paromomycin

Also known as Paramicina, Aminosidine, Humatin, Neomycin e, Paucimycin, Aminosidin, R-400, (1R,2R,3S,4R,6S)-4,6-Diamino-2-{[3-O-(2,6-diamino-2,6-dideoxy-beta-L-idopyranosyl)-beta-D-ribofuranosyl]oxy}-3-hydroxycyclohexyl 2-amino-2-deoxy-alpha-D-glucopyranoside

Key facts

Drug.CAS_number: 7542-37-2
Drug.CAS_number2: 1263-89-4
Drug.type: Antibiotic ? should be class=, but not a parameter Nov 2016-->
Drug.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
Drug.image: Paromomycin structure.svg
Drug.image_class: skin-invert-image
Drug.width: 300
Drug.image2: Paromomycin ball-and-stick (cropped).png
Drug.image_class2: bg-transparent
Drug.tradename: Catenulin, Aminosidine, Humatin, others
Drug.MedlinePlus: a601098
Drug.DailyMedID: Paromomycin
Drug.pregnancy_US: N
Drug.pregnancy_category: C
Drug.legal_US: Rx-only
Drug.routes_of_administration: By mouth, intramuscular, topical
Drug.bioavailability: Poorly absorbed in the GI tract
Drug.metabolism: Not available

via Wikipedia infobox

Chemical data

Formula: C23H45N5O14
Molecular weight: 615.6 g/mol
IUPAC name: (2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(2R,3S,4R,5S)-5-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol
SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N
InChIKey: UOZODPSAJZTQNH-LSWIJEOBSA-N
XLogP: -8.7
Polar surface area: 347 Å²
H-bond donors: 13
H-bond acceptors: 19
Formal charge: 0

via PubChem

Research

2,159 papers

Paromomycin.Transactions of the Royal Society of Tropical Medicine and Hygiene · 2009
[Paromomycin preparations].The Japanese journal of antibiotics · 1983
Paromomycin in the treatment of leishmaniasis.Expert opinion on investigational drugs · 2008
Targeted modifications of neomycin and paromomycin: Towards resistance-free antibiotics?Bioorganic chemistry · 2022
Transmission potential of paromomycin-resistant Leishmania infantum and Leishmania donovani.The Journal of antimicrobial chemotherapy · 2020

via PubMed

Wikidata facts

Mass: 615.296

Show 6 more facts

chemical formula: C₂₃H₄₅N₅O₁₄
isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)CN)O)O)N)O)O)N
canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N
World Health Organisation international non-proprietary name: paromomycin
defined daily dose: 3
Commons category: Paromomycin

Sources (5)

via Wikidata · CC0

~6 min read

Article

12 sections

Contents

Medical uses
Pregnancy and breastfeeding
HIV/AIDS
Adverse effects
Interactions
Mechanism
Pharmacokinetics
Absorption
Elimination
History
References
External links

Paromomycin is an antimicrobial used to treat a number of parasitic infections including amebiasis, giardiasis, leishmaniasis, and tapeworm infection. It is a first-line treatment for amebiasis or giardiasis during pregnancy. Otherwise, it is generally a second line treatment option. It is taken by mouth, applied to the skin, or by injection into a muscle.

Common side effects when taken by mouth include loss of appetite, vomiting, abdominal pain, and diarrhea. When applied to the skin side effects include itchiness, redness, and blisters. When given by injection there may be fever, liver problems, or hearing loss. Use during breastfeeding appears to be safe. Paromomycin is in the aminoglycoside family of medications and causes microbe death by stopping the creation of bacterial proteins.