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Identification
NameThiorphan
Accession NumberDB08626  (DB01654)
TypeSmall Molecule
GroupsExperimental
Description

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

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number76721-89-6
WeightAverage: 253.317
Monoisotopic: 253.077264041
Chemical FormulaC12H15NO3S
InChI KeyLJJKNPQAGWVLDQ-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentN-acyl-alpha Amino Acids
Alternative parentsPhenylpropylamines; Secondary Carboxylic Acid Amides; Polyamines; Enolates; Carboxylic Acids; Alkylthiols
Substituentsphenylpropylamine; benzene; secondary carboxylic acid amide; carboxamide group; alkylthiol; enolate; polyamine; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the n-acyl-alpha amino acids. These are compounds containing an alpha amino acid which bears an acyl group at his terminal nitrogen atom.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.937
Blood Brain Barrier + 0.806
Caco-2 permeable - 0.6428
P-glycoprotein substrate Non-substrate 0.7192
P-glycoprotein inhibitor I Non-inhibitor 0.9402
P-glycoprotein inhibitor II Non-inhibitor 0.9827
Renal organic cation transporter Non-inhibitor 0.9466
CYP450 2C9 substrate Non-substrate 0.838
CYP450 2D6 substrate Non-substrate 0.8369
CYP450 3A4 substrate Non-substrate 0.8005
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.9223
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9729
Ames test Non AMES toxic 0.5567
Carcinogenicity Non-carcinogens 0.9183
Biodegradation Not ready biodegradable 0.5448
Rat acute toxicity 1.6959 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9862
hERG inhibition (predictor II) Non-inhibitor 0.927
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.445ALOGPS
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
Spectra
SpectraNot 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 ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC01619
PubChem Compound4369380
PubChem Substance99445097
ChemSpider3571959
BindingDB21641
HETTIO
WikipediaThiorphan
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Neprilysin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Neprilysin P08473 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on September 15, 2010 15:33 / Updated on September 16, 2013 18:10