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81103-11-9 molecular structure
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(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: 153977
Molecular Formular: C38H69NO13
Molecular Mass: 747.95336
Monoisotopic Mass: 747.47689127
SMILES and InChIs

SMILES:
CC[C@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]1C[C@@]([C@H]([C@@H](O1)C)O)(C)OC)C)O[C@H]1[C@@H]([C@H](C[C@H](O1)C)N(C)C)O)(C)OC)C)C)O)(C)O
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

Cite this record

CBID:153977 http://www.chembase.cn/molecule-153977.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
Synonyms
Clarithromycin
CAS Number
81103-11-9
MDL Number
MFCD00865140
PubChem SID
162248116
PubChem CID
84029

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 84029 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.458389  H Acceptors 13 
H Donor LogD (pH = 5.5) 0.4510266 
LogD (pH = 7.4) 2.2163913  Log P 3.2395153 
Molar Refractivity 190.7883 cm3 Polarizability 77.6621 Å3
Polar Surface Area 182.91 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Product Information Bioassay(PubChem)
RTECS
KF4997000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95% (HPLC) expand Show data source
Suitability
suitable for 1694 per US EPA expand Show data source
Pharmacopeia Traceability
traceable to BP 833 expand Show data source
traceable to PhEur Y0000320 expand Show data source
traceable to USP 1134379 expand Show data source
Empirical Formula (Hill Notation)
C38H69NO13 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - C9742 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Clarithromycin is a macrolide antibiotic. It prevents bacterial growth by interfering with protein synthesis. Clarithromycin is an acid-stable version of erythromycin and is particularly effective against gram-negative bacteria.3 It has a short half-life4, however its metabolite, 14-hydroxy clarithromycin is nearly twice as active as clarithromycin against certain bacteria.5
Clarithromycin inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation. Clarithromycin is first metabolized to 14-OH clarithromycin, which is active and works synergistically with its parent compound. Clarithromycin penetrates the bacteria cell wall and reversibly binds to domain V of the 23S ribosomal RNA of the 50S subunit of the bacterial ribosome, blocking translocation of aminoacyl transfer-RNA and polypeptide synthesis. Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump.
Application
Clarithromycin is a semisynthetic macrolide antibiotic that is derived from erythromycin. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration . Clarithromycin may be used to attenuate cardiac transplantation rejection via matrix metalloproteinase suppression1. Clarithromycin has been used to study inflammatory markers in chronic obstructive pulmonary disease (COPD)2. It is used to study bacterial protein synthesis and peptide translation.
Sigma Aldrich - 16632 external link
Biochem/physiol Actions
Clarithromycin is a macrolide antibiotic. It prevents bacterial growth by interfering with protein synthesis. Clarithromycin is an acid-stable version of erythromycin and is particularly effective against gram-negative bacteria.1 It has a short half-life2, however its metabolite, 14-hydroxy clarithromycin is nearly twice as active as clarithromycin against certain bacteria.3

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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