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Roxithromycin

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Name

Roxithromycin

EINECS 617-007-5
CAS No. 80214-83-1 Density 1.25 g/cm3
PSA 216.89000 LogP 2.20960
Solubility Soluble in water to 18µg/ml Melting Point 111-118 °C
Formula C41H76N2O15 Boiling Point 864.7 °C at 760 mmHg
Molecular Weight 837.059 Flash Point 476.7 °C
Transport Information N/A Appearance white crystalline powder
Safety 26 Risk Codes 22
Molecular Structure Molecular Structure of 80214-83-1 (Roxithromycin) Hazard Symbols HarmfulXn
Synonyms

Roxithromycin,Stearyl Glycyrrhetinate;Roxithromycin EP;RU 965;Rulide (TN);Roxithromycinum [Latin];RU 28965;9-(O-((2-Methoxyethoxy)methyl)oxime)erythromycin;Roxithromycin (JP14/USAN);Roxithromycine [French];(3R,4S,5S,6R,7R,9R,10Z,11S,12R,13R,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-10-(2-methoxyethoxymethoxyimino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one;Roxitromicina [Spanish];Rulide;Prestwick_1046;Erythromycin, 9-(O-((2-methoxyethoxy)methyl)oxime), (9E)-;

Article Data 3

Roxithromycin Synthetic route

3970-21-6

2-Methoxyethoxymethyl chloride

13127-18-9

(9-E)-deoxo-9-hydroximinoerythromycin A

80214-83-1

roxithromycin

Conditions
ConditionsYield
With sodium ethanolate In acetone at 0 - 5℃; for 0.416667h;
80214-83-1

roxithromycin

214902-82-6

Decladinoseroxithromycin

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; for 12h;98%
80214-83-1

roxithromycin

(E)-N-Demethylroxithromycin

Conditions
ConditionsYield
With sodium hydroxide; iodine; sodium acetate In methanol; water at 48℃;80%
With sodium hydroxide; water; iodine; sodium acetate In methanol at 48℃; for 0.5h;80%
Stage #1: roxithromycin With sodium acetate In methanol; water at 51℃; for 0.1h;
Stage #2: With iodine In methanol; water for 0.333333h;
Stage #3: With sodium hydroxide In methanol; water at 51℃; for 11.6667h;
68%
108-30-5

succinic acid anhydride

80214-83-1

roxithromycin

C45H80N2O18

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 72h; Inert atmosphere;65%
80214-83-1

roxithromycin

C25H47NO10

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane; water at 50℃; for 24h;

Roxithromycin Specification

The IUPAC name of Roxithromycin is (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. With the CAS registry number 80214-83-1, it is also named as Erythromycin 9-(O-((2-methoxyethoxy)methyl)oxime). The product's categories are Antibiotic Explorer; Intermediates & Fine Chemicals; Pharmaceuticals; Veterinary Medicine, Soluble Powder; Peptide Synthesis/Antibiotics. Besides, it is white crystalline powder, which should be stored at 2-8 °C. In addition, its molecular formula is C41H76N2O15 and molecular weight is 837.05.When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.
 

The other characteristics of Roxithromycin can be summarized as:
 (1)ACD/LogP: 3.73; (2)# of Rule of 5 Violations: 3; (3)#H bond acceptors: 17; (4)#H bond donors: 5; (5)#Freely Rotating Bonds: 18; (6)Polar Surface Area: 161.89 Å2; (7)Index of Refraction: 1.535; (8)Molar Refractivity: 207.49 cm3; (9)Molar Volume: 666.3 cm3; (10)Polarizability: 82.25×10-24cm3; (11)Surface Tension: 39.7 dyne/cm; (12)Density: 1.25 g/cm3; (13)Flash Point: 476.7 °C; (14)Enthalpy of Vaporization: 142.8 kJ/mol; (15)Boiling Point: 864.7 °C at 760 mmHg; (16)Vapour Pressure: 7.17E-35 mmHg at 25 °C.

Preparation of Roxithromycin:
This chemical can be prepared by erythromycin. The reaction is as follows:
Preparation of Roxithromycin

Uses of Roxithromycin:
This chemical is a semi-synthetic macrolide antibiotic that is used for the treatment of respiratory tract, urinary and soft tissue infections. It can also be used to prevent bacteria from growing, by interfering with their protein synthesis.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C3O[C@H](CC)[C@](O)(C)[C@H](O)[C@H](C(=NOCOCCOC)[C@H](C)C[C@](O)(C)[C@H](O[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O)[C@H]([C@H](O[C@@H]2O[C@H]([C@H](O)[C@](OC)(C2)C)C)[C@H]3C)C)C
(2)InChI: InChI=1/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1
(3)InChIKey: RXZBMPWDPOLZGW-HITVVWEBBY

The toxicity data of Roxithromycin is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 0.2gm/kg (200mg/kg)   Drugs in Japan Vol. -, Pg. 1471, 1995.
mouse LD50 intraperitoneal 148mg/kg (148mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 33, Pg. 787, 1991.
mouse LD50 oral 665mg/kg (665mg/kg)   Drugs in Japan Vol. -, Pg. 1471, 1995.
rat LD50 intraperitoneal 171mg/kg (171mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 33, Pg. 787, 1991.
rat LD50 oral 830mg/kg (830mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 36(Suppl,

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