Grundinformationen
- CAS
2013-58-3- Standard-SMILES
C=C1c2c(Cl)ccc(O)c2C(O)=C2C(=O)[C@]3(O)C(O)=C(C(N)=O)C(=O)[C@@H](N(C)C)[C@@H]3[C@@H](O)[C@H]12- InChIKey
RNIADBXQDMCFEN-IWVLMIASSA-N- Summenformel
- C22H21ClN2O8
- Durchschnittliche Molmasse
- 476,9 g/mol
- Monoisotopische Masse
- 476,0986433
Überblick
Meclocycline is a member of tetracyclines.
Namen und Bezeichner
- Bevorzugter Name
- Meclocycline
- IUPAC
- (4S,4aR,5S,5aR,12aR)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
- Lokaler Name
- Meclocyclin
- Englischer Name
- meclocycline
- Summenformel
- C22H21ClN2O8
- Molmasse
- 476.86
Namen und Synonyme
meclocycline2013-58-3MeclociclinaGS-298923Q8M2HE6SMeclocyclinumGS 29897-Chloro-6-methylene-5-oxytetracycline(4S,4aR,5S,5aR,12aR)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamideNSC-785027-Cloro-6-metilene-5-ossitetraciclina
Weitere Namen anzeigen
Aids043973Aids-043973MECLOCYLINEMeclocycline baseMeclocycline(usan)Chlormethylenecyclinemeclocycline USP/EP/BP
(4S,4aR,5S,5aR,12aS)-7-chloro-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamideMeclociclina [Italian]Meclocyclinum [INN-Latin]Meclociclina [INN-Spanish]Meclocycline [USAN:INN:BAN]Meclocycline [USAN]EINECS 217-938-3NSC 78502
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,9
- Polarare Oberfläche (TPSA)
- 182 Ų
- H-Brücken-Donoren
- 6
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 33
- Formalladung
- 0
- Komplexität
- 1.040
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
SolubilitySoluble
Physikochemische Eigenschaften
- Schmelzpunkt
- 167 °C · >167°C (dec.)
- Siedepunkt
- 837 · 837.0±65.0 °C(Predicted)
- Dichte
- 1.72 · 1.72±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- pka
- 4.5 · 4.50±1.00(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Yellow to Dark Yellow
- Stabilität
- Light Sensitive
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- Toxizität
- LD50 in mice (mg/kg): >5000 orally, 425 i.p. (Bernardi)
Chemie und Industrie
Pharmakologische Informationen
Protein BindingEstimated plasma protein binding of ~75-91% based on that of demeclocycline due to structural similarity.
PharmacodynamicsTetracyclines such as meclocycline are broad spectrum bacteriostatic agents. Meclocyclin likely inhibits the growth of bacterial species present in the damaged oral mucosa, allowing the immune system to more easily eliminate infections.
Mechanism of Action
As a tetracycline, meclocycline likely works by reversably associating with the 30s subint of the bacterial ribosome. A likely binding site for tetracyclines has been identified on protein S7 of this subunit. This association blocks the association of aminoacyl-tRNA with the ribosome, inhibiting protein synthesis. Ultimately this inhibits bacterial growth due to a lack of proteins necessary for reproduction.
Biological Half-LifeHalf life estimated to be ~5.6h based on that of chlortetracycline due to structural similarity.
Metabolism/MetabolitesMost tetracyclines are not metabolized. It is unlikely that meclocycline would be metabolized.
Absorption, Distribution and Excretion
Estimated oral bioavailability of ~66% and tmax of 4h based on that of demeclocycline due to structural similarity.
Estimated urinary excretion of ~40% and fecal excretion of ~43% based on that of demeclocycline due to structural similarity.
Estimated Vd of 121L based on that of demeclocycline due to structural similarity.
Anwendungen
VerwendenMeclocycline is a semi-synthetic tetracycline prepared by dehydration of the 6-hydroxy group of chlortetracycline to yield an exocyclic 6-methylene. Meclocyline is a close structural analogue of methacycline. Like all tetracyclines, meclocycline shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis. Meclocycline has been extensively cited in the literature with over 400 references.
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