NAV

Methadyl acetate

Identification

Generic Name
Methadyl acetate
DrugBank Accession Number
DB01433
Background

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

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 353.4977
Monoisotopic: 353.235479241
Chemical Formula
C23H31NO2
Synonyms
  • Acetilmetadol
  • Acetylmethadol
  • Acetylmethadolum
  • Methadyl acetate
External IDs
  • ACSCN-9601
  • IDS-NA-004
  • NIH-2953

Pharmacology

Indication

Used mainly in the treatment of narcotic dependence.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Methadyl 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 action

Methadyl Acetate is primarily a mu-type opioid receptor agonist. It functions similarily to methadone.

TargetActionsOrganism
AMu-type opioid receptor
agonist
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Methadyl Acetate Action PathwayDrug action
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.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Methadyl acetate is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Methadyl acetate.
AcetophenazineThe risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Methadyl acetate.
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Methadyl acetate.
AgomelatineThe risk or severity of CNS depression can be increased when Methadyl acetate is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Methadyl acetate.
AlimemazineThe risk or severity of hypotension and CNS depression can be increased when Alimemazine is combined with Methadyl acetate.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Methadyl acetate.
AlmotriptanThe risk or severity of CNS depression can be increased when Almotriptan is combined with Methadyl acetate.
AlosetronThe risk or severity of CNS depression can be increased when Alosetron is combined with Methadyl acetate.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Methadyl acetate hydrochloride3ZD9WAO92T38821-43-1UXBPQRGCVJOTNT-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Aralkylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Amine / Amino acid or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Diphenylmethane / Hydrocarbon derivative / Monocarboxylic acid or derivatives
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
L59OC40KWJ
CAS number
509-74-0
InChI Key
XBMIVRRWGCYBTQ-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

References

General References
Not Available
Human Metabolome Database
HMDB0015502
PubChem Compound
10517
PubChem Substance
46505532
ChemSpider
10080
BindingDB
50027391
RxNav
6814
ChEBI
135491
ChEMBL
CHEMBL170179
Therapeutic Targets Database
DAP001137
PharmGKB
PA164746889
Wikipedia
Acetylmethadol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP4.27HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00179 mg/mLALOGPS
logP4.78ALOGPS
logP4.88Chemaxon
logS-5.3ALOGPS
pKa (Strongest Basic)9.87Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area29.54 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity117.86 m3·mol-1Chemaxon
Polarizability40.82 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9965
Blood Brain Barrier+0.9648
Caco-2 permeable+0.7459
P-glycoprotein substrateSubstrate0.5822
P-glycoprotein inhibitor IInhibitor0.8472
P-glycoprotein inhibitor IINon-inhibitor0.8897
Renal organic cation transporterNon-inhibitor0.6473
CYP450 2C9 substrateNon-substrate0.7976
CYP450 2D6 substrateNon-substrate0.8641
CYP450 3A4 substrateSubstrate0.6658
CYP450 1A2 substrateInhibitor0.5619
CYP450 2C9 inhibitorNon-inhibitor0.8153
CYP450 2D6 inhibitorInhibitor0.7123
CYP450 2C19 inhibitorNon-inhibitor0.7312
CYP450 3A4 inhibitorInhibitor0.5242
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5811
Ames testNon AMES toxic0.9016
CarcinogenicityCarcinogens 0.7025
BiodegradationNot ready biodegradable0.9792
Rat acute toxicity3.3406 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9706
hERG inhibition (predictor II)Inhibitor0.7157
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

Targets

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Details1. Mu-type opioid receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
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-Apr;19(2):169-77. doi: 10.1111/j.1521-0391.2009.00025.x. [Article]
  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. [Article]
  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. doi: 10.1055/s-0028-1083818. Epub 2009 Jan 19. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at July 24, 2007 20:16 / Updated at February 21, 2021 18:51