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Roxithromycin

HCID 6915744
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
80214-83-1
Standard-SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)/C(=N\OCOCCOC)[C@H](C)[C@@H](O)[C@]1(C)O
InChIKey
RXZBMPWDPOLZGW-XMRMVWPWSA-N
Summenformel
C41H76N2O15
Durchschnittliche Molmasse
837 g/mol
Monoisotopische Masse
836,52456972

Überblick

Roxithromycin is semisynthetic derivative of erythromycin A. It has a role as an antibacterial drug. It is a macrolide, an erythromycin derivative and a semisynthetic derivative. It is functionally related to an erythromycin A.

Namen und Bezeichner

Bevorzugter Name
Roxithromycin
IUPAC
(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
Englischer Name
Roxithromycin
Summenformel
C41H76N2O15
Molmasse
837.05

Namen und Synonyme

roxithromycinRulide80214-83-1RulidRU 28965RU 965InfectoroxitRU-965Roxi-paed 1A PharmaRoxitromycinRoxitromycineDTXSID8041117
Weitere Namen anzeigen
RoxidRoxithromycin (Roxl-150)Roxithromycin Solution, 100ppmBrilidOveralSurlidAssoralForilin
NSC-75844321KOF230FACHEBI:48935RU-28965(9E)-erythromycin 9-(O-((2-methoxyethoxy)methyl)oxime)DTXCID6021117CHEBI:48844Erythromycin, 9-(O-((2-methoxyethoxy)methyl)oxime), (9E)-

Datenbank-Bezeichner

CAS
80214-83-1
PubChem CID
6915744
ChEMBL
CHEMBL1214185
ChEBI
CHEBI:48844
UNII
21KOF230FA
EC Number
617-007-5

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,1
Polarare Oberfläche (TPSA)
217 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
17
Frei drehbare Bindungen
13
Schwere Atome
58
Formalladung
0
Komplexität
1.310

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

LogP3.46
Human DrugsBreast Feeding; Lactation; Anti-Bacterial Agents; Anti-Infective Agents; Macrolides
Dissociation Constants9.27
Collision Cross Section285.66 Ų [M+Na]+

Physikochemische Eigenschaften

Schmelzpunkt
111 · 111-118C
Siedepunkt
864.7 · 864.7±75.0 °C(Predicted)
Dichte
1.25 · 1.25±0.1 g/cm3(Predicted)
Flammpunkt
110 ° · >110°(230°F)
storage temp.
2 · Sealed in dry,2-8°C
Löslichkeit
10 mg/mL · chloroform: soluble10mg/mL
pka
9.27 · pKa 9.27±0.01(H2O t = 25.0 I = 0.15 (KCl)) (Uncertain)
Aggregatzustand
powder
Farbe
White to off-white
Wasserlöslichkeit
18 · Soluble in water to 18µg/ml
Merck
14 · 14,8276
Major Application
pharmaceutical (small molecule)
InChIKey
RXZBMPWDPOLZGW-HEWSMUCTSA-N
SMILES
CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC3OC(C)CC(C3O)N(C)C)C(C)(O)CC(C)C(=N/OCOCCOC)\C(C)C(O)C1(C)O
CAS Datenbank
80214 · 80214-83-1
EPA chemische Informationen
9 · Erythromycin, 9-[O-[(2-methoxyethoxy)methyl]oxime], (9E)- (80214-83-1)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 67 reports by companies from 2 notifications to the ECHA C&L Inventory.

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Regulatory InformationRoxithromycin: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories · 2 Einträge

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

ROXITHROMYCIN

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
3
hs_code
29415000
RTECS-Nr.
KF4990000
risk_code
22
hazard_code
Xn
safety_code
26-24/25
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 Oral

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding96%, mainly to alpha1-acid glycoproteins
Pharmacodynamics · 1 Eintrag

Roxithromycin has the following antibacterial spectrum <i>in vitro</i>: <i>Streptococcus agalactiae</i>, <i>Streptococcus pneumoniae</i> (Pneumococcus), <i>Neisseria meningitides</i> (Meningococcus), <i>Listeria monocytogenes</i>, <i>Mycoplasma pneumoniae</i>, <i>Chlamydia trachomatis</i>, <i>Ureaplasma urealyticum</i>, <i>Legionella pneumophila</i>, <i>Helicobacter</i> (Campylobacter), <i>Gardnerella vaginalis</i>, <i>Bordetella pertussis</i>, <i>Moraxella catarrhalis</i> (<i>Branhamella Catarrhalis</i>), and <i>Haemophilus ducreyi</i>. Roxithromycin is highly concentrated in polymorphonuclear leukocytes and macrophages, achieving intracellular concentrations greater than those outside the cell. Roxithromycin enhances the adhesive and chemotactic functions of these cells which in the presence of infection produce phagocytosis and bacterial lysis. Roxithromycin also possesses intracellular bactericidal activity.

Mechanism of ActionRoxithromycin prevents bacterial growth by interfering with their protein synthesis. It binds to the 50S subunit of bacterial ribosomes and inhibits the translocation of peptides.
Biological Half-Life12 hours
Metabolism/Metabolites · 1 Eintrag

Hepatic. Roxithromycin is only partially metabolised, more than half the parent compound being excreted unchanged. Three metabolites have been identified in urine and faeces: the major metabolite is descladinose roxithromycin, with N-mono and N-di-demethyl roxithromycin as minor metabolites. The respective percentage of roxithromycin and these three metabolites is similar in urine and faeces.

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionVery rapidly absorbed and diffused into most tissues and phagocytes.

Verwendung und Herstellung

UsesUse (kg) in Switzerland (2009): >10
Anwendungen · 2 Einträge

BeschreibungRoxithromycin, an oxime ether derivative of erythromycin, is a new macrolide antibiotic of high potency and long duration. Its in v i m activity spectrum is similar to that of erythromycin, but is superior to the latter against Legionella, Mycoplasma and Chlamydia.

VerwendenRoxithromycin was one of the new generation erythromycins introduced in the 1980s. Improved acid stability was achieved by converting the 9-keto group to the more stable oxime and alkylation of the oxime to provide the methoxyethoxymethyl ether oxime. In vivo, roxithromycin exhibits higher tissue levels and a longer half-life while being slightly less potent than erythromycin in vitro.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

EthanolN,N-DimethylformamidN,N-Diethylethanamin1-Chlor-2,5-dioxahexanMethanolHydroxylammoniumchloridErythromycinERYTHROMYCIN OXIME

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