14-hydroxyclarithromycin is a major metabolite of clarithromycin, an antibiotic in the macrolide class. It has been shown to exhibit antimicrobial activity against a range of bacteria, including Helicobacter pylori, which is responsible for peptic ulcers. Its synthesis involves the oxidation of clarithromycin at the 14-position. Studies have shown that 14-hydroxyclarithromycin exhibits similar antibacterial activity to clarithromycin, but with potentially improved pharmacokinetic properties. The compound's importance lies in its potential for developing new and effective treatments for bacterial infections, particularly those resistant to conventional antibiotics. Research on 14-hydroxyclarithromycin focuses on understanding its pharmacodynamics, pharmacokinetics, and potential clinical applications. These studies are driven by the need to find novel and effective therapies against emerging antibiotic resistance.'
14-hydroxyclarithromycin: major metabolite of A 56268; RN given refers to cpd without isomeric designation
ID Source | ID |
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PubMed CID | 84020 |
CHEMBL ID | 3544830 |
CHEBI ID | 189888 |
MeSH ID | M0157775 |
Synonym |
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14-hydroxyclarithromycin |
CHEBI:189888 |
110671-78-8 |
(3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-12,13-dihydroxy-14-(1-hydroxyethyl)-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecan |
14-oh-clarithromycin |
14-hydroxy-6-0-methylerthromycin a |
14-hydroxy-6-o-methylerythromycin |
unii-cdj36rhc67 |
erythromycin, 14-hydroxy-6-o-methyl- |
cdj36rhc67 , |
a-62671 |
CHEMBL3544830 |
14-hydroxy-6-o-methyl-erythromycin |
DTXSID50892932 |
antibiotic a 62671 |
An in vitro pharmacodynamic chamber model (PDCM) was used to generate bacterial time-kill curves for clarithromycin and 14-hydroxyclarithromyin against Haemophilus influenzae at three pH values: 7.5, 91-183, and 1746.
Excerpt | Reference | Relevance |
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" Because the differences in parent and metabolite pharmacokinetic parameters were small and the increase in circulating drug concentrations was well tolerated (no increase in incidence or severity of adverse events), adjustments in clarithromycin dosing regimens may not be necessary solely on the basis of age." | ( Clarithromycin pharmacokinetics in healthy young and elderly volunteers. Chu, SY; Craft, C; Guay, DR; Wilson, DS, 1992) | 0.28 |
"An in vitro pharmacodynamic model was used to simulate the in vivo pharmacokinetics of clarithromycin and 14-hydroxyclarithromycin in order to generate time-kill curves for three clinical isolates of Haemophilus influenzae (isolates 2019, 91-183, and 1746)." | ( Evaluation of antimicrobial activities of clarithromycin and 14-hydroxyclarithromycin against three strains of Haemophilus influenzae by using an in vitro pharmacodynamic model. Larsson, AJ; Rotschafer, JC; Walker, KJ; Zabinski, RA, 1994) | 0.74 |
"The pharmacokinetic and safety profiles of clarithromycin (C) and its 14-hydroxy-clarithromycin (HC) metabolite were determined after a multiple-dose oral clarithromycin regimen (250 mg twice daily for five doses) in six healthy subjects and seven patients with moderate or severe hepatic impairment (Pugh grades B and C)." | ( Effect of moderate or severe hepatic impairment on clarithromycin pharmacokinetics. Chu, SY; Decourt, JP; Fourtillan, JB; Girault, J; Granneman, GR; Pichotta, PJ, 1993) | 0.29 |
" Analysis of the patients indicated that the addition of steady-state concentrations of zafirlukast did not significantly alter the pharmacokinetic parameters of or overall exposure (based on the area under the concentration-time curve) to azithromycin, clarithromycin, and 14-OHC." | ( Lack of effect of zafirlukast on the pharmacokinetics of azithromycin, clarithromycin, and 14-hydroxyclarithromycin in healthy volunteers. Amsden, GW; Garey, KW; Godo, PG; Nafziger, AN; Peloquin, CA, 1999) | 0.52 |
"This study investigated the steady-state pharmacokinetic interaction between the HIV protease inhibitor, darunavir (TMC114), administered with low-dose ritonavir (darunavir/ritonavir), and clarithromycin in HIV-negative healthy volunteers." | ( Darunavir/ritonavir pharmacokinetics following coadministration with clarithromycin in healthy volunteers. De Paepe, E; De Pauw, M; Hoetelmans, RM; Lefebvre, E; Sekar, VJ; Spinosa-Guzman, S; Vangeneugden, T, 2008) | 0.35 |
Excerpt | Reference | Relevance |
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" The relative bioavailability was evaluated by comparing area under the plasma concentration-time curve (AUC) of the pure CLM with that of its cyclodextrin-citric acid ternary complexes those were filled into hard gelatin capsules." | ( Bioavailability of clarithromycin cyclodextrin ternary complexes upon oral administration to healthy beagle dogs. Chen, X; Li, S; Zhang, X; Zhong, D; Zou, M, 2008) | 0.35 |
" After RIF comedication, relative bioavailability of CLR decreased by more than 90%." | ( Oral absorption of clarithromycin is nearly abolished by chronic comedication of rifampicin in foals. Block, W; Freyer, J; Grube, M; Kroemer, HK; Lämmer, M; Lütjohann, D; Oswald, S; Peters, J; Siegmund, W; Venner, M, 2011) | 0.37 |
Excerpt | Relevance | Reference |
---|---|---|
" Because the differences in parent and metabolite pharmacokinetic parameters were small and the increase in circulating drug concentrations was well tolerated (no increase in incidence or severity of adverse events), adjustments in clarithromycin dosing regimens may not be necessary solely on the basis of age." | ( Clarithromycin pharmacokinetics in healthy young and elderly volunteers. Chu, SY; Craft, C; Guay, DR; Wilson, DS, 1992) | 0.28 |
" Food intake immediately before dosing increased the extent of absorption from the 500-mg tablet formulation by approximately 25%." | ( Drug-food interaction potential of clarithromycin, a new macrolide antimicrobial. Cavanaugh, JC; Chu, S; Locke, C; Park, Y; Wilson, DS, 1992) | 0.28 |
" Otherwise, no dosage adjustment for C appears necessary for subjects with moderate or severe hepatic impairment provided that renal function is not impaired." | ( Effect of moderate or severe hepatic impairment on clarithromycin pharmacokinetics. Chu, SY; Decourt, JP; Fourtillan, JB; Girault, J; Granneman, GR; Pichotta, PJ, 1993) | 0.29 |
" Twelve healthy subjects were administered single doses of clarithromycin alone and with oral cimetidine dosed to steady state." | ( Oral cimetidine prolongs clarithromycin absorption. Amsden, GW; Cheng, KL; Nafziger, AN; Peloquin, CA, 1998) | 0.3 |
Class | Description |
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aminoglycoside | |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 3 (5.45) | 18.7374 |
1990's | 37 (67.27) | 18.2507 |
2000's | 10 (18.18) | 29.6817 |
2010's | 4 (7.27) | 24.3611 |
2020's | 1 (1.82) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (11.33) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 14 (23.73%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 45 (76.27%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |