Lexithromycin , CAS No.53066-26-5

CAS: 53066-26-5 Cat. No.: L329331 Fórmula: C₃₈H₇₀N₂O₁₃ Peso molecular: 763

Synonyms

Brodimoprime [INN-French] | SCHEMBL193597 | Erythromycin methyloxime | Lexithromycinum | 7QKO29734U | Lexithromycin [USAN:INN] | Erythromycin, 9-(O-methyloxime) | Lexithromycine [INN-French] | LEXITHROMYCIN [INN] | 2,6-Xylidid der 2-pyridon-3-carboxylsaur

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

Lexithromycin is an early semi-synthetic erythromycin, prepared by reaction of the 9-keto moiety to methyl oxime. The structural change improves the pH stability profile and hydrophobicity of lexithromycin for better in vivo absorption. This same rationale was used to greater effect with roxithromycin and, as a result, lexithromycin was quickly superseded and has not been not extensively studied. Like all tetracyclines, lexithromycin shows broad spectrum antibacterial and antiprotozoan activity and acts by binding to the 30S and 50S ribosomal sub-units, blocking protein synthesis.

Specifications

Sinónimos

Brodimoprime [INN-French] | SCHEMBL193597 | Erythromycin methyloxime | Lexithromycinum | 7QKO29734U | Lexithromycin [USAN:INN] | Erythromycin, 9-(O-methyloxime) | Lexithromycine [INN-French] | LEXITHROMYCIN [INN] | 2,6-Xylidid der 2-pyridon-3-carboxylsaur

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

Sorrisos canónicos

CCC1C(C(C(C(=NOC)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O

IUPAC Name

(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-methoxyimino-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one

InChIKey

HPZGUSZNXKOMCQ-SQYJNGITSA-N

INCHI

1S/C38H70N2O13/c1-15-26-38(10,46)31(42)21(4)28(39-48-14)19(2)17-36(8,45)33(53-35-29(41)25(40(11)12)16-20(3)49-35)22(5)30(23(6)34(44)51-26)52-27-18-37(9,47-13)32(43)24(7)50-27/h19-27,29-33,35,41-43,45-46H,15-18H2,1-14H3/b39-28+/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1

SMILES isoméricas

CC[C@@H]1[C@@]([C@@H]([C@H](/C(=N/OC)/[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O

Peso molecular

763

Reaxy-Rn

25648401

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25648401&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides
• Direct Parent: Aminoglycosides
• Alternative Parents: Macrolides and analogues O-glycosyl compounds Monosaccharides Oxanes Tertiary alcohols Secondary alcohols Amino acids and derivatives Carboxylic acid esters Lactones Trialkylamines 1,2-aminoalcohols Oxime ethers Polyols Monocarboxylic acids and derivatives Dialkyl ethers Oxacyclic compounds Acetals Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Aminoglycoside core - Macrolide - Glycosyl compound - O-glycosyl compound - Monosaccharide - Oxane - Tertiary alcohol - 1,2-aminoalcohol - Amino acid or derivatives - Carboxylic acid ester - Lactone - Oxime ether - Secondary alcohol - Tertiary aliphatic amine - Tertiary amine - Acetal - Monocarboxylic acid or derivatives - Polyol - Organoheterocyclic compound - Oxacycle - Ether - Dialkyl ether - Carboxylic acid derivative - Carbonyl group - Alcohol - Organopnictogen compound - Organonitrogen compound - Amine - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Aliphatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Alvos associados (não humanos)

Bacillus subtilis (32866 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Toxoplasma gondii (4585 Activities)

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Mecanismos de ação

Propriedades químicas e físicas

• Peso molecular: 763.000 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 8
• Exact Mass: 762.488 Da
• Monoisotopic Mass: 762.488 Da
• Topological Polar Surface Area: 198.000 Ų
• Heavy Atom Count: 53
• Formal Charge: 0
• Complexity: 1230.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 18
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1