Synonym
Antibiotic 66-40 sulfate; Baymicine; Extramycin; Pathomycin; Sisomicin sulfate
IUPAC/Chemical Name
bis((2R,3R,4R,5R)-2-(((1S,2S,3R,4S,6R)-4,6-diamino-3-(((2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol) pentakis(sulfate)
InChi Key
CIKNYWFPGZCHDL-ZHFUJENKSA-N
InChi Code
InChI=1S/2C19H37N5O7.5H2O4S/c2*1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;5*1-5(2,3)4/h2*3,9-18,24-27H,4-7,20-23H2,1-2H3;5*(H2,1,2,3,4)/t2*9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+;;;;;/m11...../s1
SMILES Code
CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]3OC(=CC[C@H]3N)CN)[C@@H]2O)OC[C@]1(C)O.CN[C@@H]4[C@@H](O)[C@@H](O[C@H]5[C@H](N)C[C@H](N)[C@@H](O[C@H]6OC(=CC[C@H]6N)CN)[C@@H]5O)OC[C@]4(C)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
1,385.43
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: Guan S, Li Y, Cheng C, Gao X, Gu X, Han X, Ye H. Manufacture of pH- and HAase-responsive hydrogels with on-demand and continuous antibacterial activity for full-thickness wound healing. Int J Biol Macromol. 2020 Dec 1;164:2418-2431. doi: 10.1016/j.ijbiomac.2020.08.108. Epub 2020 Aug 13. PMID: 32798544.
2: Yuan C, Wang J, Liang Z, Xin N. [Determination of sisomicin in body fluid by high performance liquid chromatography-indirect photometric detection method]. Se Pu. 1998 Sep;16(5):445-7. Chinese. PMID: 11498926.
3: Matsukawa S, Suh JH, Hashimoto Y, Kato M, Satoh D, Saito S, Endo K, Saishu T. Neuromuscular blocking actions of the aminoglycoside antibiotics sisomicin and micronomicin in the rabbit. Tohoku J Exp Med. 1997 Apr;181(4):471-3. doi: 10.1620/tjem.181.471. PMID: 9210254.
4: Fukuda M, Sasaki K. Changes in the antibacterial activity of melanin-bound drugs. Ophthalmic Res. 1990;22(2):123-7. doi: 10.1159/000267011. PMID: 2111531.
5: Tamura K, Araki Y, Amamoto T, Seita M. [Clinical experience of sisomicin sulfate by intravenous drip infusion for the treatment of infection complicated by malignant disease]. Jpn J Antibiot. 1984 Jul;37(7):1237-40. Japanese. PMID: 6593472.
6: Egorenko GG, Berezina EK, Berezhinskaia VV, Dolgova GV, Kovalenko LP. IZuchenie obshchetoksicheskikh i organotropnykh svoĭstv sizomitsina sul'fata v khronicheskikh opytakh na zhivotnykh [General toxic and organotropic properties of sisomicin sulfate in chronic experiments on animals]. Antibiotiki. 1983 Sep;28(9):678-82. Russian. PMID: 6605712.
7: Matsuzawa T, Nakata M, Tsushima M, Miura H, Akiyoshi M. Audiotoxicosis in newborn guinea pigs from pregnant ones given sisomicin. Toxicology. 1980;17(1):67-71. doi: 10.1016/0300-483x(80)90028-1. PMID: 7434369.
8: Rodríquez Torres A. Sulfato de sisomicina: su eficacia en el tratamiento de las infecciones urológicas [Sisomicin sulfate: its efficacy in the treatment of urologic infections]. Arch Esp Urol. 1979 Jul-Aug;32(4):387-96. Spanish. PMID: 485572.
9: Varela Rico J, Monroy López J, Núñez Díaz A, Ortega González M. Nuevo aminoglucosido en infecciones del aparato urogenital. Estudio clínico del sulfato de sisomicina [A new aminoglucoside in infections of the urogenital system. Clinical study of sisomicin sulfate]. Prensa Med Mex. 1978 Jul- Aug;43(7-8):258-60. Spanish. PMID: 392493.
