Basic information
- Name:
Isepamicin sulfate
- CAS No.:
67814-76-0
- Molecular Structure:
- Formula:
- C22H43N5O12.H2SO4
- Synonyms:
- (2S)-3-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxy-oxan-2-yl]oxy-2-[(2R,3R,4R,5S)-3,5-dihydroxy-5-methyl-4-methylamino-oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-propanamide sulfate
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Chemistry
Molecular Formula: C22H45N5O16S
Molar mass: 667.68 g/mol
Product categories of Isepamicin sulfate (67814-76-0): Antibacterial
Structure of Isepamicin sulfate (67814-76-0):
H-Bond Donor: 14
H-Bond Acceptor: 20
IUPAC Name: (2S)-3-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,4S,5S,
6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-2-[(2R,3R,4R,5R)-3,
5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-
2-hydroxypropanamide; sulfuric acid
Canonical SMILES: CC1(COC(C(C1NC)O)OC2C(CC(C(C2O)OC3C(C(C(C(O3)CN)O)O)O)N)NC(=O)C(CN)O)O.OS(=O)(=O)O
Isomeric SMILES: C[C@@]1(CO[C@@H]([C@@H]([C@H]1NC)O)O[C@H]2[C@@H](C[C@@H]([C@H]([C@@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)O)N)NC(=O)[C@H](CN)O)O.OS(=O)(=O)O
InChI: InChI=1S/C22H43N5O12.H2O4S/c1-22(35)6-36-20(15(33)18(22)26-2)39-17-8(27-19(34)9(28)4-23)3-7(25)16(14(17)32)38-21-13(31)12(30)11(29)10(5-24)37-21;1-5(2,3)4/h7-18,20-21,26,28-33,35H,3-6,23-25H2,1-2H3,(H,27,34);(H2,1,2,3,4)/t7-,8+,9-,10+,11+,12-,13+,14-,15+,16+,17-,18+,20+,21+,22-;/m0./s1
InChIKey: DDXRHRXGIWOVDQ-MGAUJLSLSA-N
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | intramuscular | > 1800mg/kg (1800mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) GASTROINTESTINAL: NAUSEA OR VOMITING | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
| dog | LD50 | intravenous | 720mg/kg (720mg/kg) | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. | |
| mouse | LD50 | intramuscular | 2508mg/kg (2508mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
| mouse | LD50 | intraperitoneal | 2244mg/kg (2244mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
| mouse | LD50 | intravenous | 234mg/kg (234mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
| mouse | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. -, Pg. 109, 1990. | |
| mouse | LD50 | subcutaneous | 3320mg/kg (3320mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
| rat | LD50 | intramuscular | 2088mg/kg (2088mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
| rat | LD50 | intraperitoneal | 1591mg/kg (1591mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
| rat | LD50 | intravenous | 476mg/kg (476mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
| rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. -, Pg. 109, 1990. | |
| rat | LD50 | subcutaneous | 3392mg/kg (3392mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Japanese Journal of Antibiotics. Vol. 39, Pg. 3164, 1986. |
Safety Profile
Moderately toxic by intraperitoneal and intramuscular route. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx. See also SULFATES.
Specification
Isepamicin sulfate (67814-76-0) also can be called Isepacin ; 1-N-(S-3-Amino-2-hydroxypropionyl)-gentamicin B sulfate and HAPA-B sulfate .
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