Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H43N5O7.H2O4S |
Molecular Weight | 575.674 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.[H][C@]1(CC[C@@H](N)[C@@]([H])(O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1)[C@@H](C)NC
InChI
InChIKey=NWQISSNHRDDWRM-FDJABWOBSA-N
InChI=1S/C21H43N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;/m1./s1
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C21H43N5O7 |
Molecular Weight | 477.5954 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdfhttps://www.drugbank.ca/drugs/DB00798Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26083124
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/062366s033lbl.pdfhttps://www.drugbank.ca/drugs/DB00798
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26083124
Gentamicin C1 is a part of gentamicin C complex, containing gentamicin C1, gentamicin C1a, and gentamicin C2 which compose approximately 80% of gentamicin and have been found to have the highest antibacterial activity. Commercial gentamicin C is a mixture of gentamicin C1, C1a, and C2. Gentamicin C1 has a methyl group in the 6' position of the 2-amino-hexose ring and is N methylated at the same position. Gentamicin is a broad spectrum aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses. Aminoglycosides like gentamicin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically gentamicin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes. Gentamicin complex is used for treatment of serious infections caused by susceptible strains of the following microorganisms: P. aeruginosa, Proteus species (indole-positive and indole-negative), E. coli, Klebsiella-Enterobactor-Serratia species, Citrobacter species and Staphylococcus species (coagulase-positive and coagulase-negative).
CNS Activity
Sources: https://books.google.ru/books?id=tMfQvYKNVz4C&pg=PA5&lpg=PA5&dq=gentamicin+not+readily+crosses+the+blood-brain+barrier&source=bl&ots=1t9bQV5WFT&sig=4pWiwGUCNf8NuKWscVRE6Ag9aHI&hl=ru&sa=X&ved=0ahUKEwivs63J9u_LAhWrCpoKHUZgA90Q6AEIQzAE#v=onepage&q=gentamicin%20not%20readily%20crosses%20the%20blood-brain%20barrier&f=falsehttps://www.ncbi.nlm.nih.gov/pubmed/6431059
Curator's Comment: In studies of 70 rats, the permeability of the normal blood-brain barrier to gentamicin was shown to be poor.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20970332 |
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Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20970332 |
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Target ID: 30S subunit of the bacterial ribosome |
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Target ID: CHEMBL614640 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9822590 |
2.0 µM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
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Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
|||
Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
|||
Curative | GARAMYCIN Approved UseGentamicin sulfate ophthalmic solution, USP is indicated in the topical treatment of ocular bacterial infections including conjunctivitis, keratitis, keratoconjunctivitis, corneal ulcers, blepharitis, blepharoconjunctivitis, acute meibomianitis, and dacryocystitis, caused by susceptible strains of the following microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Streptococcus pneumoniae, Enterobacter aerogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Serratia marcescens. Launch Date1970 |
PubMed
Title | Date | PubMed |
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Proceedings: Hearing loss due to gentamicin therapy. | 1975 |
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[Letter: Cauda equina syndrome due to intrathecal gentamicin]. | 1975 Jan 18 |
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[Evaluation of ototoxicity of amikacin (BB-K8) by animal test (author's transl)]. | 1975 Jun |
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[The intratympanic treatment of Menière's disease with ototoxic antibiotics. A follow-up study of 55 cases (author's transl)]. | 1977 May |
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Effects of desoxycorticosterone acetate (DOCA) plus saline drinking on gentamicin-mediated nephropathy in rats. | 1992 |
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Comparison of methods for prediction of nephrotoxicity during development. | 1992 |
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Reactive oxygen metabolites in toxic acute renal failure. | 1992 |
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An investigation of the acute effect of gentamicin on the renal handling of electrolytes in the rat. | 1992 Apr |
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Sense of smell after gentamicin nose-drops. | 1992 Feb 1 |
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Chrononephrotoxicity in rat of a vancomycin and gentamicin combination. | 1992 Jul |
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Calcium supplementation and thyroid hormone protect against gentamicin-induced inhibition of proximal tubular Na+,K(+)-ATPase activity and other renal functional changes. | 1992 Jun |
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Effects of aminoglycoside antibiotics on the auditory brainstem response and post rotatory nystagmus in rats. | 1992 May |
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Detection of uremic peaks in dogs by anion exchange high performance liquid chromatography. | 1992 Oct |
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Gentamicin-induced hypercalciuria in the rat: assessment of nephron site involved. | 1992 Oct |
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Changes in concentration of essential metals in kidneys and urine as indices of gentamicin nephrotoxicity in female Wistar rats. | 1992 Sep |
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Aortic root replacement in a patient with vancomycin-resistant Enterococcus faecium endocarditis and leukemia. | 2001 Nov |
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Quantitative and qualitative scintigraphic measurement of renal function in dogs exposed to toxic doses of Gentamicin. | 2001 Nov-Dec |
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FGFR3 expression during development and regeneration of the chick inner ear sensory epithelia. | 2001 Oct 15 |
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Protective effect of Pongamia pinnata flowers against cisplatin and gentamicin induced nephrotoxicity in rats. | 2003 Jan |
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Intratympanic gentamicin for intractable Meniere's disease: 5-year follow-up. | 2003 Oct |
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Gentamicin-induced correction of CFTR function in patients with cystic fibrosis and CFTR stop mutations. | 2003 Oct 9 |
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Hearing loss after intratympanic gentamicin therapy for unilateral Ménière's Disease. | 2003 Sep |
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Inhibition of nuclear factor-kappaB activation attenuates tubulointerstitial nephritis induced by gentamicin. | 2004 |
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Plasma protein extravasation and vascular endothelial growth factor expression with endothelial nitric oxide synthase induction in gentamicin-induced acute renal failure in rats. | 2004 Apr |
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Absence of dystrophin in mice reduces NO-dependent vascular function and vascular density: total recovery after a treatment with the aminoglycoside gentamicin. | 2004 Apr |
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alpha-L-iduronidase premature stop codons and potential read-through in mucopolysaccharidosis type I patients. | 2004 Apr 30 |
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Effects of some antibiotics on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro and in vivo study. | 2004 Aug |
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Efficacy of the combination ampicillin plus ceftriaxone in the treatment of a case of enterococcal endocarditis due to Enterococcus faecalis highly resistant to gentamicin: efficacy of the "ex vivo" synergism method. | 2004 Aug |
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Effect of tempol (4-hydroxy tempo) on gentamicin-induced nephrotoxicity in rats. | 2004 Feb |
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Influence of spironolactone treatment on gentamicin-induced nephrotoxicity in rats. | 2004 Jul |
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Altered NMDA receptor expression in renal toxicity: Protection with a receptor antagonist. | 2004 Jul |
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Gentamicin treatment induces simultaneous mesangial proliferation and apoptosis in rats. | 2004 Jun |
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Identification of putative gene based markers of renal toxicity. | 2004 Mar |
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Evaluation of factors to decrease bioavailability of cyclosporin A in rats with gentamicin-induced acute renal failure. | 2004 Mar |
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Hematopoietic and nonhematopoietic potentials of Hoechst(low)/side population cells isolated from adult rat kidney. | 2004 May |
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Deficiency of polycystin-2 reduces Ca2+ channel activity and cell proliferation in ADPKD lymphoblastoid cells. | 2004 May |
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Correction of ATM gene function by aminoglycoside-induced read-through of premature termination codons. | 2004 Nov 2 |
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Delayed diagnosis of penicillin-resistant Streptococcus mitis endocarditis following single-dose amoxicillin prophylaxis in a child. | 2004 Oct |
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Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center. | 2004 Oct |
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In vivo efficacy of linezolid in combination with gentamicin for the treatment of experimental endocarditis due to methicillin-resistant Staphylococcus aureus. | 2004 Oct |
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Early gene expression in the organ of Corti exposed to gentamicin. | 2004 Sep |
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Protective effect of L-arginine intake on the impaired renal vascular responses in the gentamicin-treated rats. | 2005 |
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Efficacy of a non-vancomycin-based peritoneal dialysis peritonitis protocol. | 2005 Apr |
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Role of the renin-angiotensin system on the parathyroid hormone-related protein overexpression induced by nephrotoxic acute renal failure in the rat. | 2005 Apr |
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Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing. | 2005 Apr 20 |
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Pyomyositis caused by methicillin-resistant Staphylococcus aureus. | 2005 Apr 7 |
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[Expression of heat shock protein 70 mRNA in guinea pig cochlea with ototoxicity of gentamicin]. | 2005 Jun 25 |
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Aminoglycosides induce acute cell signaling and chronic cell death in renal cells that express the calcium-sensing receptor. | 2005 May |
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Aminoglycoside suppression of nonsense mutations in severe hemophilia. | 2005 Nov 1 |
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Gentamicin induces Jun-AP1 expression and JNK activation in renal glomeruli and cultured mesangial cells. | 2005 Sep 16 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Gentamicin injection may be given IM or IV. Gentamicin is recommended to be administered in three equal doses every eight hours. For adult patients with life-threatening infections, dosages up to 5 mg/kg/day may be administered in three or four equal doses.
Adults: 3 mg/kg/day
Adult patients with life-threatening infections: 5 mg/kg/day
Children: 6 to 7.5 mg/kg/day
Infants and Neonates: 7.5 mg/kg/day
Premature or Full-Term Neonates One Week of Age or Less: 5 mg/kg/day
Route of Administration:
Other
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/4790564/
Serratia marcescens was susceptible to gentamicin (mean MIC, 0.34±0.14 μg/ml).
Substance Class |
Chemical
Created
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Edited
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Record UNII |
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PARENT -> SALT/SOLVATE |