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
USP · ERYTHROMYCIN BASE · em · Erythro · ERYTHROMYCIN A · erytromycin · erythrocin · (-)-Erythromycin
Identifiers & Physical Properties
| CAS No. | 114-07-8 |
|---|---|
| Molecular formula | C37H67NO13 |
| Average molar mass | 733.9 g/mol |
| Monoisotopic mass | 733.4612412 g/mol |
| SMILES | CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC2OC(C)CC(N(C)C)C2O)C(C)(O)CC(C)C(=O)C(C)C(O)C1(C)O |
| InChIKey | ULGZDMOVFRHVEP-UHFFFAOYSA-N |
| PubChem CID | 3255 |
| ChEMBL | CHEMBL1671887 |
| DTXSID | DTXSID90859206 |
Chemical & Physical Properties
| XLogP | 2.7 |
|---|---|
| Topological polar surface area | 194 |
| Hydrogen bond donors | 5 |
| Hydrogen bond acceptors | 14 |
| Rotatable bonds | 7 |
| Heavy atoms | 51 |
| Formal charge | 0 |
| Complexity | 1,180 |
| Drugs | Pharmaceuticals |
| Melting point | 133 °C |
| alpha | -74.5 º (c=2, ethanol) |
| Boiling point | 719.69°C (rough estimate) |
| Density | 1.1436 (rough estimate) |
| Refractive index | -74 ° (C=2, EtOH) |
| Storage conditions | Inert atmosphere,Room Temperature |
| Solubility | ethanol: solubleSoluble in water at 2mg/ml |
| Physical state | powder |
| pKa (acidity coefficient) | 8.8(at 25℃) |
| Color | white to faint yellow |
| Biological source | Streptomyces erythreus |
| optical activity | [α]/D -78 to --71° |
| Merck | 14,3681 |
| BRN | 8183758 |
| Major applications | pharmaceutical (small molecule) |
| InChIKey | HIYRERIGRWIODP-PNFGZDISSA-N |
| FDA 21 CFR | 556.230558.248558.4 |
| EWG's Food Scores | 1 |
| FDA UNII | 63937KV33D |
| NCI Drug Dictionary | E-Mycin |
| ATC code | D10AF02,D10AF52,J01FA01,S01AA17 |
| EPA Substance Registry System | Erythromycin (114-07-8) |
| UNSPSC Code | 51282304 |
| NACRES | NB.43 |
| Protein binding | 70-95% |
| Excreted unchanged in urine | 2-15% |
| Volume of distribution | 0.6-1.2 (increased in CKD 5) |
| Biological half-life | 1.5-2 / 4-7 |
| GHS pictogram | GHS02,GHS08 |
| Signal word | Warning |
| GHS hazard statements | H225-H333-H371 |
| GHS precautionary statements | P210-P260-P280a-P303+P361+P353-P405-P501a |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 42/43-36/37/38 |
| Safety statements (S) | 45-37-24-36-26-24/25 |
| Water hazard class (WGK) | 2 |
| RTECS number | KF4375000 |
| F | 3-4.3-10 |
| Hazard class | 3 |
| Customs code | 29415000 |
| Storage class | 11 - Combustible Solids |
| Hazardous substances data | 114-07-8(Hazardous Substances Data) |
| Toxicity | LD50 oral in rat: 4600mg/kg |
| REACH registrations | Active |
Safety & Regulations
| F | 3-4.3-10 |
|---|---|
| Water hazard class (WGK) | 2 |
| RTECS number | KF4375000 |
| Customs code | 29415000 |
| Toxicity | LD50 oral in rat: 4600mg/kg |
| Risk statements (R) | 42/43-36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS02,GHS08 |
| Hazard symbols | Xn,Xi |
| Safety statements (S) | 45-37-24-36-26-24/25 |
| Hazard class | 3 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H225-H333-H371 |
| REACH registrations | Active |
| GHS precautionary statements | P210-P260-P280a-P303+P361+P353-P405-P501a |
| Hazardous substances data | 114-07-8(Hazardous Substances Data) |
Applications & Uses
Description
Erythromycin ethyl succinate is a mixed double ester pro-drug in which one carboxyl of succinic acid esterifies the C-2′ hydroxyl of erythromycin and the other ethanol. This pro-drug frequently is used in an oral suspension for pediatric use largely to mask the bitter taste of the drug. Film-coated tablets also are used to deal with this. Some cholestatic jaundice is associated with the use of EES.
Description
Erythromycin is a macrolide antibiotic that inhibits bacterial protein synthesis by targeting the 50S ribosomal subunit, blocking the progression of nascent polypeptide chains. It is active against a host of bacterial genera, including Streptococcus, Staphylococcus, and Haemophilus (MIC90s = 0.015-2.0 mg/l). Erythromycin (10-40 mg/kg) dose-dependently inhibits the growth of S. aureus in a mouse model of thigh infection. It also inhibits the cytochrome P450 (CYP450) isoform CYP3A4 in vitro with IC50 values of 33 and 27.3 μM for α-hydroxytriazolam and 4-hydroxytriazolam formation, respectively, following administration of triazolam, which is known to be metabolized primarily by CYP3A4. Formulations containing erythromycin have been used in the treatment of bacterial respiratory and skin infections, pertussis, and a variety of other bacterial infections.
Uses
For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases: respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct to antitoxin in infections
Uses
Macrolide antibacterial
Uses
Erythromycin A is a 14-membered macrocyclic lactone with broad spectrum antibiotic activity, isolated from Saccharopolyspora erythraea (formerly Streptomyces erythreus) in 1952. Erythromycin is one of only a handful of microbial metabolites to have profoundly shaped the treatment of bacterial disease in the last 50 years. Erythromycin has given rise to new generations of semi-synthetic derivatives with improved stability and potency. Our product has been HPLC-purified to remove contaminants and degradation products.
Uses
Labeled Erythromycin, intended for use as an internal standard for the quantification of Erythromycin by GC- or LC-mass spectrometry.
General Description
Early in 1952, McGuire et al. reported the isolation oferythromycin (E-Mycin, Erythrocin, Ilotycin) fromStreptomyces erythraeus. It achieved rapid early acceptanceas a well-tolerated antibiotic of value for the treatment ofvarious upper respiratory and soft-tissue infections causedby Gram-positive bacteria. It is also effective against manyvenereal diseases, including gonorrhea and syphilis, andprovides a useful alternative for the treatment of many infectionsin patients allergic to penicillins. More recently,erythromycin was shown to be effective therapy for Eatonagent pneumonia (Mycoplasma pneumoniae), venereal diseasescaused by Chlamydia, bacterial enteritis caused byCampylobacter jejuni, and Legionnaires disease.The commercial product is erythromycin A, whichdiffers from its biosynthetic precursor, erythromycin B,in having a hydroxyl group at the 12-position of theaglycone. The chemical structure of erythromycin A was reportedby Wiley et al.197 in 1957 and its stereochemistry byCelmer198 in 1965. An elegant synthesis of erythronolide A,the aglycone present in erythromycin A, was described byCorey et al.The amino sugar attached through a glycosidic link to C-5 is desosamine, a structure found in several other macrolideantibiotics. The tertiary amine of desosamine (3,4,6-trideoxy-3-dimethylamino-D-xylo-hexose) confers a basiccharacter to erythromycin and provides the means by whichacid salts may be prepared. The other carbohydrate structurelinked as a glycoside to C-3 is called cladinose (2,3,6-trideoxy-3-methoxy-3-C-methyl-L-ribo-hexose) and isunique to the erythromycin molecule.