S-Ethylisothiourea

Identification

Generic Name
S-Ethylisothiourea
DrugBank Accession Number
DB02234
Background

S-Ethylisothiourea is a nitric oxide synthase inhibitor.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 104.174
Monoisotopic: 104.040818956
Chemical Formula
C3H8N2S
Synonyms
  • 2-Ethyl-2-thiopseudourea
  • CARBAMIMIDOTHIOIC ACID, ETHYL ESTER
  • Ethyron
  • Etiron
  • S-ETHYLISOTHIOURONIUM

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase oxygenaseNot AvailableStaphylococcus aureus (strain MW2)
UNitric oxide synthase, inducibleNot AvailableHumans
UNitric oxide synthase, endothelialNot AvailableHumans
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
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when S-Ethylisothiourea is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with S-Ethylisothiourea.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with S-Ethylisothiourea.
AgomelatineThe risk or severity of CNS depression can be increased when S-Ethylisothiourea is combined with Agomelatine.
AlfentanilThe risk or severity of CNS depression can be increased when Alfentanil is combined with S-Ethylisothiourea.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
S-Ethyl isothiouronium bromideT9389OA11M1071-37-0SWXXKWPYNMZFTE-UHFFFAOYSA-N
S-ethylisothiouronium diethyl phosphateCTD25O6OBI21704-46-1CSYSULGPHGCBQD-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as isothioureas. These are organic compounds containing the isothiourea group, with the general structure R1SC(=NR2)N(R3)R4 (R1,R2,R3,R4=H, alkyl, aryl).
Kingdom
Organic compounds
Super Class
Organosulfur compounds
Class
Isothioureas
Sub Class
Not Available
Direct Parent
Isothioureas
Alternative Parents
Sulfenyl compounds / Carboximidamides / Organopnictogen compounds / Imines / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Carboximidamide / Hydrocarbon derivative / Imine / Isothiourea / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Sulfenyl compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
236P47H4VR
CAS number
2986-20-1
InChI Key
VFIZBHJTOHUOEK-UHFFFAOYSA-N
InChI
InChI=1S/C3H8N2S/c1-2-6-3(4)5/h2H2,1H3,(H3,4,5)
IUPAC Name
(ethylsulfanyl)methanimidamide
SMILES
CCSC(N)=N

References

General References
Not Available
Human Metabolome Database
HMDB0257399
PubChem Compound
5139
PubChem Substance
46508006
ChemSpider
4955
BindingDB
50055281
ChEMBL
CHEMBL321691
ZINC
ZINC000003806245
PDBe Ligand
ITU
PDB Entries
1df1 / 1dmi / 1dmj / 1dmk / 1mjt / 1nse / 2nsi / 3nse / 4nos

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2WithdrawnTreatmentCardiopulmonary Bypass / Hypotension1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.77 mg/mLALOGPS
logP0.03ALOGPS
logP0.67Chemaxon
logS-1.3ALOGPS
pKa (Strongest Basic)10.59Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.87 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity39.78 m3·mol-1Chemaxon
Polarizability10.96 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002f-9000000000-51fd97bf7873b43d0447
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a70-9600000000-a1d6bc833d582cdffa77
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-62d1427197f92066e14f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-9000000000-e400d2f57000c624eebf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-015b0f32c3eedb4f8b34
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-314f9bc1edbb1d3ff37b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-9000000000-f9eedcb07fb48561bb43
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-126.038994
predicted
DeepCCS 1.0 (2019)
[M+H]+127.934395
predicted
DeepCCS 1.0 (2019)
[M+Na]+135.48917
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Staphylococcus aureus (strain MW2)
Pharmacological action
Unknown
General Function
Nitric-oxide synthase activity
Specific Function
Catalyzes the production of nitric oxide.
Gene Name
nos
Uniprot ID
P0A094
Uniprot Name
Nitric oxide synthase oxygenase
Molecular Weight
41709.935 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
Molecular Weight
133287.62 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 28, 2023 05:48