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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/25 16:43:33」(JST)
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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (July 2015) (Learn how and when to remove this template message) |
Ribostamycin
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| Systematic (IUPAC) name |
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(1R,2R,3S,4R,6S)-4,6-diamino-3-hydroxy-2-(β-D-ribofuranosyloxy)cyclohexyl 2,6-diamino-2,6-dideoxy-α-D-glucopyranoside
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| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| Identifiers |
| CAS Number |
53797-35-6 |
| ATC code |
J01GB10 (WHO) |
| PubChem |
CID 33042 |
| ChemSpider |
30581 |
| UNII |
2Q5JOU7T53 N |
| ChEMBL |
CHEMBL221572 N |
| Synonyms |
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol |
| Chemical data |
| Formula |
C17H34N4O10 |
| Molar mass |
454.47266 g/mol |
SMILES
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C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)O)N
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InChI
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InChI=1S/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1
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Key:NSKGQURZWSPSBC-VVPCINPTSA-N
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| NY (what is this?) (verify) |
Ribostamycin is an aminoglycoside-aminocyclitol antibiotic isolated from a streptomycete, Streptomyces ribosidificus, originally identified in a soil sample from Tsu City of Mie Prefecture in Japan.[1] It is made up of 3 ring subunits: 2-deoxystreptamine (DOS), neosamine C, and ribose.[2] Ribostamycin, along with other aminoglycosides with the DOS subunit, is an important broad-spectrum antibiotic with important use against human immunodeficiency virus and is considered a critically important antimicrobial by the World Health Organization.,[3][4] Resistance against aminoglycoside antibiotics, such as ribostamycin, is a growing concern. The resistant bacteria contain enzymes that modify the structure through phosphorylation, adenylation, and acetylation and prevent the antibiotic from being able to interact with the bacterial ribosomal RNAs.[5]
Biosynthesis
The biosynthesis of ribostamycin begins with the sugar, D-glucose, which is phosphorylated at the 6 position to form glucose-6-phosphate. Enzyme rbmA contains a genetic sequence that corresponds to NAD+ binding and catalyzes the formation of 2-deoxy-scyllo-inosose. Enzyme rmbB then catalyzes the transamination of 2-deoxy-scyllo-inosose to 2-deoxy-scyllo-inosamine with L-glutamine and pyridoxal phosphate (PLP). Enzyme rbmC oxidizes the ring to 2-deoxy-3-amino-scyllo-inosose, which is then transaminated by enzyme rmbB to DOS. DOS is then glycosylated by the glycosyltransferase rmbD with uridine diphosphate N-acetylglucosamine (UDP-Glc-NAc) to form 2’-N-acetylparomamine. The deacetylase, racJ, removes the acetyl group and forms paromamine. Paromamine is oxidized by enzyme rbmG and then enzyme rmbH transaminates to produce neamine. Neamine is then ribosylated to form ribostamycin.,[2][3]
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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
- Oxytetracycline
- Penimepicycline
- Rolitetracycline
- Tetracycline
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| Glycylcyclines |
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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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| EF-G |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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References
- ^ Shomura, T.; Ezaki, N.; Tsuruoka, T.; Niwa, T.; Akita, E.; Niida, T.; Studies on Antibiotic SF-733, a New Antibiotic. I Taxonomy, Isolation and Characterization. The Journal of Antibiotics. 1970, 23 (3), 155-161.
- ^ a b Subba, B.; Kharel, M.K.; Lee, H.C.; Liou, K.; Kim, B.G; Sohng, J.K.; The Ribostamycin Biosynthetic Gene Cluster in Streptomyces ribosidificus: Comparison With Butirosin Biosynthesis. Molecules and Cells. 2005, 20 (1), 90-96.
- ^ a b Kurumbang N.P.; Liou, K.; Sohng, J.K.; Biosynthesis of Ribostamycin Derivatives by Reconstitution and Heterologous Expression of Required Gene Sets. Applied Biochemistry and Biotechnology. 2011, 163, 373-382.
- ^ World Health Organization. Critically Important Antimicrobials for Human Medicine 3rd revision. 2011
- ^ Kudo, F.; Eguchi, T.; Biosynthetic Genes for Aminoglycoside Antibiotics. The Journal of Antibiotics. 2009, 62, 471-481.
English Journal
- Mycobacterium massiliense outbreak after intramuscular injection, South Korea.
- Kim HJ, Cho Y, Lee S, Kook Y, Lee D, Lee J, Park BJ.SourceDepartment of Preventive Medicine, Seoul National University College of Medicine, Seoul, Republic of Korea.
- Epidemiology and infection.Epidemiol Infect.2012 Jan 4:1-8. [Epub ahead of print]
- SUMMARYWe conducted an epidemic investigation to discover the route of transmission and the host factors of an outbreak of post-injection abscesses. Of the 2984 patients who visited a single clinic, 77 cases were identified and 208 age- and sex-matched controls were selected for analysis. Injected m
- PMID 22217328
- Leishmania major protein disulfide isomerase as a drug target : Enzymatic and functional characterization.
- Ben Khalaf N, De Muylder G, Louzir H, McKerrow J, Chenik M.SourceLaboratory of Immunopathology Vaccinology and Molecular Genetics (LIVGM), Institut Pasteur de Tunis, 13, Place Pasteur, 1002, Tunis-Belvédère, Tunisia.
- Parasitology research.Parasitol Res.2011 Dec 9. [Epub ahead of print]
- Leishmaniasis is a major health problem worldwide and tools available for their control are limited. Effective vaccines are still lacking, drugs are toxic and expensive, and parasites develop resistance to chemotherapy. In this context, new antimicrobials are urgently needed to control the disease i
- PMID 22160278
Japanese Journal
- HILIC-MS-MSによる血漿中アミノグリコシド系抗菌薬の簡易迅速分析法
- Enzymatic preparation of neomycin C from ribostamycin
- 12 アミノ配糖体抗生物質ネオマイシンCの全生合成の解明(口頭発表の部)
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