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Roxithromycin

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Identification
Molecular formula
C41H76N2O15
CAS number
80214-83-1
IUPAC name
6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
State
State
Roxithromycin is a solid at room temperature, typically prepared as oral tablets.
Melting point (Celsius)
115.00
Melting point (Kelvin)
388.15
Boiling point (Celsius)
795.86
Boiling point (Kelvin)
1 068.99
General information
Molecular weight
837.05g/mol
Molar mass
837.0490g/mol
Density
1.3512g/cm3
Appearence

Roxithromycin is a semi-synthetic macrolide antibiotic and appears as a white or slightly yellowish powder. It is commonly available in tablet form for oral use. It is insoluble in water but soluble in organic solvents such as chloroform and dichloromethane.

Comment on solubility

Solubility of 6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione (C41H76N2O15)

The solubility of this complex compound can be significantly influenced by its unique structural features. Here, we examine the factors affecting its solubility:

  • Molecular Structure: The presence of multiple hydroxyl (-OH) groups typically enhances solubility in polar solvents, particularly water.
  • Hydrophobic Regions: The long hydrocarbon chains within the compound may render it less soluble in water, but more soluble in organic solvents.
  • Functional Groups: Tertiary amine functionality (from the dimethylamino group) can participate in hydrogen bonding, potentially increasing solubility in specific polar solvents.

Overall, the solubility can be characterized as follows:

  1. Expected to be moderately soluble in water due to the presence of hydroxyl groups.
  2. Likely more soluble in organic solvents, such as ethanol or acetone, due to hydrophobic interactions.
  3. Solubility behavior may vary significantly with changes in pH, temperature, and solvent type.

As with many organic compounds of this complexity, empirical solubility data is essential for practical applications, emphasizing that theoretical predictions must be validated through experimentation.

Interesting facts

Interesting Facts about 6-[4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl)oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

This complex compound showcases the fascinating interplay of organic chemistry and molecular design. With its elaborate structure, it serves multiple pathways for research and exploration. Here are some intriguing aspects:

  • Diverse Functional Groups: The compound is rich in functional groups, including hydroxyl (-OH) and ether groups (-O-), that contribute to its chemical reactivity and biological activity.
  • Molecular Complexity: Containing numerous rings and branches, its intricate formation mirrors natural products found in various biological systems, illustrating a window into nature's synthetic strategy.
  • Potential Applications: Its structure suggests potential applications in pharmacology. The presence of tertiary amines could relate to neurological studies, while the extensive hydroxyl groups might indicate possibilities in therapeutic developments.
  • Natural Analogues: Compounds with similar motifs often occur in the realm of natural products, suggesting this compound could serve as a synthetic variant or lead for developing novel drugs.

As a student of chemistry, one might appreciate the depth of study required to understand such a compound. The synthesis and characterization alone could lead to engaging laboratory experiences. It opens discussions on:

  • The significance of chirality in drug design.
  • The use of organic synthesis strategies to build complex molecules.
  • The role of chemical modifications in enhancing biological activities.

"Understanding complex compounds is like solving a puzzle; each piece contributes to the whole." This statement embodies the thrill and challenge that compounds such as this one present to chemists and students alike.

Synonyms
Erythrogran
Erythromid
Propiocine
Abboticin
Dotycin
Erycinum
Ilocaps
Erycin
Kesso-Mycin
Taimoxin-F
ERYTHROMYCIN A DIHYDRATE
erythro
Eritrocina
Erythroguent
Staticin
Retcin
adecane-2,10-dione (non-preferred name)
959119-26-7
IndermRetcin
Erythromycin D3
6-{[4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy]-3,5,7,9,11,13-hexamethyloxacyclotetr
Erythromycin, sodium salt
CHEMBL1671887
component of Drixin (Salt/Mix)
SCHEMBL15263177
BDBM86313
component of T-stat (Salt/Mix)
DTXSID90859206
Erythromycin sodium lauryl sulfate
ULGZDMOVFRHVEP-UHFFFAOYSA-N
BBL028236
NSC_12560
STK249736
AKOS005423023
CAS_114-07-8
FE176617
SY070227
DB-041196
NS00076487
component of Benzedrex nasal spray (Salt/Mix)
(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]oxacyclotetradecane-2,10-dione
[3R-(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)]-4-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]oxacyclotetradecane-2,10-dione
6-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6 dimethyl-oxan-2-yl)oxy-3,5,7,9,11,13-hexamethyl-1 oxacyclotetradecane-2,10-dione
6-{[4-(Dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-[(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy]-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
Oxacyclotetradecane-2, 4-[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-, [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12S*,13S*)]-
Oxacyclotetradecane-2,10-dione, 4-[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-, [3R-(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)]-
Pentadecanoic acid, 3-[(2,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-6,11,12,13-tetrahydroxy-2,4,6,8,10,12-hexamethyl-9-oxo-5-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-, .mu.-lactone, [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12S*,13S*)]-
Pentadecanoic acid,6-dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-6,11,12,13-tetrahydroxy-2,4,6,8,10,12-hexamethyl-9-oxo-5-[[3,4,6-trideoxy-3-(dimethylamino)-.beta.-D-xylo-hexopyranosyl]oxy]-, .mu.-lactone, [2R-(2R*,3S*,4S*,5R*,6R*,8R*,10R*,11R*,12S*,13S*)]-
WLN: T-14-VO GVTJ C2 DQ D1 EQ F1 H1 JQ J1 L1 N1 KO-BT6OTJ CQ DN1 & 1 F1 & MO-FT6OTJ B1 CQ DO1 D1