CLARITHROMYCIN LACTOBIONATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H69NO13.C12H22O12
Molecular Weight	1106.2492
Optical Activity	UNSPECIFIED
Defined Stereocenters	27 / 27
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of CLARITHROMYCIN LACTOBIONATE

Structure Search

SMILES

OC[C@@H](O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@@H](O)C(O)=O.CC[C@H]2OC(=O)[C@H](C)[C@@H](O[C@H]3C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[C@H](C)[C@@H](O[C@@H]4O[C@H](C)C[C@@H]([C@H]4O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]2(C)O)OC

InChI

InChIKey=RWVXTLPOSMQGRC-BDHJQFRQSA-N

InChI=1S/C38H69NO13.C12H22O12/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;13-1-3(15)10(7(18)8(19)11(21)22)24-12-9(20)6(17)5(16)4(2-14)23-12/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3;3-10,12-20H,1-2H2,(H,21,22)/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-;3-,4-,5+,6+,7-,8-,9-,10-,12+/m11/s1

HIDE SMILES / InChI

Molecular Formula	C12H22O12
Molecular Weight	358.2959
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Antibiotic resistance and antibiotic sensitivity based treatment in Helicobacter pylori infection: advantages and outcome.	2001-05	11316688
Prospective evaluation of the impact of amoxicillin, clarithromycin and their combination on human gastrointestinal colonization by Candida species.	2001-04-18	11306791
Bacterial adhesiveness: effects of the SH metabolite of erdosteine (mucoactive drug) plus clarithromycin versus clarithromycin alone.	2001-04-18	11306790
Rifabutin-associated hypopyon uveitis in human immunodeficiency virus-negative immunocompetent individuals.	2001-04	11297492
Postoperative proprionibacterium acnes endophthalmitis.	2001-04	11297461
Plasma and BAL fluid concentrations of antimicrobial peptides in patients with Mycobacterium avium-intracellulare infection.	2001-04	11296180
Comparative efficacy of new investigational agents against Helicobacter pylori.	2001-04	11284777
In vitro activity of telithromycin (HMR 3647) against 502 strains of anaerobic bacteria.	2001-04	11266423
Analysis of metronidazole, clarithromycin and tetracycline resistance of Helicobacter pylori isolates from Korea.	2001-04	11266421
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.	2001-04	11266411
Molecular resistance testing of Helicobacter pylori in gastric biopsies.	2001-04	11260622
Six cases of confluent and reticulated papillomatosis alleviated by various antibiotics.	2001-04	11260541
[Buruli ulcer in Togo: 21 cases].	2001-03-24	11317927
Pericarditis after allogeneic peripheral blood stem cell transplantation caused by Legionella pneumophila (non-serogroup 1).	2001-03-23	11261761
Evaluation of the clinical microbiology profile of moxifloxacin.	2001-03-15	11249830
What have we learned from pharmacokinetic and pharmacodynamic theories?	2001-03-15	11249828
Comparative in vitro activity of moxifloxacin by E-test against Streptococcus pyogenes.	2001-03-15	11249826
[HIV: a guide on management of seropositive patients].	2001-03-03	11268903
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.	2001-03	11303370
Clarithromycin and CNS disturbances.	2001-03	11288564
Antibiotic resistance rates and macrolide resistance phenotypes of viridans group streptococci from the oropharynx of healthy Greek children.	2001-03	11282264
Effect of genotypic differences in CYP2C19 on cure rates for Helicobacter pylori infection by triple therapy with a proton pump inhibitor, amoxicillin, and clarithromycin.	2001-03	11240980
Phenotypic consequences of red-white colony type variation in Mycobacterium avium.	2001-03	11238960
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication.	2001-03	11231401
Clarithromycin and risk of Clostridium difficile-associated diarrhoea.	2001-03	11222572
[Phlebitis due to intravenous administration of macrolide antibiotics. A comparative study of erythromycin versus clarithromycin].	2001-02-03	11222159
[Acute delirium, probably precipitated by clarithromycin].	2001-02-03	11219151
Evaluation of the immunomodulatory effects of the macrolide antibiotic, clarithromycin, in female B6C3F1 mice: a 28-day oral gavage study.	2001-02	11307632
[Eradication therapy of Helicobacter pylori infection].	2001-02	11307304
[The history of Helicobacter pylori].	2001-02	11307300
Breakthrough Streptococcus pneumoniae meningitis during clarithromycin therapy for acute otitis media.	2001-02	11305469
A rare case of osteomyelitis of the sternum in an adult with sickle cell disease.	2001-02	11300345
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.	2001-02	11293500
Acute fatal colchicine intoxication in a patient on continuous ambulatory peritoneal dialysis (CAPD). Possible role of clarithromycin administration.	2001-02	11269688
Multicenter study of incidence of Mycobacterium marinum in humans in Spain.	2001-02	11258515
Mycobacterium abscessus wound infection.	2001-02	11233716
Do some patients with Helicobacter pylori infection benefit from an extension to 2 weeks of a proton pump inhibitor-based triple eradication therapy?	2001-02	11232676
Comparison of the efficacy and safety of different formulations of omeprazole-based triple therapies in the treatment of Helicobacter pylori-positive peptic ulcer.	2001-02	11227677
Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication.	2001-02	11227668
Fixed drug eruption due to clarithromycin.	2001-01	11260179
[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege].	2001-01	11256133
Antibiotic susceptibilities of Helicobacter pylori.	2001-01	11255612
Acute community-acquired pneumonia: current diagnosis and treatment.	2001-01	11227252
Treatment of canine leproid granuloma syndrome: preliminary findings in seven dogs.	2001-01	11221566
Comparison of 5-day, short-course gatifloxacin therapy with 7-day gatifloxacin therapy and 10-day clarithromycin therapy for acute exacerbation of chronic bronchitis.	2001-01	11219483
Comparison of the efficacy of extended-release clarithromycin tablets and amoxicillin/clavulanate tablets in the treatment of acute exacerbation of chronic bronchitis.	2001-01	11219481
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	11310801
Antimicrobial activity of thiamphenicol-glycinate-acetylcysteinate and other drugs against Chlamydia pneumoniae.	2001	11304944
Molecular diagnosis of a Mycobacterium chelonae infection.	2001	11261816
The successful treatment of prurigo pigmentosa with macrolide antibiotics.	2001	11244235

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 17:51:06 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:06 GMT 2025`
Record UNII	4108JKI097
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLARITHROMYCIN LACTOBIONATE

Common Name

English

ERYTHROMYCIN, 6-O-METHYL-, 4-O-.BETA.-D-GALACTOPYRANOSYL-D-GLUCONATE (1:1)

Preferred Name

English

Clarithromycin lactobionate [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

178265