Dihydrostreptomycin sulfateProduct ingredient for Dihydrostreptomycin

Name
Dihydrostreptomycin sulfate
Drug Entry
Dihydrostreptomycin

Dihydrostreptomycin is an aminoglycoside antibiotic. In humans, the use of dihydrostreptomycin has been associated with ototoxicity. The FDA withdrew its approval for the use of all drug products containing dihydrostreptomycin sulfate.11

Accession Number
DBSALT001676
Structure
Synonyms
Dihydrostreptomycin sulfate / Dihydrostreptomycin sulphate
UNII
T7D4876IUE
CAS Number
5490-27-7
Weight
Average: 1461.41
Monoisotopic: 1460.464778732
Chemical Formula
C42H88N14O36S3
InChI Key
CZWJCQXZZJHHRH-YCRXJPFRSA-N
InChI
InChI=1S/2C21H41N7O12.3H2O4S/c2*1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35;3*1-5(2,3)4/h2*5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;;;/m00.../s1
IUPAC Name
bis(N-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine); tris(sulfuric acid)
SMILES
OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]2NC(N)=N)O[C@@H](C)[C@]1(O)CO.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](NC(N)=N)[C@@H](O)[C@@H]2NC(N)=N)O[C@@H](C)[C@]1(O)CO
ChemSpider
20352
ChEMBL
CHEMBL3188576
Wikipedia
Dihydrostreptomycin_sulfate
Predicted Properties
PropertyValueSource
Water Solubility16.0 mg/mLALOGPS
logP-3ALOGPS
logP-7.3Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.11Chemaxon
pKa (Strongest Basic)11.31Chemaxon
Physiological Charge3Chemaxon
Hydrogen Acceptor Count19Chemaxon
Hydrogen Donor Count15Chemaxon
Polar Surface Area334.59 Å2Chemaxon
Rotatable Bond Count18Chemaxon
Refractivity150.45 m3·mol-1Chemaxon
Polarizability56.69 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon