chloramphenicol succinate: inactive precursor (PRODRUGS) of chloramphenicol; used for parenteral administration of chloramphenicol; RN given refers to (R-(R*,R*))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 656580 |
| CHEMBL ID | 1201281 |
| CHEBI ID | 3606 |
| SCHEMBL ID | 12495640 |
| MeSH ID | M0085881 |
| Synonym |
|---|
| CHEMBL1201281 |
| DIVK1C_000689 |
| KBIO1_000689 |
| succinic acid mono-[2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propyl] ester |
| 4-[(2r,3r)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxo-butanoic acid |
| SPECTRUM_000122 |
| chloramphenicol hemisuccinate |
| chloramphenicol icn (tn) |
| D07675 |
| IDI1_000689 |
| SPECTRUM5_000679 |
| BSPBIO_001973 |
| 3544-94-3 |
| chloramphenicol succinate |
| KBIOGR_000768 |
| KBIO2_000582 |
| KBIOSS_000582 |
| KBIO2_005718 |
| KBIO2_003150 |
| KBIO3_001193 |
| SPECTRUM4_000274 |
| SPBIO_000006 |
| NINDS_000689 |
| SPECTRUM2_000083 |
| SPECTRUM3_000337 |
| SPECTRUM1500173 |
| NCGC00094619-03 |
| chloramphenicol hydrogen succinate |
| chloramphenicol acid succinate |
| succinic acid, alpha-monoester with d-threo-(-)-2,2-dichloro-n-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide |
| chronicin foam |
| einecs 222-590-0 |
| kemicetine succinate |
| succinato de cloranfenicol [spanish] |
| levomycetin succinate |
| chloromycetin succinate |
| levomycetin hemisuccinate |
| chloramphenicol monosuccinate |
| paraxin succinate |
| (2-((dichloroacetyl)amino)-3-hydroxy-3-(4-nitrophenyl)propyl) hydrogen (r-(r*,r*))-succinate |
| brn 3228488 |
| HMS2091C06 |
| DB07565 |
| HMS502C11 |
| HMS1920M17 |
| NCGC00094619-04 |
| nsc756676 |
| nsc-756676 |
| pharmakon1600-01500173 |
| CCG-40017 |
| unii-zcx619u9a1 |
| nsc 756676 |
| succinato de cloranfenicol |
| 4-13-00-02756 (beilstein handbook reference) |
| zcx619u9a1 , |
| 4-[(2r,3r)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid |
| chloramphenicol hemisuccinate [who-dd] |
| succinic acid hydrogen 1-((2r,3r)-3-(4-nitrophenyl)-2-(dichloroacetylamino)-3-hydroxypropan-1-yl) ester |
| SCHEMBL12495640 |
| DTXSID8048155 |
| CHEBI:3606 |
| butanedioic acid, 1-[(2r,3r)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] ester |
| LIRCDOVJWUGTMW-ZWNOBZJWSA-N |
| SBI-0051278.P003 |
| 4-{[(2r,3r)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl]oxy}-4-oxobutanoic acid |
| Q27096784 |
| chloramphenicol-sodium-succinate |
| 4-((2r,3r)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy)-4-oxobutanoic acid |
| EN300-33341413 |
| HY-N7114 |
| CS-0013524 |
| AKOS040746697 |
Chloramphenicol succinate acts as a prodrug, being converted to active chloramphen Nicol while it is circulating in the body.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Chloramphenicol succinate acts as a prodrug, being converted to active chloramphenicol while it is circulating in the body." | ( Clinical pharmacokinetics of chloramphenicol and chloramphenicol succinate. Ambrose, PJ, ) | 1.11 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " We studied the relationship between steady-state chloramphenicol serum concentration and hematologic adverse effects in 45 pediatric patients." | ( Serum concentrations and adverse effects of chloramphenicol in pediatric patients. Nahata, MC, 1987) | 0.27 |
| " Until now, elucidation of the mechanisms involved and any attempt at amelioration of the toxic effects have been hampered by the lack of an animal model." | ( The myelotoxicity of chloramphenicol: in vitro and in vivo studies: II: In vivo myelotoxicity in the B6C3F1 mouse. Andrews, CM; Holt, DE; Payne, JP; Turton, JA; Williams, TC, 1998) | 0.3 |
The bioavailability of chloramphenicol and the pharmacokinetics were studied in 5 premature infants, 8 full-term infants and 4 children. The relative bioavailability was compared in 18 children, age 2 months to 14 years. Incomplete bioavailability explains the need for individualizing doses to achieve thrapeutic effect.
| Excerpt | Reference | Relevance |
|---|---|---|
| " Pancreatic enzyme replacement had little effect on the biodisposition parameters for the CAP-base and CAP-S formulation, but significantly increased the peak concentration and bioavailability of the CAP-P formulation." | ( The effect of exocrine pancreatic function on chloramphenicol pharmacokinetics in patients with cystic fibrosis. Aronoff, SC; Blumer, JL; Dickinson, CJ; Reed, MD; Stern, RC; Yamashita, TS, 1988) | 0.27 |
| "Because it is thought that chloramphenicol is poorly absorbed after intramuscular administration, we compared blood levels of chloramphenicol after intramuscular administration with those after intravenous administration in children with a variety of diagnoses." | ( Absorption of chloramphenicol sodium succinate after intramuscular administration in children. Barker, J; Crinis, N; Gratten, M; Linnemann, V; Mackenzie, A; Shann, F, 1985) | 0.27 |
| " The bioavailability of oral crystalline chloramphenicol and chloramphenicol palmitate is approximately 80%." | ( Clinical pharmacokinetics of chloramphenicol and chloramphenicol succinate. Ambrose, PJ, ) | 0.39 |
| "The comparative bioavailability of chloramphenicol from intravenous succinate, oral palmitate, and oral base preparations was studied in a crossover manner in 12 adult patients." | ( Comparative bioavailability of intravenous and oral chloramphenicol in adults. Ericsson, CD; Kramer, WG; Pickering, LK; Rensimer, ER, 1984) | 0.27 |
| "The bioavailability of chloramphenicol and the pharmacokinetics of chloramphenicol and chloramphenicol succinate were studied in 5 premature infants (group A), 8 full-term infants (group B) and 4 children (group C) receiving intravenous chloramphenicol succinate at steady-state." | ( Comparative bioavailability and pharmacokinetics of chloramphenicol after intravenous chloramphenicol succinate in premature infants and older patients. Nahata, MC; Powell, DA, 1983) | 0.71 |
| "0% of the dose, was recovered unchanged in the urine indicating that the bioavailability of CAP from a dose of intravenous chloramphenicol succinate is not complete." | ( Pharmacokinetics of intravenous chloramphenicol sodium succinate in adult patients with normal renal and hepatic function. Blum, MR; Burke, JT; Sanders, KL; Sarubbi, FA; Sherertz, RJ; Wargin, WA, 1982) | 0.47 |
| " Incomplete bioavailability of chloramphenicol and the more than 10-fold variability in clearance of both chloramphenicol and chloramphenicol succinate explain the need for individualizing doses to achieve thrapeutic effect and minimize the risk to toxicity." | ( Bioavailability and clearance of chloramphenicol after intravenous chloramphenicol succinate. Nahata, MC; Powell, DA, 1981) | 0.7 |
| "The relative bioavailability of intravenously administered chloramphenicol succinate and orally administered chloramphenicol palmitate was compared in 18 children, age 2 months to 14 years." | ( Relative bioavailability of intravenous chloramphenicol succinate and oral chloramphenicol palmitate in infants and children. Aravind, MK; Buckley, JA; Dajani, AS; Kauffman, RE; Thirumoorthi, MC, 1981) | 0.77 |
| " Variable hydrolysis and renal elimination of nonhydrolyzed chloramphenicol-S reduces the bioavailability of the antibiotic and appears to contribute substantially to the wide variation in apparent half-life and poor correlation between dose and serum concentration of free chloramphenicol." | ( Pharmacokinetics of chloramphenicol and chloramphenicol succinate in infants and children. Buckley, JA; Dajani, AS; Done, AK; Kauffman, RE; Miceli, JN; Strebel, L, 1981) | 0.53 |
| " Seventeen % of the dose (range 0-51%) was recovered in urine as intact prodrug, indicating incomplete and variable bioavailability of chloramphenicol." | ( Decreased chloramphenicol clearance in malnourished Ethiopian children. Alemayehu, E; Ashton, M; Bolme, P; Eriksson, M; Paalzow, L, 1993) | 0.29 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Regardless of dosage form or route of administration, plasma chloramphenicol concentrations remained in the therapeutic range (5 to 25 mg/liter) for the entire dosage interval, implying that no change needs to be made when changing dosage form or route of administration." | ( Comparative bioavailability of intravenous and oral chloramphenicol in adults. Ericsson, CD; Kramer, WG; Pickering, LK; Rensimer, ER, 1984) | 0.27 |
| " The dosage had to be increased in all preterm neonates from 25 mg/kg/day to 50 mg/kg/day to obtain adequate serum levels during therapy." | ( Use of chloramphenicol palmitate in neonates. Kauffman, RE; Shankaran, S, 1984) | 0.27 |
| " In these, general dosage guidelines are almost impossible in newborns; monitoring the serum concentrations is mandatory." | ( Antibiotic pharmacokinetics in newborns. Smith, AL, 1982) | 0.26 |
| " Dosage adjustments of intravenous chloramphenicol in children must be made in relation to the trough chloramphenicol plasma concentration, renal elimination of CAP-S, and possible saturation of chloramphenicol metabolism." | ( Chloramphenicol dosage and pharmacokinetics in infants and children. Barrett, FF; Burckart, GJ; Della Valle, R; Meyer, MC, ) | 0.13 |
| " The method has also been applied to determine chloramphenicol and its esters as well as chloramphenical in the presence of combination drugs in dosage forms." | ( Spectrophotometric determination of chloramphenicol and its esters in complex drug mixtures. Devani, MB; Doshi, KJ; Shah, AK; Shishoo, CJ, 1981) | 0.26 |
| " The possibility of using a single point measurement of plasma chloramphenicol as a guide to individualized dosage are discussed." | ( Decreased chloramphenicol clearance in malnourished Ethiopian children. Alemayehu, E; Ashton, M; Bolme, P; Eriksson, M; Paalzow, L, 1993) | 0.29 |
| " Mice were dosed with CAPS at 1400 mg/kg for 10 days and sampled at 1, 4 and 15 days after the last dose." | ( Haemotoxicity of chloramphenicol succinate in the CD-1 mouse and Wistar Hanover rat. Andrews, CM; Fagg, R; Turton, JA; Williams, TC; Yallop, D; York, M, 1999) | 0.64 |
| " Urine collected during the dosing interval in nine patients contained 35% (mean) of the administered dose." | ( Chloramphenicol succinate kinetics in infants and young children. Koup, JR; Neeley, N; Opheim, KE; Sack, CM; Smith, AL, 1982) | 1.71 |
| " When these results were compared with susceptibility data for human Chlamydia isolates, the expected efficacy of the current chloramphenicol dosing regimen used in koalas to treat chlamydiosis remains uncertain and at odds with clinical observations." | ( Pharmacokinetics of chloramphenicol following administration of intravenous and subcutaneous chloramphenicol sodium succinate, and subcutaneous chloramphenicol, to koalas (Phascolarctos cinereus). Black, LA; Gillett, A; Govendir, M; Griffith, JE; Higgins, DP; Krockenberger, MB; McLachlan, AJ, 2013) | 0.39 |
| Class | Description |
|---|---|
| amphetamines | Amines that constitute a class of central nervous system stimulants based on the structure of the parent amphetamine 1-phenylpropan-2-amine. |
| hemisuccinate | A succinate ester in which only one of the carboxy groups of succinic acid has been esterified. |
| [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] | |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1617219 | Cytotoxicity in human HEK293 cells assessed as reduction in cell viability at 20 uM incubated up to 72 hrs relative to chloramphenicol | 2019 | Journal of medicinal chemistry, 11-27, Volume: 62, Issue:22 | Structure-Activity Relationship of Peptide-Conjugated Chloramphenicol for Inhibiting |
| AID1617203 | Drug metabolism in human serum assessed as formation of chloramphenicol at 200 pM at 37 degC after 24 hrs by LC-MS analysis relative to control | 2019 | Journal of medicinal chemistry, 11-27, Volume: 62, Issue:22 | Structure-Activity Relationship of Peptide-Conjugated Chloramphenicol for Inhibiting |
| AID1617217 | Cytotoxicity in human HS5 cells assessed as reduction in cell viability at 20 uM to 2 mM incubated up to 72 hrs relative to chloramphenicol | 2019 | Journal of medicinal chemistry, 11-27, Volume: 62, Issue:22 | Structure-Activity Relationship of Peptide-Conjugated Chloramphenicol for Inhibiting |
| AID1617197 | Antibacterial activity against Escherichia coli K-12 assessed as reduction in bacterial growth incubated for 16 hrs | 2019 | Journal of medicinal chemistry, 11-27, Volume: 62, Issue:22 | Structure-Activity Relationship of Peptide-Conjugated Chloramphenicol for Inhibiting |
| AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
| AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
| AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal of biomolecular screening, Jul, Volume: 21, Issue:6 | A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 74 (74.00) | 18.7374 |
| 1990's | 7 (7.00) | 18.2507 |
| 2000's | 9 (9.00) | 29.6817 |
| 2010's | 10 (10.00) | 24.3611 |
| 2020's | 0 (0.00) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (31.73) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 4 (3.64%) | 5.53% |
| Reviews | 3 (2.73%) | 6.00% |
| Case Studies | 5 (4.55%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 98 (89.09%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
| Trial | Phase | Enrollment | Study Type | Start Date | Status | ||
|---|---|---|---|---|---|---|---|
| Prospective Randomized Study to Compare Clinical Outcomes in Patients With Osteomyelitis Treated With Intravenous Antibiotics Versus Intravenous Antibiotics With an Early Switch to Oral Antibiotics [NCT02099240] | Early Phase 1 | 11 participants (Actual) | Interventional | 2014-03-06 | Terminated(stopped due to Not enough patient enrollment and lack of staffing) | ||
| [information is prepared from clinicaltrials.gov, extracted Sep-2024] | |||||||