CAS 81103-11-9|Clarithromycin|Clarem|Infex|(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-hydro...

General Information

Structure

Molecular Formula

C₃₈H₆₉NO₁₃

Molecular Mass

747.95336

Exact Mass

747.47689127

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

LogD (pH = 7.4)

1.63

LogD (pH = 5.5)

0.04

Log P

3.24

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

9.00

Polar Surface Area

182.91

Polarizability

82.01

Molar Refractivity

190.79

LOG S

-2.42

Data Source

Names and Identifiers

Synonyms

ClarithromycinClaremInfexKlaricidKlabaxClacidClariClaridarClaceeCrixanFromilidClaripenVikrolAntibiotic TE 316-O-Methylerythromycin AClarisA 56268Antibiotic A 56268ClaritekClarithroCRIXAN ODZeclarClamicinClathromycinClarithFascarKelamycinAbbott 56268ClarithromycinTE 031MacladinKlarithran MRVeclamBiaxinKlacidKlaribac6-O-MethylerythromycinNaxyClaricBIAXIN XLMavid;NaxyCyllindClarithromycin(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-dioneClarithromycinCLARITHROMYCINCLAclarithromycin6-O-methylerythromycin6-O-methylerythromycin A

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

International Nonproprietary Name (INN)

clarithromycinumclarithromycinclarithromycineclarithromycina

Names and Identifiers

Registration numbers

CAS Number

81103-11-9

PubChem SID

16203766399313627

PubChem CID

84029

CHEBI ID

CHEBI:41676CHEBI:442148CHEBI:670147CHEBI:3732

Protein Data Bank

6u181j5a5igw5igj

PDBeChem Database

CTY

Drug Central Database

668

MetaboLights Database

MTBLS1693MTBLS2633MTBLS1455MTBLS4967MTBLS2871MTBLS3750

PubMed Citation Links

16387493

UniProt Database

Q8NIN9P42039Q8NJ52Q8WTV0P0C0Y5P40918P50344P51679P40108Q9ZGH6P42040P42059

MassBank Database

EA019113EA019109EA019101EA019110EA019102EA019114EA019103EA019104EA019105EA019111EA019107EA019112EA019108EA019106

BKMS React Database

22929722099229298

BRENDA Database

2.7.1.1363.1.8.17.6.2.2

BRENDA Ligand Database

Beilstein Number

ACToR Database

CompTox Database

SureChEMBL Database

Reaxys Registry

Patent number

BindingDB Database

CHEMBL

DrugBank ID

KEGG ID

KEGG DRUG Database

LINCS Database

LIPID MAPS Instance

Registration numbers

Properties

Safety Information

Storage Condition

-20°C

-20°C Freezer

MSDS Link

Download link

Pharmacology Properties

Target

DNA/RNA

Mechanism of Action

Inhibitor of the translation of bacterial peptides

Product Information

Free Base

Download link

Antibacterial agent

Shows superior pharmacokinetic props. to erythromycin and about twice the activity, with a similar spectrum of activity

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

TRC

C559750

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

ChEBI

CHEBI:3732

The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.

Molecule Details

References

PubChem Literature

From Data Sources

• Niemi M et al. Clin Pharmacol Ther. 2001 Jul; 70(1):58-65.

• Benson, C., et al.: Eur. J. Clin. Microbiol., 6, 173 (1987)

• Boyanova, L., et al.: J. Med. Microb., 61, 85 (1987)

• Lin, Z., et al.: Toxicol. Sci., 126, 114 (1987)

• Clark, R.K. et al., Antibiot. Chemother. (Washington, D.C.), 1955, 5, 206, (struct)

• Morimoto, S. et al., J. Antibiot., 1984, 37, 187, (Clarithromycin)

• Washington, J.A. et al., Mayo Clin. Proc., 1985, 60, 189, (rev, pharmacol, metab)

• Ager, D.J. et al., Magn. Reson. Chem., 1987, 25, 948, (cmr)

• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, EDH500

• Gribble, M.J. et al., Med. Clin. North Am., 1982, 66, 79, (rev, pharmacol)

• Paterson, I. et al., Tetrahedron, 1985, 41, 3569, (synth, rev)

• Donadio, S. et al., Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 7119-7123, (6,7-Anhydroerythromycin C)

• Langtry, H.D. et al., Drugs, 1997, 53, 973-1004, (rev, Clarithromycin)

• Terui, Y. et al., Tet. Lett., 1975, 2583, (cmr)

• Cane, D.E. et al., J.A.C.S., 1986, 108, 4957, (biosynth)

• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 3, 171, (rev)

• Kirst, H.A., Prog. Med. Chem., 1993, 30, 57, (rev)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 189

• Awan, A. et al., J.C.S. Perkin 2, 2000, 1645-1652, (Erythromycin A, Clarithromycin, pmr, conformn)

• Wiley, P.F. et al., J.A.C.S., 1955, 77, 3422; 1957, 79, 6062; 6074, (struct)

• Majer, J. et al., J.A.C.S., 1977, 99, 1620, (pmr)

• Belg. Pat., 1985, 901 411; CA, 104, 19776

• Fernandes, P.B. et al., Antimicrob. Agents Chemother., 1986, 30, 865; 1987, 31, 328; 343; 463; 640, (Clarithromycin)

• Concia, P.M. et al., J. Int. Med. Res., 1986, 14, 137, (RV11)

• Barber, J. et al., J.C.S. Perkin 2, 1991, 1489, (pmr, cmr, tautom, conformn)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 11577; 11628; 11659; 11757

• Oleinick, N.L., Antibiotics (N.Y.), 1975, 3, 396, (rev)

• Everett, J.R. et al., J.C.S. Perkin 2, 1987, 1659; 1988, 325; 1989, 1719, (pmr, cmr, conformn, cryst struct)

• Gasc, J.-C. et al., J. Antibiot., 1991, 44, 313, (synth, pmr, activity)

• Weber, J.M. et al., Science (Washington, D.C.), 1991, 252, 114-117, (6-Deoxyerythromycins)

• Shida, Y. et al., Tetrahedron, 1993, 49, 9221, (ms)

• Tyson, P. et al., J. Chem. Res., Synop., 1998, 727, (pmr, cmr)

• Tadanier, J. et al., J.O.C., 1978, 43, 2351, (synth)

• Hunt, E. et al., J.C.S. Perkin 2, 1990, 2157, (synth, ir, pmr)

• Sturgill, M.G. et al., Ann. Pharmacother., 1992, 26, 1099, (rev)

• Iwasaki, H. et al., Acta Cryst. C, 1993, 49, 1227, (cryst struct, Clarithromycin)

• Fraschiui, F. et al., Clin. Pharmacokinet., 1993, 25, 189, (Clarithromycin, rev)

• Martin, S.F. et al., J.A.C.S., 1997, 119, 3193, (synth)

• Watanabe, Y. et al., Heterocycles, 1990, 31, 2121, (Clarithromycin)

• Piscitelli, S.C. et al., Clin. Pharm., 1992, 11, 137, (Clarithromycin, rev)

• Pat. Coop. Treaty (WIPO), 1993, 93 13 663; CA, 119, 219166t, (derivs)

• Gates, P.J. et al., Rapid Commun. Mass Spectrom., 1999, 13, 242-246, (ms)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, EDH500; EDJ000; EDI500; EDJ500

• Koch, W.L. et al., Anal. Profiles Drug Subst., 1979, 8, 159, (rev)

• Chater, K.F., Bacteria, 1986, 9, 119, (rev, biosynth)

• Stanton, J., Angew. Chem., Int. Ed., 1991, 30, 1302, (rev, biosynth)

• Muelzer, J., Angew. Chem., Int. Ed., 1991, 30, 1452, (rev, synth)

• Shepherd, M.J., Food Contaminants: Sources and Surveillance, Royal Society of Chemistry, 1991, 145, (anal)

• Toshima, K. et al., Tet. Lett., 1991, 32, 6155, (synth)

• Peters, D.H. et al., Drugs, 1992, 44, 117, (Clarithromycin)

• Watanabe, Y. et al., J. Antibiot., 1993, 46, 1163, (Clarithromycin)

References

Bioactivity

PubChem BioAssay

Bioactivity