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Betaprodine

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Overview

Structure
DrugBank ID
DB01473
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
Betaprodine
DrugBank Accession Number
DB01473
Background

An opioid analgesic chemically related to and with an action resembling that of meperidine, but more rapid in onset and of shorter duration. It has been used in obstetrics, as pre-operative medication, for minor surgical procedures, and for dental procedures. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1067)

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 261.365
Monoisotopic: 261.172878985
Chemical Formula
C16H23NO2
Synonyms
  • beta-Prodine
  • Betaprodina
  • Betaprodine
  • Betaprodinum
External IDs
  • DEA No. 9611
  • NU-1779
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Benzyloxycarbonyls / Aralkylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
21J54X4Z4Z
CAS number
468-59-7
InChI Key
UVAZQQHAVMNMHE-CZUORRHYSA-N
InChI
InChI=1S/C16H23NO2/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2/h5-9,13H,4,10-12H2,1-3H3/t13-,16-/m1/s1
IUPAC Name
(3R,4R)-1,3-dimethyl-4-phenylpiperidin-4-yl propanoate
SMILES
[H][C@@]1(C)CN(C)CC[C@]1(OC(=O)CC)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
5284516
PubChem Substance
46507695
ChemSpider
4447576
ChEMBL
CHEMBL3187964
ZINC
ZINC000004626727
Wikipedia
Betaprodine

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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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
PropertyValueSource
Water Solubility0.475 mg/mLALOGPS
logP3.24ALOGPS
logP2.78Chemaxon
logS-2.7ALOGPS
pKa (Strongest Basic)8.9Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area29.54 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity76.41 m3·mol-1Chemaxon
Polarizability30 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9942
Blood Brain Barrier+0.9778
Caco-2 permeable+0.7392
P-glycoprotein substrateSubstrate0.768
P-glycoprotein inhibitor IInhibitor0.9203
P-glycoprotein inhibitor IIInhibitor0.6555
Renal organic cation transporterInhibitor0.6195
CYP450 2C9 substrateNon-substrate0.8428
CYP450 2D6 substrateNon-substrate0.6067
CYP450 3A4 substrateSubstrate0.7028
CYP450 1A2 substrateNon-inhibitor0.8298
CYP450 2C9 inhibitorNon-inhibitor0.897
CYP450 2D6 inhibitorInhibitor0.6364
CYP450 2C19 inhibitorNon-inhibitor0.9007
CYP450 3A4 inhibitorInhibitor0.5
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8595
Ames testNon AMES toxic0.8872
CarcinogenicityNon-carcinogens0.8008
BiodegradationNot ready biodegradable0.9764
Rat acute toxicity2.8945 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6126
hERG inhibition (predictor II)Inhibitor0.6841
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0490000000-52dcc6f0158209576cf7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-6090000000-2e14e827f6e09cd4ece9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052r-2940000000-b8f4cc6d7da4d5e7dbef
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2490000000-c8c5b6f8604adac84676
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-bf6d5dbaf956185c868b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-059i-5930000000-6b1fb0eeb03313cea8cd
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.1414783
predicted
DarkChem Lite v0.1.0
[M-H]-159.70819
predicted
DeepCCS 1.0 (2019)
[M+H]+172.6392783
predicted
DarkChem Lite v0.1.0
[M+H]+162.0662
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.3199783
predicted
DarkChem Lite v0.1.0
[M+Na]+168.66054
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:09 / Updated at February 21, 2021 18:51