CLARITHROMYCIN CITRATE

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MDRWXDRMSKEMRE-AZFLODHXSA-N

InChI=1S/C38H69NO13.C6H8O7/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27;7-3(8)1-6(13,5(11)12)2-4(9)10/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 179 Target ID: CHEMBL2363135 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050662s054,050698s033,050775s002lbl.pdf	Binding Agent 1064		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 8429	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 8429	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 8429	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 8429	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 8429	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 8429	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 8429	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 8429	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 8429	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
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 1587 inducer 781 substrate 1737	inhibitor 1767 substrate 1037	inhibitor 1852 substrate 1217	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT2 145 P-gp 1461 OATP1B1 788 OATP1B3 706 OAT1 599 OAT3 642 OCT1 512 OCT2 647 MATE1 306 MATE2 263 BCRP 699 MRP2 383 MRP3 157 BSEP 402 CYP1A2 1524 UGT1A1 204 UGT1A3 84 UGT1A4 77 UGT1A6 108 UGT1A7 21 UGT1A8 36 UGT1A9 116 UGT1A10 32 UGT2B4 19 UGT2B7 146 UGT2B10 25 UGT2B15 64 UGT2B17 18 aldehyde oxidase 7 FMO 7 CES1 3 CES2 3	OATP1B1 406 OATP1B3 350 OATP2B1 104 OCT1 327 CYP2C19 991 CYP1A2 1054 CYP2E1 667 CYP2A6 543 CYP1A1 349 CYP2B6 664 CYP2C8 693 CYP4A11 119	CYP3A5 76

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
UGT1A1 254	inhibitor 3277 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 41	inhibitor 3277 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 93	inhibitor 3277 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 80	inhibitor 3277 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 141	inhibitor 3277 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 23	inhibitor 3277 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 121	inhibitor 3277 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 27	inhibitor 3277 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 64	inhibitor 3277 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 20	inhibitor 3277 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 19	inhibitor 3277 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 157	inhibitor 3277 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 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MATE1 308	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MATE2 263	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
OCT2 648	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	no [IC50 >50 uM]
CES1 3	inhibitor 3277 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 3277 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 1925	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15735612/	no
CYP3A5 130	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15735612/	no
FMO 7	inhibitor 3277 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 1692	inhibitor 3277 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 1819	inhibitor 3277 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 1891	inhibitor 3277 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 1925	inhibitor 3277 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 147	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15708966/	weak
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/ \| https://pubmed.ncbi.nlm.nih.gov/17296622/	yes [IC50 14 uM]
UGT1A8 48	inhibitor 3277 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 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	yes [IC50 5.3 uM]
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/26668209/	yes [IC50 59 uM]
aldehyde oxidase 8	inhibitor 3277 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 1650	inhibitor 3277 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 41	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	yes
UGT1A8 48	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/25834030/	yes

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9152603/ \| https://pubmed.ncbi.nlm.nih.gov/15618724/	no
CYP4A11 119	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15618724/	no
OATP1B1 406	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OATP1B3 350	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OATP2B1 104	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
OCT1 327	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25106415/	no
CYP3A4 1737	substrate 3367 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 1647	inhibitor 1626 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
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
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
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
[Mechanism of drug resistance in Helicobacter pylori].	2001 Feb	11218414
[A strategy for second-line anti-Helicobacter pylori therapy in patients with previously failed treatment].	2001 Feb	11218406
[Usefulness of new triple therapy containing PPI].	2001 Feb	11218404
[Selection of antibiotics and planning of eradication for H. pylori infection].	2001 Feb	11218403
[Antimicrobial resistant test of H. pylori].	2001 Feb	11218400
[Recent guidelines for the management of Helicobacter pylori infection].	2001 Feb	11218393
[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
[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
Favourable effect of an acidified milk (LC-1) on Helicobacter pylori gastritis in man.	2001 Jan	11204805
Rhabdomyolysis secondary to a drug interaction between simvastatin and clarithromycin.	2001 Jan	11197581
Adverse reactions to rifabutin.	2001 Jan	11196537
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
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
Five-day proton pump inhibitor-based quadruple therapy regimen is more effective than 7-day triple therapy regimen for Helicobacter pylori infection.	2001 Mar	11207518
Clarithromycin vs. furazolidone in quadruple therapy regimens for the treatment of Helicobacter pylori in a population with a high metronidazole resistance rate.	2001 Mar	11207517
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
Evaluation of the clinical microbiology profile of moxifloxacin.	2001 Mar 15	11249830
[Buruli ulcer in Togo: 21 cases].	2001 Mar 24	11317927
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 `Sat Dec 16 10:04:50 GMT 2023` Edited by `admin` on `Sat Dec 16 10:04:50 GMT 2023`
Record UNII	16K08R7NG0
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CLARITHROMYCIN CITRATE

Common Name

English

CLARITHROMYCIN CITRATE (1:1)

Common Name

English

ERYTHROMYCIN, 6-O-METHYL-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (SALT) (1:1)

Common Name

English

Clarithromycin citrate [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

71587811