Erythromycylamine
Basic information
- CAS
26116-56-3- 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@H](N)[C@H](C)[C@@H](O)[C@]1(C)O- InChIKey
XCLJRCAJSCMIND-JCTYMORFSA-N- Molecular formula
- C37H70N2O12
- Average molar mass
- 735 g/mol
- Monoisotopic mass
- 734.49287567
Overview
(9S)-erythromycyclamine is a macrolide antibiotic that is erythromycin A in which the ketone group has been converted into the corresponding imine and then reduced to give the corresponding amino compound (the 9S diastereoisomer).
Names & identifiers
- Preferred name
- Erythromycylamine
- IUPAC
- (3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-10-amino-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-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan-2-one
- English name
- (9S)-9-Amino-9-deoxoerythromycin
- Molecular formula
- C37H70N2O12
- Molecular weight
- 734.96
Names & synonyms
Erythromycylamine26116-56-3(9S)-9-Amino-9-deoxoerythromycin9(S)-Erythromycylamine9-EpierythromycylamineBRN 4241492(9S)-9-amino-9-deoxyerythromycinYX9KV1OMA4erythromyclamine, (9S)-BRL-42852ERLY-024410RefChem:405596
Show more names
LY 024410BRL 42852ERErythromycilamine9-()-Eythromyeyamine9-(S)-AMINOERYTHROMYCIN
406-790-7(9S)-erythromycyclamineDirithromycin EP Impurity AEpierythromycyl-A-amineErythromycin, 9-amino-9-deoxo-, (9S)-MFCD00872156CHEMBL290242(3R,4S,5S,6R,7R,9R,10S,11S,12R,13S,14R)-10-amino-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecan-2-one
Database identifiers
- CAS
26116-56-3
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 203 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 7
- Heavy atoms
- 51
- Formal charge
- 0
- Complexity
- 1,140
Experimental & physicochemical properties
LogP3.0
Physicochemical properties
- Melting point
- 123 · 123-127°C
- Boiling point
- 810.3 · 810.3±65.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- 15 mg/ml; · DMF: 15 mg/ml; DMSO: 15 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2) (1:1): 0.5 mg/ml
- form
- A solid
- pka
- 13.41 · 13.41±0.70(Predicted)
- color
- White to off-white
- optical activity
- Consistent with structure
- InChIKey
- XCLJRCAJSCMIND-FLSDEJNQNA-N
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 9 KV1OMA4 · YX9KV1OMA4
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P273, P280, P305+P354+P338, P317, P391, and P501 (click each P-code to see the statement)
Danger
H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P273, P280, P305+P354+P338, P317, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory InformationREACH registered substance: (9S)-9-amino-9-deoxyerythromycin (EC: 406-790-7)
Hazard Classes and Categories
Eye Dam. 1 (100%)
Eye damage - category 1
Eye Dam. 1
Safety data
- Toxicity
- mouse,LD50,intraperitoneal,120mg/kg (120mg/kg),European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 13, Pg. 83, 1978.
- risk_code
- 41-50/53
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS09
- hazard_code
- Xi,N
- safety_code
- 26-39-60-61
- Hazard statements
- H318-H410
- REACH Registrations
- Inactive
- Precautionary statements
- P280-P305+P351+P338-P310-P273-P391-P501
Chemistry & industry
Applications
Uses(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.
UsesErythromycylamine 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.
Uses(9S)-9-Amino-9-deoxoerythromycin is a metabolite of Dirithromycin; an antibiotic
Additional notes
DefinitionChEBI: 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).
Related reactions
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Compound notes
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