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 cat. ? (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 YesY
ATC code A07AA06
PubChem CID 441375
DrugBank DB01421
ChemSpider 390117 YesY
ChEBI CHEBI:7934 YesY
ChEMBL CHEMBL370143 N
Chemical data
Formula C23H47N5O18S 
Mol. mass 615.629 g/mol
 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]

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 like 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 non-resistant 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 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". 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.