Chloramphenicol succinate
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Basic information
- CAS
3544-94-3- Standard SMILES
O=C(O)CCC(=O)OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc([N+](=O)[O-])cc1- InChIKey
LIRCDOVJWUGTMW-ZWNOBZJWSA-N- Molecular formula
- C15H16Cl2N2O8
- Average molar mass
- 423.2 g/mol
- Monoisotopic mass
- 422.0283709
Overview
Chloramphenicol succinate is a hemisuccinate and a member of amphetamines.
Names & identifiers
- Preferred name
- Chloramphenicol succinate
- IUPAC
- 4-[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid
- English name
- Chloramphenicol hemisuccinate
- Molecular formula
- C15H16Cl2N2O8
- Molecular weight
- 423.2
Names & synonyms
CHLORAMPHENICOL SUCCINATE3544-94-3chloramphenicol hemisuccinateLevomycetin succinateChloramphenicol monosuccinateChloromycetin succinateZCX619U9A1NSC-756676DTXSID80481554-[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxo-butanoic acid4-((2R,3R)-2-((2,2-dichloroacetyl)amino)-3-hydroxy-3-(4-nitrophenyl)propoxy)-4-oxo-butanoic acidRefChem:125272
Show more names
Chloramphenicol 3-succinate
DTXCID4028129222-590-0Chronicin foam4-((2R,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy)-4-oxobutanoic acid4-[(2R,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acidKemicetine succinateParaxin succinateLevomycetin hemisuccinate
Database identifiers
- CAS
3544-94-3- PubChem CID
- 656580
- DTXSID
Properties
Computed structural propertiesFilling in
- XLogP
- 1.1
- Topological polar surface area
- 159 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 10
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 546
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 127 °C · 127 °C
- Boiling point
- 716.3 · 716.3±60.0 °C(Predicted)
- Density
- 1.6769 · 1.6769 (rough estimate)
- refractive index
- 1.735 · 1.7350 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
- form
- A solid
- pka
- 4.36 · 4.36±0.17(Predicted)
- FDA UNII
- 619 U9A1 · ZCX619U9A1
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H302-H332-H335-H319
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P308+P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationREACH registered substance: [2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl] hydrogen [R-(R*,R*)]-succinate (EC: 222-590-0)
Hazard Classes and CategoriesAcute Tox. 4 (66.7%)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H302-H332-H335-H319
- REACH Registrations
- Active
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P261-P271-P304+P340-P312-P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
Protein BindingChloramphenicol succinate is 57-92% protein bound in plasma.
Pharmacodynamics
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.
Mechanism of Action
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.
Biological Half-LifeThe half life of chloramphenicol succinate in patients with normal renal and hepatic function is 0.6-2.7h.
Metabolism/Metabolites
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.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
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.
Related reactions
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Compound notes
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