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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H69NO13.C6H8O7
Molecular Weight 940.0769
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLARITHROMYCIN CITRATE

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.[H][C@@]2(O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(OC)[C@]([H])(O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@H]2C

InChI

InChIKey=MDRWXDRMSKEMRE-AZFLODHXSA-N
InChI=1S/C38H69NO13.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
9.5 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BIAXIN
Curative
BIAXIN
Curative
BIAXIN
Curative
BIAXIN
Curative
BIAXIN
Curative
BIAXIN
Curative
BIAXIN
Curative
BIAXIN
Curative
BIAXIN

Cmax

ValueDoseCo-administeredAnalytePopulation
2.21 mg/L
500 mg 2 times / day steady-state, oral
CLARITHROMYCIN plasma
Homo sapiens
1.09 mg/L
250 mg single, oral
CLARITHROMYCIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
26.81 mg × h/L
500 mg 2 times / day steady-state, oral
CLARITHROMYCIN plasma
Homo sapiens
4.45 mg × h/L
250 mg single, oral
CLARITHROMYCIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.7 h
500 mg 2 times / day steady-state, oral
CLARITHROMYCIN plasma
Homo sapiens
1.9 h
250 mg single, oral
CLARITHROMYCIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
23.1%
500 mg 2 times / day steady-state, oral
CLARITHROMYCIN plasma
Homo sapiens
28.7%
250 mg single, oral
CLARITHROMYCIN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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).