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Home > Encyclopedia > Chloramphenicol succinate

Chloramphenicol succinate

pharmaceutical raw materials
Chloramphenicol succinate structure

Chloramphenicol succinate 

structure
  • CAS No:

    3544-94-3

  • Formula:

    C15H16Cl2N2O8

  • Chemical Name:

    Chloramphenicol succinate

  • Synonyms:

    Butanedioic acid,mono[(2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] ester;Succinic acid,α-monoester with D-threo-(-)-2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]acetamide;Butanedioic acid,mono[2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] ester,[R-(R*,R*)]-;Succinic acid,ester with chloramphenicol;Acetamide,2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-,α-(hydrogen succinate),D-(-)-threo-;Chloramphenicol hemisuccinate;Chloramphenicol hydrogen succinate;Chloramphenicol succinate;Chloromycetin succinate;Kemicetine succinate;Levomycetin hemisuccinate;Chloramphenicol acid succinate;Chloramphenicol monosuccinate;Levomycetin succinate;Paraxin succinate;Chronicin foam;Chloramphenicol 3-monosuccinate;53906-65-3

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Chloramphenicol succinate is a member of amphetamines and a hemisuccinate.|Chloramphenicol succinate is an ester prodrug of [chloramphenicol]. Chloramphenicol is a bacteriostatic antibiotic. Use of chloramphenicol succinate and chloramphenicol has decreased due to the risk of potentially fatal blood dyscrasias. Chloramphenicol succinate was granted FDA approval on 20 February 1959.

Chloramphenicol succinate Basic Attributes

423.20200

423.20

222-590-0

ZCX619U9A1

756676

DTXSID8048155

Characteristics

162.24000

2.68820

1.536g/cm3

127 °C

716.3ºC at 760mmHg

387ºC

1.589

0.01 M

Safety Information

P260, P264, P270, P309+P311, P405, P501

H371

|Warning|H302 (66.67%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P309+P311, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Patients experiencing an overdose may present with shock, cyanosis, and coma. Treat patients with symptomatic and supportive measures which may include administration of fluids, exchange transfusions, and administration of dopamine.

Chloramphenicol succinate is 57-92% protein bound in plasma.

Drug Information

Chloramphenicol succinate is indicated to treat serious and susceptible bacterial infections where less dangerous drugs are ineffective or contraindicated.

Chloramphenicol succinate is a prodrug of chloramphenicol, which binds to bacterial ribosomes and prevents translation. It has a narrow therapeutic index and a moderate duration of action. Patients should be counselled regarding the risk of serious fatal blood dyscrasias.

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Chloramphenicol succinate has a high degree of interpatient variability, with a Tmax of 18 minutes to 3 hours. A 1g oral chloramphenicol succinate dose every 6-8 hours reaches a mean Cmax of 11.2µg/mL with a Tmax of 1 hour.|6-80% of chloramphenicol succinate is eliminated unchanged in the urine, though this is highly variable between patients. On average, 30% of chloramphenicol succinate is eliminated unchanged in the urine and 10% is eliminated as the active chloramphenicol in the urine.|Chloramphenicol succinate has a volume of distribution of 0.2-3.1L/kg.|Chloramphenicol succinate's total clearance is 530-540mL/min in patients with normal renal and hepatic function, and 354mL/min in patients with renal or hepatic dysfunction. Chloramphenicol succinate's renal clearance is 222-260mL/min in patients with normal renal and hepatic function, and 66mL/min in patients with renal or hepatic dysfunction.

Chloramphenicol succinate is hydrolyzed to chloramphenicol. The propane-diol moiety of chloramphenicol can be metabolised through a number of pathways including glucuronidation, sulfate conjugation, phosphorylation, acetylation, and oxidation. The dichloroacetate moiety can be metabolised through hydrolysis of the amide group and dechlorination. The nitro functional group can also be metabolised to an aryl amine and aryl amide metabolite.

The half life of chloramphenicol succinate in patients with normal renal and hepatic function is 0.6-2.7h.

Chloramphenicol succinate is hydrolyzed into the active chloramphenicol. Chloramphenicol resembles uridine-5'-phosphate. It binds to the residues A2451 and A2452 in the 23S rRNA of the 50S ribosomal subunit of _E. coli_, which prevents translation.

chloramphenicol hemisuccinate

Chloramphenicol succinate Use and Manufacturing

Chloramphenicol succinate is prepared by acylation of chloramphenicol with succinic anhydride to provide a water soluble pro-drug. Chloramphenicol succinate represents an alternative pro-drug strategy for chloramphenicol that has found a niche in surface antibiotic treatment in surgery. Chloramphenicol succinate is significantly less active than chloramphenicol but acts as a prodrug, forming chloramphenicol in the presence of succinate dehydrogenase.

Computed Properties

Molecular Weight:423.2
XLogP3:1.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:10
Exact Mass:422.0283709
Monoisotopic Mass:422.0283709
Topological Polar Surface Area:159
Heavy Atom Count:27
Complexity:546
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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