CAS 62013-04-1|Dirithromycin|(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-meth...

General Information

Structure

Molecular Formula

C₄₂H₇₈N₂O₁₄

Molecular Mass

835.07372

Exact Mass

834.54530519

Charge

InChI

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

InChIKey

WLOHNSSYAXHWNR-PBIGORBISA-N

Canonic Smiles

COCCOC[C@@H]1N[C@H]2[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@H](C)[C@@H]([C@@H](C(=O)O[C@@H]([C@@]([C@@H](O1)[C@@H]2C)(C)O)CC)C)O[C@@H]1O[C@@H](C)[C@@H]([C@](C1)(C)OC)O

Isomeric Smiles

O1[C@H]2[C@@H]([C@@H](N[C@H]1COCCOC)[C@@H](C[C@@](O)([C@H](O[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C)[C@@H]([C@H](O[C@@H]1O[C@H]([C@H](O)[C@](OC)(C1)C)C)[C@@H](C(=O)O[C@@H]([C@]2(O)C)CC)C)C)C)C)C

Calculated Properties

JChem

Acid pKa

12.485339

H Acceptors

H Donor

LogD (pH = 5.5)

-2.8307562

LogD (pH = 7.4)

0.45715556

Log P

2.9477377

Molar Refractivity

212.9535

Polarizability

87.141304

Polar Surface Area

196.33

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

2.9

LOG S

-3.56

Solubility (Water)

2.30e-01 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Dirithromycin

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

Brand Name

Dynabac

IUPAC Traditional name

Names and Identifiers

Registration numbers

CAS Number

62013-04-1

PubChem SID

160964293

PubChem CID

70789200

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

1.6

Solubility

Poor

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00954

Drug Groups

approved

Description

Dirithromycin 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.

Indication

For the treatment of the following mild-to-moderate infections caused by susceptible strains of microorganisms: acute bacterial exacerbations of chronic bronchitis, secondary bacterial infection of acute bronchitis, community-acquired pneumonia, pharyngitis/tonsilitis, and uncomplicated skin and skin structure infections.

Pharmacology

Dirithromycin is a pro-drug which is converted non-enzymatically during intestinal absorption into the microbiologically active moiety erythromycylamine. Erythromycylamine exerts its activity by binding to the 50S ribosomal subunits of susceptible mircoorganisms resulting in inhibition of protein synthesis. Dirithromycin/erythromycylamine has been shown to be active against most strains of the following microorganisms both in vitro and in clinical infections: Staphylococcus aureus (methicillin-susceptible strains only), Streptococcus pneumoniae, Streptococcus pyogenes, Haemophilus influenzae, Legionella pneumophila, Moraxella catarrhalis, and Mycoplasma pneumoniae.

Toxicity

The toxic symptoms following an overdose of a macrolide antibiotic may include nausea, vomiting, epigastric distress, and diarrhea.

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

Dirithromycin is converted by nonenzymatic hydrolysis during absorption to the active compound, erythromycylamine. Sixty to 90% of a dose is hydrolyzed to erythromycylamine within 35 minutes after dosing, and conversion is nearly complete after 1.5 hours. Erythromycylamine undergoes little or no hepatic biotransformation. No other metabolites of dirithromycin have been detected in the serum.

Absorption

Oral dirithromycin is rapidly absorbed, with an absolute bioavailability of approximately 10%. Dietary fat has little or no effect on the bioavailability of dirithromycin.

Half Life

The mean plasma half-life of erythromycylamine was estimated to be about 8 h (2 to 36 h), with a mean urinary terminal elimination half-life of about 44 h (16 to 65 h) in patients with normal renal function.

Protein Binding

15 to 30% for erythromycylamine, the active compound.

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]

• Wintermeyer SM, Abdel-Rahman SM, Nahata MC: Dirithromycin: a new macrolide. Ann Pharmacother. 1996 Oct;30(10):1141-9. [Pubmed]

• Sides GD, Cerimele BJ, Black HR, Busch U, DeSante KA: Pharmacokinetics of dirithromycin. J Antimicrob Chemother. 1993 Mar;31 Suppl C:65-75. [Pubmed]

• 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]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Brogden RN, Peters DH: Dirithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1994 Oct;48(4):599-616. Pubmed

• Wintermeyer SM, Abdel-Rahman SM, Nahata MC: Dirithromycin: a new macrolide. Ann Pharmacother. 1996 Oct;30(10):1141-9. Pubmed

• Sides GD, Cerimele BJ, Black HR, Busch U, DeSante KA: Pharmacokinetics of dirithromycin. J Antimicrob Chemother. 1993 Mar;31 Suppl C:65-75. PubmedCounter 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Synonyms

• IUPAC name

• Brand Name

• IUPAC Traditional name

Registration numbers

• CAS Number

• PubChem SID

• PubChem CID

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Synonyms

Dirithromycin

IUPAC name

IUPAC Traditional name

CAS Number

62013-04-1

PubChem SID

160964293

PubChem CID

70789200

Physical Property

Hydrophobicity(logP)

1.6

Solubility

Poor

DrugBank

DB00954

Drug Groups

approved

Description

Dirithromycin 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.

Indication

Pharmacology

Toxicity

The toxic symptoms following an overdose of a macrolide antibiotic may include nausea, vomiting, epigastric distress, and diarrhea.

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

Absorption

Oral dirithromycin is rapidly absorbed, with an absolute bioavailability of approximately 10%. Dietary fat has little or no effect on the bioavailability of dirithromycin.

Half Life

Protein Binding

15 to 30% for erythromycylamine, the active compound.

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]

• Wintermeyer SM, Abdel-Rahman SM, Nahata MC: Dirithromycin: a new macrolide. Ann Pharmacother. 1996 Oct;30(10):1141-9. [Pubmed]

• Sides GD, Cerimele BJ, Black HR, Busch U, DeSante KA: Pharmacokinetics of dirithromycin. J Antimicrob Chemother. 1993 Mar;31 Suppl C:65-75. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

From Data Sources

• Brogden RN, Peters DH: Dirithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1994 Oct;48(4):599-616. Pubmed

• Wintermeyer SM, Abdel-Rahman SM, Nahata MC: Dirithromycin: a new macrolide. Ann Pharmacother. 1996 Oct;30(10):1141-9. Pubmed

Molecule

ID:830