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| CAS No.: | 1264-62-6 |
|---|---|
| Name: | Erythromycin ethylsuccinate |
| Molecular Structure: | |
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| Formula: | C43H75NO16 |
| Molecular Weight: | 862.066 |
| Synonyms: | Durapaediat;Eritrocina;EryPed;ErythroES;Erythro-Holz;Erythrocin ethyl succinate;Esinol;Evesin;Refkas;Sigapedil;Erythromycinethyl succinate (6CI);Erythromycin, 2'-(ethyl succinate) (7CI);Succinic acid, monoethyl ester, monoester with erythromycin;Anamycin; |
| EINECS: | 215-033-8 |
| Density: | 1.212 g/cm3 |
| Melting Point: | 219-224 °C |
| Boiling Point: | 874.107 °C at 760 mmHg |
| Flash Point: | 482.442 °C |
| Solubility: | Freely soluble in organic solvents, practically insoluble in water |
| Appearance: | white to yellowish crystalline solid |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 42/43-36/37/38 |
| Safety: | 36-26 |
| PSA: | 226.28000 |
| LogP: | 2.67980 |
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Specification
The Erythromycin ethylsuccinate, with the CAS registry number 1264-62-6, is also known as Succinic acid, monoethyl ester, monoester with erythromycin. It belongs to the product categories of Organics; Interferes with Protein Synthesis Antibiotics; A - K Antibiotics; Antibacterial; Antibiotics A to; Antibiotics A-F Antibiotics; Chemical Structure Class; Macrolides; Mechanism of Action; Spectrum of Activity. Its EINECS number is 215-033-8. This chemical's molecular formula is C43H75NO16 and molecular weight is 862.05. What's more, its systematic name is (2S,3R,4S,6R)-4-(Dimethylamino)-2-{[(3S,4R,5R,6S,7S,9S,11S,12S,13R,14S)-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexame thyl-2,10-dioxooxacyclotetradecan-6-yl]oxy}-6-methyltetrahydro-2H-pyran-3-yl ethyl succinate. Its classification codes are: (1)Anti-Bacterial Agents; (2)Anti-Infective Agents; (3)Antibacterial; (4)Drug / Therapeutic Agent; (5)Enzyme inhibitors; (6)Gastrointestinal agents; (7)Human Data; (8)Protein synthesis inhibitors. This chemical is a macrolide antibiotic, produced by Streptomyces erythreus. This compound is an ester of erythromycin base and succinic acid. It acts primarily as a bacteriostatic agent. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.
Physical properties of Erythromycin ethylsuccinate are: (1)ACD/LogP: 4.103; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 2.05; (4)ACD/LogD (pH 7.4): 3.70; (5)ACD/BCF (pH 5.5): 6.80; (6)ACD/BCF (pH 7.4): 302.25; (7)ACD/KOC (pH 5.5): 35.73; (8)ACD/KOC (pH 7.4): 1589.13; (9)#H bond acceptors: 17; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 18; (12)Polar Surface Area: 226.28 Å2; (13)Index of Refraction: 1.528; (14)Molar Refractivity: 219.135 cm3; (15)Molar Volume: 711.003 cm3; (16)Polarizability: 86.872×10-24cm3; (17)Surface Tension: 51.04 dyne/cm; (18)Density: 1.212 g/cm3; (19)Flash Point: 482.442 °C; (20)Enthalpy of Vaporization: 144.332 kJ/mol; (21)Boiling Point: 874.107 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Uses of Erythromycin ethylsuccinate: it can be used to produce succinic acid 4-dimethylamino-2-[5-ethyl-3-hydroxy-9-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-2,4,8,10,12,14-hexamethyl-7-oxo-6,15,16-trioxa-tricyclo[10.2.1.11,4]hexadec-11-yloxy] at the ambient temperature. It will need reagent aq. HCl with the reaction time of 1 hour. The yield is about 42%.
![Erythromycin ethylsuccinate can be used to produce succinic acid 4-dimethylamino-2-[5-ethyl-3-hydroxy-9-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-2,4,8,10,12,14-hexamethyl-7-oxo-6,15,16-trioxa-tricyclo[10.2.1.11,4]hexadec-11-yloxy] at the ambient temperature](/UserFilesUpload/Uses of Erythromycin ethylsuccinate(1).jpeg)
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It may cause sensitisation by inhalation and skin contact. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: CCOC(=O)CCC(=O)O[C@@H]3[C@H](C[C@@H](C)O[C@H]3O[C@H]2[C@H](C)[C@@H](O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@H](C)C(=O)O[C@@H](CC)[C@](C)(O)[C@@H](O)[C@H](C)C(=O)[C@@H](C)C[C@]2(C)O)N(C)C
(2)Std. InChI: InChI=1S/C43H75NO16/c1-15-29-43(11,52)36(48)24(5)33(47)22(3)20-41(9,51)38(25(6)34(26(7)39(50)57-29)59-32-21-42(10,53-14)37(49)27(8)56-32)60-40-35(28(44(12)13)19-23(4)55-40)58-31(46)18-17-30(45)54-16-2/h22-29,32,34-38,40,48-49,51-52H,15-21H2,1-14H3/t22-,23+,24+,25+,26-,27-,28-,29-,32-,34+,35+,36-,37-,38-,40-,41-,42+,43-/m0/s1
(3)Std. InChIKey: NSYZCCDSJNWWJL-XJHUJGFMSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| child | TDLo | oral | 420mg/kg/7D-I (420mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: OTHER CHANGES | Canadian Medical Association Journal. Vol. 129, Pg. 411, 1983. |
| man | TDLo | oral | 5714ug/kg (5.714mg/kg) | BEHAVIORAL: ATAXIA | American Journal of Emergency Medicine. Vol. 10, Pg. 616, 1992. |
| mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Drugs in Japan Vol. 6, Pg. 126, 1982. | |
| rat | LD50 | subcutaneous | 4167mg/kg (4167mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Toxicology and Applied Pharmacology. Vol. 9, Pg. 445, 1966. |