Basic information
- CAS
3847-29-8- Standard 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](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O.O=C(O)[C@H](O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO- InChIKey
NNRXCKZMQLFUPL-WBMZRJHASA-N- Molecular formula
- C49H89NO25
- Average molar mass
- 1,092.2 g/mol
- Monoisotopic mass
- 1,091.57236735
Overview
Erythromycin Lactobionate is the lactobionate salt form of erythromycin, a broad-spectrum, topical macrolide antibiotic with antibacterial activity. Erythromycin lactobionate diffuses through the bacterial cell membrane and reversibly binds to the 50S subunit of the bacterial ribosome. This prevents bacterial protein synthesis. Erythromycin lactobionate may be bacteriostatic or bactericidal in action, depending on the concentration of the drug at the site of infection and the susceptibility of the organism involved.
Names & identifiers
- Preferred name
- Erythromycin Lactobionate
- IUPAC
- (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;(2R,3R,4R,5R)-2,3,5,6-tetrahydroxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoic acid
- English name
- ERYTHROMYCIN LACTOBIONATE (200 MG)
- Molecular formula
- C37H67NO13.C12H22O12
- Molecular weight
- 1092.22
Names & synonyms
erythromycin lactobionate3847-29-833H58I7GLQErythromycini lactobionasErythromycin mono(4-O-beta-D-galactopyranosyl-D-gluconate) (salt)DTXSID801009322Erythrocin LactobionateRefChem:55127DTXCID401436149(2R,3S,4S,5R,6R,8R,10R,11R,12S,13R)-5-(3,4,6-Trideoxy-3-dimethylamino-beta-D-xylo-hexopyranosyloxy)-3-(2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyloxy)-6,11,12-trihydroxy-2,4,6,8,10,12-hexamethyl-9-oxopentadecan-13-olide mono(4-O-beta-D-galactopyranosyl-D-gluconate)223-348-7n-2,10-dion(1:1)
Show more names
Azithromycin lactobionateERYTHROMYCIN LACTOBIONATE USP(CRM STANDARD)Lactose azithroMycinC37H67NO13.C12H22O12Erythomycin lactobionateMoxifloxacin Impurity 146Erythromycin lactobionate CRS
Erythromycin lactobionate (1:1) (salt)Erythromycin lactobionate [JAN]EINECS 223-348-7Erythrocin Lactobionate IVUNII-33H58I7GLQErythromycin A Lactobionate; (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-l-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-ss-d-xylo-hexopyranosyl]oxy]oxacyclotetradecane-2,10-dione 4-O-ss-d-galactopyranosyl-d-gluconateErythromycin lactobionate [USP:BAN:JAN]Erythromycin iactobionate
Properties
Computed structural properties
- Topological polar surface area
- 412 Ų
- Hydrogen bond donors
- 14
- Hydrogen bond acceptors
- 26
- Rotatable bonds
- 15
- Heavy atoms
- 75
- Formal charge
- 0
- Complexity
- 1,580
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 145 · 145-150°
- Density
- 0.9083 · 0.9083 (rough estimate)
- refractive index
- 1.53 · 1.5300 (estimate)
- storage temp.
- Refrigerator
- solubility
- Soluble in water, freely soluble in anhydrous ethanol and in methanol, very slightly soluble in acetone and in methylene chloride.
- form
- Solid
- color
- White to Off-White
- Water Solubility
- 20 g/L · >20g/L(21 ºC)
- Major Application
- USP Biologicspharmaceutical (small molecule)
- InChIKey
- NNRXCKZMQLFUPL-FACXKIDONA-N
- FDA UNII
- 33 H58I7GLQ · 33H58I7GLQ
- UNSPSC Code
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Other Safety InformationIMAP assessments - D-Gluconic acid, 4-O-.beta.-D-galactopyranosyl-, compound with erythromycin (1:1): Environment tier I assessment
Safety data
- wgk
- WGK 3
- hs_code
- 2941500000
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
ERYTHROMYCIN LACTOBIONATE
Macrolides [CS]; Decreased Sebaceous Gland Activity [PE]; Macrolide [EPC]; Macrolide Antimicrobial [EPC]
MeSH Pharmacological Classification
Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionErythromycin is a macrolide antibiotic that inhibits bacterial protein synthesis by targeting the 50S ribosomal subunit, blocking the progression of nascent polypeptide chains. It is effective against a host of bacterial genera, including Streptococcus, Staphylococcus, and Haemophilus (MIC90s range from 0.015-2.0 mg/l). Erythromycin is known to potently inhibit the cytochrome P450 isoform CYP3A4, which can affect the metabolism of numerous clinically relevant medications. Erythromycin lactobionate is a soluble salt of erythromycin that is typically used for intraperitoneal or intravenous injections.
UsesErythromycin Lactobionate is an antibiotic used to reduce the prevalence of drug resistant bacteria as well as keeping constant the efficacy of other antibacterial drugs.
UsesMacrolide antibacterial.
General DescriptionErythromycin lactobionate is a water-soluble salt preparedby reacting erythromycin base with lactobiono-σ-lactone. Itoccurs as an amorphous powder that is freely soluble inwater and alcohol and slightly soluble in ether. It is intended,after reconstitution in sterile water, for intravenousadministration to achieve high plasma levels in the treatmentof serious infections.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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