Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C11H12Cl2N2O5.C4H6O4.C2H7NO |
Molecular Weight | 502.301 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCO.OC(=O)CCC(O)=O.OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O
InChI
InChIKey=GLOVPJIOQKHINH-UONRGADFSA-N
InChI=1S/C11H12Cl2N2O5.C4H6O4.C2H7NO/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20;5-3(6)1-2-4(7)8;3-1-2-4/h1-4,8-10,16-17H,5H2,(H,14,18);1-2H2,(H,5,6)(H,7,8);4H,1-3H2/t8-,9-;;/m1../s1
Molecular Formula | C11H12Cl2N2O5 |
Molecular Weight | 323.129 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C2H7NO |
Molecular Weight | 61.0831 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C4H6O4 |
Molecular Weight | 118.088 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Date-5.63328E10 |
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 |
|
Numerical methods for handling uncertainty in microarray data: an example analyzing perturbed mitochondrial function in yeast. | 2001 |
|
Comparative review of topical ophthalmic antibacterial preparations. | 2001 |
|
The adverse neuro-developmental effects of postnatal steroids in the preterm infant: a systematic review of RCTs. | 2001 |
|
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 |
|
Toxicity of natural tear substitutes in a fully defined culture model of human corneal epithelial cells. | 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 |
|
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 |
|
Determination of assay and impurities of gamma irradiated chloramphenicol in eye ointment. | 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 |
|
Anti-anaerobic activity of antibacterial agents. | 2001 Feb |
|
Crystallization and preliminary X-ray diffraction analysis of the chloramphenicol acetyltransferase from Tn2424. | 2001 Feb |
|
Resistance patterns of non-O157 Shiga toxin-producing Escherichia coli (STEC) strains isolated from animals, food and asymptomatic human carriers in Switzerland. | 2001 Feb |
|
Antibiotic susceptibility of Kingella kingae isolates from respiratory carriers and patients with invasive infections. | 2001 Feb |
|
A limited loss of DNA compaction accompanying the release of cytoplasm from cells of Escherichia coli. | 2001 Jan |
|
Shigella and Salmonella strains isolated from children under 5 years in Gaborone, Botswana, and their antibiotic susceptibility patterns. | 2001 Jan |
|
Mesophyll-specific, light and metabolic regulation of the C4 PPCZm1 promoter in transgenic maize. | 2001 Jan |
|
Clonal relationships among penicillin-susceptible, multiresistant serotype 6B Streptococcus pneumoniae isolates recovered in Greece and France. | 2001 Jan |
|
Bacteraemia and mortality among adult medical admissions in Malawi--predominance of non-typhi salmonellae and Streptococcus pneumoniae. | 2001 Jan |
|
[Pneumococcal antibiotic resistance in 1999. Results from 19 registries for 1999]. | 2001 Jan |
|
DNA circle formation in Neisseria gonorrhoeae: a possible intermediate in diverse genomic recombination processes. | 2001 Jan |
|
Adhesion to a polymeric biomaterial affects the antibiotic resistance of Staphylococcus epidermidis. | 2001 Jan |
|
Lack of evidence for chloramphenicol resistance in Neisseria meningitidis, Africa. | 2001 Jan-Feb |
|
[Methods of determining chloramphenicol in the workplace air]. | 2001 Jan-Feb |
|
[Lactobacillus paracasei endocarditis in an 18-yeard-old patient with trisomy 21, atrioventricular septal defect and Eisenmenger complex: therapeutic problems]. | 2001 Jan-Feb |
|
Secretion of the virulence-associated Campylobacter invasion antigens from Campylobacter jejuni requires a stimulatory signal. | 2001 Jun 1 |
|
Analysis of a conserved hydrophobic pocket important for the thermostability of Bacillus pumilus chloramphenicol acetyltransferase (CAT-86). | 2001 Mar |
|
Antimicrobial susceptibility of Listeria monocytogenes isolated from meningoencephalitis in sheep. | 2001 Mar |
|
Antimicrobial resistance of Enterococci in Lebanon. | 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 |
|
Patterns of antibiotic resistance, serotype distribution, and patient demographics of Streptococcus pneumoniae in Hong Kong. | 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 |
|
Chromate tolerant bacteria isolated from tannery effluent. | 2001 May |
|
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 |
|
Methicillin-resistant staphylococci and ofloxacin-resistant bacteria from clinically healthy conjunctivas. | 2001 May-Jun |
|
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 16 18:20:59 UTC 2022
by
admin
on
Fri Dec 16 18:20:59 UTC 2022
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Record UNII |
FMO6OC31WV
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Record Status |
Validated (UNII)
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Record Version |
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-
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Systematic Name | English |
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131801044
Created by
admin on Fri Dec 16 18:20:59 UTC 2022 , Edited by admin on Fri Dec 16 18:20:59 UTC 2022
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PRIMARY | |||
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FMO6OC31WV
Created by
admin on Fri Dec 16 18:20:59 UTC 2022 , Edited by admin on Fri Dec 16 18:20:59 UTC 2022
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20369-85-1
Created by
admin on Fri Dec 16 18:20:59 UTC 2022 , Edited by admin on Fri Dec 16 18:20:59 UTC 2022
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