Basic information
- Standard 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- Molecular formula
- C43H75NO16
- Average molar mass
- 862.1 g/mol
- Monoisotopic mass
- 861.50858532
Overview
Erythromycin ethylsuccinate is a erythromycin derivative that is erythromycin A in which the hydroxy group at position 3R is substituted by a (4-ethoxy-4-oxobutanoyl)oxy group. It is used for the treatment of a wide variety of bacterial infections. It is an ethyl ester, a succinate ester, a cyclic ketone and an erythromycin derivative. It is functionally related to an erythromycin A.
Names & identifiers
- Preferred name
- Erythromycin ethyl succinate
- IUPAC
- 4-O-[(2S,3R,4S,6R)-4-(dimethylamino)-2-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-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-2,10-dioxo-oxacyclotetradec-6-yl]oxy]-6-methyloxan-3-yl] 1-O-ethyl butanedioate
- English name
- Erythromycin ethylsuccinate
- Molecular formula
- C43H75NO16
- Molecular weight
- 862.05
Names & synonyms
erythromycin ethylsuccinate1264-62-6Erythromycin ethyl succinateErythrocin ethyl succinateanamycinarpimycinWyamycinERY-PEDPEDIAMYCIN 400Erythromycin, ethyl succinateErythromycin 2'-(ethyl butanedioate)Esinol
Show more names
EvesinE-Mycin eMonomycinSigapedilWyamycin E
DTXSID40229931014KSJ86FErythromycin, mono(ethyl succinate)Erythromycin, mono(ethyl succinate) (ester)NSC-756758ERYLIQUIDREFKASSuccinic acid, monoethyl ester, monoester with erythromycin
Database identifiers
- CAS
1264-62-6、41342-53-4- PubChem CID
- 443953
- DTXSID
DTXSID4022993- ChEMBL
CHEMBL1200688- ChEBI
CHEBI:31555- UNII
- 1014KSJ86F
- EC Number
- 215-033-8
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 226 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 17
- Rotatable bonds
- 14
- Heavy atoms
- 60
- Formal charge
- 0
- Complexity
- 1,450
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
LipidsPolyketides [PK] -> Ansamycins and related polyketides [PK05]
OdorODORLESS OR PRACTICALLY SO
TastePRACTICALLY TASTELESS
Color/FormWHITE OR SLIGHTLY YELLOW, CRYSTALLINE POWDER
Solubility
FREELY SOL IN ACETONE & CHLOROFORM; SOL IN 95% ETHANOL & BENZENE; SPARINGLY SOL IN ETHER; VERY SLIGHTLY SOL IN WATER
FREELY SOLUBLE IN ALC, SOL IN POLYETHYLENE GLYCOL
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Refractive IndexINDEX OF REFRACTION: 1.490 (ALPHA), 1.515 (BETA), 1.567 (GAMMA)
Stability/Shelf Life
AFTER RECONSTITUTION OF COMMERCIALLY AVAILABLE POWDER, SUSPENSIONS ARE STABLE FOR 10 DAYS @ 2-8 °C
COMMERCIALLY AVAILABLE TABLETS & POWDER FOR ORAL SUSPENSION HAVE EXPIRATION DATES OF 2 YR FOLLOWING DATES OF MANUFACTURE
COMMERCIALLY AVAILABLE SUSPENSIONS HAVE EXPIRATION DATES OF 18 MONTHS FOLLOWING DATES OF MANUFACTURE
ERYTHROMYCIN ETHYLSUCCINATE IM INJECTION HAS AN EXPIRATION DATE OF 18 MONTHS FOLLOWING DATE OF MFR
Dissociation ConstantsPKA 7.1
Collision Cross Section257.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 219 · 219-224 C
- Boiling point
- 778.19 °C · 778.19°C (rough estimate)
- Density
- 1.1417 · 1.1417 (rough estimate)
- refractive index
- 1.528 · 1.5280 (estimate)
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 50 mg/mL · ethanol: soluble50mg/mL
- form
- solid
- pka
- 13.09 · 13.09±0.70(Predicted)
- color
- white
- Water Solubility
- Freely soluble in organic solvents, practically insoluble in water
- Stability
- Hygroscopic
- Major Application
- 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 · 1264-62-6
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1014 KSJ86F · 1014KSJ86F
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 317 · H317-H334
- Precautionary statements
- 261 · P261-P280-P284-P304+P340-P342+P311
- Hazard Codes
- Xn,Xi
- Risk Statements
- 42 · 42/43-36/37/38
- Safety Statements
- 36 · 36-26
- WGK Germany
- 2 · 2
- RTECS
- 9800000 · WM9800000
- HS Code
- 29419000 · 29419000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 Skin · Resp. Sens. 1Skin Sens. 1
- Hazardous Substances Data
- 1264 · 1264-62-6(Hazardous Substances Data)
- Toxicity
- 50 oral · LD50 oral in mouse: > 10gm/kg
Safety & regulation
GHS classification
GHS Classification
Danger
H317 (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.
Hazard information
Other Safety InformationIMAP assessments - Erythromycin, 2'-(ethyl butanedioate): Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (29.9%)
Toxicology
Human Toxicity Excerpts
AMONG HYPERSENSITIVITY REACTIONS ARE FEVER, EOSINOPHILIA, & SKIN ERUPTIONS, EACH OF WHICH MAY OCCUR ALONE OR IN COMBINATION; THEY 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.
Safety data
- wgk
- 2
- rtecs
- WM9800000
- hs_code
- 29419000
- Toxicity
- LD50 oral in mouse: > 10gm/kg
- risk_code
- 42/43-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xn,Xi
- safety_code
- 36-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H334
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- Precautionary statements
- P261-P280-P284-P304+P340-P342+P311
- Hazardous Substances Data
- 1264-62-6(Hazardous Substances Data)
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
ERYTHROMYCIN ETHYLSUCCINATE
Macrolides [CS]; Decreased Sebaceous Gland Activity [PE]; Macrolide [EPC]; Macrolide Antimicrobial [EPC]
MeSH Pharmacological Classification
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Substances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
ERYTHROMYCIN ETHYLSUCCINATE IS PARTIALLY DISSOCIATED IN INTESTINE; BOTH ERYTHROMYCIN & UNDISSOCIATED ESTER ARE ABSORBED &, IN THE BLOOD, THE ESTER IS HYDROLYZED TO RELEASE FREE ERYTHROMYCIN.
ERYTHROMYCIN ETHYLSUCCINATE...IS ADEQUATELY ABSORBED FOLLOWING ORAL ADMINISTRATION, PARTICULARLY WHEN THE STOMACH IS EMPTY. PEAK CONCENTRATIONS IN PLASMA ARE 1.5 UG/ML (0.5 UG/ML OF BASE) 1 TO 2 HR AFTER ADMINISTRATION OF A 500 MG TABLET.
IN PATIENTS, MEAN BILE LEVELS OF ERYTHROMYCIN WERE APPROXIMATELY 10 TIMES HIGHER THAN CORRESPONDING SERUM CONCN 1 HR AFTER IV (ERYTHROMYCIN LACTOBIONATE) & IM (ERYTHROMYCIN SUCCINATE) INJECTION.
IN HEALTHY ADULT SUBJECTS & IN ADULT PATIENTS WITH BRONCHIAL INFECTIONS, PHARMACOKINETICS OF VARIOUS FORMULATIONS OF ERYTHROMYCIN WERE STUDIED. ERYTHROMYCIN ETHYLSUCCINATE WAS BETTER THAN ERYTHROMYCIN STEARATE FOR ORAL TREATMENT IN THAT IT WAS RAPIDLY & CONSISTENTLY ABSORBED.
Uses & manufacturing
UsesMEDICATION
Methods of ManufacturingERYTHROMYCIN IS ESTERIFIED AT THE 2' POSITION BY REACTING IT WITH ETHYL 3-CHLOROFORMYLPROPIONATE [CLCOCH2CH2CO2ET] IN DRY ACETONE IN THE PRESENCE OF SODIUM BICARBONATE.
Formulations/PreparationsPEDIAMYCIN (EES 400): TABLETS (CHEWABLE) 200 MG; GRANULES FOR DROPS (SUSPENSION) 100 MG/2.5 ML; GRANULES FOR SUSPENSION 200 MG/5 ML; SUSPENSION 200 MG/5 ML. ERYTHROCIN ETHYLSUCCINATE: INJECTION (SOLUTION) 50 MG/ML.
General Manufacturing Information
ERYTHROMYCIN ETHYLSUCCINATE INJECTION, USP (ERYTHROCIN ETHYLSUCCINATE-IM), CONTAINS 50 MG/ML IN 2- & 10-ML CONTAINERS FOR IM INJECTION. THIS PREPN INCL BUTYL AMINOBENZOATE (2%) AS LOCAL ANESTHETIC.
...USED IN FLAVORED ORAL "SUSPENSIONS" FOR PEDIATRIC USE.
...CONTAINS THE EQUIVALENT OF NOT LESS THAN 76.5% OF ERYTHROMYCIN BASE.
WHILE CROSS-RESISTANCE BETWEEN ERYTHROMYCIN & OTHER ANTIMICROBIAL AGENTS DOES NOT USUALLY OCCUR, IT HAS BEEN NOTED BETWEEN LINCOMYCIN & ERYTHROMYCIN IN STRAINS OF VIRIDANS GROUP OF STREPTOCOCCI ISOLATED FROM PT TREATED WITH EITHER AGENT. /ERYTHROMYCIN/
INCIDENCE OF ERYTHROMYCIN-RESISTANT STRAINS OF STAPH AUREUS HAS BEEN INCR; IN SOME HOSPITALS 50% OF STRAINS ARE NOT INHIBITED BY DRUG. OCCASIONAL STRAINS OF STREPTOCOCCUS PYOGENES & STREP (D) PNEUMONIAE RESISTANT TO DRUG HAVE BEEN RECOVERED FROM PT. /ERYTHROMYCIN/
Applications
UsesA broad spectrum antibiotic commonly targeting bacteria responsible for respiratory tract infections
General DescriptionErythromycin 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.
Upstream & downstream products
Upstream raw materials
Suppliers11 total
Shenzhen Monkono Technology Co.,Ltd+86-17063441314 · [email protected]
Jai Radhe Sales+(91)-(79)-26431096/65255722 · [email protected]
武汉卡诺斯科技有限公司027-83238443 15327105076 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
PT CHEM GROUP LIMITED+86-85511178; +86-85511178 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
陕西缔都医药化工有限公司029-81154043 17391733319 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
山东康鸿新材料科技有限公司17686625089; 17686625089
Additional notes
DefinitionChEBI: Erythromycin ethylsuccinate is a erythromycin derivative that is erythromycin A in which the hydroxy group at position 3R is substituted by a (4-ethoxy-4-oxobutanoyl)oxy group. It is used for the treatment of a wide variety of bacterial infections. It is a succinate ester, a cyclic ketone, an erythromycin derivative and an ethyl ester. It is functionally related to an erythromycin A.
Related reactions
2 records
Linked notes
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