Dirithromycin (CHEM020172)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:52:49 UTC
Update Date2016-11-09 01:16:09 UTC
Accession NumberCHEM020172
Identification
Common NameDirithromycin
ClassSmall Molecule
DescriptionDirithromycin is a macrolide glycopeptide antibiotic. Dirithromycin (Dynabac) is a more lipid-soluble prodrug derivative of 9S-erythromycyclamine prepared by condensation of the latter with 2-(2-methoxyethoxy)acetaldehyde. The 9N, 11O-oxazine ring thus formed is a hemi-aminal that is unstable under both acidic and alkaline aqueous conditions and undergoes spontaneous hydrolysis to form erythromycyclamine. Erythromycyclamine is a semisynthetic derivative of erythromycin in which the 9-ketogroup of the erythronolide ring has been converted to an amino group. Erythromycyclamine retains the antibacterial properties of erythromycin oral administration. The prodrug, dirithromycin, is provided as enteric coated tablets to protect it from acid catalyzed hydrolysis in the stomach. Orally administered dirithromycin is absorbed rapidly into the plasma, largely from the small intestine. Spontaneous hydrolysis to erythromycyclamine occurs in the plasma. Oral bioavailability is estimated to be about 10%, but food does not affect absorption of the prodrug.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
NortronMeSH
DynabacMeSH
(9S)-9-Deoxo-11-deoxy-9,11-(imino((1R)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycinMeSH
Dista brand OF dirithromycinMeSH
Lilly brand OF dirithromycinMeSH
muro Brand OF dirithromycinMeSH
Pharmafarm brand OF dirithromycinMeSH
DirithromycinMeSH
Chemical FormulaC42H78N2O14
Average Molecular Mass835.086 g/mol
Monoisotopic Mass834.545 g/mol
CAS Registry Number62013-04-1
IUPAC Name(1S,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-3-ethyl-2,10-dihydroxy-7-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
Traditional Namedirithromycin
SMILES[H][C@@]1(C)C[C@]([H])(N(C)C)[C@@]([H])(O)[C@]([H])(O[C@]2([H])[C@@]([H])(C)[C@]([H])(O[C@@]3([H])C[C@@](C)(OC)[C@@]([H])(O)[C@]([H])(C)O3)[C@@]([H])(C)C(=O)O[C@]([H])(CC)[C@@](C)(O)[C@@]3([H])O[C@]([H])(COCCOC)N[C@]([H])([C@]3([H])C)[C@]([H])(C)C[C@@]2(C)O)O1
InChI IdentifierInChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37+,39+,40-,41-,42-/m1/s1
InChI KeyWLOHNSSYAXHWNR-NXPDYKKBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • O-glycosyl compound
  • Glycosyl compound
  • Monosaccharide
  • 1,3-oxazinane
  • Oxane
  • Oxazinane
  • Tertiary alcohol
  • Tertiary amine
  • Lactone
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Hemiaminal
  • Carboxylic acid ester
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Alcohol
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organopnictogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP2.9ALOGPS
logP2.95ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area196.33 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity212.95 m³·mol⁻¹ChemAxon
Polarizability92.05 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r9-0100029040-49367042a9336b3d37c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cdi-1300096000-1d4a0c073ba9a565ce0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9103152000-32a89788297a874b8d73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-1712046290-12246cb49830aeef5c4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00pi-3600149420-9c7b1608dcd2f85d1b15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-3400097100-7216dc15237b8e349359Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDirithromycin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6917067
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available