CLARITHROMYCIN

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 Search

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

Molecular Formula	C38H69NO13
Molecular Weight	747.9534
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	18 / 18
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf
Curator's Comment: description was created based on several sources, including www.ncbi.nlm.nih.gov/pubmed/10760175

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 Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 180 Target ID: CHEMBL2363135 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Binding Agent 1076		9.5 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Acute bacterial exacerbation of chronic bronchitis 31 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991
Acute bacterial maxillary sinusitis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991
Community-acquired pneumonia 47 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991
Bacterial pharyngitis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991
Bacterial tonsillitis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991
Uncomplicated skin and skin-structure infections 21 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991
Acute bacterial otitis media 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991
Disseminated mycobacterial infections 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991
Helicobacter pylori infection 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8583	BIAXIN Approved Use BIAXIN is a macrolide antimicrobial indicated for mild to moderate infections caused by designated, susceptible bacteria in the following: Acute Bacterial Exacerbation of Chronic Bronchitis in Adults; Acute Maxillary Sinusitis; Community-Acquired Pneumonia; Pharyngitis/Tonsillitis; Uncomplicated Skin and Skin Structure Infections; Acute Otitis Media in Pediatric Patients; Treatment and Prophylaxis of Disseminated Mycobacterial Infections; Helicobacter pylori Infection and Duodenal Ulcer Disease in Adults. Launch Date 1991

C_max

Value	Dose	Co-administered	Analyte	Population
1.09 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17606673/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CLARITHROMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.21 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17606673/	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CLARITHROMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
4.45 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17606673/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CLARITHROMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
26.81 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17606673/	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CLARITHROMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17606673/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CLARITHROMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17606673/	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CLARITHROMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
28.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17606673/	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:		CLARITHROMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
23.1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17606673/	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CLARITHROMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/	unhealthy, 33 - 51 years Health Status: unhealthy Age Group: 33 - 51 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/	Other AEs: Taste metallic, Gastrointestinal pain... Other AEs: Taste metallic (19 patients) Gastrointestinal pain (4 patients) Nausea (5 patients) Vomiting (3 patients) Diarrhea (2 patients) Headache (7 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/
2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	Other AEs: Abdominal pain, Diarrhea... Other AEs: Abdominal pain (7.5%) Diarrhea (9.4%) Flatulence (7.5%) Headache (7.5%) Nausea (28.3%) Rash (9.4%) Taste perversion (18.9%) Vomiting (24.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf

AEs

AE	Significance	Dose	Population
Taste metallic	19 patients	500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/	unhealthy, 33 - 51 years Health Status: unhealthy Age Group: 33 - 51 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/
Diarrhea	2 patients	500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/	unhealthy, 33 - 51 years Health Status: unhealthy Age Group: 33 - 51 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/
Vomiting	3 patients	500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/	unhealthy, 33 - 51 years Health Status: unhealthy Age Group: 33 - 51 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/
Gastrointestinal pain	4 patients	500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/	unhealthy, 33 - 51 years Health Status: unhealthy Age Group: 33 - 51 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/
Nausea	5 patients	500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/	unhealthy, 33 - 51 years Health Status: unhealthy Age Group: 33 - 51 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/
Headache	7 patients	500 mg 2 times / day steady, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: steady Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/	unhealthy, 33 - 51 years Health Status: unhealthy Age Group: 33 - 51 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/
Taste perversion	18.9%	2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Vomiting	24.5%	2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Nausea	28.3%	2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Abdominal pain	7.5%	2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Flatulence	7.5%	2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Headache	7.5%	2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Diarrhea	9.4%	2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Rash	9.4%	2000 mg 2 times / day steady, oral Highest studied dose Dose: 2000 mg, 2 times / day Route: oral Route: steady Dose: 2000 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087 substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT2 153 P-gp 1741 OATP1B1 1079 OATP1B3 961 OAT1 725 OAT3 747 OCT1 620 OCT2 779 MATE1 415 MATE2 267 BCRP 910 MRP2 499 MRP3 246 BSEP 550 CYP1A2 2153 UGT1A1 246 UGT1A3 89 UGT1A4 98 UGT1A6 136 UGT1A7 23 UGT1A8 37 UGT1A9 148 UGT1A10 37 UGT2B4 23 UGT2B7 197 UGT2B10 31 UGT2B15 84 UGT2B17 31 aldehyde oxidase 5 FMO 7 CES1 7 CES2 6	OATP1B1 503 OATP1B3 435 OATP2B1 122 OCT1 393 CYP2C19 1119 CYP1A2 1197 CYP2E1 729 CYP2A6 626 CYP1A1 389 CYP2B6 776 CYP2C8 810 CYP4A11 137	CYP3A5 92

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
UGT1A1 303	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT1A10 46	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT1A3 99	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT1A4 100	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT1A6 171	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT1A7 25	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT1A9 155	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT2B10 33	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT2B15 84	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT2B17 33	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT2B4 23	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
UGT2B7 210	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no [IC50 >100 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MATE2 267	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
CES1 7	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no
CES2 6	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15735612/	no
CYP3A5 201	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15735612/	no
FMO 7	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11408369/	no	no (co-administration study) Comment: Administration of CLARITHROMYCIN had no effect on caffeine PK Sources: https://pubmed.ncbi.nlm.nih.gov/11408369/
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11408369/	no	no (co-administration study) Comment: Administration of CLARITHROMYCIN had no effect on tolbutamide (CYP2C9 probe) PK Sources: https://pubmed.ncbi.nlm.nih.gov/11408369/
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11408369/	no	no (co-administration study) Comment: Administration of CLARITHROMYCIN had no effect on dextromethorphan (CYP2D6 probe) PK Sources: https://pubmed.ncbi.nlm.nih.gov/11408369/
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050662s044s050,50698s026s030,050775s015s019lbl.pdf	strong	yes (co-administration study) Comment: Serious adverse reactions have been reported in patients taking larithromycin concomitantly with CYP3A4 substrates. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050662s044s050,50698s026s030,050775s015s019lbl.pdf
OAT2 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15708966/	weak
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/ \| https://pubmed.ncbi.nlm.nih.gov/17296622/	yes [IC50 14 uM]
UGT1A8 49	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	yes [IC50 43.5 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	yes [IC50 5.3 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	yes [IC50 59 uM]
aldehyde oxidase 5	inhibitor 4027 Sources: https://www.xenotech.com/wp-content/uploads/2020/05/ISSX_In-Vitro-Ketoconazole-Clinical-CYP3A45-Inhibitors-Ritonavir-Clarithromycin-Itraconazole-Non-CYP-Enzymes.pdf	yes [IC50 61.7 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/ \| https://pubmed.ncbi.nlm.nih.gov/25907295/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050662s044s050,50698s026s030,050775s015s019lbl.pdf	yes [IC50 8.9 uM]	yes (co-administration study) Comment: Elevated digoxin serum concentrations in patients receiving clarithromycin and digoxin concomitantly have been reported in post-marketing surveillance Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/ \| https://pubmed.ncbi.nlm.nih.gov/25907295/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/050662s044s050,50698s026s030,050775s015s019lbl.pdf
UGT1A10 46	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	yes
UGT1A8 49	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
OATP1B1 503	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OATP1B3 435	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OATP2B1 122	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OCT1 393	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/12065733/ \| https://pubmed.ncbi.nlm.nih.gov/14674677/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3732	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3732
ChemicalBook	CB2225614	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2225614
eMolecules	4775688	https://www.emolecules.com/cgi-bin/more?vid=4775688
MolPort	MolPort-002-507-425	https://www.molport.com/shop/molecule-link/MolPort-002-507-425
Selleck Chemicals	clarithromycin	http://www.selleckchem.com/products/clarithromycin.html
ZINC	ZINC000085534098	http://zinc15.docking.org/substances/ZINC000085534098

PubMed

Title	Date	PubMed
MiRP1 forms IKr potassium channels with HERG and is associated with cardiac arrhythmia.	1999 Apr 16	10219239
Disseminated Mycobacterium genavense infection in a patient with acquired immunodeficiency syndrome: first case report in Taiwan.	1999 Jan	10063276
Antimicrobial activity of thiamphenicol-glycinate-acetylcysteinate and other drugs against Chlamydia pneumoniae.	2001	11304944
In vitro activity of telithromycin (HMR 3647) against 502 strains of anaerobic bacteria.	2001 Apr	11266423
Molecular resistance testing of Helicobacter pylori in gastric biopsies.	2001 Apr	11260622
Six cases of confluent and reticulated papillomatosis alleviated by various antibiotics.	2001 Apr	11260541
Effect of the treatment of Helicobacter pylori infection on gastric emptying and its influence on the glycaemic control in type 1 diabetes mellitus.	2001 Apr	11182211
Evaluation of the immunomodulatory effects of the macrolide antibiotic, clarithromycin, in female B6C3F1 mice: a 28-day oral gavage study.	2001 Feb	11307632
[Eradication therapy of Helicobacter pylori infection].	2001 Feb	11307304
[The history of Helicobacter pylori].	2001 Feb	11307300
Breakthrough Streptococcus pneumoniae meningitis during clarithromycin therapy for acute otitis media.	2001 Feb	11305469
A rare case of osteomyelitis of the sternum in an adult with sickle cell disease.	2001 Feb	11300345
Mycobacterium abscessus wound infection.	2001 Feb	11233716
Do some patients with Helicobacter pylori infection benefit from an extension to 2 weeks of a proton pump inhibitor-based triple eradication therapy?	2001 Feb	11232676
[Antimicrobial resistant test of H. pylori].	2001 Feb	11218400
[Recent guidelines for the management of Helicobacter pylori infection].	2001 Feb	11218393
[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege].	2001 Jan	11256133
Rhabdomyolysis secondary to a drug interaction between simvastatin and clarithromycin.	2001 Jan	11197581
Adverse reactions to rifabutin.	2001 Jan	11196537
Clarithromycin and CNS disturbances.	2001 Mar	11288564
Effect of genotypic differences in CYP2C19 on cure rates for Helicobacter pylori infection by triple therapy with a proton pump inhibitor, amoxicillin, and clarithromycin.	2001 Mar	11240980
Phenotypic consequences of red-white colony type variation in Mycobacterium avium.	2001 Mar	11238960
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication.	2001 Mar	11231401
One-week ranitidine bismuth citrate-based triple therapy for the eradication of Helicobacter pylori in Hong Kong with high prevalence of metronidazole resistance.	2001 Mar	11207516
What have we learned from pharmacokinetic and pharmacodynamic theories?	2001 Mar 15	11249828
Comparative in vitro activity of moxifloxacin by E-test against Streptococcus pyogenes.	2001 Mar 15	11249826
[Buruli ulcer in Togo: 21 cases].	2001 Mar 24	11317927
Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication.	2001 Mar-Apr	11182043
c-myc gene mutation in gastric mucosa-associated lymphoid tissue (MALT) lymphoma and diffuse large B-cell lymphoma.	2001 Mar-Apr	11182042
Antibiotic resistance and antibiotic sensitivity based treatment in Helicobacter pylori infection: advantages and outcome.	2001 May	11316688
Prospective evaluation of the impact of amoxicillin, clarithromycin and their combination on human gastrointestinal colonization by Candida species.	2001 May-Jun	11306791
Bacterial adhesiveness: effects of the SH metabolite of erdosteine (mucoactive drug) plus clarithromycin versus clarithromycin alone.	2001 May-Jun	11306790
A multicenter study of the antimicrobial susceptibility of Haemophilus influenzae, Streptococcus pneumoniae, and Moraxella catarrhalis isolated from patients with community-acquired lower respiratory tract infections in 1999 in Portugal.	2001 Spring	11310801

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:05 GMT 2025`
Record UNII	H1250JIK0A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLARITHROMYCIN

Official Name

English

CLARITHROMYCIN IDENTITY

Preferred Name

English

CLARITHROMYCIN [MI]

Common Name

English

6-O-Methylerythromycin

Common Name

English

CLARITHROMYCIN [MART.]

Common Name

English

NAXY

Brand Name

English

Clarithromycin [WHO-DD]

Common Name

English

CLARITHROMYCIN IDENTITY [USP-RS]

Common Name

English

CLARITHROMYCIN [USP MONOGRAPH]

Common Name

English

clarithromycin [INN]

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

CLARITHROMYCIN [EP MONOGRAPH]

Common Name

English

ZECLAR

Brand Name

English

TE-031

Code

English

VECLAM

Brand Name

English

CLARITHROMYCIN [VANDF]

Common Name

English

CYLLIND

Brand Name

English

A-56268

Code

English

NSC-758704

Code

English

CLARITHROMYCIN [JAN]

Common Name

English

MAVID

Brand Name

English

ERYTHROMYCIN, 6-O-METHYL-

Common Name

English

CLARITHROMYCIN [USP-RS]

Common Name

English

CLARITHROMYCIN [USP IMPURITY]

Common Name

English

KLACID

Brand Name

English

CLARITHROMYCIN [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

WHO-ATC

A02BD09