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(3R,4S,5S,6R,7R,9R,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

HCID 444037
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Basic information

CAS
80214-83-1
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(=NOCOCCOC)[C@H](C)[C@@H](O)[C@]1(C)O
InChIKey
RXZBMPWDPOLZGW-HITVVWEBSA-N
Molecular formula
C41H76N2O15
Average molar mass
837 g/mol
Monoisotopic mass
836.52456972

Names & identifiers

Preferred name
(3R,4S,5S,6R,7R,9R,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
IUPAC
(3R,4S,5S,6R,7R,9R,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
English name
Roxithromycin
Molecular formula
C41H76N2O15
Molecular weight
837.05

Names & synonyms

MLS001304008Spectrum_001653Spectrum2_001551Spectrum3_001159Spectrum4_000200SCHEMBL65986KBioGR_000779KBioSS_002133(3R,4S,5S,6R,7R,9R,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-oneDivK1c_000382SPBio_001422CHEMBL1476500
Show more names
RoxidRulidRoxithromycin (Roxl-150)Roxithromycin Solution, 100ppmBrilidOveralRU 965SurlidAssoralForilin
BCBcMAP01_000131KBio1_000382KBio2_002133KBio2_004701KBio2_007269KBio3_002217NINDS_000382HMS2236F08

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
217 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
17
Rotatable bonds
13
Heavy atoms
58
Formal charge
0
Complexity
1,310

Experimental & physicochemical properties

LogP1.7
Solubility1.87e-01 g/L
Human DrugsPharmaceuticals
Physical DescriptionSolid
Collision Cross Section280.7 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID8041117]

Physicochemical properties

Melting point
111 · 111-118C
Boiling point
864.7 · 864.7±75.0 °C(Predicted)
alpha
25 · D25 -77.5 ±2° (c = 0.45 in chloroform)
Density
1.25 · 1.25±0.1 g/cm3(Predicted)
Flash point
110 ° · >110°(230°F)
storage temp.
2 · Sealed in dry,2-8°C
solubility
10 mg/mL · chloroform: soluble10mg/mL

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
rtecs
KF4990000
hs_code
29415000
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
26-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P501

Chemistry & industry

Pharmacology

Cellular LocationsMembrane
Metabolite PathwaysRoxithromycin Action Pathway

Uses & manufacturing

Use ClassificationPharmaceuticals
Applications · 5 items

Uses1. It belongs to macrolide antibiotics, being a kind of erythromycin derivative with the antibacterial spectrum being similar as erythromycin but having a 6 times stronger effect on erythromycin with high bioavailability. It is used for the treatment of respiratory tract infection, such as pneumonia, acute bronchitis, acute infection of chronic bronchitis, atypical pneumonia, and genitourinary system infection, skin and soft tissue infections, having good therapeutic effect and tolerance with smaller adverse reactions than erythromycin. 2. As the new generation of macrolide antibiotics; 3. The product belongs to a new generation of macrolide antibiotics, mainly used for Gram-positive bacteria, anaerobes, chlamydia and mycoplasma. Its antibacterial activity in vitro is similar as erythromycin with its in vivo effect being 1-4 times stronger than erythromycin. Pharmacological effects and indications 1, it has strong bactericidal effect on Gram-negative bacteria and some Gram-negative bacteria (meningococcus, Neisseria gonorrhoeae, influenza bacilli, pertussis, Brucella) and spirochetes, Mycoplasma pneumoniae and Rickettsia. Legionella is sensitive to it; its effect against mycoplasma and chlamydia is further enhanced. 4. 2, antibacterial mechanism: it can bind to the bacterial ribosome 50S subunit, through blocking the peptidyl transfer and MRNA displacement, further inhibiting the protein synthesis. 3, this product has excellent oral absorption and quick efficacy with stronger bioavailability and plasma concentrations than erythromycin. According to reports, oral administration of 150 mg can lead to a peak plasma concentration of up to 6.6~7.9 ug/ml while the value for erythromycin under the same conditions is only 0.2~0.4ug/ml; roxithromycin is mainly distributed in body fluids and tissues, with high and durable tissue concentration and cell concentration. Moreover, it has a half-life of up to 12 h while the value for erythromycin is only 1.5~2.0h. 4, in clinical medicine, it is the first-choice drug for the treatment of drug-resistance Staphylococcus aureus and hemolytic streptococcus. In veterinary clinical practice, it is used for the treatment of penicillin-resistant staphylococcus aureus caused severe infection, pneumonia, uterine inflammation and poultry chronic respiratory disease. 5, the goods are mainly used for the treatment of livestock and poultry chronic respiratory disease with good efficacy in the treatment of livestock and poultry staphylococcus and streptococcal disease, chlamydia, spirocheal disease (swine dysentery), infectious pleurisy and rhinitis. 6, indications: avian neck swelling, local heat, pain, difficulty breathing, mouth and nose flow white foam, mucous membranes and skin cyanosis and other symptoms.

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Compound notes

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Database identifiers

CAS
80214-83-1
PubChem CID
444037
DTXSID
DTXSID8041117
ChEMBL
CHEMBL1476500
pka
9.27 · pKa 9.27±0.01(H2O t = 25.0 I = 0.15 (KCl)) (Uncertain)
form
powder
color
White to off-white
Water Solubility
18 · Soluble in water to 18µg/ml
Merck
14 · 14,8276
Major Application
pharmaceutical (small molecule)
InChIKey
RXZBMPWDPOLZGW-HEWSMUCTSA-N
SMILES
CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC3OC(C)CC(C3O)N(C)C)C(C)(O)CC(C)C(=N/OCOCCOC)\C(C)C(O)C1(C)O
CAS DataBase Reference
80214 · 80214-83-1
FDA UNII
21 KOF230FA · 21KOF230FA
ATC code
1 FA06 · J01FA06
EPA Substance Registry System
9 · Erythromycin, 9-[O-[(2-methoxyethoxy)methyl]oxime], (9E)- (80214-83-1)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P501
Hazard Codes
Xn
Risk Statements
22 · 22
Safety Statements
26 · 26-24/25
WGK Germany
3 · 3
RTECS
4990000 · KF4990000
HS Code
29415000 · 29415000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral

DescriptionRoxithromycin, an oxime ether derivative of erythromycin, is a new macrolide antibiotic of high potency and long duration. Its in v i m activity spectrum is similar to that of erythromycin, but is superior to the latter against Legionella, Mycoplasma and Chlamydia.

UsesRoxithromycin was one of the new generation erythromycins introduced in the 1980s. Improved acid stability was achieved by converting the 9-keto group to the more stable oxime and alkylation of the oxime to provide the methoxyethoxymethyl ether oxime. In vivo, roxithromycin exhibits higher tissue levels and a longer half-life while being slightly less potent than erythromycin in vitro.

Usesanesthetic (local)

UsesSemisynthetic erythromycin derivative. Antibacterial

Upstream & downstream products

Upstream raw materials

EthanolN,N-DimethylformamideTriethylamine2-Methoxyethoxymethyl chlorideMethanolHydroxylamine hydrochlorideErythromycinERYTHROMYCIN OXIME

Additional notes

DefinitionChEBI: Roxithromycin is semisynthetic derivative of erythromycin A. It has a role as an antibacterial drug. It is an erythromycin derivative, a macrolide and a semisynthetic derivative. It is functionally related to an erythromycin A.