CLARITHROMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H69NO13
Molecular Weight	747.9548
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@]1([H])[C@](C)([C@@]([H])([C@@]([H])(C)C(=O)[C@]([H])(C)C[C@](C)([C@@]([H])([C@@]([H])(C)[C@@]([H])([C@@]([H])(C)C(=O)O1)O[C@@]2([H])C[C@](C)([C@]([H])([C@]([H])(C)O2)O)OC)O[C@@]3([H])[C@@]([H])([C@]([H])(C[C@@]([H])(C)O3)N(C)C)O)OC)O)O

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	747.9548
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 172 Target ID: CHEMBL2363135 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Binding Agent 996		9.5 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Acute bacterial exacerbation of chronic bronchitis 24 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.8886718E11
Acute bacterial maxillary sinusitis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.887808E11
Community-acquired pneumonia 39 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.887808E11
Bacterial pharyngitis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.887808E11
Bacterial tonsillitis 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.887808E11
Uncomplicated skin and skin-structure infections 20 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.887808E11
Acute bacterial otitis media 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.887808E11
Disseminated mycobacterial infections 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.887808E11
Helicobacter pylori infection 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Curative	Approved 8043	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 6.887808E11

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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
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

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 n = 41 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 33 - 51 years Sex: M+F Population Size: 41 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 (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 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 n = 41 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 33 - 51 years Sex: M+F Population Size: 41 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 n = 41 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 33 - 51 years Sex: M+F Population Size: 41 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 n = 41 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 33 - 51 years Sex: M+F Population Size: 41 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 n = 41 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 33 - 51 years Sex: M+F Population Size: 41 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 n = 41 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 33 - 51 years Sex: M+F Population Size: 41 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 n = 41 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: 33 - 51 years Sex: M+F Population Size: 41 Sources: https://pubmed.ncbi.nlm.nih.gov/17355733/
Taste perversion	18.9%	2000 mg 2 times / day steady, oral (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Vomiting	24.5%	2000 mg 2 times / day steady, oral (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Nausea	28.3%	2000 mg 2 times / day steady, oral (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 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 (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Flatulence	7.5%	2000 mg 2 times / day steady, oral (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Headache	7.5%	2000 mg 2 times / day steady, oral (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Diarrhea	9.4%	2000 mg 2 times / day steady, oral (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf
Rash	9.4%	2000 mg 2 times / day steady, oral (max) 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 n = 53 Health Status: unhealthy Condition: HIV disease Age Group: adult Sex: unknown Population Size: 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/050662s042,050698s024,050775s013lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1467 inducer 707 substrate 1601	inhibitor 1604 substrate 936	inhibitor 1702 substrate 1118	inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT2 131 P-gp 1330 OATP1B1 733 OATP1B3 657 OAT1 554 OAT3 588 OCT1 480 OCT2 594 MATE1 290 MATE2 251 BCRP 643 MRP2 346 MRP3 150 BSEP 376 CYP1A2 1383 UGT1A1 192 UGT1A3 82 UGT1A4 74 UGT1A6 104 UGT1A7 20 UGT1A8 33 UGT1A9 113 UGT1A10 29 UGT2B4 18 UGT2B7 141 UGT2B10 24 UGT2B15 61 UGT2B17 17 aldehyde oxidase 7 FMO 7 CES1 3 CES2 3	OATP1B1 370 OATP1B3 319 OATP2B1 101 OCT1 302 CYP2C19 910 CYP1A2 972 CYP2E1 606 CYP2A6 485 CYP1A1 325 CYP2B6 616 CYP2C8 634 CYP4A11 93	CYP3A5 71

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
UGT1A1 240	inhibitor 3045 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 38	inhibitor 3045 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 91	inhibitor 3045 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 77	inhibitor 3045 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 136	inhibitor 3045 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 22	inhibitor 3045 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 118	inhibitor 3045 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 26	inhibitor 3045 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 61	inhibitor 3045 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 19	inhibitor 3045 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 18	inhibitor 3045 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 152	inhibitor 3045 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 713	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MATE1 292	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MATE2 251	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MRP2 434	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MRP3 200	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OAT1 558	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OAT3 590	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OCT1 495	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OCT2 595	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
CES1 3	inhibitor 3045 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 3	inhibitor 3045 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 1772	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/15735612/	no
CYP3A5 122	inducer 1440 Sources: https://pubmed.ncbi.nlm.nih.gov/15735612/	no
FMO 7	inhibitor 3045 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 1532	inhibitor 3045 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 1648	inhibitor 3045 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 1738	inhibitor 3045 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 1772	inhibitor 3045 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 133	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/15708966/	weak
OATP1B3 666	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/ \| https://pubmed.ncbi.nlm.nih.gov/17296622/	yes [IC50 14 uM]
UGT1A8 45	inhibitor 3045 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 748	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	yes [IC50 5.3 uM]
BSEP 377	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	yes [IC50 59 uM]
aldehyde oxidase 8	inhibitor 3045 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 1514	inhibitor 3045 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 38	activator 202 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	yes
UGT1A8 45	activator 202 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 325	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP1A2 972	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2A6 485	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2B6 616	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C19 910	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C8 634	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C9 936	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2D6 1118	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2E1 606	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP4A11 93	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
OATP1B1 370	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OATP1B3 319	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OATP2B1 101	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OCT1 302	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
CYP3A4 1601	substrate 3113 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 1507	inhibitor 1489 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
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
eMolecules	4775688	https://www.emolecules.com/cgi-bin/more?vid=4775688

PubMed

Title	Date	PubMed
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
Rifabutin-associated hypopyon uveitis in human immunodeficiency virus-negative immunocompetent individuals.	2001 Apr	11297492
Postoperative proprionibacterium acnes endophthalmitis.	2001 Apr	11297461
Plasma and BAL fluid concentrations of antimicrobial peptides in patients with Mycobacterium avium-intracellulare infection.	2001 Apr	11296180
Comparative efficacy of new investigational agents against Helicobacter pylori.	2001 Apr	11284777
In vitro activity of telithromycin (HMR 3647) against 502 strains of anaerobic bacteria.	2001 Apr	11266423
Analysis of metronidazole, clarithromycin and tetracycline resistance of Helicobacter pylori isolates from Korea.	2001 Apr	11266421
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.	2001 Apr	11266411
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
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
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.	2001 Feb	11293500
Acute fatal colchicine intoxication in a patient on continuous ambulatory peritoneal dialysis (CAPD). Possible role of clarithromycin administration.	2001 Feb	11269688
Multicenter study of incidence of Mycobacterium marinum in humans in Spain.	2001 Feb	11258515
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
Comparison of the efficacy and safety of different formulations of omeprazole-based triple therapies in the treatment of Helicobacter pylori-positive peptic ulcer.	2001 Feb	11227677
Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication.	2001 Feb	11227668
[Phlebitis due to intravenous administration of macrolide antibiotics. A comparative study of erythromycin versus clarithromycin].	2001 Feb 3	11222159
[Acute delirium, probably precipitated by clarithromycin].	2001 Feb 3	11219151
Fixed drug eruption due to clarithromycin.	2001 Jan	11260179
[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege].	2001 Jan	11256133
Antibiotic susceptibilities of Helicobacter pylori.	2001 Jan	11255612
Acute community-acquired pneumonia: current diagnosis and treatment.	2001 Jan	11227252
Treatment of canine leproid granuloma syndrome: preliminary findings in seven dogs.	2001 Jan	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 Jan	11219483
Comparison of the efficacy of extended-release clarithromycin tablets and amoxicillin/clavulanate tablets in the treatment of acute exacerbation of chronic bronchitis.	2001 Jan	11219481
Pericarditis after allogeneic peripheral blood stem cell transplantation caused by Legionella pneumophila (non-serogroup 1).	2001 Jan-Feb	11261761
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.	2001 Mar	11303370
Clarithromycin and CNS disturbances.	2001 Mar	11288564
Antibiotic resistance rates and macrolide resistance phenotypes of viridans group streptococci from the oropharynx of healthy Greek children.	2001 Mar	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 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
Clarithromycin and risk of Clostridium difficile-associated diarrhoea.	2001 Mar	11222572
Evaluation of the clinical microbiology profile of moxifloxacin.	2001 Mar 15	11249830
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
[HIV: a guide on management of seropositive patients].	2001 Mar 3	11268903
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 `Fri Jun 25 21:01:09 UTC 2021` Edited by `admin` on `Fri Jun 25 21:01:09 UTC 2021`
Record UNII	H1250JIK0A
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CLARITHROMYCIN

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 [USP MONOGRAPH]

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

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

CLARITHROMYCIN [USP]

Common Name

English

MAVID

Brand Name

English

CLARITHROMYCIN IDENTITY

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