Basic information
- CAS
15301-48-1- Standard SMILES
CCC(=O)n1c(=O)n(C2CCN(CCC(C#N)(c3ccccc3)c3ccccc3)CC2)c2ccccc21- InChIKey
FLKWNFFCSSJANB-UHFFFAOYSA-N- Molecular formula
- C31H32N4O2
- Average molar mass
- 492.6 g/mol
- Monoisotopic mass
- 492.25252628
Overview
Bezitramide is a nitrile.
Names & identifiers
- Preferred name
- Bezitramide
- IUPAC
- 4-[4-(2-oxo-3-propanoylbenzimidazol-1-yl)piperidin-1-yl]-2,2-diphenylbutanenitrile
- English name
- bezitramide
- Molecular formula
- C31H32N4O2
- Molecular weight
- 492.61
Names & synonyms
BEZITRAMIDEBurgodinBezitramida15301-48-1BezitramidumR-4845R 4845Bezitramide [INN:BAN:DCF]3KXW0Y310IIDS-NB-007N02AC051-(1-(3-Cyano-3,3-diphenylpropyl)-4-piperidyl)-3-propionyl-2-benzimidazolinone
Show more names
FLKWNFFCSSJANB-UHFFFAOYSA-N1-[1-(3-Cyano-3,3-diphenylpropyl)-4-piperidinyl]-1,3-dihydro-3-(1-oxopropyl)-2H-benzimidazol-2-one1-Piperidinebutanenitrile, 4-[2,3-dihydro-2-oxo-3-(1-oxopropyl)-1H-benzimidazol-1-yl]-α,α-diphenyl-
1-(3-Cyano-3,3-diphenylpropyl)-4-(2-oxo-3-propionyl-1-benzimidazolinyl)piperidineDTXSID90165197Bezitramide (INN:BAN:DCF)RefChem:119583DTXCID2087688239-335-44-(4-(2-oxo-3-propanoyl-2,3-dihydro-1H-1,3-benzodiazol-1-yl)piperidin-1-yl)-2,2-diphenylbutanenitrileBenzitramide
Database identifiers
- CAS
15301-48-1- PubChem CID
- 61791
- DTXSID
DTXSID90165197- ChEMBL
CHEMBL2104149
Properties
Computed structural properties
- XLogP
- 5
- Topological polar surface area
- 67.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 827
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Narcotic Analgesics
DEA Schedule II Controlled Substance -> Opiates
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
LogP4.8
SolubilityPoor water solubility
Melting Point145-149 °C
Physicochemical properties
- Melting point
- 145 · 145-149°; mp 124.5-126°
- Boiling point
- 586.35 °C · 586.35°C (rough estimate)
- Density
- 1.147 · 1.1470 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- solubility
- 10 mg/ml · DMSO: Soluble: = 10 mg/ml
- pka
- 8.21 · 8.21±0.10(Predicted)
- color
- White, crystalline powder
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationDEA schedule II controlled substance
Safety data
- Toxicity
- LD50 orally in mice, rats: 2101, 141 mg/kg (Janssen)
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Bezitramide acts in the body to relieve pain with a potency 20 times that of methadone. Its duration of action is relatively long, lasting up to 12 hours post oral administration, after the achievement of steady state. Its onset of action is slow, with a peak in analgesic effect noted between 2.5-3.5 hours after dosing. It is noted to illicit a strong antitussive effect, which could be of benefit to patients with bronchial carcinoma.
Biological Half-Life11-24h.
Metabolism/Metabolites
Bezitramide is a prodrug which undergoes rapid hydrolysis of a proprionyl-group to form the major metabolite, R-4618. R-4618 has analgesic properties similar to the parent compound. Metabolism occurs in the gastrointestinal tract under both acidic and alkaline conditions.
MeSH Pharmacological ClassificationCompounds capable of relieving pain without the loss of CONSCIOUSNESS.
Absorption, Distribution and Excretion
Bezitramide has poor water solubility, thus administration is restricted to the oral route.
Less than 0.3% of the dose was excreted unchanged in the urine. High concentrations in feces suggested incomplete absorption of biliary excretion. Experiments in rats demonstrated extensive (up to 70%) biliary excretion, and less than 3% urinary excretion.
Applications
UsesBezitramide is a narcotic analgesic agonist with modified pipiridine N-substituents whose binding affinity to the ORL1 and N-methyl-D-aspartate (NMDA) receptors is of research interest.
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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