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Identification
NameThiorphan
Accession NumberDB08626  (DB01654)
TypeSmall Molecule
GroupsExperimental
DescriptionA potent inhibitor of membrane metalloendopeptidase (enkephalinase). Thiorphan potentiates morphine-induced analgesia and attenuates naloxone-precipitated withdrawal symptoms.
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIB79L7B5X3Z
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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
NeprilysinProteinunknown
inhibitor
HumanP08473 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
Interactions
Drug Interactions
DrugInteractionDrug group
AbacavirThe serum concentration of Abacavir can be decreased when it is combined with Thiorphan.Approved, Investigational
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Thiorphan.Approved, Investigational
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Thiorphan.Approved, Illicit, Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be decreased when it is combined with Thiorphan.Experimental
AmineptineThe serum concentration of Amineptine can be increased when it is combined with Thiorphan.Illicit, Withdrawn
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Thiorphan.Approved
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Thiorphan.Approved
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Thiorphan.Approved
BoceprevirThe serum concentration of Thiorphan can be decreased when it is combined with Boceprevir.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Thiorphan.Approved, Investigational
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Thiorphan.Approved
CarbamazepineThe metabolism of Thiorphan can be increased when combined with Carbamazepine.Approved, Investigational
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Thiorphan.Withdrawn
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Thiorphan.Approved, Investigational, Withdrawn
ClarithromycinThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Thiorphan.Approved
ClomipramineThe serum concentration of Clomipramine can be increased when it is combined with Thiorphan.Approved, Vet Approved
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be decreased when it is combined with Thiorphan.Approved
CyclobenzaprineThe serum concentration of Cyclobenzaprine can be increased when it is combined with Thiorphan.Approved
CyclophosphamideThe risk or severity of adverse effects can be increased when Thiorphan is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Thiorphan.Approved, Investigational, Vet Approved
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Thiorphan.Approved
DesipramineThe serum concentration of Desipramine can be increased when it is combined with Thiorphan.Approved
DienestrolThe serum concentration of Dienestrol can be decreased when it is combined with Thiorphan.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Thiorphan.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Thiorphan.Approved
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Thiorphan.Approved
DiltiazemThe metabolism of Diltiazem can be decreased when combined with Thiorphan.Approved
DosulepinThe serum concentration of Dosulepin can be increased when it is combined with Thiorphan.Approved
DoxepinThe serum concentration of Doxepin can be increased when it is combined with Thiorphan.Approved
DyphyllineThe serum concentration of Dyphylline can be decreased when it is combined with Thiorphan.Approved
EnfuvirtideThe serum concentration of Enfuvirtide can be increased when it is combined with Thiorphan.Approved, Investigational
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Thiorphan.Approved
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Thiorphan.Approved
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Thiorphan.Approved
EsmirtazapineThe serum concentration of Esmirtazapine can be increased when it is combined with Thiorphan.Investigational
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Thiorphan.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Estramustine can be decreased when it is combined with Thiorphan.Approved
Estrogens, esterifiedThe serum concentration of Estrogens, esterified can be decreased when it is combined with Thiorphan.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be decreased when it is combined with Thiorphan.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Thiorphan.Approved
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Thiorphan.Approved
GarlicThe serum concentration of Thiorphan can be decreased when it is combined with Garlic.Approved
HexestrolThe serum concentration of Hexestrol can be decreased when it is combined with Thiorphan.Withdrawn
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Thiorphan.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Thiorphan.Approved, Investigational
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Thiorphan.Approved
MethallenestrilThe serum concentration of Methallenestril can be decreased when it is combined with Thiorphan.Experimental
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Thiorphan.Approved, Illicit
MirtazapineThe serum concentration of Mirtazapine can be increased when it is combined with Thiorphan.Approved
NefazodoneThe serum concentration of Nefazodone can be increased when it is combined with Thiorphan.Approved, Withdrawn
NortriptylineThe serum concentration of Nortriptyline can be increased when it is combined with Thiorphan.Approved
OpipramolThe serum concentration of Opipramol can be increased when it is combined with Thiorphan.Investigational
PethidineThe risk or severity of adverse effects can be increased when Thiorphan is combined with Pethidine.Approved
PimozideThe serum concentration of Pimozide can be increased when it is combined with Thiorphan.Approved
ProtriptylineThe serum concentration of Protriptyline can be increased when it is combined with Thiorphan.Approved
RiociguatThe serum concentration of Riociguat can be increased when it is combined with Thiorphan.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Thiorphan.Approved
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Thiorphan.Approved, Investigational
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Thiorphan.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Thiorphan.Approved
St. John's WortThe metabolism of Thiorphan can be increased when combined with St. John's Wort.Nutraceutical
Synthetic Conjugated Estrogens, AThe serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Thiorphan.Approved
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Thiorphan.Approved, Investigational
TemsirolimusThe risk or severity of adverse effects can be increased when Thiorphan is combined with Temsirolimus.Approved
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Thiorphan.Approved
TianeptineThe serum concentration of Tianeptine can be increased when it is combined with Thiorphan.Approved
TipranavirThe serum concentration of Thiorphan can be decreased when it is combined with Tipranavir.Approved, Investigational
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Thiorphan.Approved
TrimipramineThe serum concentration of Trimipramine can be increased when it is combined with Thiorphan.Approved
Valproic AcidThe serum concentration of Valproic Acid can be decreased when it is combined with Thiorphan.Approved, Investigational
VerapamilThe metabolism of Verapamil can be decreased when combined with Thiorphan.Approved
ZidovudineThe serum concentration of Zidovudine can be decreased when it is combined with Thiorphan.Approved
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-aliphatic-alpha amino acids. These are alpha amino acids carrying a N-acylated aliphatic chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-aliphatic-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-aliphatic-alpha amino acid
  • Phenylpropylamine
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Monocyclic benzene moiety
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Targets

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 peptides such as Met- and Leu-enkephalins by cleavage of a Gly-Phe bond (PubMed:17101991). Able to cleave angiotensin-1, angiotensin-2 and angiotensin 1-9 (PubMed:15283675). Involved in the degradation of at...
Gene Name:
MME
Uniprot ID:
P08473
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 ]
Comments
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Drug created on September 15, 2010 15:33 / Updated on August 17, 2016 12:24