| Common Name |
Dirithromycin
| Description |
Dirithromycin is only found in individuals that have used or taken this drug. It is a macrolide glycopeptide antibiotic. It is used to treat many different types of bacterial infections, such as bronchitis, pneumonia, tonsillitis, and even skin infections.Dirithromycin prevents bacteria from growing, by interfering with their protein synthesis. Dirithromycin binds to the 50S subunit of the 70S bacterial ribosome, and thus inhibits the translocation of peptides. Dirithromycin has over 10 times higher affinity to the subunit 50S than erythromycin. In addition, dirithromycin binds simlitaneously in to two domains of 23S RNA of the ribosomal subunit 50S, where older macrolides bind only in one. Dirithromycin can also inhibit the formation of ribosomal subunits 50S and 30S.
| Structure |
| Synonyms |
| Value |
Source |
Lilly brand OF dirithromycinMeSH
Pharmafarm brand OF dirithromycinMeSH
Dista brand OF dirithromycinMeSH
muro Brand OF dirithromycinMeSH
DynabacMeSH
NortronMeSH
| Chemical Formlia |
C42H78N2O14
| Average Molecliar Weight |
835.0737
| Monoisotopic Molecliar Weight |
834.545305214
| IUPAC Name |
(1S,2R,3R,6R,7R,8R,9R,10R,12R,13S,15R,17R)-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 Name |
dynabac
| CAS Registry Number |
62013-04-1
| SMILES |
CC[C@H]1OC(=O)[C@H](C)[C@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)[C@@H]2N[C@@H](COCCOC)O[C@@H]([C@@H]2C)[C@]1(C)O
| InChI Identifier |
InChI=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 Key |
WLOHNSSYAXHWNR-PBIGORBISA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as aminoglycosides. These are moleclies or a portion of a moleclie composed of amino-modified sugars.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic oxygen compounds
| Sub Class |
Organooxygen compounds
| Direct Parent |
Aminoglycosides
| Alternative Parents |
Macrolides and analogues
O-glycosyl compounds
Monosaccharides
Oxanes
1,3-oxazinanes
Tertiary alcohols
Amino acids and derivatives
Carboxylic acid esters
Hemiaminals
Lactones
Trialkylamines
1,2-aminoalcohols
Secondary alcohols
Azacyclic compounds
Monocarboxylic acids and derivatives
Acetals
Oxacyclic compounds
Dialkyl ethers
Carbonyl compounds
Hydrocarbon derivatives
Organic oxides
Organopnictogen compounds
| Substituents |
Aminoglycoside core
Macrolide
O-glycosyl compound
Glycosyl compound
1,3-oxazinane
Monosaccharide
Oxane
Oxazinane
Tertiary alcohol
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
Hemiaminal
Lactone
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Acetal
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Alcohol
Amine
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound
| Molecliar Framework |
Aliphatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Bacterial Agents
Anti-Infectives
Macrolides
| Application |
Pharmaceutical
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.30e-01 g/LNot Available
LogP1.6Not Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.23 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity212.95 m3·mol-1ChemAxon
Polarizability91.59 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00954
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00954
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB00954
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
26329512
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Dirithromycin
| NuGOwiki Link |
HMDB15089
| Metagene Link |
HMDB15089
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: BTS
References |
| Synthesis Reference |
# Counter FT, Ensminger PW, Preston DA, Wu CY, Greene JM, Felty-Duckworth AM, Paschal JW, Kirst HA: Synthesis and antimicrobial evaluation of dirithromycin (AS-E 136; LY237216), a new macrolide antibiotic derived from erythromycin. Antimicrob Agents Chemother. 1991 Jun;35(6):1116-26. Pubmed:http://www.ncbi.nlm.nih.gov/pubmed/1929252 |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Brogden RN, Peters DH: Dirithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1994 Oct;48(4):599-616. [PubMed:7528132 ]
- Sides GD, Cerimele BJ, Black HR, Busch U, DeSante KA: Pharmacokinetics of dirithromycin. J Antimicrob Chemother. 1993 Mar;31 Suppl C:65-75. [PubMed:8478313 ]
- Wintermeyer SM, Abdel-Rahman SM, Nahata MC: Dirithromycin: a new macrolide. Ann Pharmacother. 1996 Oct;30(10):1141-9. [PubMed:8893122 ]
|
PMID: 22886304
