Paromomycin

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 category	US: N (Not classified yet)
Legal status	US: ℞-only
Routes of administration	Oral, intramuscular
Pharmacokinetic data
Bioavailability	None
Metabolism	None
Biological half-life	?
Excretion	Fecal
Identifiers
CAS Number	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
Molecular 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
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
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Paromomycin is an aminoglycoside antibiotic, first isolated from Streptomyces krestomuceticus in the 1950s. It was discovered by Parke Davis now Pfizer and introduced as Humatin in 1960. It is also called monomycin and aminosidine;

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.

Medical uses

It is an antibiotic used to treat intestinal infections such as cryptosporidiosis and amoebiasis, and other diseases such as leishmaniasis. 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.

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.

Mechanism

Paromomycin is a protein synthesis inhibitor in nonresistant cells by binding to 16S ribosomal RNA. 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.