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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyThiorphan
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
- 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
Target Actions Organism UNeprilysin inhibitorHumans - 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
- 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.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
- PDB Entries
- 1zdp / 5v48
Clinical Trials
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
Property Value Source Water Solubility 0.445 mg/mL ALOGPS logP 1.78 ALOGPS logP 1.46 ChemAxon logS -2.8 ALOGPS pKa (Strongest Acidic) 4.02 ChemAxon pKa (Strongest Basic) -1.8 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 66.4 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 67.15 m3·mol-1 ChemAxon Polarizability 25.93 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available 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
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
- Kind
- Protein
- Organism
- Humans
- 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
- 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 December 02, 2019 08:19