Erythromycinethylsuccinat

Erythromycin ethyl succinate

HCID 443953CAS 1264-62-6

Grundinformationen

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
Summenformel
C43H75NO16
Durchschnittliche Molmasse
862,1 g/mol
Monoisotopische Masse
861,50858532

Überblick

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.

Namen und Bezeichner

Bevorzugter 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
Lokaler Name
Erythromycinethylsuccinat
Englischer Name
Erythromycin ethylsuccinate
Summenformel
C43H75NO16
Molmasse
862.05

Namen und Synonyme

erythromycin ethylsuccinate1264-62-6Erythromycin ethyl succinateErythrocin ethyl succinateanamycinarpimycinWyamycinERY-PEDPEDIAMYCIN 400Erythromycin, ethyl succinateErythromycin 2'-(ethyl butanedioate)Esinol
Weitere Namen anzeigen
EvesinE-Mycin eMonomycinSigapedilWyamycin E
DTXSID40229931014KSJ86FErythromycin, mono(ethyl succinate)Erythromycin, mono(ethyl succinate) (ester)NSC-756758ERYLIQUIDREFKASSuccinic acid, monoethyl ester, monoester with erythromycin

Datenbank-Bezeichner

CAS
1264-62-6、41342-53-4
PubChem CID
443953
DTXSID
DTXSID4022993
ChEMBL
CHEMBL1200688
ChEBI
CHEBI:31555
UNII
1014KSJ86F
EC Number
215-033-8

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,4
Polarare Oberfläche (TPSA)
226 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
17
Frei drehbare Bindungen
14
Schwere Atome
60

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Antibiotics
LipidsPolyketides [PK] -> Ansamycins and related polyketides [PK05]
OdorODORLESS OR PRACTICALLY SO
TastePRACTICALLY TASTELESS
Color/FormWHITE OR SLIGHTLY YELLOW, CRYSTALLINE POWDER
Solubility · 2 Einträge

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

Physikochemische Eigenschaften

Schmelzpunkt
219 · 219-224 C
Siedepunkt
778.19 °C · 778.19°C (rough estimate)
Dichte
1.1417 · 1.1417 (rough estimate)
Brechungsindex
1.528 · 1.5280 (estimate)
Flammpunkt
110 ° · >110°(230°F)
storage temp.
Sealed in dry,Room Temperature

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Other Safety InformationIMAP assessments - Erythromycin, 2'-(ethyl butanedioate): Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (29.9%)

Toxikologische Informationen

Human Toxicity Excerpts · 3 Einträge

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.

Sicherheitsdaten

wgk
2
hs_code
29419000
RTECS-Nr.
WM9800000
risk_code
42/43-36/37/38
Toxizität
LD50 oral in mouse: > 10gm/kg
hazard_code
Xn,Xi

Chemie und Industrie

Pharmakologische Informationen

FDA Pharmacological Classification · 2 Einträge

ERYTHROMYCIN ETHYLSUCCINATE

Macrolides [CS]; Decreased Sebaceous Gland Activity [PE]; Macrolide [EPC]; Macrolide Antimicrobial [EPC]

MeSH Pharmacological Classification · 4 Einträge

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 · 4 Einträge

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.

Verwendung und Herstellung

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 · 5 Einträge

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/

Vor- und nachgelagerte Produkte

Anbieter11 Anbieter

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]

Zugehörige Reaktionen

2

Verknüpfte Notizen

Wird geladen…