Paromomycin sulfate

Paromomycin

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
ChEMBL	CHEMBL370143 N
Chemical data
Formula	C23H47N5O18S
Mol. mass	615.629 g/mol
SMILES	eMolecules & PubChem
InChI 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
N(what is this?)  sulfate (verify)

Paromomycin (brand name Humatin) is an aminoglycoside antibiotic, first isolated from Streptomyces krestomuceticus in the 1950s.^[1] It is also called monomycin and aminosidine^[2];

Uses

It is an antibiotic designed to fight intestinal infections such as cryptosporidiosis,^[3] amoebiasis,^[4] and leishmaniasis.^[5]

The route of administration is intramuscular injection and capsule.

Mechanism

Paromomycin inhibits protein synthesis by binding to 16S ribosomal RNA.^[6]

History and availability

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.^[2]

It was developed as a therapeutic against visceral leishmaniasis by the Institute for OneWorld Health. Paromomycin was granted orphan drug status in 2005^[7] and was approved by the Drug Controller General of India in September 2006 for treatment of visceral leishmaniasis.^[8]

As of February 5th, 2008, King Pharmaceuticals is discontinuing the sale of Humatin. Paromomycin continues to be available in the United States from another manufacturer.^[9]

References

1. ^ 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. 
2. ^ ^{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. 
3. ^ Sweetman S.C. (Editor). (2002). Martindale: the complete drug reference. 33rd ed. London: Pharmaceutical Press
4. ^ "paromomycin" at Dorland's Medical Dictionary
5. ^ 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. http://content.nejm.org/cgi/pmidlookup?view=short&pmid=17582067&promo=ONFLNS19. 
6. ^ 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. http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6VSR-43VBX2W-C&_user=10&_coverDate=08%2F31%2F2001&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=1b1e19d11ca34e14eca1603c2be009d5. Retrieved 2007-02-10. 
7. ^ "Institute for OneWorld Health Drug Receives “Orphan” Designation From U.S. and European Regulatory Agencies" (Press release). Institute for OneWorld Health. 23 May 2005. http://www.oneworldhealth.org/media/details.php?prID=115. Retrieved 2007-02-10. 
8. ^ "New cure for deadly visceral leishmaniasis (kala-azar) approved by government of India" (Press release). Institute for OneWorld Health. 8 September 2006. http://www.oneworldhealth.org/media/details.php?prID=154. Retrieved 2007-02-10. 
9. ^ Food and Drug Administration (2010). "Drugs to be Discontinued". http://www.fda.gov/Drugs/DrugSafety/DrugShortages/ucm050794.htm.