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Identification
NameMethadyl Acetate
Accession NumberDB01433
Typesmall molecule
Groupsapproved, illicit
Description

A narcotic analgesic with a long onset and duration of action. It is used mainly in the treatment of narcotic dependence. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
AcetilmetadolSpanishINN
AcetylmethadolNot AvailableNot Available
AcetylmethadolumLatinINN
BetamethadolNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number509-74-0
WeightAverage: 353.4977
Monoisotopic: 353.235479241
Chemical FormulaC23H31NO2
InChI KeyXBMIVRRWGCYBTQ-UHFFFAOYSA-N
InChI
InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3
IUPAC Name
6-(dimethylamino)-4,4-diphenylheptan-3-yl acetate
SMILES
CCC(OC(C)=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassDiphenylmethanes
Direct parentDiphenylmethanes
Alternative parentsPhenylpropylamines; Tertiary Amines; Carboxylic Acid Esters; Ethers; Enolates; Polyamines
Substituentsphenylpropylamine; tertiary amine; carboxylic acid ester; enolate; ether; carboxylic acid derivative; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Pharmacology
IndicationUsed mainly in the treatment of narcotic dependence.
PharmacodynamicsMethadyl Acetate is a narcotic analgesic with a long onset and duration of action. The drug decreases a patients opioid use by preventing opioid withdrawal and in how it can mimic some of the effects of opioids.
Mechanism of actionMethadyl Acetate is primarily a mu-type opioid receptor agonist. It functions similarily to methadone.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Methadyl Acetate Action PathwayDrug actionSMP00678
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9965
Blood Brain Barrier + 0.9648
Caco-2 permeable + 0.7459
P-glycoprotein substrate Substrate 0.5822
P-glycoprotein inhibitor I Inhibitor 0.8472
P-glycoprotein inhibitor II Non-inhibitor 0.8897
Renal organic cation transporter Non-inhibitor 0.6473
CYP450 2C9 substrate Non-substrate 0.7976
CYP450 2D6 substrate Non-substrate 0.8641
CYP450 3A4 substrate Substrate 0.6658
CYP450 1A2 substrate Inhibitor 0.5619
CYP450 2C9 substrate Non-inhibitor 0.8153
CYP450 2D6 substrate Inhibitor 0.7123
CYP450 2C19 substrate Non-inhibitor 0.7312
CYP450 3A4 substrate Inhibitor 0.5242
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5811
Ames test Non AMES toxic 0.9016
Carcinogenicity Carcinogens 0.7025
Biodegradation Not ready biodegradable 0.9792
Rat acute toxicity 3.3406 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9706
hERG inhibition (predictor II) Inhibitor 0.7157
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP4.27HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.79e-03 g/lALOGPS
logP4.78ALOGPS
logP4.88ChemAxon
logS-5.3ALOGPS
pKa (strongest basic)9.87ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area29.54ChemAxon
rotatable bond count9ChemAxon
refractivity117.86ChemAxon
polarizability40.82ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound10517
PubChem Substance46505532
ChemSpider10080
BindingDB50027391
Therapeutic Targets DatabaseDAP001137
PharmGKBPA164746889
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

References:

  1. Mancino MJ, McGaugh J, Feldman Z, Poling J, Oliveto A: Effect of PTSD diagnosis and contingency management procedures on cocaine use in dually cocaine- and opioid-dependent individuals maintained on LAAM: a retrospective analysis. Am J Addict. 2010 Mar;19(2):169-77. Pubmed
  2. Walczak SA, Makman MH, Gardner EL: Acetylmethadol metabolites influence opiate receptors and adenylate cyclase in amygdala. Eur J Pharmacol. 1981 Jul 10;72(4):343-9. Pubmed
  3. Wolstein J, Gastpar M, Finkbeiner T, Heinrich C, Heitkamp R, Poehlke T, Scherbaum N: A randomized, open-label trial comparing methadone and Levo-Alpha-Acetylmethadol (LAAM) in maintenance treatment of opioid addiction. Pharmacopsychiatry. 2009 Jan;42(1):1-8. Epub 2009 Jan 19. Pubmed
  4. 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 July 24, 2007 14:16 / Updated on September 16, 2013 17:14