CAS 81103-11-9|(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-dimethyloxa...

基本信息

化学结构

分子式

C₃₈H₆₉NO₁₃

分子量

747.95336

精确质量

747.47689127

电荷

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

计算属性

JChem

LogD (pH = 7.4)

1.63

LogD (pH = 5.5)

0.04

Log P

3.24

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

false

Acid pKa

9.00

极化表面积

182.91

极化性

82.01

摩尔折射率

190.79

LOG S

-2.42

数据来源

名称和标识

别名

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标准名

(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传统名

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

国际非专利药品(INN)

clarithromycinumclarithromycinclarithromycineclarithromycina

名称和标识

数据登录号

CAS号

81103-11-9

PubChem SID

16203766399313627

PubChem CID

84029

MetaboLights数据库

MTBLS1693MTBLS1455MTBLS2633MTBLS4967MTBLS3750MTBLS2871

SureChEMBL数据库

SCHEMBL38125

BRENDA Ligand数据库

22929722099229298

MassBank数据库

EA019107EA019114EA019101EA019105EA019111EA019102EA019110EA019109EA019113EA019104EA019103EA019112EA019106EA019108

BKMS React数据库

22929722099229298

CHEBI ID

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

PDB数据库

6u181j5a5igw5igj

UniProt数据库

Q8NJ52Q8NIN9P42039P40918P0C0Y5Q8WTV0P40108P51679P50344P42059Q9ZGH6P42040

ACToR数据库

专利号

Reaxys Registry

Beilstein号

BRENDA数据库

2.7.1.1363.1.8.17.6.2.2

Drug Central Database

PubMed文献链接

CompTox数据库

PDBeChem数据库

KEGG ID

DrugBank ID

KEGG DRUG Database

LINCS数据库

CHEMBL

BindingDB数据库

LIPID MAPS Instance

数据登录号

化合物性质

安全信息

保存条件

-20°C

-20°C Freezer

MSDS下载

下载链接

药理学性质

作用靶点

DNA/RNA

生物活性机理

Inhibitor of the translation of bacterial peptides

产品相关信息

Free Base

下载链接

Antibacterial agent

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

化合物性质

分子相关蛋白质

分子图谱

暂无数据

点击上传数据

描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

• 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)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

参考文献

生物活性

PubChem BioAssay

生物活性