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Prothionamide

CAT: 0804-HY-B0306-02Size: 1 gDry Ice: NoHazardous: No
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Description
Prothionamide is an orally active thioamide antibacterial agent. Prothionamide is a substrate of OCT1 with a Km value of 805.8 μM. Prothionamide reacts with NAD to form a covalent adduct, with the adduct being a tight-binding inhibitor of Mycobacterium tuberculosis and Mycobacterium leprae InhA. Prothionamide can effectively inhibit the growth of Mycobacterium tuberculosis (MIC = ~0.5 µg/mL) and Mycobacterium leprae. Prothionamide is used in the research of tuberculosis and leprosy[1][2][3][4][5].
CAS Number
14222-60-7
Product Name Alternative
Protionamide
UNSPSC
12352005
Hazard Statement
H302
Target
Bacterial
Type
Reference compound
Related Pathways
Anti-infection
Applications
Neuroscience-Neuromodulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/prothionamide.html
Purity
99.94
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
S=C(C1=CC(CCC)=NC=C1)N
Molecular Formula
C9H12N2S
Molecular Weight
180.28
Precautions
H302
References & Citations
[1]Wang F, et al. Mechanism of thioamide drug action against tuberculosis and leprosy.J Exp Med. 2007 Jan 22;204 (1) :73-8.|[2]Fajardo TT, et al. A clinical trial of ethionamide and prothionamide for treatment of lepromatous leprosy. Am J Trop Med Hyg. 2006 Mar;74 (3) :457-61.|[3]Parvez MM, et al. Comprehensive Substrate Characterization of 22 Antituberculosis Drugs for Multiple Solute Carrier (SLC) Uptake Transporters In Vitro. Antimicrob Agents Chemother. 2018 Aug 27;62 (9) :e00512-18.|[4]Grosset , et al. The role of low dosage prothionamide with and without 4, 4'-diaminio dipheimyl sulphone for use with isoniazld in the treatment of experimental mouse tuberculosis. Tubercle, 1982, 63 (1) : 37-43.|[5]Krasavin M, et al. Conjugation of a 5-nitrofuran-2-oyl moiety to aminoalkylimidazoles produces non-toxic nitrofurans that are efficacious in vitro and in vivo against multidrug-resistant Mycobacterium tuberculosis. Eur J Med Chem. 2018 Sep 5;157:1115-1126.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Prothionamide

Prothionamide is a member of pyridines.

CAS Number14222-60-7
PubChem CID666418
IUPAC Name2-propylpyridine-4-carbothioamide
Molecular FormulaC9H12N2S
Molecular Weight180.27
XLogP1.5
Topological Polar Surface Area71
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Heavy Atom Count12
Formal Charge0
Complexity159
SMILES
CCCC1=NC=CC(=C1)C(=S)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)
InChIKey
VRDIULHPQTYCLN-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Prothionamide
CAS: 14222-60-7
CID: 666418
Formula: C9H12N2S
MW: 180.27
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight180.27
XLogP31.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass180.07211956
Monoisotopic Mass180.07211956
Topological Polar Surface Area71 Ų
Heavy Atom Count12
Formal Charge0
Complexity159
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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