Dextromoramide
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Identification
- Generic Name
- Dextromoramide
- DrugBank Accession Number
- DB01529
- Background
An opioid analgesic structurally related to methadone and used in the treatment of severe pain. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1070)
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
- Weight
- Average: 392.543
Monoisotopic: 392.246378278 - Chemical Formula
- C25H32N2O2
- Synonyms
- (+)-1-(3-methyl-4-morpholino-2,2-diphenylbutyryl)pyrrolidine
- (+)-4-(2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl)morpholine
- 1-((3S)-3-methyl-4-(4-morpholinyl)-1-oxo-2,2-diphenylbutyl)pyrrolidine
- 4-(2-methyl-4-oxo-3,3-diphenyl-4-(1-pyrrolidinyl)butyl)morpholine
- D-2,2-diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine
- dextromoramida
- Dextromoramide
- dextromoramidum
- palphium
- Pyrrolamidol
- External IDs
- ACSCN-9613
- IDS-ND-003
- MCP-875
- R-875
- SKF-5137
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Dextromoramide is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Dextromoramide. Acetophenazine The risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Dextromoramide. Aclidinium The risk or severity of adverse effects can be increased when Aclidinium is combined with Dextromoramide. Agomelatine The risk or severity of CNS depression can be increased when Dextromoramide is combined with Agomelatine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- palfium
Categories
- ATC Codes
- N02AC01 — Dextromoramide
- 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
- Phenylacetamides / Phenylpropanes / N-acylpyrrolidines / Aralkylamines / Morpholines / Tertiary carboxylic acid amides / Trialkylamines / Amino acids and derivatives / Oxacyclic compounds / Dialkyl ethers show 5 more
- Substituents
- Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkyl ether / Diphenylmethane show 19 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- N-acylpyrrolidine, morpholines (CHEBI:74274)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 9S4S6CIY83
- CAS number
- 357-56-2
- InChI Key
- INUNXTSAACVKJS-OAQYLSRUSA-N
- InChI
- InChI=1S/C25H32N2O2/c1-21(20-26-16-18-29-19-17-26)25(22-10-4-2-5-11-22,23-12-6-3-7-13-23)24(28)27-14-8-9-15-27/h2-7,10-13,21H,8-9,14-20H2,1H3/t21-/m1/s1
- IUPAC Name
- (3S)-3-methyl-4-(morpholin-4-yl)-2,2-diphenyl-1-(pyrrolidin-1-yl)butan-1-one
- SMILES
- C[C@H](CN1CCOCC1)C(C(=O)N1CCCC1)(C1=CC=CC=C1)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D07287
- PubChem Compound
- 92943
- PubChem Substance
- 46507896
- ChemSpider
- 83901
- 3290
- ChEBI
- 74274
- ChEMBL
- CHEMBL2365707
- ZINC
- ZINC000029402224
- Wikipedia
- Dextromoramide
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 182 °C PhysProp logP 3.61 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0175 mg/mL ALOGPS logP 4.17 ALOGPS logP 3.75 Chemaxon logS -4.4 ALOGPS pKa (Strongest Basic) 7.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 32.78 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 117.37 m3·mol-1 Chemaxon Polarizability 44.36 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9941 Blood Brain Barrier + 0.986 Caco-2 permeable + 0.5628 P-glycoprotein substrate Substrate 0.6229 P-glycoprotein inhibitor I Inhibitor 0.6781 P-glycoprotein inhibitor II Non-inhibitor 0.573 Renal organic cation transporter Inhibitor 0.525 CYP450 2C9 substrate Non-substrate 0.8056 CYP450 2D6 substrate Non-substrate 0.7581 CYP450 3A4 substrate Substrate 0.6149 CYP450 1A2 substrate Non-inhibitor 0.9177 CYP450 2C9 inhibitor Non-inhibitor 0.9297 CYP450 2D6 inhibitor Inhibitor 0.5 CYP450 2C19 inhibitor Non-inhibitor 0.6691 CYP450 3A4 inhibitor Non-inhibitor 0.6655 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7777 Ames test Non AMES toxic 0.801 Carcinogenicity Non-carcinogens 0.919 Biodegradation Not ready biodegradable 0.9549 Rat acute toxicity 3.7072 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8914 hERG inhibition (predictor II) Non-inhibitor 0.6829
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0159000000-32af6dc12a5d6e0065fd Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0005-9103000000-390368a46a27ddf2c624 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0596-9346000000-1640fd48a548d611eb13 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0005-9000000000-c6c74910677024144675 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fr2-2911000000-fffc1340e10621afff4d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01ox-6947000000-f95257e3485afaf83b8c Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.9246 predictedDeepCCS 1.0 (2019) [M+H]+ 194.28262 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.8191 predictedDeepCCS 1.0 (2019)
Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51