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Identification
NameDezocine
Accession NumberDB01209  (APRD00912)
TypeSmall Molecule
GroupsApproved
Description

Dezocine is a partial opiate drug and is used for pain management. Dezocine is a very effective alternative to fentanyl when administered during outpatient laparoscopy, although is associated with an increased incidence of postoperative nausea.

Structure
Thumb
Synonyms
(-)-13beta-amino-5,6,7,8,9,10,11alpha,12-Octahydro-5alpha-methyl-5,11-methanobenzocyclodecen-3-ol
Dezocina
Dezocinum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DalganNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIVHX8K5SV4X
CAS number53648-55-8
WeightAverage: 245.3599
Monoisotopic: 245.177964363
Chemical FormulaC16H23NO
InChI KeyInChIKey=VTMVHDZWSFQSQP-VBNZEHGJSA-N
InChI
InChI=1S/C16H23NO/c1-16-8-4-2-3-5-12(15(16)17)9-11-6-7-13(18)10-14(11)16/h6-7,10,12,15,18H,2-5,8-9,17H2,1H3/t12-,15-,16+/m0/s1
IUPAC Name
(1R,9S,15S)-15-amino-1-methyltricyclo[7.5.1.0²,⁷]pentadeca-2,4,6-trien-4-ol
SMILES
[H][C@@]12CC3=CC=C(O)C=C3[C@@](C)(CCCCC1)[[email protected]]2N
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTetralins
Sub ClassNot Available
Direct ParentTetralins
Alternative Parents
Substituents
  • Tetralin
  • Aralkylamine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationIndicated in the treatment of moderate to severe pain.
PharmacodynamicsDezocine is a parenteral narcotic analgesic possessing both agonist and antagonist activity. It is similar to morphine with respect to analgesic potency and onset and duration of action. The narcotic antagonist activity is greater than that of pentazocine.
Mechanism of actionDezocine is a opioid analgesic drug of mixed agonist-antagonist type. It binds with stereospecific receptors at many sites within the central nervous system (CNS) to alter processes affecting both the perception of pain and the emotional response to pain. At least 2 of these types of receptors (mu and kappa) mediate analgesia. Mu receptors are widely distributed throughout the CNS, especially in the limbic system (frontal cortex, temporal cortex, amygdala, and hippocampus), thalamus, striatum, hypothalamus, and midbrain as well as laminae I, II, IV, and V of the dorsal horn in the spinal cord. Kappa receptors are localized primarily in the spinal cord and in the cerebral cortex.
Related Articles
AbsorptionRapid and complete following intramuscular administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic, via conjugation (glucuronidation).

Route of eliminationNot Available
Half lifeElimination half-life following intramuscular administration averages 2.2 hours. Elimination half-life following a 5mg intravenous dose averages 1.7 to 2.6 hours (range 0.6 to 4.4 hours) while a 10mg dose averages 2.4 to 2.6 hours (range 1.2 to 7.4 hours). In patients with hepatic cirrhosis, the half-life is increased by 30 to 50%.
ClearanceNot Available
ToxicitySymptoms of overdose include cold and clammy skin, confusion, nervousness, or severe restlessness, convulsions (seizures), severe dizziness, severe drowsiness, low blood pressure, pinpoint pupils of eyes, slow heartbeat, slow or troubled breathing and severe weakness.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Dezocine Action PathwayDrug actionSMP00676
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9932
Blood Brain Barrier+0.9403
Caco-2 permeable+0.6275
P-glycoprotein substrateSubstrate0.6181
P-glycoprotein inhibitor INon-inhibitor0.9556
P-glycoprotein inhibitor IINon-inhibitor0.8905
Renal organic cation transporterNon-inhibitor0.7672
CYP450 2C9 substrateNon-substrate0.7337
CYP450 2D6 substrateNon-substrate0.6473
CYP450 3A4 substrateSubstrate0.5845
CYP450 1A2 substrateInhibitor0.5521
CYP450 2C9 inhibitorNon-inhibitor0.7985
CYP450 2D6 inhibitorNon-inhibitor0.8933
CYP450 2C19 inhibitorNon-inhibitor0.7939
CYP450 3A4 inhibitorNon-inhibitor0.7701
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.7561
CarcinogenicityNon-carcinogens0.8934
BiodegradationNot ready biodegradable0.9865
Rat acute toxicity2.4549 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8997
hERG inhibition (predictor II)Inhibitor0.6053
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 mg/mLALOGPS
logP3.77ALOGPS
logP3.23ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)10.43ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity74.19 m3·mol-1ChemAxon
Polarizability28.49 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesN02AX03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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. Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociati...
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular Weight:
44778.855 Da
References
  1. Picker MJ: Discriminative stimulus effects of the mixed-opioid agonist/antagonist dezocine: cross-substitution by mu and delta opioid agonists. J Pharmacol Exp Ther. 1997 Dec;283(3):1009-17. [PubMed:9399970 ]
  2. Barrett AC, Cook CD, Terner JM, Craft RM, Picker MJ: Importance of sex and relative efficacy at the mu opioid receptor in the development of tolerance and cross-tolerance to the antinociceptive effects of opioids. Psychopharmacology (Berl). 2001 Nov;158(2):154-64. [PubMed:11702089 ]
  3. Cook CD, Barrett AC, Roach EL, Bowman JR, Picker MJ: Sex-related differences in the antinociceptive effects of opioids: importance of rat genotype, nociceptive stimulus intensity, and efficacy at the mu opioid receptor. Psychopharmacology (Berl). 2000 Jul;150(4):430-42. [PubMed:10958085 ]
  4. Gharagozlou P, Demirci H, David Clark J, Lameh J: Activity of opioid ligands in cells expressing cloned mu opioid receptors. BMC Pharmacol. 2003 Jan 4;3:1. Epub 2003 Jan 4. [PubMed:12513698 ]
  5. Morgan D, Cook CD, Smith MA, Picker MJ: An examination of the interactions between the antinociceptive effects of morphine and various mu-opioids: the role of intrinsic efficacy and stimulus intensity. Anesth Analg. 1999 Feb;88(2):407-13. [PubMed:9972766 ]
  6. Jacobs AM, Youngblood F: Opioid receptor affinity for agonist-antagonist analgesics. J Am Podiatr Med Assoc. 1992 Oct;82(10):520-4. [PubMed:1361946 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Opioid receptor activity
Specific Function:
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates th...
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular Weight:
42644.665 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J: Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacol. 2006 Jan 25;6:3. [PubMed:16433932 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13