Thiorphan

Targets (1)Biointeractions (1)

Identification

Name
Thiorphan
Accession Number
DB08626  (DB01654)
Type
Small Molecule
Groups
Experimental
Description

A potent inhibitor of membrane metalloendopeptidase (enkephalinase). Thiorphan potentiates morphine-induced analgesia and attenuates naloxone-precipitated withdrawal symptoms.

Structure
Thumb
3D
Similar Structures
Synonyms
Not Available
Categories
UNII
B79L7B5X3Z
CAS number
76721-89-6
Weight
Average: 253.317
Monoisotopic: 253.077264041
Chemical Formula
C12H15NO3S
InChI Key
LJJKNPQAGWVLDQ-SNVBAGLBSA-N
InChI
InChI=1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)/t10-/m1/s1
IUPAC Name
2-[(2S)-2-benzyl-3-sulfanylpropanamido]acetic acid
SMILES
[H][C@](CS)(CC1=CC=CC=C1)C(=O)NCC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNeprilysin
inhibitor
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Mohammad R. Masjedizadeh, Shao-Yong Wu, "PROCESS FOR SYNTHESIS OF TRITIATED AND DEUTERATED THIORPHAN AND ACETORPHAN." U.S. Patent US20110319656, issued December 29, 2011.

US20110319656
General References
Not Available
External Links
KEGG Compound
C01619
PubChem Compound
4369380
PubChem Substance
99445097
ChemSpider
3571959
BindingDB
50024102
ChEMBL
CHEMBL298827
HET
TIO
Wikipedia
Thiorphan
PDB Entries
1zdp / 5v48

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.445 mg/mLALOGPS
logP1.78ALOGPS
logP1.46ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity67.15 m3·mol-1ChemAxon
Polarizability25.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.937
Blood Brain Barrier+0.806
Caco-2 permeable-0.6428
P-glycoprotein substrateNon-substrate0.7192
P-glycoprotein inhibitor INon-inhibitor0.9402
P-glycoprotein inhibitor IINon-inhibitor0.9827
Renal organic cation transporterNon-inhibitor0.9466
CYP450 2C9 substrateNon-substrate0.838
CYP450 2D6 substrateNon-substrate0.8369
CYP450 3A4 substrateNon-substrate0.8005
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9223
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9729
Ames testNon AMES toxic0.5567
CarcinogenicityNon-carcinogens0.9183
BiodegradationNot ready biodegradable0.5448
Rat acute toxicity1.6959 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9862
hERG inhibition (predictor II)Non-inhibitor0.927
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids
Alternative Parents
Fatty amides / Benzene and substituted derivatives / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Alkylthiols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
N-acyl-alpha-amino acid / Monocyclic benzene moiety / Fatty amide / Fatty acyl / Benzenoid / Carboxamide group / Secondary carboxylic acid amide / Alkylthiol / Carboxylic acid / Monocarboxylic acid or derivatives
show 10 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Details1. Neprilysin
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Thermolysin-like specificity, but is almost confined on acting on polypeptides of up to 30 amino acids (PubMed:15283675, PubMed:8168535). Biologically important in the destruction of opioid peptide...
Gene Name
MME
Uniprot ID
P08473
Uniprot Name
Neprilysin
Molecular Weight
85513.225 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on September 15, 2010 15:33 / Updated on November 02, 2018 06:52