ジヒドロストレプトマイシン
- 関
- dihydrostreptomycin sulfate
WordNet
- antibiotic consisting of a hydrogenated form of streptomycin; used against tuberculosis and tularemia and Gram-negative organisms
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/11/09 16:06:33」(JST)
[Wiki en表示]
Dihydrostreptomycin
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Clinical data |
AHFS/Drugs.com |
International Drug Names |
ATC code |
- S01AA15 (WHO) QA07AA90 (WHO) QJ01GA90 (WHO) QJ51GA90 (WHO)
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Identifiers |
IUPAC name
- 2-[(1S,2R,3R,4S,5R,6R)-5-(Diaminomethylideneamino)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)- 4,5-dihydroxy-6-(hydroxymethyl)-3-methylaminooxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)- 5-methyloxolan-2-yl]oxy-3,4,6-trihydroxycyclohexyl]guanidine
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CAS Number |
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PubChem CID |
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ChemSpider |
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UNII |
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ChEMBL |
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ECHA InfoCard |
100.004.445 |
Chemical and physical data |
Formula |
C21H41N7O12 |
Molar mass |
583.59 g/mol |
3D model (JSmol) |
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SMILES
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C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)NC(=N)N)O)NC(=N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O
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InChI
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InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
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Key:ASXBYYWOLISCLQ-HZYVHMACSA-N
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(verify) |
Dihydrostreptomycin is a derivative of streptomycin that has a bactericidal property.[1] It's a semisynthetic aminoglycoside antibiotic used in the treatment of tuberculosis.[2]
It acts by irreversibly binding the S12 protein in the bacterial 30S ribosomal subunit, after being actively transported across the cell membrane, which interferes with the initiation complex between the mRNA and the bacterial ribosome. This leads to the synthesis of defective non-functional proteins, which results in the bacterial cell's death.[1]
It causes ototoxicity,[3] which is why it is no longer used in humans.
See also
- Streptomycin
- Translation (biology)
References
- ^ a b "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016.
- ^ "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016.
- ^ Harrison, Wiley H. (1954). "Ototoxicity of dihydrostreptomycin". Quarterly bulletin. Northwestern University (Evanston, Ill.). Medical School. 28 (3): 271–3. PMC 3803976 . PMID 13186082.
External links
- Dihydrostreptomycin | C21H41N7O12 - PubChem
Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)
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30S |
Aminoglycosides
(initiation inhibitors) |
-mycin (Streptomyces) |
- Streptomycin#
- Dihydrostreptomycin
- Neomycin#
- Framycetin
- Paromomycin
- Ribostamycin
- Kanamycin#
- Amikacin#
- Arbekacin
- Bekanamycin
- Dibekacin
- Tobramycin
- Spectinomycin#
- Hygromycin B
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-micin (Micromonospora) |
- Gentamicin#
- Netilmicin
- Sisomicin
- Plazomicin†
- Isepamicin
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Tetracycline antibiotics
(tRNA binding) |
Tetracyclines |
- Doxycycline#
- Chlortetracycline
- Clomocycline
- Demeclocycline
- Lymecycline
- Meclocycline
- Metacycline
- Minocycline
- Omadacycline†
- Oxytetracycline
- Penimepicycline
- Rolitetracycline
- Sarecycline†
- Tetracycline
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Glycylcyclines |
|
Fluorocyclines |
|
|
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50S |
Oxazolidinone
(initiation inhibitors) |
- Eperezolid
- Linezolid#
- Posizolid
- Radezolid
- Ranbezolid
- Sutezolid
- Tedizolid
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Peptidyl transferase |
Amphenicols |
- Chloramphenicol#
- Azidamfenicol
- Thiamphenicol
- Florfenicol
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Pleuromutilins |
- Retapamulin
- Tiamulin
- Valnemulin
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MLS (transpeptidation/translocation) |
Macrolides |
- Azithromycin#
- Clarithromycin#
- Dirithromycin
- Erythromycin#
- Flurithromycin
- Josamycin
- Midecamycin
- Miocamycin
- Oleandomycin
- Rokitamycin
- Roxithromycin
- Spiramycin
- Troleandomycin
- Tylosin
- Ketolides
- Telithromycin
- Cethromycin
- Solithromycin†
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Lincosamides |
- Clindamycin#
- Lincomycin
- Pirlimycin
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Streptogramins |
- Pristinamycin
- Quinupristin/dalfopristin
- Virginiamycin
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|
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EF-G |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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English Journal
- Use of experimental design to optimize a triple-potential waveform to develop a method for the determination of streptomycin and dihydrostreptomycin in pharmaceutical veterinary dosage forms by HPLC-PAD.
- Martínez-Mejía MJ1, Rath S2.
- Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2015 Feb;104:81-9. doi: 10.1016/j.jpba.2014.11.026. Epub 2014 Nov 22.
- An HPLC-PAD method using a gold working electrode and a triple-potential waveform was developed for the simultaneous determination of streptomycin and dihydrostreptomycin in veterinary drugs. Glucose was used as the internal standard, and the triple-potential waveform was optimized using a factorial
- PMID 25497889
- Risk factors for antimicrobial resistance in fecal Escherichia coli from preweaned dairy calves.
- Duse A1, Waller KP2, Emanuelson U3, Unnerstad HE4, Persson Y5, Bengtsson B4.
- Journal of dairy science.J Dairy Sci.2015 Jan;98(1):500-16. doi: 10.3168/jds.2014-8432. Epub 2014 Nov 14.
- The primary objective of this study was to investigate calf and farm factors associated with antimicrobial-resistant Escherichia coli in the feces of preweaned dairy calves in Sweden. In particular, we investigated the effects of feeding calves colostrum and milk from cows treated with antimicrobial
- PMID 25465547
- Unraveling Antimicrobial Resistance Genes and Phenotype Patterns among Enterococcus faecalis Isolated from Retail Chicken Products in Japan.
- Hidano A1, Yamamoto T2, Hayama Y2, Muroga N2, Kobayashi S2, Nishida T3, Tsutsui T2.
- PloS one.PLoS One.2015 Mar 17;10(3):e0121189. doi: 10.1371/journal.pone.0121189. eCollection 2015.
- Multidrug-resistant enterococci are considered crucial drivers for the dissemination of antimicrobial resistance determinants within and beyond a genus. These organisms may pass numerous resistance determinants to other harmful pathogens, whose multiple resistances would cause adverse consequences.
- PMID 25781022
Japanese Journal
- 2003~2009年にブリ類から分離された類結節症原因菌<I>Photobacterium damselae</I> subsp. <I>piscicida</I>の薬剤感受性およびRAPD解析による分類
- Prevalence and Mechanism of Antimicrobial Resistance in Staphylococcus aureus Isolates from Diseased Cattle, Swine and Chickens in Japan
- 我が国の養豚場における抗菌性物質の使用と薬剤耐性大腸菌の分布との関係
Related Links
- Dihydrostreptomycin definition, an antibiotic, C 21 H 41 N 7 O 12 , derived by organic synthesis from and believed to be less toxic than streptomycin: used in the form of its sulfate chiefly in the treatment of tuberculosis. See more. ...
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