HuagongsheHuagongshe Chemistry Print Report · For research reference only
Erythromycin ethyl succinate
Esinol · Evesin · Refkas · Anamycin · Arpimycin · E-Mycin e · Eryliquid · Monomycin
Identifiers & Physical Properties
| CAS No. | 1264-62-6 |
|---|---|
| Molecular formula | C43H75NO16 |
| Average molar mass | 862.1 g/mol |
| Monoisotopic mass | 861.50858532 g/mol |
| SMILES | CCOC(=O)CCC(=O)O[C@H]1[C@H](O[C@@H]2[C@@H](C)[C@H](O[C@H]3C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[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)O[C@H](C)C[C@@H]1N(C)C |
| InChIKey | NSYZCCDSJNWWJL-YXOIYICCSA-N |
| PubChem CID | 443953 |
| ChEMBL | CHEMBL1200688 |
| ChEBI | CHEBI:31555 |
| EC No. | 215-033-8 |
| DTXSID | DTXSID4022993 |
Chemical & Physical Properties
| XLogP | 3.4 |
|---|---|
| Topological polar surface area | 226 |
| Hydrogen bond donors | 4 |
| Hydrogen bond acceptors | 17 |
| Rotatable bonds | 14 |
| Heavy atoms | 60 |
| Formal charge | 0 |
| Complexity | 1,450 |
| Drugs | Pharmaceuticals -> Antibiotics |
| Lipids | Polyketides [PK] -> Ansamycins and related polyketides [PK05] |
| Odor | ODORLESS OR PRACTICALLY SO |
| Taste | PRACTICALLY TASTELESS |
| Color/Form | WHITE OR SLIGHTLY YELLOW, CRYSTALLINE POWDER |
| Solubility | FREELY SOL IN ACETONE & CHLOROFORMSOL IN 95% ETHANOL & BENZENESPARINGLY SOL IN ETHERVERY SLIGHTLY SOL IN WATERFREELY SOLUBLE IN ALC, SOL IN POLYETHYLENE GLYCOLethanol: soluble50mg/mLFreely soluble in organic solvents, practically insoluble in water |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Refractive index | INDEX OF REFRACTION: 1.490 (ALPHA), 1.515 (BETA), 1.567 (GAMMA)1.5280 (estimate) |
| Stability/Shelf Life | AFTER RECONSTITUTION OF COMMERCIALLY AVAILABLE POWDER, SUSPENSIONS ARE STABLE FOR 10 DAYS @ 2-8 °CCOMMERCIALLY AVAILABLE TABLETS & POWDER FOR ORAL SUSPENSION HAVE EXPIRATION DATES OF 2 YR FOLLOWING DATES OF MANUFACTURECOMMERCIALLY AVAILABLE SUSPENSIONS HAVE EXPIRATION DATES OF 18 MONTHS FOLLOWING DATES OF MANUFACTUREERYTHROMYCIN ETHYLSUCCINATE IM INJECTION HAS AN EXPIRATION DATE OF 18 MONTHS FOLLOWING DATE OF MFR |
| Dissociation Constants | PKA 7.1 |
| Collision Cross Section | 257.7 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Melting point | 219-224 C |
| Boiling point | 778.19°C (rough estimate) |
| Density | 1.1417 (rough estimate) |
| Flash point | >110°(230°F) |
| Storage conditions | Sealed in dry,Room Temperature |
| Physical state | solid |
| pKa (acidity coefficient) | 13.09±0.70(Predicted) |
| Color | white |
| Stability | Hygroscopic |
| Major applications | pharmaceuticalpharmaceutical small molecule |
| InChIKey | NSYZCCDSJNWWJL-UHFFFAOYSA-N |
| SMILES | C1(OC(=O)CCC(OCC)=O)C(N(C)C)CC(C)OC1OC1C(CC(C(C(C(O)C(O)(C)C(CC)OC(=O)C(C)C(OC2OC(C)C(O)C(C)(OC)C2)C1C)C)=O)C)(O)C |
| CAS DataBase Reference | 1264-62-6 |
| EWG's Food Scores | 1 |
| FDA UNII | 1014KSJ86F |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS08 |
| Signal word | Danger |
| GHS hazard statements | H317-H334 |
| GHS precautionary statements | P261-P280-P284-P304+P340-P342+P311 |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 42/43-36/37/38 |
| Safety statements (S) | 36-26 |
| Water hazard class (WGK) | 2 |
| RTECS number | WM9800000 |
| Customs code | 29419000 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Resp. Sens. 1Skin Sens. 1 |
| Hazardous substances data | 1264-62-6(Hazardous Substances Data) |
| Toxicity | LD50 oral in mouse: > 10gm/kg |
Safety & Regulations
| GHS classification | DangerH317 (29.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]P233, P260, P261, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P321, P333+P317, P337+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 144 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Other safety information | IMAP assessments - Erythromycin, 2'-(ethyl butanedioate): Environment tier I assessment |
| Hazard Classes and Categories | Skin Sens. 1 (29.9%) |
| Human Toxicity Excerpts | AMONG HYPERSENSITIVITY REACTIONS ARE FEVER, EOSINOPHILIA, & SKIN ERUPTIONS, EACH OF WHICH MAY OCCUR ALONE OR IN COMBINATIONTHEY DISAPPEAR SHORTLY AFTER THERAPY IS STOPPED. ...MAY PRODUCE IRRITATIVE EFFECTS. ORAL ADMIN...FREQUENTLY ACCOMPANIED BY EPIGASTRIC DISTRESS, WHICH MAY BE QUITE SEVERE. /ERYTHROMYCIN/IM INJECTION OF QUANTITIES LARGER THAN 100 MG PRODUCES...SEVERE PAIN... PERSISTS FOR HR: IV PERFUSIONS OF 1-G DOSES...ALMOST REGULARLY IS FOLLOWED BY THROMBOPHLEBITIS. ...6 PT...DEVELOPED DIFFICULTY IN HEARING WHILE BEING TREATED WITH 4 G/DAY...IV. ... CESSATION...LED TO COMPLETE RETURN OF NORMAL HEARING... /ERYTHROMYCIN/A CASE REPORT OF HEPATOTOXICITY RESULTING FROM ERYTHROMYCIN ETHYLSUCCINATE THERAPY IN 60-YR-OLD FEMALE IS DESCIRBED. |
| Water hazard class (WGK) | 2 |
| RTECS number | WM9800000 |
| Customs code | 29419000 |
| Toxicity | LD50 oral in mouse: > 10gm/kg |
| Risk statements (R) | 42/43-36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS08 |
| Hazard symbols | Xn,Xi |
| Safety statements (S) | 36-26 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H317-H334 |
| Hazard class | Resp. Sens. 1Skin Sens. 1 |
| GHS precautionary statements | P261-P280-P284-P304+P340-P342+P311 |
| Hazardous substances data | 1264-62-6(Hazardous Substances Data) |
Applications & Uses
Uses
A broad spectrum antibiotic commonly targeting bacteria responsible for respiratory tract infections
General Description
Erythromycin ethylsuccinate (EES, Pediamycin, EryPed) isthe ethylsuccinate mixed ester of erythromycin in which the2＇-hydroxyl group of the desosamine is esterified. It isabsorbed as the ester and hydrolyzed slowly in the body toform erythromycin. It is somewhat acid labile, and itsabsorption is enhanced by the presence of food. The ester isinsoluble in water but soluble in alcohol and ether.