U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H69NO13
Molecular Weight 747.9534
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLARITHROMYCIN

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]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O)OC

InChI

InChIKey=AGOYDEPGAOXOCK-KCBOHYOISA-N
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

HIDE SMILES / InChI

Description

Clarithromycin is an antibacterial drug which is used either in combination with lansoprazole and amoxicillin (Prevpac), in combination with omeprazole and amoxicillin (Omeclamox) or alone (Biaxin) for the treatment of broad range of infections. The drug exerts its action by binding to 23s rRNA (with nucleotides in domains II and V). The binding leads to the protein synthesis inhibition and the cell death.

Approval Year

PubMed

PubMed

TitleDatePubMed
Postoperative proprionibacterium acnes endophthalmitis.
2001 Apr
Plasma and BAL fluid concentrations of antimicrobial peptides in patients with Mycobacterium avium-intracellulare infection.
2001 Apr
Comparative efficacy of new investigational agents against Helicobacter pylori.
2001 Apr
In vitro activity of telithromycin (HMR 3647) against 502 strains of anaerobic bacteria.
2001 Apr
Analysis of metronidazole, clarithromycin and tetracycline resistance of Helicobacter pylori isolates from Korea.
2001 Apr
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.
2001 Apr
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.
2001 Feb
Acute fatal colchicine intoxication in a patient on continuous ambulatory peritoneal dialysis (CAPD). Possible role of clarithromycin administration.
2001 Feb
Clarithromycin and CNS disturbances.
2001 Mar
Antibiotic resistance rates and macrolide resistance phenotypes of viridans group streptococci from the oropharynx of healthy Greek children.
2001 Mar
[HIV: a guide on management of seropositive patients].
2001 Mar 3
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dosages of clarithromycin tablets for the treatment of mild to moderate infections in adults are: 250 mg or 500 mg every 12 hours for 7–14 days; 500 mg every 8 or 12 hours for 10-14 days (H.pylori, in in combination with lansoprazole/amoxicillin, in combination with omeprazole/amoxicillin or omeprazole); 500 mg every 12 hours (Mycobacterial Infections).
Route of Administration: Oral
In Vitro Use Guide
The MIC values for clarithromycin were: 0.12-0.5 ug/ml (Staphylococcus aureus ATCC 29213), 0.03-0.12 ug/ml (Streptococcus pneumoniae ATCC 49619), 4-16 ug/ml (Haemophilus influenzae ATCC 49247), 0.015-0.12 ug/ml (Helicobacter pylori ATCC 43504), 1-4 ug/ml (M. avium ATCC 700898).
Name Type Language
CLARITHROMYCIN
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
CLARITHROMYCIN [MI]
Common Name English
6-O-METHYLERYTHROMYCIN
Common Name English
CLARITHROMYCIN [MART.]
Common Name English
NAXY
Brand Name English
CLARITHROMYCIN COMPONENT OF PREVPAC
Common Name English
CLARITHROMYCIN IDENTITY [USP-RS]
Common Name English
CLARITHROMYCIN [INN]
Common Name English
CLARITHROMYCIN [WHO-DD]
Common Name English
PREVPAC COMPONENT CLARITHROMYCIN
Common Name English
BIAXIN
Brand Name English
CLAROSIP
Brand Name English
ABBOTT-56268
Code English
MACLADIN
Brand Name English
KLARICID
Brand Name English
ZECLAR
Brand Name English
TE-031
Code English
VECLAM
Brand Name English
CLARITHROMYCIN [VANDF]
Common Name English
CYLLIND
Brand Name English
CLARITHROMYCIN [EP]
Common Name English
A-56268
Code English
CLARITHROMYCIN [JAN]
Common Name English
CLARITHROMYCIN [USP]
Common Name English
CLARITHROMYCIN [USAN]
Common Name English
MAVID
Brand Name English
CLARITHROMYCIN IDENTITY
USP-RS  
Common Name English
ERYTHROMYCIN, 6-O-METHYL-
Common Name English
CLARITHROMYCIN [USP-RS]
Common Name English
KLACID
Brand Name English
CLARITHROMYCIN [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-ATC A02BD09
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-ATC A02BD07
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-VATC QA02BD05
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-VATC QJ01FA09
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
NDF-RT N0000007529
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-VATC QA02BD04
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-ATC J01FA09
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.2
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
NDF-RT N0000007529
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
FDA ORPHAN DRUG 338811
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
NDF-RT N0000007529
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
LIVERTOX 214
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-ATC A02BD05
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-ATC A02BD06
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-VATC QA02BD06
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
NDF-RT N0000175935
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-VATC QA02BD07
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-ATC A02BD04
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
WHO-ATC A02BD11
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
NCI_THESAURUS C261
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
Code System Code Type Description
MERCK INDEX
M3608
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY Merck Index
NDF-RT
N0000190114
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY Cytochrome P450 3A Inhibitors [MoA]
NDF-RT
N0000182141
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
HSDB
81103-11-9
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
ChEMBL
CHEMBL1741
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
NDF-RT
N0000185503
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
CAS
81103-11-9
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
DRUG BANK
DB01211
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
EPA CompTox
81103-11-9
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
LactMed
81103-11-9
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
NCI_THESAURUS
C1054
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
INN
6252
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
WIKIPEDIA
CLARITHROMYCIN
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
RXCUI
21212
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY RxNorm
EVMPD
SUB06641MIG
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
MESH
D017291
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY
PUBCHEM
84029
Created by admin on Mon Oct 21 19:49:57 UTC 2019 , Edited by admin on Mon Oct 21 19:49:57 UTC 2019
PRIMARY