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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H16Cl2N2O8
Molecular Weight 423.202
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLORAMPHENICOL SUCCINATE

SMILES

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=LIRCDOVJWUGTMW-ZWNOBZJWSA-N
InChI=1S/C15H16Cl2N2O8/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/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21)/t10-,13-/m1/s1

HIDE SMILES / InChI
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CHLOROPTIC

Approved Use

Indications 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 Date

1968
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
16.9 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
59.1 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
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
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
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

Doses

DosePopulationAdverse 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...
Other AEs:
Swollen eyelid (1 patient)
Sources:
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)
120 mg/kg/day
Sources:
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
nafcillin
Sources:
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

AEs

AESignificanceDosePopulation
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)
120 mg/kg/day
Sources:
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
nafcillin
Sources:
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Survey of yeast mastitis in dairy herds of small-type farms in the Lublin region, Poland.
2001
Carbon and nitrogen removal from a wastewater of an industrial dairy laboratory with a coupled anaerobic filter-sequencing batch reactor system.
2001
Numerical methods for handling uncertainty in microarray data: an example analyzing perturbed mitochondrial function in yeast.
2001
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA.
2001
Amplification of the Escherichia coli lacZ gene in Bacillus subtilis and its expression on a by-product growth medium.
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
Strain differences in haematological response to chloramphenicol succinate in mice: implications for toxicological research.
2001 Apr
Randomised controlled trial of ketorolac in the management of corneal abrasions.
2001 Apr
Plasmid transfer and susceptibility to antibiotics in the halophilic phototrophs Rhodovibrio salinarum and Rhodothalassium salexigens.
2001 Apr 1
UV-induced increase in RNA polymerase activity in Xanthomonas oryzae pathovar oryzae.
2001 Aug
Liposome-mediated DNA uptake and transient expression in Thermotoga.
2001 Feb
Molecular epidemiology of multiple drug resistant type 6B Streptococcus pneumoniae in the Northern Territory and Queensland, Australia.
2001 Feb
A limited loss of DNA compaction accompanying the release of cytoplasm from cells of Escherichia coli.
2001 Jan
Chloramphenicol treatment for vancomycin-resistant Enterococcus faecium bacteremia.
2001 Jan
Interaction of human aldehyde dehydrogenase with aromatic substrates and ligands.
2001 Jan 30
Drug resistant Haemophilus influenzae from respiratory tract infection in a tertiary care hospital in north India.
2001 Jan-Mar
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
Secretion of the virulence-associated Campylobacter invasion antigens from Campylobacter jejuni requires a stimulatory signal.
2001 Jun 1
[Susceptibility of non-typhi Salmonella spp. at the Galdakao Hospital (1992-1998)].
2001 Mar
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
Antimicrobial resistance of Enterococci in Lebanon.
2001 Mar
Clostridium sordelii corneal ulcer.
2001 Mar-Apr
Induction of complement sensitivity in Escherichia coli by citric acid and low pH.
2001 May
Natural antibiotic susceptibility of Klebsiella pneumoniae, K. oxytoca, K. planticola, K. ornithinolytica and K. terrigena strains.
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
Neisseria meningitidis with decreased susceptibility to penicillin in Ontario, Canada 1997-2000.
2001 May 1
Successful treatment of vancomycin-resistant Enterococcus endocarditis with oral linezolid.
2001 May 1
Increased mitochondrial-encoded gene transcription in immortal DF-1 cells.
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
Worldwide prevalence of antimicrobial resistance in Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis in the SENTRY Antimicrobial Surveillance Program, 1997-1999.
2001 May 15
Decreased susceptibility to ciprofloxacin in Salmonella enterica serotype typhi, United Kingdom.
2001 May-Jun
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

Chloramphenicol 0.5% Eye Drops
Route of Administration: Topical
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).
Name Type Language
CHLORAMPHENICOL SUCCINATE
Common Name English
CHLORAMPHENICOL HEMISUCCINATE
WHO-DD  
Common Name English
NSC-756676
Code English
SUCCINIC ACID HYDROGEN 1-((2R,3R)-3-(4-NITROPHENYL)-2-(DICHLOROACETYLAMINO)-3-HYDROXYPROPAN-1-YL) ESTER
Common Name English
Chloramphenicol hemisuccinate [WHO-DD]
Common Name English
Code System Code Type Description
CAS
3544-94-3
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
EVMPD
SUB01205MIG
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
DRUG CENTRAL
4653
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
RXCUI
20769
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID8048155
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
WIKIPEDIA
Chloramphenicol succinate
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
NSC
756676
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
PUBCHEM
656580
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
DRUG BANK
DB07565
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
SMS_ID
100000084708
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
FDA UNII
ZCX619U9A1
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
222-590-0
Created by admin on Fri Dec 15 19:39:44 GMT 2023 , Edited by admin on Fri Dec 15 19:39:44 GMT 2023
PRIMARY