Paromomycin
Identification
- Name
- Paromomycin
- Accession Number
- DB01421
- Description
An oligosaccharide antibiotic produced by various streptomyces. [PubChem]
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Paromomycin (DB01421)
- Weight
- Average: 615.6285
Monoisotopic: 615.296301173 - Chemical Formula
- C23H45N5O14
- Synonyms
- (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
- Aminosidin
- Aminosidine
- Catenulin
- Crestomycin
- Estomycin
- Hydroxymycin
- Monomycin A
- Neomycin E
- Paromomicina
- Paromomycin
- Paromomycin I
- Paromomycine
- Paromomycinum
- Paucimycin
- Paucimycinum
- Zygomycin A1
- External IDs
- ANTIBIOTIC 503-3
- ANTIBIOTIC SF 767B
- R 400
- R-400
Pharmacology
- Indication
For the treatment of acute and chronic intestinal amebiasis (it is not effective in extraintestinal amebiasis). Also for the management of hepatic coma as adjunctive therapy.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Paromomycin is a broad spectrum aminoglycoside antibiotic produced by Streptomyces rimosus var. paromomycinus. The in vitro and in vivo antibacterial action of paromomycin closely parallels that of neomycin.
- Mechanism of action
Paromomycin inhibits protein synthesis by binding to 16S ribosomal RNA. Bacterial proteins are synthesized by ribosomal RNA complexes which are composed of 2 subunits, a large subunit (50s) and small (30s) subunit, which forms a 70s ribosomal subunit. tRNA binds to the top of this ribosomal structure. Paramomycin binds to the A site, which causes defective polypeptide chains to be produced. Continuous production of defective proteins eventually leads to bacterial death.
Target Actions Organism A30S ribosomal protein S10 inhibitorThermus thermophilus (strain HB8 / ATCC 27634 / DSM 579) A16S ribosomal RNA inhibitorEnteric bacteria and other eubacteria - Absorption
Poorly absorbed after oral administration, with almost 100% of the drug recoverable in the stool.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
Pathway Category Paromomycin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Paromomycin may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Paromomycin may decrease the excretion rate of Acarbose which could result in a higher serum level. Aceclofenac The risk or severity of nephrotoxicity can be increased when Paromomycin is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Paromomycin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Paromomycin is combined with Acenocoumarol. Acetaminophen Paromomycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylcholine The therapeutic efficacy of Acetylcholine can be decreased when used in combination with Paromomycin. Acetyldigitoxin The risk or severity of adverse effects can be increased when Paromomycin is combined with Acetyldigitoxin. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Paromomycin. Aclidinium Paromomycin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with food.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Product Ingredients
Ingredient UNII CAS InChI Key Paromomycin sulfate 845NU6GJPS 1263-89-4 LJRDOKAZOAKLDU-UDXJMMFXSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataHumatin Capsule 250 mg/1 Oral Physicians Total Care, Inc. 1994-03-11 2011-05-31 US 
Humatin Cap 250mg Capsule Oral Erfa Canada 2012 Inc 1994-12-31 Not applicable Canada 
Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataHumatin Capsule 250 mg/1 Oral Monarch Pharmaceuticals, Inc. 1981-01-03 2008-11-11 US Paromomycin Sulfate Capsule 250 mg/1 Oral Central Texas Community Health Centers 2009-10-22 Not applicable US Paromomycin Sulfate Capsule, gelatin coated 250 mg/1 Oral X Gen Pharmaceuticals, Inc. 2007-12-17 2009-05-01 US Paromomycin Sulfate Capsule 250 mg/1 Oral Sun Pharmaceutical Industries, Inc. 1997-06-30 2017-06-30 US Paromomycin Sulfate Capsule 250 mg/1 Oral Department Of State Health Services, Pharmacy Branch 2009-10-22 Not applicable US Paromomycin Sulfate Capsule 250 mg/1 Oral Heritage 2009-10-22 Not applicable US Paromomycin Sulfate Capsule 250 mg/1 Oral Physicians Total Care, Inc. 1997-10-01 2010-06-30 US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Humatin Paromomycin sulfate (250 mg/1) Capsule Oral Physicians Total Care, Inc. 1994-03-11 2011-05-31 US
Categories
- ATC Codes
- A07AA06 — Paromomycin
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Alimentary Tract and Metabolism
- Amebicides
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antidiarrheals, Intestinal Antiinflammatory/antiinfective Agents
- Antiparasitic Agents
- Antiprotozoals
- Carbohydrates
- Drugs that are Mainly Renally Excreted
- Glycosides
- Intestinal Antiinfectives
- Nephrotoxic agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- 4,5-disubstituted 2-deoxystreptamines
- Alternative Parents
- O-glycosyl compounds / Disaccharides / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Tetrahydrofurans / 1,2-aminoalcohols / Oxacyclic compounds / Acetals show 4 more
- Substituents
- 1,2-aminoalcohol / 4,5-disubstituted 2-deoxystreptamine / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives / Cyclohexanol show 16 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- aminoglycoside antibiotic, amino cyclitol glycoside (CHEBI:7934)
Chemical Identifiers
- UNII
- 61JJC8N5ZK
- CAS number
- 7542-37-2
- InChI Key
- UOZODPSAJZTQNH-LSWIJEOBSA-N
- InChI
- 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
- 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]oxy}oxane-3,4-diol
- SMILES
- NC[[email protected]@H]1O[[email protected]](O[[email protected]@H]2[[email protected]@H](CO)O[[email protected]@H](O[[email protected]@H]3[[email protected]@H](O)[[email protected]](N)C[[email protected]](N)[[email protected]]3O[[email protected]]3O[[email protected]](CO)[[email protected]@H](O)[[email protected]](O)[[email protected]]3N)[[email protected]@H]2O)[[email protected]](N)[[email protected]@H](O)[[email protected]@H]1O
References
- Synthesis Reference
Federico Arcamone, Giuseppe Cassinelli, "Paromomycin derivatives and process for the preparation thereof." U.S. Patent US4021601, issued October, 1967.
US4021601- General References
- Vicens Q, Westhof E: Crystal structure of paromomycin docked into the eubacterial ribosomal decoding A site. Structure. 2001 Aug;9(8):647-58. [PubMed:11587639]
- External Links
- Human Metabolome Database
- HMDB0015490
- KEGG Compound
- C00832
- PubChem Compound
- 165580
- PubChem Substance
- 46505391
- ChemSpider
- 145115
- BindingDB
- 50240054
- 7934
- ChEBI
- 7934
- ChEMBL
- CHEMBL370143
- ZINC
- ZINC000060183170
- Therapeutic Targets Database
- DAP000407
- PharmGKB
- PA164784023
- PDBe Ligand
- PAR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Paromomycin_sulfate
- AHFS Codes
- 08:30.04 — Amebicides
- PDB Entries
- 1fjg / 1fyp / 1ibk / 1ibl / 1j7t / 1n32 / 1n33 / 1vvj / 1xmo / 1xmq … show 79 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Visceral Leishmaniasis 1 3 Active Not Recruiting Treatment Visceral Leishmaniasis 1 3 Completed Treatment Leishmaniasis, Cutaneous 2 3 Completed Treatment Visceral Leishmaniasis 6 2 Completed Treatment Cryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections 1 2 Completed Treatment Leishmaniasis, Cutaneous 3 2 Recruiting Treatment PKDL - Post-Kala-Azar Dermal Leishmanioid 1 2 Terminated Treatment Leishmaniasis, Cutaneous 3 2, 3 Completed Treatment Leishmania Braziliensis Complex / Leishmaniasis, American / Leishmaniasis, Cutaneous / Leishmaniasis; American, Cutaneous 1 2, 3 Recruiting Treatment Cutaneous Leishmaniasis, American 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Caraco Pharmaceutical Labs
- Heritage Pharmaceuticals
- Kaiser Foundation Hospital
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Syrup Oral Tablet, film coated Oral Injection 0.5 g Capsule Oral 250 mg/1 Capsule Oral 250 MG Syrup Oral 2.5 g/100ml Syrup Oral 25 MG/ML Powder, for solution Oral 1 g Capsule Oral Capsule, gelatin coated Oral 250 mg/1 - Prices
Unit description Cost Unit Paromomycin 250 mg capsule 5.67USD capsule Humatin 250 mg capsule 2.67USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 79.7 mg/mL ALOGPS logP -2.9 ALOGPS logP -8.3 ChemAxon logS -0.89 ALOGPS pKa (Strongest Acidic) 12.23 ChemAxon pKa (Strongest Basic) 9.94 ChemAxon Physiological Charge 5 ChemAxon Hydrogen Acceptor Count 19 ChemAxon Hydrogen Donor Count 13 ChemAxon Polar Surface Area 347.32 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 134.24 m3·mol-1 ChemAxon Polarizability 60.4 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8617 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.7502 P-glycoprotein substrate Non-substrate 0.5164 P-glycoprotein inhibitor I Non-inhibitor 0.8023 P-glycoprotein inhibitor II Non-inhibitor 0.8764 Renal organic cation transporter Non-inhibitor 0.7886 CYP450 2C9 substrate Non-substrate 0.8231 CYP450 2D6 substrate Non-substrate 0.8041 CYP450 3A4 substrate Non-substrate 0.6473 CYP450 1A2 substrate Non-inhibitor 0.9157 CYP450 2C9 inhibitor Non-inhibitor 0.9147 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9034 CYP450 3A4 inhibitor Non-inhibitor 0.9471 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8446 Ames test Non AMES toxic 0.6934 Carcinogenicity Non-carcinogens 0.9505 Biodegradation Not ready biodegradable 0.8587 Rat acute toxicity 1.4850 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9728 hERG inhibition (predictor II) Non-inhibitor 0.81
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Thermus thermophilus (strain HB8 / ATCC 27634 / DSM 579)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Trna binding
- Specific Function
- Part of the top of the 30S subunit head.
- Gene Name
- rpsJ
- Uniprot ID
- Q5SHN7
- Uniprot Name
- 30S ribosomal protein S10
- Molecular Weight
- 11929.82 Da
References
- Dlugosz M, Trylska J: Aminoglycoside association pathways with the 30S ribosomal subunit. J Phys Chem B. 2009 May 21;113(20):7322-30. doi: 10.1021/jp8112914. [PubMed:19438282]
Yes
Inhibitor
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Konno T, Kurita D, Takahashi T, Muto A, Himeno H: Initiation-shift of trans-translation by aminoglycosides. Nucleic Acids Symp Ser (Oxf). 2004;(48):299-300. [PubMed:17150597]
- Chao PW, Chow CS: Monitoring aminoglycoside-induced conformational changes in 16S rRNA through acrylamide quenching. Bioorg Med Chem. 2007 Jun 1;15(11):3825-31. Epub 2007 Mar 13. [PubMed:17399988]
Drug created on July 24, 2007 04:03 / Updated on November 25, 2020 15:47
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