This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Summary
Protionamide is an antitubercular thioamide-derivative used in the treatment of multi-drug resistant (MDR) tuberculosis and leprosy.
- Generic Name
- Protionamide
- DrugBank Accession Number
- DB12667
- Background
Prothionamide has been used in trials studying the treatment of MDR-TB and HIV Infections.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Protionamide (DB12667)
- Weight
- Average: 180.27
Monoisotopic: 180.072119568 - Chemical Formula
- C9H12N2S
- Synonyms
- Prothionamide
- Protionamida
- Protionamide
- Protionamidum
- External IDs
- RP 9778
- RP-9778
- TH 1321
- TH-1321
Pharmacology
- Indication
Not Available
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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
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- 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 softwareAcenocoumarol The risk or severity of bleeding can be increased when Protionamide is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Protionamide is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Protionamide is combined with Articaine. Bacillus calmette-guerin substrain russian BCG-I live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Protionamide. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Protionamide. Benzocaine The risk or severity of methemoglobinemia can be increased when Protionamide is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Protionamide is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Protionamide is combined with Bupivacaine. Butacaine The risk or severity of methemoglobinemia can be increased when Protionamide is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Protionamide is combined with Butamben. 
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- Not Available
Products
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- Ektebin / Peteha / Trevintix
Categories
- ATC Codes
- J04AD01 — Protionamide
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Not Available
- Direct Parent
- Pyridines and derivatives
- Alternative Parents
- Thioamides / Heteroaromatic compounds / Thiocarboxylic acid amides / Azacyclic compounds / Thiocarbonyl compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Organosulfur compound / Pyridine / Thioamide
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 76YOO33643
- CAS number
- 14222-60-7
- InChI Key
- VRDIULHPQTYCLN-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12)
- IUPAC Name
- 2-propylpyridine-4-carbothioamide
- SMILES
- CCCC1=CC(=CC=N1)C(N)=S
References
- General References
- TITCK Product Information: Promid (protionamide) coated tablets for oral use [Link]
- External Links
- KEGG Drug
- D01195
- PubChem Compound
- 666418
- PubChem Substance
- 347828871
- ChemSpider
- 579891
- BindingDB
- 50499814
- 8871
- ChEBI
- 32066
- ChEMBL
- CHEMBL1378024
- ZINC
- ZINC000003874803
- Wikipedia
- Prothionamide
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Recruiting Treatment Multidrug Resistant Tuberculosis 1 3 Active Not Recruiting Treatment Multidrug Resistant Tuberculosis 1 1 Completed Treatment Healthy Subjects (HS) 1 Not Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / Human Immunodeficiency Virus (HIV) Infections 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated 250 mg Tablet, coated Oral 250 mg Tablet, coated Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.296 mg/mL ALOGPS logP 2.25 ALOGPS logP 1.77 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 11.89 Chemaxon pKa (Strongest Basic) 4.97 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 38.91 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 54.79 m3·mol-1 Chemaxon Polarizability 20.09 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key 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 LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-001i-1900000000-4e2e325a8024a29d1946 MS/MS Spectrum - , positive LC-MS/MS splash10-0udi-3900000000-ebf07b82c23f40b432ab
Drug created at October 20, 2016 23:32 / Updated at June 08, 2021 11:32