Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H16Cl2N2O8.C6H14N4O2 |
Molecular Weight | 597.403 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CCCNC(N)=N)C(O)=O.O[C@@H]([C@@H](COC(=O)CCC(O)=O)NC(=O)C(Cl)Cl)C1=CC=C(C=C1)[N+]([O-])=O
InChI
InChIKey=VVVYDMROIIOUOA-PZMRBAAZSA-N
InChI=1S/C15H16Cl2N2O8.C6H14N4O2/c16-14(17)15(24)18-10(7-27-12(22)6-5-11(20)21)13(23)8-1-3-9(4-2-8)19(25)26;7-4(5(11)12)2-1-3-10-6(8)9/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21);4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t10-,13-;4-/m10/s1
Molecular Formula | C15H16Cl2N2O8 |
Molecular Weight | 423.202 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C6H14N4O2 |
Molecular Weight | 174.201 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Chloramphenicol is a broad-spectrum antibiotic that was first isolated from
Streptomyces venezuelae in 1947. The drug was subsequently chemically synthesized. It has both a bacteriostatic and bactericidal effect; in the usual therapeutic concentrations it is bacteriostatic. Chloramphenicol is used for the treatment of serious gram-negative, gram-positive, and anaerobic infections. It is especially useful in the treatment of meningitis, typhoid fever, and cystic fibrosis. It should be reserved for infections for which other drugs are ineffective or contraindicated. Chloramphenicol, a small inhibitor of bacterial protein synthesis, is active against a variety of bacteria and readily enters the CSF. It has been used extensively in the last decades for the treatment of bacterial meningitis. In industrialized countries, chloramphenicol is restricted mostly to topical uses because of the risk of induction of aplastic anemia. However, it remains a valuable reserve antibiotic for patients with allergy to β-lactam antibiotics or with CNS infections caused by multiresistant pathogens.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: intestinal esterase Sources: https://www.iasj.net/iasj?func=article&aId=41875 |
|||
Target ID: CHEMBL2363135 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | CHLOROPTIC Approved UseIndications and Usage In accord with the concepts in the Warning Box and this section, chloramphenicolmust be used only in those serious infections for which less potentially dangerous drugs are ineffective or contraindicated. However, chloramphenicol may be chosen to initiate antibiotic therapy on the clinical impression that one of the conditions below is believed to be present; in vitro sensitivity tests should be performed concurrently so that the drug may be discontinued as soon as possible if less potentially dangerous agents are indicated by such tests. The decision to continue use of chloramphenicol rather than another antibiotic when both are suggested by in vitro studies to be effective against a specific pathogen should be based upon severity of the infection, susceptibility of the pathogen to the various antimicrobial drugs, efficacy of the various drugs in the infection, and the important additional concepts contained in the Warning Box above. 1. Acute infections caused by Salmonella typhi* It is not recommended for the routine treatment of the typhoid carrier state. 2. Serious infections caused by susceptible strains in accordance with the concepts expressed above: a) Salmonella species b) H. influenzae, specially meningeal infections c) Rickettsia d) Lymphogranuloma-psittacosis group e) Various gram-negative bacteria causing bacteremia, meningitis, or other serious gram-negative infections f) Other susceptible organisms which have been demonstrated to be resistant to all other appropriate antimicrobial agents. 3. Cystic fibrosis regimens *In treatment of typhoid fever some authorities recommend that chloramphenicol be administered at therapeutic levels for 8 to 10 days after the patient has become afebrile to lessen the possibility of relapse. Launch Date1968 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2713219/ |
500 mg 4 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
59.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2713219/ |
500 mg 4 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2713219/ |
500 mg 4 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL blood | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7463235/ |
25 mg/kg 4 times / day multiple, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL serum | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7463235/ |
25 mg/kg 4 times / day multiple, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CHLORAMPHENICOL SUCCINATE serum | Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.5 % 4 times / day multiple, ophthalmic Recommended Dose: 0.5 %, 4 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 4 times / day Sources: |
unhealthy, 0.5 - 12 years n = 163 Health Status: unhealthy Condition: acute infective conjunctivitis Age Group: 0.5 - 12 years Sex: unknown Population Size: 163 Sources: |
Other AEs: Swollen eyelid... |
0.25 g 1 times / 3 months multiple, intramuscular Recommended Dose: 0.25 g, 1 times / 3 months Route: intramuscular Route: multiple Dose: 0.25 g, 1 times / 3 months Sources: |
unhealthy, 11 years n = 1 Health Status: unhealthy Condition: infection Age Group: 11 years Sex: F Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 4, 1 patient) Sources: |
70 mg/kg 1 times / day steady, intravenous Recommended Dose: 70 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 70 mg/kg, 1 times / day Co-administed with:: (meropenem) Sources: 120 mg/kg/day |
unhealthy, 15 years n = 1 Health Status: unhealthy Condition: Cystic Fibrosis and infection Age Group: 15 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hyperlactatemia... AEs leading to discontinuation/dose reduction: Hyperlactatemia (1 patient) Sources: |
3 g 1 times / day multiple, intravenous Recommended Dose: 3 g, 1 times / day Route: intravenous Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, 23 years n = 1 Health Status: unhealthy Condition: infection Age Group: 23 years Sex: M Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 5, 1 patient) Sources: |
2.5 g 1 times / day multiple, intravenous Recommended Dose: 2.5 g, 1 times / day Route: intravenous Route: multiple Dose: 2.5 g, 1 times / day Sources: |
unhealthy, 27 years n = 1 Health Status: unhealthy Condition: infection Age Group: 27 years Sex: F Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 4, 1 patient) Sources: |
1 g 1 times / day multiple, parenteral Recommended Dose: 1 g, 1 times / day Route: parenteral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 39 years n = 1 Health Status: unhealthy Condition: infection Age Group: 39 years Sex: M Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 4, 1 patient) Sources: |
750 mg 4 times / day steady, intravenous Recommended Dose: 750 mg, 4 times / day Route: intravenous Route: steady Dose: 750 mg, 4 times / day Co-administed with:: tobramycin Sources: nafcillin |
unhealthy, 54 years n = 1 Health Status: unhealthy Condition: purulent drainage from the surgical wound Age Group: 54 years Sex: M Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 5, 1 patient) Sources: |
4 g 1 times / day multiple, intravenous Recommended Dose: 4 g, 1 times / day Route: intravenous Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy, 61 years n = 1 Health Status: unhealthy Condition: infection Age Group: 61 years Sex: M Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 5, 1 patient) Sources: |
1 g 1 times / day multiple, intramuscular Recommended Dose: 1 g, 1 times / day Route: intramuscular Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 68 years n = 1 Health Status: unhealthy Condition: infection Age Group: 68 years Sex: F Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 4, 1 patient) Sources: |
2 g 1 times / day multiple, parenteral Recommended Dose: 2 g, 1 times / day Route: parenteral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 71 years n = 1 Health Status: unhealthy Condition: infection Age Group: 71 years Sex: F Population Size: 1 Sources: |
Disc. AE: Aplastic anemia... AEs leading to discontinuation/dose reduction: Aplastic anemia (grade 5, 1 patient) Sources: |
3 % 1 times / day multiple, topical Recommended Dose: 3 %, 1 times / day Route: topical Route: multiple Dose: 3 %, 1 times / day Sources: |
unhealthy, adult n = 23 Health Status: unhealthy Condition: cancer patients with (EGFRI)-induced papulopustular rash Age Group: adult Sex: unknown Population Size: 23 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Swollen eyelid | 1 patient | 0.5 % 4 times / day multiple, ophthalmic Recommended Dose: 0.5 %, 4 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 4 times / day Sources: |
unhealthy, 0.5 - 12 years n = 163 Health Status: unhealthy Condition: acute infective conjunctivitis Age Group: 0.5 - 12 years Sex: unknown Population Size: 163 Sources: |
Aplastic anemia | grade 4, 1 patient Disc. AE |
0.25 g 1 times / 3 months multiple, intramuscular Recommended Dose: 0.25 g, 1 times / 3 months Route: intramuscular Route: multiple Dose: 0.25 g, 1 times / 3 months Sources: |
unhealthy, 11 years n = 1 Health Status: unhealthy Condition: infection Age Group: 11 years Sex: F Population Size: 1 Sources: |
Hyperlactatemia | 1 patient Disc. AE |
70 mg/kg 1 times / day steady, intravenous Recommended Dose: 70 mg/kg, 1 times / day Route: intravenous Route: steady Dose: 70 mg/kg, 1 times / day Co-administed with:: (meropenem) Sources: 120 mg/kg/day |
unhealthy, 15 years n = 1 Health Status: unhealthy Condition: Cystic Fibrosis and infection Age Group: 15 years Sex: F Population Size: 1 Sources: |
Aplastic anemia | grade 5, 1 patient Disc. AE |
3 g 1 times / day multiple, intravenous Recommended Dose: 3 g, 1 times / day Route: intravenous Route: multiple Dose: 3 g, 1 times / day Sources: |
unhealthy, 23 years n = 1 Health Status: unhealthy Condition: infection Age Group: 23 years Sex: M Population Size: 1 Sources: |
Aplastic anemia | grade 4, 1 patient Disc. AE |
2.5 g 1 times / day multiple, intravenous Recommended Dose: 2.5 g, 1 times / day Route: intravenous Route: multiple Dose: 2.5 g, 1 times / day Sources: |
unhealthy, 27 years n = 1 Health Status: unhealthy Condition: infection Age Group: 27 years Sex: F Population Size: 1 Sources: |
Aplastic anemia | grade 4, 1 patient Disc. AE |
1 g 1 times / day multiple, parenteral Recommended Dose: 1 g, 1 times / day Route: parenteral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 39 years n = 1 Health Status: unhealthy Condition: infection Age Group: 39 years Sex: M Population Size: 1 Sources: |
Aplastic anemia | grade 5, 1 patient Disc. AE |
750 mg 4 times / day steady, intravenous Recommended Dose: 750 mg, 4 times / day Route: intravenous Route: steady Dose: 750 mg, 4 times / day Co-administed with:: tobramycin Sources: nafcillin |
unhealthy, 54 years n = 1 Health Status: unhealthy Condition: purulent drainage from the surgical wound Age Group: 54 years Sex: M Population Size: 1 Sources: |
Aplastic anemia | grade 5, 1 patient Disc. AE |
4 g 1 times / day multiple, intravenous Recommended Dose: 4 g, 1 times / day Route: intravenous Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy, 61 years n = 1 Health Status: unhealthy Condition: infection Age Group: 61 years Sex: M Population Size: 1 Sources: |
Aplastic anemia | grade 4, 1 patient Disc. AE |
1 g 1 times / day multiple, intramuscular Recommended Dose: 1 g, 1 times / day Route: intramuscular Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 68 years n = 1 Health Status: unhealthy Condition: infection Age Group: 68 years Sex: F Population Size: 1 Sources: |
Aplastic anemia | grade 5, 1 patient Disc. AE |
2 g 1 times / day multiple, parenteral Recommended Dose: 2 g, 1 times / day Route: parenteral Route: multiple Dose: 2 g, 1 times / day Sources: |
unhealthy, 71 years n = 1 Health Status: unhealthy Condition: infection Age Group: 71 years Sex: F Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 375.9 uM] | ||||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
no | |||
Page: Product Information Sheet in Japanese) 18 |
yes [IC50 32 uM] | |||
yes [IC50 48.1 uM] |
PubMed
Title | Date | PubMed |
---|---|---|
Survey of yeast mastitis in dairy herds of small-type farms in the Lublin region, Poland. | 2001 |
|
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA. | 2001 |
|
The adverse neuro-developmental effects of postnatal steroids in the preterm infant: a systematic review of RCTs. | 2001 |
|
Disposition kinetics of florfenicol in goats by using two analytical methods. | 2001 Apr |
|
Prevalence of penicillin-resistant Streptococcus pneumoniae in Kuwait. | 2001 Apr |
|
Antimicrobial resistance of Streptococcus pneumoniae at a university hospital in Saudi Arabia. | 2001 Apr |
|
Randomised controlled trial of ketorolac in the management of corneal abrasions. | 2001 Apr |
|
Activity of moxifloxacin against clinical isolates of Streptococcus pneumoniae from England and Wales. | 2001 Apr |
|
The epithelial flap for photorefractive keratectomy. | 2001 Apr |
|
The Bhaktapur eye study: ocular trauma and antibiotic prophylaxis for the prevention of corneal ulceration in Nepal. | 2001 Apr |
|
Sex-related differences in antinociception and tolerance development following chronic intravenous infusion of morphine in the rat: modulatory role of testosterone via morphine clearance. | 2001 Apr |
|
An outbreak of Salmonella enteritidis infection in pygmy hogs (Sus salvanius). | 2001 Apr |
|
Streptococcus pneumoniae nasopharyngeal carriage prevalence, serotype distribution, and resistance patterns among children on Lombok Island, Indonesia. | 2001 Apr 1 |
|
Yes-associated protein and p53-binding protein-2 interact through their WW and SH3 domains. | 2001 Apr 27 |
|
UV-induced increase in RNA polymerase activity in Xanthomonas oryzae pathovar oryzae. | 2001 Aug |
|
Molecular epidemiology of multiple drug resistant type 6B Streptococcus pneumoniae in the Northern Territory and Queensland, Australia. | 2001 Feb |
|
Improved high performance liquid chromatographic analysis of omeprazole in human plasma. | 2001 Feb |
|
Phenotypic and genotypic characterization of antibiotic-resistant Propionibacterium acnes isolated from acne patients attending dermatology clinics in Europe, the U.S.A., Japan and Australia. | 2001 Feb |
|
Vibrio parahaemolyticus associated with cholera-like diarrhea among patients in North Jakarta, Indonesia. | 2001 Feb |
|
A limited loss of DNA compaction accompanying the release of cytoplasm from cells of Escherichia coli. | 2001 Jan |
|
Inactivation of chloramphenicol by Staphylococcus aureus biotype C from humans & animals. | 2001 Jan |
|
Shigella and Salmonella strains isolated from children under 5 years in Gaborone, Botswana, and their antibiotic susceptibility patterns. | 2001 Jan |
|
Interaction of human aldehyde dehydrogenase with aromatic substrates and ligands. | 2001 Jan 30 |
|
Antibacterial activity of 4,5-dihydroxy-2-cyclopentan-1-one (DHCP) and cloning of a gene conferring DHCP resistance in Escherichia coli. | 2001 Jul |
|
A novel heat shock protein plays an important role in thermal stress management in cyanobacteria. | 2001 Jul 6 |
|
Cloning and functional analysis of a phosphopantetheinyl transferase superfamily gene associated with jadomycin biosynthesis in Streptomyces venezuelae ISP5230. | 2001 Jun |
|
Distribution of resistance genes tet(M), aph3'-III, catpC194 and the integrase gene of Tn1545 in clinical Streptococcus pneumoniae harbouring erm(B) and mef(A) genes in Spain. | 2001 Jun |
|
External quality assessment of antimicrobial susceptibility testing in Europe. | 2001 Jun |
|
Screening of antibiotic resistant inhibitors from local plant materials against two different strains of Pseudomonas aeruginosa. | 2001 Jun |
|
Analysis of a conserved hydrophobic pocket important for the thermostability of Bacillus pumilus chloramphenicol acetyltransferase (CAT-86). | 2001 Mar |
|
Occurrence of the vanA and vanC2/C3 genes in Enterococcus species isolated from poultry sources in Malaysia. | 2001 Mar |
|
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998. | 2001 Mar |
|
Antimicrobial susceptibility of Listeria monocytogenes isolated from meningoencephalitis in sheep. | 2001 Mar |
|
Factors involved in the (near) anoxic survival time of Cerastoderma edule: associated bacteria vs. endogenous fuel. | 2001 Mar |
|
Improved agar diffusion method for detecting residual antimicrobial agents. | 2001 Mar |
|
Clostridium sordelii corneal ulcer. | 2001 Mar-Apr |
|
Induction of complement sensitivity in Escherichia coli by citric acid and low pH. | 2001 May |
|
In vitro susceptibility of Vibrio spp. isolated from the environment. | 2001 May |
|
High prevalence of carriage of antibiotic-resistant Streptococcus pneumoniae in children in Kampala Uganda. | 2001 May |
|
In vitro susceptibility to 15 antibiotics of vibrios isolated from penaeid shrimps in Northwestern Mexico. | 2001 May |
|
Carriage of antibiotic-resistant bacteria by healthy children. | 2001 May |
|
Comparative study of the influence of melatonin and vitamin E on the surface characteristics of Escherichia coli. | 2001 May |
|
Chromate tolerant bacteria isolated from tannery effluent. | 2001 May |
|
Neisseria meningitidis with decreased susceptibility to penicillin in Ontario, Canada 1997-2000. | 2001 May 1 |
|
Clinical prevalence, antimicrobial susceptibility, and geographic resistance patterns of enterococci: results from the SENTRY Antimicrobial Surveillance Program, 1997-1999. | 2001 May 15 |
|
Methicillin-resistant staphylococci and ofloxacin-resistant bacteria from clinically healthy conjunctivas. | 2001 May-Jun |
|
Prevalence of serotypes and molecular epidemiology of Streptococcus pneumoniae strains isolated from children in Beijing, China: identification of two novel multiply-resistant clones. | 2001 Spring |
|
Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center. | 2001 Spring |
|
In vitro activity of 19 antimicrobial agents against enterococci from healthy subjects and hospitalized patients and use of an ace gene probe from Enterococcus faecalis for species identification. | 2001 Spring |
|
Variation in clonality and antibiotic-resistance genes among multiresistant Salmonella enterica serotype typhimurium phage-type U302 (MR U302) from humans, animals, and foods. | 2001 Spring |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15227603
The highest activity of chloramphenicol was documented for isolates of Stenotrophomonas maltophilia (76,5 % susceptible, MIC50 = 4 mg/L, MIC90 = 16 mg/L) and of Staphylococcus aureus (76,2 % susceptible, MIC50 = 8 mg/L, MIC90 = 16 mg/L).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 20:14:17 GMT 2023
by
admin
on
Fri Dec 15 20:14:17 GMT 2023
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Record UNII |
0IQ3P295UA
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Record Status |
Validated (UNII)
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Record Version |
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DTXSID30187893
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0IQ3P295UA
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34327-18-9
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m3347
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