Paromomycin

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Paromomycin
Paromomycin structure.svg
Paromomycin ball-and-stick.png
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
category
  • US: N (Not classified yet)
Legal status
Routes of
administration
Oral, intramuscular
Pharmacokinetic data
Bioavailability None
Metabolism None
Biological half-life ?
Excretion Fecal
Identifiers
CAS Number 1263-89-4 YesY
ATC code A07AA06
PubChem CID 441375
DrugBank DB01421 YesY
ChemSpider 390117 YesY
ChEBI CHEBI:7934 YesY
ChEMBL CHEMBL370143 N
Chemical data
Formula C23H47N5O18S
Molar mass 615.629 g/mol
 NYesY (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[edit]

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[edit]

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[edit]

  1. ^ 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. 
  2. ^ Marshall Sittig (1988). Pharmaceutical Manufacturing Encyclopedia (PDF) 1. Noyes Publications. p. 1166. ISBN 9780815511441. 
  3. ^ 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. 
  4. ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 2014-04-22. 
  5. ^ Sweetman S, ed. (2002). Martindale: The Complete Drug Reference (33rd ed.). London: Pharmaceutical Press. ISBN 978-0-85369-499-1. 
  6. ^ "paromomycin" at Dorland's Medical Dictionary
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ "Paromomycin" (pdf). Toku-E. 2010-01-12. Retrieved 2012-06-11.