(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione

• ChemBase ID: 72742
• Molecular Formular: C38H69NO13
• Molecular Mass: 747.95336
• Monoisotopic Mass: 747.47689127
• SMILES: [C@@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](C(=O)[C@@H]([C@H]1O)C)C)(OC)C)O[C@@H]1O[C@@H](C[C@@H]([C@H]1O)N(C)C)C)C)O[C@@H]1O[C@H]([C@@H]([C@](C1)(C)OC)O)C)C)CC)(O)C
• Canonical SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@H]([C@@H](O2)C)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C[C@H](C(=O)[C@@H]([C@H]([C@]1(C)O)O)C)C)(C)OC
• InChI: InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
• InChIKey: AGOYDEPGAOXOCK-KCBOHYOISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• IUPAC Traditional name: clarithromycin; (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• Synonyms: 6-O-Methylerythromycin; 6-O-Methylerythromycin A; A 56268; Abbott 56268; Antibiotic A 56268; Antibiotic TE 31; BIAXIN XL; Biaxin; CRIXAN OD; Clamicin; Claric; Claris; Claritek; Clarith; Clarithro; Clarithromycin; Clathromycin; Fascar; Kelamycin; Klacid; Klaribac; Klarithran MR; Macladin; Naxy; TE 031; Veclam; Zeclar; Crixan; Klaricid; Klabax; Claripen; Clarem; Claridar; Fromilid; Clacid; Clacee; Vikrol; Infex; Clari; Clarithromycin; (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetra hydro-2H-pyran-2-yl)oxy)-7-methoxy-3,5,7,9,11,13-hexame thyloxacyclotetradecane-2,10-dione; Cyllind; Mavid;Naxy; Clarithromycin

Database IDs

• CAS Number: 81103-11-9
• PubChem SID: 162037663
• PubChem CID: 84029

CALCULATED PROPERTIES

• Acid pKa: 12.458389
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): 0.4510266
• LogD (pH = 7.4): 2.2163913
• Log P: 3.2395153
• Molar Refractivity: 190.7883 cm^3
• Polarizability: 77.6621 Å^3
• Polar Surface Area: 182.91 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 217-220°C (dec.)

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Pharmacology Properties

• Target: DNA/RNA
• Mechanism of Action: Inhibitor of the translation of bacterial peptides

Product Information

• Salt Data: Free Base
• Application(s): Antibacterial agent; Shows superior pharmacokinetic props. to erythromycin and about twice the activity, with a similar spectrum of activity

DETAILS

Selleck Chemicals - S2555

Research Area: Cancer
Biological Activity:
Clarithromycin (Biaxin, Klacid) is a macrolide antibiotic and a CYP3A4 substrate and inhibitor. Clarithromycin (Biaxin, Klacid) prevents bacteria from growing by interfering with their protein synthesis. Clarithromycin (Biaxin, Klacid) binds to the subunit 50S of the bacterial ribosome and thus inhibits the translation of peptides. Clarithromycin (Biaxin, Klacid) has similar antimicrobial spectrum as erythromycin but is more effective against certain gram-negative bacteria, particularly Legionella pneumophila. Clarithromycin (Biaxin, Klacid) is used to treat pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia (especially atypical pneumonias associated with Chlamydia pneumoniae or TWAR), skin and skin structure infections. Besides, clarithromycin (Biaxin, Klacid)is a substrate and inhibitor of CYP3A4. Inhibitors of CYP3A4 may increase clarithromycin (Biaxin, Klacid) serum concentrations. Inducers of CYP3A4 substrates may decrease clarithromycin (Biaxin, Klacid) serum concentrations. [1][2]

Toronto Research Chemicals - C559750

Clarithromycin is a semi-synthetic macrolide antibiotic. Clarithromycin is a derivative of Erythromycin (E650000).

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