U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H45N5O14.H2O4S
Molecular Weight 713.707
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PAROMOMYCIN SULFATE

SMILES

OS(O)(=O)=O.[H][C@@]3(O[C@@H]1[C@@H](O)[C@H](N)C[C@H](N)[C@@]1([H])O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2N)O[C@H](CO)[C@@H](O[C@@]4([H])O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]4N)[C@H]3O

InChI

InChIKey=LJRDOKAZOAKLDU-UDXJMMFXSA-N
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

HIDE SMILES / InChI

Molecular Formula C23H45N5O14
Molecular Weight 615.6285
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 19 / 19
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O4S
Molecular Weight 98.078
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Paromomycin is a broad spectrum aminoglycoside antibiotic produced by by Streptomyces rimosus var. paromomycinus and used to treat intestinal infections such as cryptosporidiosis and amoebiasis, and other diseases such as leishmaniasis. Paromomycin is also used for the management of hepatic coma as adjunctive therapy. Paromomycin inhibits protein synthesis by binding to bacterial or protozoal 16S ribosomal RNA which causes defective polypeptide chains to be produced. Continuous production of defective proteins eventually leads to bacterial death. Gastrointestinal side effects include nausea, vomiting, diarrhea, and abdominal discomfort.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PAROMOMYCIN SULFATE
Secondary
PAROMOMYCIN SULFATE

Cmax

ValueDoseCo-administeredAnalytePopulation
331 ng/mL
150 mg single, topical
PAROMOMYCIN plasma
Homo sapiens
1000 ng/mL
150 mg 1 times / day multiple, topical
PAROMOMYCIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2180 ng × h/mL
150 mg single, topical
PAROMOMYCIN plasma
Homo sapiens
8575 ng × h/mL
150 mg 1 times / day multiple, topical
PAROMOMYCIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.04 h
150 mg single, topical
PAROMOMYCIN plasma
Homo sapiens
5.96 h
150 mg 1 times / day multiple, topical
PAROMOMYCIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
PAROMOMYCIN unknown
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Intestinal amebiasis: 25 to 35 mg/kg body weight daily, administered in three doses with meals, for five to ten days. Management of hepatic coma: 4 g daily in divided doses, given at regular intervals for five to six days.
Route of Administration: Oral
In Vitro Use Guide
1184 mg/L
Substance Class Chemical
Record UNII
845NU6GJPS
Record Status Validated (UNII)
Record Version