Identification
- Summary
Paromomycin is an aminoglycoside antibiotic used in the treatment of acute and chronic intestinal amebiasis, and as an adjunct for the management of hepatic coma.
- Brand Names
- Humatin
- Generic Name
- Paromomycin
- DrugBank Accession Number
- DB01421
- Background
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.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
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Not Available
- 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 Integrate drug-drug
interactions in your softwareAbacavir Paromomycin may decrease the excretion rate of Abacavir 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. Acrivastine Paromomycin may decrease the excretion rate of Acrivastine which could result in a higher serum level. 
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- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Humatin Capsule 250 mg/1 Oral Physicians Total Care, Inc. 1994-03-11 2011-05-31 US 
Humatin Cap 250mg Capsule 250 mg Oral Erfa Canada 2012 Inc 1994-12-31 Not applicable Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Humatin Capsule 250 mg/1 Oral Monarch Pharmaceuticals, Inc. 1981-01-03 2008-11-11 US Humatin Capsule 250 mg/1 Oral Waylis Therapeutics LLC 2021-04-08 Not applicable US Humatin Capsule 250 mg/1 Oral Woodward Pharma Services Llc 2021-02-19 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 Central Texas Community Health Centers 2009-10-22 Not applicable 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 Sun Pharmaceutical Industries, Inc. 1997-06-30 2017-06-30 US Paromomycin Sulfate Capsule 250 mg/1 Oral Physicians Total Care, Inc. 1997-10-01 2010-06-30 US Paromomycin Sulfate Capsule 250 mg/1 Oral Heritage Pharmaceuticals Inc. d/b/a Avet Pharmaceuticals Inc. 2009-10-22 2024-03-31 US - 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
- 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)
- Affected organisms
- Enteric bacteria and other eubacteria
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[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]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@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. [Article]
- 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
- PDB Entries
- 1fjg / 1fyp / 1ibk / 1ibl / 1j7t / 1n32 / 1n33 / 1vvj / 1xmo / 1xmq … show 82 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Visceral Leishmaniasis 1 3 Completed Treatment Leishmaniasis, Cutaneous 2 3 Completed Treatment Visceral Leishmaniasis 7 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, Cutaneous / Leishmaniasis; American / Leishmaniasis; American, Cutaneous 1 2, 3 Completed Treatment Leishmaniasis; American, Cutaneous 1 0 Completed Supportive Care Leishmaniasis, Cutaneous 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Caraco Pharmaceutical Labs
- Heritage Pharmaceuticals
- Kaiser Foundation Hospital
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Tablet Syrup Oral Tablet, film coated Oral Injection Capsule Oral Capsule Oral 250 mg/1 Syrup Oral 2.5 g/100ml Syrup Oral 25 MG/ML Powder, for solution Oral 1 g Capsule Oral 250 mg 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
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- 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. [Article]
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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Drug created at July 24, 2007 10:03 / Updated at January 16, 2022 18:54