3'' in butirosin biosynthesis by an NAD(+) -dependent dehydrogenase BtrE and an NADPH-dependent reductase BtrF. Chembiochem. 2015 Feb 9;16(3):487-95. doi: 10.1002/cbic.201402612. Epub 2015 Jan 19. PMID: 25600434.
3: Dowding JE. Susceptibility to butirosin and neomycin B in Bacillus circulans, the butirosin-producing organism. J Gen Microbiol. 1979 Dec;115(2):385-9. doi: 10.1099/00221287-115-2-385. PMID: 93616.
4: Kudo F, Eguchi T. Biosynthetic enzymes for the aminoglycosides butirosin and neomycin. Methods Enzymol. 2009;459:493-519. doi: 10.1016/S0076-6879(09)04620-5. PMID: 19362652.
5: DiGiammarino EL, Draker KA, Wright GD, Serpersu EH. Solution studies of isepamicin and conformational comparisons between isepamicin and butirosin A when bound to an aminoglycoside 6'-N-acetyltransferase determined by NMR spectroscopy. Biochemistry. 1998 Mar 17;37(11):3638-44. doi: 10.1021/bi972778b. PMID: 9521682.
6: Llewellyn NM, Li Y, Spencer JB. Biosynthesis of butirosin: transfer and deprotection of the unique amino acid side chain. Chem Biol. 2007 Apr;14(4):379-86. doi: 10.1016/j.chembiol.2007.02.005. PMID: 17462573.
7: Kudo F, Fujii T, Kinoshita S, Eguchi T. Unique O-ribosylation in the biosynthesis of butirosin. Bioorg Med Chem. 2007 Jul 1;15(13):4360-8. doi: 10.1016/j.bmc.2007.04.040. Epub 2007 Apr 25. PMID: 17482823.
8: Heifetz CL, Chodubski JA, Pearson IA, Silverman CA, Fisher MW. Butirosin compared with gentamicin in vitro and in vivo. Antimicrob Agents Chemother. 1974 Aug;6(2):124-35. doi: 10.1128/aac.6.2.124. PMID: 15828182; PMCID: PMC444617.
9: Aubert-Pivert E, el-Samaraie A, von Döhren H. A 4-amino-2-hydroxybutyrate activating enzyme from butirosin-producing Bacillus circulans. Biochem Biophys Res Commun. 1993 Dec 30;197(3):1334-9. doi: 10.1006/bbrc.1993.2623. PMID: 7506542.
10: Takeda K, Kinumaki A, Hayasaka H, Yamaguchi T, Ito Y. Mutational biosynthesis of butirosin analogs. II. 3', 4'-Dideoxy-6'-N-methylbutirosins, new semisynthetic aminoglycosides. J Antibiot (Tokyo). 1978 Oct;31(10):1031-8. doi: 10.7164/antibiotics.31.1031. PMID: 81823.
