26116-56-3

Basic information

• Product Name: (9S)-9-Amino-9-deoxoerythromycin
• Synonyms: (9S)-9-Amino-9-deoxoerythromycin;9-(S)-AMINOERYTHROMYCIN;9-(S)-ERYTHROMYCYLAMINE:9-AMINO-9-DEOXO-ERYTHROMYCIN;(9S)-9-Deoxy-9-aminoerythromycin A;(9S)-Erythromycylamine A;BRL 42852ER;Erythromycylamine;LY 024410
• CAS NO: 26116-56-3
• Molecular Formula: C₃₇H₇₀N₂O₁₂
• Molecular Weight: 734.962
• EINECS: 406-790-7
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 26116-56-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 123-127°C
• Boiling Point: 810.3 °C at 760 mmHg
• Flash Point: 443.8 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 2.15E-30mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: -20°C Freezer
• PKA: 13.41±0.70(Predicted)
• CAS DataBase Reference: (9S)-9-Amino-9-deoxoerythromycin(CAS DataBase Reference)
• NIST Chemistry Reference: (9S)-9-Amino-9-deoxoerythromycin(26116-56-3)
• EPA Substance Registry System: (9S)-9-Amino-9-deoxoerythromycin(26116-56-3)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-50/53
• Safety Statements: 26-39-60-61
• Hazardous Substances Data: 26116-56-3(Hazardous Substances Data)

Usage

Chemical Properties

(9S)-9-Amino-9-deoxoerythromycin is White Solid

Uses

Different sources of media describe the Uses of 26116-56-3 differently. You can refer to the following data:
1. (9S)-9-Amino-9-deoxoerythromycin is a semi-synthetic analogue of erythromycin prepared by reduction of erythromycin oxime. (9S)-9-Amino-9-deoxoerythromycin is a potent antibiotic, however the introduction of the amino- moiety increases the compound’s polarity and is disadvantageous for in vivo use. This limitation was overcome by the synthesis of dirithromycin, a Schiff base pro-drug that dissociates in vivo to erythromycylamine.
2. Erythromycylamine is a semi-synthetic analogue of erythromycin prepared by reduction of erythromycin oxime. Erythromycylamine is a potent antibiotic, however the introduction of the amino- moiety increases the compound’s polarity and is disadvantageous for in vivo use. This limitation was overcome by the synthesis of dirithromycin, a Schiff base pro-drug that dissociates in vivo to erythromycylamine.
3. (9S)-9-Amino-9-deoxoerythromycin is a metabolite of Dirithromycin; an antibiotic

Definition

ChEBI: A macrolide antibiotic that is erythromycin A in which the ketone group has been converted to the corresponding imine and then reduced to give the corresponding amino compound (the 9S diastereoisomer).

InChI:InChI=1/C37H70N2O12/c1-14-25-37(10,45)30(41)20(4)27(38)18(2)16-35(8,44)32(51-34-28(40)24(39(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-32,34,40-42,44-45H,14-17,38H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

Upstream product

• 13127-18-9 C₃₇H₆₈N₂O₁₃ 
• 13127-18-9 (9-E)-deoxo-9-hydroximinoerythromycin A 
• 78442-83-8 (1S,2R,4R,5R,7R,9S,10R,13R,14R,15R,19S,20S)-13-Ethyl-4,14-dihydroxy-2,4,10,14,19,20-hexamethyl-7-(2,4,6-trimethyl-phenyl)-6,8,12,16-tetraoxa-18-aza-tricyclo[13.3.1.1^5,9]icosane-11,17-dione 
• 449142-84-1 C₄₄H₆₆N₂O₁₂ 
• 78443-15-9 (1S,2R,4R,5R,7R,9S,10R,13R,14R,15R,19S,20S)-18-(Biphenyl-4-carbonyl)-13-ethyl-4,14-dihydroxy-2,4,10,14,19,20-hexamethyl-7-(2,4,6-trimethyl-phenyl)-6,8,12,16-tetraoxa-18-aza-tricyclo[13.3.1.1^5,9]icosane-11,17-dione 
• 78443-18-2 Biphenyl-4-carboxylic acid [(2R,3S,4R,5S,6S,7R,9R,10R,11S,12S,13R)-10-((2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-amide 
• 78443-16-0 Biphenyl-4-carboxylic acid [(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,15R,17S)-5-ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-3-oxo-15-(2,4,6-trimethyl-phenyl)-4,14,16-trioxa-bicyclo[11.3.1]heptadec-9-yl]-amide 
• 78479-30-8 Biphenyl-4-carboxylic acid ((2R,3S,4R,5S,6S,7R,9R,10R,11S,12S,13R)-2-ethyl-3,4,9,10,12-pentahydroxy-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl)-amide 
• 78443-17-1 (2S,3R,4S,6R)-4-(dimethylamino)-6-methyl-2-(pyrimidin-2-ylthio)tetrahydro-2H-pyran-3-yl methyl carbonate 
• 155382-14-2 (2S,3R,4S,6R)-4-Dimethylamino-6-methyl-2-(pyrimidin-2-ylsulfanyl)-tetrahydro-pyran-3-ol 
• 78443-20-6 4-O-acetyl-1-deoxy-1-(2-pyridylthio)-α-L-cladinoside 
• 111869-04-6 4-acetyl-L-cladinose 
• 801972-88-3 D-desosamine 
• 114-07-8 erythromycin 

Downstream Products

• 79617-15-5 [10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester 
• 850220-44-9 C₅₀H₈₄N₄O₁₆ 
• 79541-37-0 acetic acid 2-[10-benzyloxycarbonylamino-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-2-oxo-oxacyclotetradec-6-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester 
• 112452-09-2 9-N-(cyclohex-3-en-1-ylmethyl)erythromycylamine 
• 112452-23-0 9-N-(2-methoxyethyl)erythromycylamine 
• 119904-03-9 9-N-(1-propyl)erythromycylamine 
• 78443-18-2 Biphenyl-4-carboxylic acid [(2R,3S,4R,5S,6S,7R,9R,10R,11S,12S,13R)-10-((2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9,12-tetrahydroxy-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-amide 
• 62013-04-1 dirithromycin 
• 121329-81-5 9(S)-<tyrosyl>amino>erythromycin 
• 121329-78-0 9(S)-amino>erythromycin 
• 121329-80-4 9(S)-<glycyl>amino>erythromycin 
• 121329-84-8 9(S)-amino>erythromycin 
• 121329-85-9 9(S)-amino>erythromycin 
• 129968-13-4 9-N-(3-phenylpropargyl)erythromycylamine 

Relevant articles and documents

Synthetic method of isotope-labeled erythromycylamine

The invention discloses a synthetic method of isotope-labeled erythromycylamine, belongs to the field of drug metabolism, and provides a synthetic method which is reasonable in process design, strongin operability and high in yield, can efficiently convert isotope-labeled raw materials into labeled target products, and can realize industrial production of isotope-labeled erythromycylamine. The method takes 13CD3 labeled methyl iodide as a starting raw material, the isotope-labeled erythromycylamine is synthesized by six steps of reactions, optimal preparation steps and reaction conditions arescreened out through a large number of experiments, the whole process is reasonable in design and high in operability, the labeled raw materials can be efficiently converted into labeled target products, the chemical purity of the labeled erythromycylamine prepared through the method can reach 98.5% or above, and the labeled isotope abundance is larger than 98.5%.

9-N-ethenyl derivatives of 9(S)-erythromycylamine

The invention relates to 9-N-ethenyl derivatives of 9 (S)-erythromycylamine, new semisynthetic antibiotics of the macrolide class of the general formula (I) STR1 wherein R1 and R2 are the same or different and represent nitryl, a carboxyl group of the formula COOR3, wherein R3 represents a C1 -C4 alkyl group, or a keto group of the formula COR4, wherein R4 represents a C1 -C4 alkyl group, to their pharmaceutically acceptable addition salts with inorganic or organic acids, to a process for their preparation, to a process for the preparation of the pharmaceutical compositions as well as to the use of the obtained pharmaceutical compositions in the treatment of bacterial infections.

A MILD SINGLE-STEP REDUCTION OF OXIMES TO AMINES

A mild and convenient procedure has been developed for the reduction of oximes to amines in a single step involving treatment the oxime with TiCl3 in the presence of NaBH3CN.This method is especially useful for those substrates in which the intermeiate im