パロモマイシン
WordNet
- convert into a sulfate
- a salt or ester of sulphuric acid (同)sulphate
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/05/23 00:57:05」(JST)
[Wiki en表示]
Paromomycin
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Systematic (IUPAC) name |
(2 R,3 S,4 R,5 R,6 S)-5-amino-6-[(1 R,2 S,3 S,4 R,6 S)-
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
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Clinical data |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a601098 |
Pregnancy |
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Administration |
Oral, intramuscular |
Legal status |
Legal status |
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Pharmacokinetic data |
Bioavailability |
None |
Metabolism |
None |
Biological half-life |
? |
Excretion |
Fecal |
Identifiers |
CASRN |
1263-89-4 Y |
ATC code |
A07AA06 (WHO) |
PubChem |
CID 441375 |
DrugBank |
DB01421 Y |
ChemSpider |
390117 Y |
ChEBI |
CHEBI:7934 Y |
ChEMBL |
CHEMBL370143 N |
Chemical data |
Formula |
C23H47N5O18S |
Molar mass |
615.629 g/mol |
SMILES
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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
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Key:LJRDOKAZOAKLDU-UDXJMMFXSA-N Y
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NY (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]
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[4]
Medical uses
It is an antibiotic used to treat intestinal infections such as cryptosporidiosis[5] and amoebiasis,[6] and other diseases such as leishmaniasis.[7] 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.[8]
Mechanism
Paromomycin is a protein synthesis inhibitor in nonresistant cells by binding to 16S ribosomal RNA.[9] 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.[10]
References
- ^ Davidson RN, 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.
- ^ Marshall Sittig (1988). Pharmaceutical Manufacturing Encyclopedia (PDF) 1. Noyes Publications. p. 1166. ISBN 9780815511441.
- ^ a b Neal RA, Murphy AG, Olliaro P, Croft SL (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.
- ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 2014-04-22.
- ^ Sweetman S, ed. (2002). Martindale: The Complete Drug Reference (33rd ed.). London: Pharmaceutical Press. ISBN 978-0-85369-499-1.
- ^ "paromomycin" at Dorland's Medical Dictionary
- ^ Sundar S, Jha TK, Thakur CP, Sinha PK, Bhattacharya SK (2007). "Injectable paromomycin for visceral leishmaniasis in India". N. Engl. J. Med. 356 (25): 2571–81. doi:10.1056/NEJMoa066536. PMID 17582067.
- ^ Ben Salah A, Ben Messaoud N, Guedri E, Zaatour A, Ben Alaya N, Bettaieb J, Gharbi A, Belhadj Hamida N, et al. (2013). "Topical Paromomycin with or without Gentamicin for Cutaneous Leishmaniasis". N. Engl. J. Med. 368 (6): 524–32. doi:10.1056/NEJMoa1202657. PMID 23388004.
- ^ Vicens Q, Westhof E (2001). "Crystal Structure of Paromomycin Docked into the Eubacterial Ribosomal Decoding A Site". Structure 9 (8): 647–58. doi:10.1016/S0969-2126(01)00629-3. PMID 11587639.
- ^ "Paromomycin" (pdf). Toku-E. 2010-01-12. Retrieved 2012-06-11.
Antidiarrheals, intestinal anti-inflammatory and 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: Eluxadoline
- 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
- Crofelemer
- Octreotide
- Racecadotril
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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)
- thiazolide (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
- 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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UpToDate Contents
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English Journal
- Leishmaniasis: new insights from an old and neglected disease.
- Antinori S, Schifanella L, Corbellino M.SourceDepartment of Clinical Sciences L. Sacco, Section of Infectious Diseases and Immunopathology, Universita degli Studi di Milano, Via GB Grassi, 74, 20157, Milano, Italy, spinello.antinori@unimi.it.
- European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology.2011 May 1. [Epub ahead of print]
- Leishmaniases are a clinically heterogeneous group of diseases caused by protozoa of the genus Leishmania. There is growing evidence that the true incidence of the disease is underestimated, especially in hyperendemic regions. Moreover, climate changes together with the increasing movement of humans
- PMID 21533874
- Drug targeting to macrophages using paromomycin-loaded albumin microspheres for treatment of visceral leishmaniasis: an in vitro evaluation.
- Khan W, Kumar N.SourceDepartment of Pharmaceutics, National Institute of Pharmaceutical Education & Research (NIPER), Punjab, India.
- Journal of drug targeting.2011 May;19(4):239-50. Epub 2010 Jun 14.
- PMID 20545446
Japanese Journal
- Populations of <I>Lactobacillus acidophilus, Bifidobacterium spp</I>., and <I>Lactobacillus casei</I> in Commercial Fermented Milk Products
- Effect of Long-term Administration of Paromomycin Sulfate on the Level of Serum Albumin and γ-globulin in Human Cirrhosis
- Tokai journal of experimental and clinical medicine 8(4), 349-357, 1983-11
- NAID 110004691045
- 硫酸Paromomycinによる裂頭条虫,無鉤条虫の駆虫効果
★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
[★]
- 関
- H2SO4、inorganic sulfate、sulfate ester、sulfated、sulfation、sulfuric acid、sulfuric acid ester、sulphate、sulphuric acid
[★]
- 関
- sulfate、sulfation、sulphate
[★]
スルファ、サルファ