パロモマイシン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/01/14 17:12:58」(JST)
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Paromomycin
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Systematic (IUPAC) name |
(2R,3S,4R,5R,6S)-5-amino-6-[(1R,2S,3S,4R,6S)-
4,6-diamino-2-[(2S,3R,4R,5R)-4-[(2R,3R,4R,5R,6S)-
3-amino-6-(aminomethyl)-4,5-dihydroxy-oxan-2-yl]
oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-
3-hydroxy-cyclohexyl]oxy-2-(hydroxymethyl)oxane-3,4-diol |
Clinical data |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a601098 |
Pregnancy cat. |
B (US) |
Legal status |
Rx only U.S. |
Routes |
Oral, intramuscular |
Pharmacokinetic data |
Bioavailability |
None |
Metabolism |
None |
Half-life |
? |
Excretion |
Fecal |
Identifiers |
CAS number |
1263-89-4 Y |
ATC code |
A07AA06 |
PubChem |
CID 441375 |
DrugBank |
DB01421 |
ChemSpider |
390117 Y |
ChEBI |
CHEBI:7934 Y |
ChEMBL |
CHEMBL370143 N |
Chemical data |
Formula |
C23H47N5O18S |
Mol. mass |
615.629 g/mol |
SMILES
- O=S(=O)(O)O.O([C@H]3[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@H]1O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]1N)[C@H]2O)[C@@H](O)[C@H](N)C[C@@H]3N)[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4N)CO
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InChI
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InChI=1S/C23H45N5O14.H2O4S/c24-2-7-13(32)15(34)10(27)21(37-7)41-19-9(4-30)39-23(17(19)36)42-20-12(31)5(25)1-6(26)18(20)40-22-11(28)16(35)14(33)8(3-29)38-22;1-5(2,3)4/h5-23,29-36H,1-4,24-28H2;(H2,1,2,3,4)/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;/m1./s1 Y
Key:LJRDOKAZOAKLDU-UDXJMMFXSA-N Y
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N (what is this?) (verify) |
Paromomycin is an aminoglycoside antibiotic, first isolated from Streptomyces krestomuceticus in the 1950s.[1] It was discovered by Parke Davis now Pfizer and introduced as Humatin in 1960.[2] It is also called monomycin and aminosidine;[3]
Uses[edit]
It is an antibiotic used to treat intestinal infections such as cryptosporidiosis [4] and amoebiasis,[5] and other diseases like leishmaniasis.[6] Paromomycin was demonstrated to be effective against cutaneous leishmaniasis in clinical studies in the USSR in the 1960s, and in trials with visceral leishmaniasis in the early 1990s.[3]
The route of administration is intramuscular injection and capsule.
Paromomycin topical cream with or without gentamicin is an effective treatment for ulcerative cutaneous leishmaniasis, according to the results of a phase 3, randomized, double-blind, parallel group–controlled trial.[7]
Mechanism[edit]
Paromomycin is a protein synthesis inhibitor in non-resistant cells by binding to 16S ribosomal RNA.[8] This broad spectrum antibiotic soluble in water, is very similar in action to Neomycin. Antimicrobial activity of Paromomycin against Escherichia coli and Staphylococcus aureus has been shown.[9]
References[edit]
- ^ Davidson R.N., den Boer M., Ritmeijer K. (2008). "Paromomycin". Transactions of the Royal Society of Tropical Medicine and Hygiene 103 (7): 653–60. doi:10.1016/j.trstmh.2008.09.008. PMID 18947845.
- ^ Page 1166. http://books.google.co.in/books?id=XCsJgUnclbcC&pg=PA1257&dq=Pharmaceutical+Manufacturing+Encyclopedia,+Volume+2&hl=en&sa=X&ei=9V7iT8mqJoOIrAfe4P2zAw&ved=0CDoQ6AEwAA#v=onepage&q=Pharmaceutical%20Manufacturing%20Encyclopedia%2C%20Volume%202&f=false
- ^ a b Neal R.A. et al. (1994). "Aminosidine ointments for the treatment of experimental cutaneous leishmaniasis". Transactions of the Royal Society of Tropical Medicine and Hygiene 88 (2): 223–5. doi:10.1016/0035-9203(94)90307-7. PMID 8036682.
- ^ Sweetman S.C. (Editor). (2002). Martindale: the complete drug reference. 33rd ed. London: Pharmaceutical Press
- ^ "paromomycin" at Dorland's Medical Dictionary
- ^ Sundar S, Jha TK, Thakur CP, Sinha PK, Bhattacharya SK (June 2007). "Injectable paromomycin for visceral leishmaniasis in India". N. Engl. J. Med. 356 (25): 2571–81. doi:10.1056/NEJMoa066536. PMID 17582067.
- ^ N Engl J Med. 2013;368:524-532
- ^ Vicens, Quentin; Eric Westhof (August 2001). "Crystal Structure of Paromomycin Docked into the Eubacterial Ribosomal Decoding A Site". Structure 9 (8): 647–658. doi:10.1016/S0969-2126(01)00629-3. PMID 11587639. Retrieved 2007-02-10.
- ^ "Paromomycin" (pdf). Toku-E. 2010-01-12. Retrieved 2012-06-11.
Antidiarrheals, intestinal anti-inflammatory/anti-infective agents (A07)
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Rehydration |
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Intestinal anti-infectives |
- Antibiotics
- Amphotericin B
- Colistin
- Fidaxomicin
- Kanamycin
- Natamycin
- Neomycin
- Nystatin
- Paromomycin
- Polymyxin B
- Rifaximin
- Streptomycin
- Vancomycin
- Sulfonamides
- Phthalylsulfathiazole
- Succinylsulfathiazole
- Sulfaguanidine
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Intestinal adsorbents |
- Charcoal
- Bismuth
- Pectin
- Kaolin
- Crospovidone
- Attapulgite
- Diosmectite
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Antipropulsives (opioids) |
- Opium tincture (laudanum)
- Codeine
- Morphine
- Camphorated opium tincture (paregoric)
- crosses BBB: Diphenoxylate (Diphenoxylate/atropine)
- Difenoxin
- does not cross BBB: Loperamide
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Intestinal anti-inflammatory agents |
- corticosteroids acting locally
- Prednisolone
- Hydrocortisone
- Prednisone
- Betamethasone
- Tixocortol
- Budesonide
- Beclometasone
- antiallergic agents, excluding corticosteroids
- aminosalicylic acid and similar agents
- Sulfasalazine
- Mesalazine
- Olsalazine
- Balsalazide
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Antidiarrheal micro-organisms |
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Other antidiarrheals |
- Albumin tannate
- Ceratonia
- Octreotide
- Racecadotril
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anat (t, g, p)/phys/devp/enzy
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noco/cong/tumr, sysi/epon
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proc, drug (A2A/2B/3/4/5/6/7/14/16), blte
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Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)
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Entamoeba |
Tissue amebicides
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Nitroimidazole derivatives
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- Metronidazole#
- Tinidazole
- Ornidazole
- Nimorazole
- Secnidazole
- Azanidazole
- Propenidazole
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Other
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- isoquinoline (Emetine/Dehydroemetine)
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Luminal amebicides
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Hydroxyquinoline derivatives
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- Cl (Chlorquinaldol)
- Br (Tilbroquinol
- Broxyquinoline)
- I (Diiodohydroxyquinoline)
- I,Cl (Clioquinol)
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Dichloroacetamide derivatives
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- Diloxanide#
- Clefamide
- Etofamide
- Teclozan
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Aminoglycoside
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Other/ungrouped
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- arsenic (Arsthinol
- Difetarsone
- Glycobiarsol)
- phenanthroline (Phanquinone)
- aminoacridine (Mepacrine)
- quinazoline (Trimetrexate)
- thiazole (Tenonitrozole)
- sesquiterpene (Fumagillin)
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Acanthamoeba |
- Propamidine
- Chlorhexidine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Antiparasitics – antiprotozoal agents – Excavata antiparasitics (P01)
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Discicristata |
Trypanosomiasis
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- African trypanosomiasis: ornithine (Eflornithine#)
- arsenical (Melarsoprol#)
- benzamidine (Pentamidine#)
- naphthalenesulfonate (Suramin#)
Chagas disease: nitroimidazole (Benznidazole#)
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Leishmaniasis
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- macrolide (Amphotericin B#)
Pentavalent antimonials (Meglumine antimoniate#, Sodium stibogluconate)
- benzamidine (Pentamidine#)
- phosphorylcholine (Miltefosine)
- neomycin (Paromomycin)
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PAM
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- macrolide (Amphotericin B)
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Trichozoa |
Giardiasis
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- nitroimidazole (Metronidazole#, Tinidazole)
- benzimidazole (Albendazole)
- thiazole (Nitazoxanide)
- nitrofuran (Furazolidone)
- aminoacridine (Quinacrine)
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Trichomoniasis
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- nitroimidazole (Carnidazole, Metronidazole#, Tinidazole)
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Dientamoebiasis
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- nitroimidazole (Metronidazole
- Secnidazole)
- oxyquinoline (Iodoquinol)
- tetracycline (Doxycycline)
- neomycin (Paromomycin)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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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
- 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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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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UpToDate Contents
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English Journal
- Cryptosporidiosis: A rare and severe infection in a pediatric renal transplant recipient.
- Acikgoz Y, Ozkaya O, Bek K, Genc G, Sensoy SG, Hokelek M.SourceDepartments of Pediatric Nephrology Pediatric Infection Microbiology, Faculty of Medicine, Ondokuz Mayis University, Kurupelit, Samsun, Turkey.
- Pediatric transplantation.Pediatr Transplant.2012 Jun;16(4):E115-9. doi: 10.1111/j.1399-3046.2011.01473.x. Epub 2011 Feb 15.
- Acikgoz Y, Ozkaya O, Bek K, Genc G, Sensoy SG, Hokelek M. Cryptosporidiosis: A rare and severe infection in a pediatric renal transplant recipient. Abstract: Cryptosporidium is an intracellular protozoan parasite that causes gastroenteritis in human. In immunocompromised individuals, cryptosporid
- PMID 21320246
- Fulminant amoebic colitis mimicking intestinal vasculitis in a patient with systemic lupus erythematosus.
- Lee J, Jung HS, Nam HC, Kwok SK, Ju J, Park KS, Kim HY, Park SH.SourceDivision of Rheumatology, Department of Internal Medicine, School of Medicine, The Catholic University of Korea, South Korea.
- Lupus.Lupus.2012 May 8. [Epub ahead of print]
- Colitis in patients with systemic lupus erythematosus (SLE) is quite rare. It can be caused by intestinal vasculitis, mesenteric vascular thrombosis, concomitant inflammatory bowel disease or infectious colitis. It is important to make an accurate and early diagnosis as the treatments for each condi
- PMID 22570337
Japanese Journal
- Determination of paromomycin residues in turkey tissues by liquid chromatography/mass spectrometry
- RONA K.,KLAUSZ G.,KELLER E.,SZAKAY M.,LACZAY P.,SHEM-TOV M.,SZEKELY-KORMOCZY P.
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 877(30), 3792-3798, 2009-11-15
- NAID 10028028805
- Agrobacterium-mediated genetic transformation of radish (Raphanus sativus L.)
- CHO Mi Ae,MIN Sung Ran,KO Suk Min,LIU Jang Ryol,CHOI Pil Son
- Plant biotechnology 25(2), 205-208, 2008-03-01
- … Jin Ju Dae Pyong), hypocotyl explants were cultured on Murashige and Skoog medium containing 4 mg l−1 AgNO3, 5 mg l−1 acetosyringone, 4 mg l−1 6-benzyladenine, and 3 mg l−1 α-naphthaleneacetic acid in addition to either 10 mg l−1 hygromycin or 100 mg l−1 paromomycin after co-cultivation with disarmed Agrobacterium tumefaciens harboring a plant expression binary vector. …
- NAID 10021913172
Related Links
- Paromomycin official prescribing information for healthcare professionals. Includes: indications, dosage, adverse reactions, pharmacology and more. ... Precautions Prescribing Paromomycin Sulfate Capsules in the absence of a ...
- Paromomycin is an aminoglycoside that is active against Gram-negative and many Gram-positive bacteria as well as some protozoa and cestodes. It is out of use as ... 3. Antibacterial and antileishmanial action The antibacterial ...
Related Pictures
★リンクテーブル★
[★]
- 英
- paromomycin, PRM
- 同
- ヒドロキシマイシン hydroxymycin
- 化
- 硫酸パロモマイシン paromomycin sulfate
- 商
- アミノサイジン、アメパロモ、ヒドロキシマイシン
- 関
- 抗菌薬
分類