Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H45N5O14 |
| Molecular Weight | 615.6285 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O
InChI
InChIKey=UOZODPSAJZTQNH-LSWIJEOBSA-N
InChI=1S/C23H45N5O14/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/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8-,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
| Molecular Formula | C23H45N5O14 |
| Molecular Weight | 615.6285 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB01421Curator's Comment: Description was created based on several sources, including
http://www.drugs.com/cdi/paromomycin.html
http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20%28General%20Monographs-%20H%29/HUMATIN.html
Sources: http://www.drugbank.ca/drugs/DB01421
Curator's Comment: Description was created based on several sources, including
http://www.drugs.com/cdi/paromomycin.html
http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20%28General%20Monographs-%20H%29/HUMATIN.html
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363135 Sources: http://www.drugbank.ca/drugs/DB01421 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | PAROMOMYCIN SULFATE Approved UseParomomycin sulfate is indicated for intestinal amebiasis—acute and chronic (NOTE—It is not effective in extraintestinal amebiasis); management of hepatic coma—as adjunctive therapy. Launch Date2007 |
|||
| Secondary | PAROMOMYCIN SULFATE Approved UseParomomycin sulfate is indicated for intestinal amebiasis—acute and chronic (NOTE—It is not effective in extraintestinal amebiasis); management of hepatic coma—as adjunctive therapy. Launch Date2007 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
331 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689 |
150 mg single, topical dose: 150 mg route of administration: Topical experiment type: SINGLE co-administered: |
PAROMOMYCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1000 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689 |
150 mg 1 times / day multiple, topical dose: 150 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
PAROMOMYCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2180 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689 |
150 mg single, topical dose: 150 mg route of administration: Topical experiment type: SINGLE co-administered: |
PAROMOMYCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8575 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689 |
150 mg 1 times / day multiple, topical dose: 150 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
PAROMOMYCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.04 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689 |
150 mg single, topical dose: 150 mg route of administration: Topical experiment type: SINGLE co-administered: |
PAROMOMYCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5.96 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23877689 |
150 mg 1 times / day multiple, topical dose: 150 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
PAROMOMYCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
100% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28756612 |
PAROMOMYCIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 71.0 |
likely |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: abstract |
yes | |||
Page: abstract |
yes | yes (co-administration study) Comment: verapamil increased paromomycin exposure 1.5x Page: abstract |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Rubisco activase is required for optimal photosynthesis in the green alga Chlamydomonas reinhardtii in a low-CO(2) atmosphere. | 2003-12 |
|
| Markovian negentropies in bioinformatics. 1. A picture of footprints after the interaction of the HIV-1 Psi-RNA packaging region with drugs. | 2003-11-01 |
|
| Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step. | 2003-11 |
|
| Vibrational Markovian modelling of footprints after the interaction of antibiotics with the packaging region of HIV type 1. | 2003-11 |
|
| Efficacy of antigiardial drugs. | 2003-11 |
|
| [Liver abscess: a practical approach]. | 2003-10-08 |
|
| The molecular basis for A-site mutations conferring aminoglycoside resistance: relationship between ribosomal susceptibility and X-ray crystal structures. | 2003-10-06 |
|
| Sfp1 plays a key role in yeast ribosome biogenesis. | 2003-10 |
|
| Entamoeba histolytica: an update. | 2003-10 |
|
| Current treatment approaches to leishmaniasis. | 2003-10 |
|
| Genetic transformation of Indian bread (T. aestivum) and pasta (T. durum) wheat by particle bombardment of mature embryo-derived calli. | 2003-09-03 |
|
| Neomycin and paromomycin inhibit 30S ribosomal subunit assembly in Staphylococcus aureus. | 2003-09 |
|
| Multitarget affinity/specificity screening of natural products: finding and characterizing high-affinity ligands from complex mixtures by using high-performance mass spectrometry. | 2003-09 |
|
| Thermodynamics of aminoglycoside-rRNA recognition. | 2003-09 |
|
| Effect of antiretroviral protease inhibitors alone, and in combination with paromomycin, on the excystation, invasion and in vitro development of Cryptosporidium parvum. | 2003-09 |
|
| Evaluation of rye (Secale cereale L.) inbred lines and their crosses for tissue culture response and stable genetic transformation of homozygous rye inbred line L22 by biolistic gene transfer. | 2003-08 |
|
| Design and synthesis of paromomycin-related heterocycle-substituted aminoglycoside mimetics based on a mass spectrometry RNA-binding assay. | 2003-07-28 |
|
| Various effects of paromomycin on tmRNA-directed trans-translation. | 2003-07-25 |
|
| Selective enumeration of Lactobacillus delbrueckii ssp. bulgaricus, Streptococcus thermophilus, Lactobacillus acidophilus, bifidobacteria, Lactobacillus casei, Lactobacillus rhamnosus, and propionibacteria. | 2003-07 |
|
| Production of Hevea brasiliensis transgenic embryogenic callus lines by Agrobacterium tumefaciens: roles of calcium. | 2003-07 |
|
| Treatment of cutaneous leishmaniasis by photodynamic therapy. | 2003-06 |
|
| [Cutaneous leishmaniasis]. | 2003-06 |
|
| Effect of neomycin B on rotavirus plus- and minus-strand RNA synthesis. | 2003-06 |
|
| Aminoglycoside complexation with a DNA.RNA hybrid duplex: the thermodynamics of recognition and inhibition of RNA processing enzymes. | 2003-05-28 |
|
| Insights into the decoding mechanism from recent ribosome structures. | 2003-05 |
|
| Comparative study of the prophylactic and therapeutic effects of paromomycin, recombinant IL-12 alone or in combination against Cryptosporidium parvum infection in immunosuppressed mice. | 2003-04 |
|
| Eradication of Cryptosporidium in four children with acute lymphoblastic leukemia. | 2003-04 |
|
| The complex of a designer antibiotic with a model aminoacyl site of the 30S ribosomal subunit revealed by X-ray crystallography. | 2003-03-26 |
|
| Coupling of drug protonation to the specific binding of aminoglycosides to the A site of 16 S rRNA: elucidation of the number of drug amino groups involved and their identities. | 2003-03-07 |
|
| Long-lasting anticryptosporidial activity of nitazoxanide in an immunosuppressed rat model. | 2003-03 |
|
| Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide. | 2003-02-28 |
|
| A dispensable yeast ribosomal protein optimizes peptidyltransferase activity and affects translocation. | 2003-01-31 |
|
| HIV-1 RNA dimerization initiation site is structurally similar to the ribosomal A site and binds aminoglycoside antibiotics. | 2003-01-24 |
|
| Treatment of cutaneous leishmaniasis with either topical paromomycin or intralesional meglumine antimoniate. | 2003-01 |
|
| Comparison of X-ray crystal structure of the 30S subunit-antibiotic complex with NMR structure of decoding site oligonucleotide-paromomycin complex. | 2003-01 |
|
| Various effects of paromomycin on tmRNA-mediated trans-translation. | 2003 |
|
| Treatment of cutaneous leishmaniasis with aminosidine (paromomycin) ointment: double-blind, randomized trial in the Islamic Republic of Iran. | 2003 |
|
| Evaluation of in vitro and in vivo activity of benzindazole-4,9-quinones against Cryptosporidium parvum. | 2002-12 |
|
| Selection of tRNA by the ribosome requires a transition from an open to a closed form. | 2002-11-27 |
|
| Controlling the onset of natural cryptosporidiosis in calves with paromomycin sulphate. | 2002-11-16 |
|
| Detecting ligand binding to a small RNA target via saturation transfer difference NMR experiments in D(2)O and H(2)O. | 2002-11-13 |
|
| Footprinting and circular dichroism studies on paromomycin binding to the packaging region of human immunodeficiency virus type-1. | 2002-11 |
|
| Treatment of asymptomatic intestinal Entamoeba histolytica infection. | 2002-10-24 |
|
| Aminoglycosides suppress tRNA processing in human epidermal keratinocytes in vitro. | 2002-10-22 |
|
| The protein synthesis inhibitors, oxazolidinones and chloramphenicol, cause extensive translational inaccuracy in vivo. | 2002-09-13 |
|
| Identification of a role for actin in translational fidelity in yeast. | 2002-09 |
|
| Stereospecificity of aminoglycoside-ribosomal interactions. | 2002-08-20 |
|
| Fluconazole for the treatment of cutaneous leishmaniasis. | 2002-08-01 |
|
| "Chemotherapeutic approaches to protozoa: Giardia, Trichomonas and Entamoeba-current level of knowledge and outlook". | 2002-06 |
|
| [Considerations and results of the use of paramomycin in the prevention of infectious complications in colorectal surgery]. | 2002-04 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=22494bde-a53e-4b3c-a89b-0ccda341f28f
Curator's Comment: Additional resource:
http://www.rxlist.com/paromomycin-sulfate-drug.htm
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
Curator's Comment: Paromomycin inhibited the growth of Cryptosporidium parvum in Madin-Darby canine kidney (MDCK) cells in a dose-dependent manner. The EC50s of paromomycin against C. parvum growth in MDCK cells was 1184 mg/L.
Paromomycin at 25, 50 and 100 μg/ml, inhibited the growth of Leishmania major amastigotes by 34.5%, 61.2%, 74.9% and 85.4%, 89.9%, 95.7% on the 2nd and the 4th day of treatment in culture, respectively (http://www.sciencedirect.com/science/article/pii/S0014489406003262).
1184 mg/L
| Substance Class |
Chemical
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61JJC8N5ZK
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WHO-VATC |
QA07AA06
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WHO-ATC |
A07AA06
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WHO-ESSENTIAL MEDICINES LIST |
6.5.2
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NCI_THESAURUS |
C2363
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FDA ORPHAN DRUG |
464314
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NDF-RT |
N0000175485
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DB01421
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DTXSID8023424
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SUB09630MIG
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61JJC8N5ZK
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Paromomycin
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165580
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7934
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C61878
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PAROMOMYCIN
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TARGET ORGANISM->INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
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TARGET ORGANISM->INHIBITOR |
Approved by the FDA for the treatment of amoebiasis
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SALT/SOLVATE -> PARENT |
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TARGET ORGANISM->INHIBITOR |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
effective against a wide range of bacteria and protozoa and is licensed in Europe for parenteral therapy of bacterial infections that are thought to respond to aminoglycosides.
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