DEZOCINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H23NO
Molecular Weight	245.3599
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12CCCCC[C@@H](CC3=CC=C(O)C=C13)[C@@H]2N

InChI

InChIKey=VTMVHDZWSFQSQP-VBNZEHGJSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24263237 | https://www.drugs.com/mmx/dalgan.html

Dezocine was discovered and patented by American Home Products Corp. in 1978. Dezocine is a partial opiate drug and was used for pain management under brand name Dalgan. But then usage of this drug was discontinued in US. Dezocine acts as a partial μ-receptor agonist, a κ-receptor antagonist, and a norepinephrine and serotonin reuptake inhibitor (via norepinephrine transporter and serotonin transporter). Dezocine shares the CNS depressant and respiratory depressant effects of opioid analgesics. Dezocine has not been shown to produce clinically significant cardiovascular adverse effects.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24263237	Partial Agonist 297		3.7 nM [Ki]
Kappa opioid receptor 115 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16433932	Antagonist 2849		24.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.drugs.com/mmx/dalgan.html	Primary		Approved 8583	DALGAN Approved Use Unknown Launch Date 1989

AUC

Value	Dose	Analyte	Population
23.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709625	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	DEZOCINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
49.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709625	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	DEZOCINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
117.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709625	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	DEZOCINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709625	5 mg single, intravenous dose: 5 mg route of administration: Intravenous experiment type: SINGLE co-administered:	DEZOCINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709625	10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered:	DEZOCINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709625	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:	DEZOCINE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
10 mg single, intramuscular Highest studied dose Dose: 10 mg Route: intramuscular Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3709625	healthy, 18-52 years Health Status: healthy Age Group: 18-52 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3709625	Sources: https://pubmed.ncbi.nlm.nih.gov/3709625
10 mg single, subcutaneous Highest studied dose Dose: 10 mg Route: subcutaneous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3709625	healthy, 18-52 years Health Status: healthy Age Group: 18-52 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3709625	Sources: https://pubmed.ncbi.nlm.nih.gov/3709625
20 mg single, intravenous Highest studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3709625	healthy, 18-52 years Health Status: healthy Age Group: 18-52 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3709625	Sources: https://pubmed.ncbi.nlm.nih.gov/3709625

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1MHV5E
AvaChem Scientific	2873	http://www.avachem.com/productSearch.asp?2873
Chemspace	CSSB00102511962	https://chem-space.com/CSSB00102511962
Compound Cloud	3033053
eMolecules	46015078
mcule	MCULE-6634719835
NovoSeek	3033053
Parchem	87269	https://www.parchem.com/chemical-supplier-distributor/Dezocine-087269.aspx
Toronto Research Chemicals	D299800
ZINC	ZINC000003830683	http://zinc15.docking.org/substances/ZINC000003830683

PubMed

Title	Date	PubMed
Sevoflurane requirement during elective ankle day surgery: the effects of etirocoxib premedication, a prospective randomised study.	2008-09-11	18786254
Increased efficacy of micro-opioid agonist-induced antinociception by metabotropic glutamate receptor antagonists in C57BL/6 mice: comparison with (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959).	2008-06	18392754
Varenicline in the treatment of tobacco dependence.	2008-04	18728741
Pharmacological profiles of opioid ligands at kappa opioid receptors.	2006-01-25	16433932
The effect of preoperative ketorolac on WBC response and pain in laparoscopic surgery for endometriosis.	2005-12-31	16385658
Effects of opioids in morphine-treated pigeons trained to discriminate among morphine, the low-efficacy agonist nalbuphine, and saline.	2004-07	15044559
Capsaicin-induced hyperalgesia and mu-opioid-induced antihyperalgesia in male and female Fischer 344 rats.	2003-10	12954802
Activity of opioid ligands in cells expressing cloned mu opioid receptors.	2003-01-04	12513698
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.	2002-11-18	12437765
Sex-related differences in mechanical nociception and antinociception produced by mu- and kappa-opioid receptor agonists in rats.	2002-10-04	12354566
Influence of gonadectomy on the antinociceptive effects of opioids in male and female rats.	2002-09	12202965
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.	2001-11	11702089
Cocaine-like discriminative stimulus effects and [3H]dopamine uptake inhibition produced by selected partial opioid agonists.	2001-07	11548108
Three-choice discrimination in pigeons is based on relative efficacy differences among opioids.	2001-06	11441428

Patents

Sample Use Guides

In Vivo Use Guide

Intravenous: 5-mg dose, 10-mg dose and 20-mg dose

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

DALGAN

Preferred Name

English

DEZOCINE

Official Name

English

DEZOCINE [MART.]

Common Name

English

DEZOCINE [USAN]

Common Name

English

WY-16225

Code

English

DOZOCINE

Common Name

English

WY-16,225

Code

English

dezocine [INN]

Common Name

English

DEZOCINE [VANDF]

Common Name

English

DOCOZINE

Common Name

English

5,11-METHANOBENZOCYCLODECEN-3-OL, 13-AMINO-5,6,7,8,9,10,11,12-OCTAHYDRO-5-METHYL-, (5.ALPHA.,11.ALPHA.,13S*)

Common Name

English

DEZOCINE [ORANGE BOOK]

Common Name

English

DEZOCINE [MI]

Common Name

English

(-)-13.BETA.-AMINO-5,6,7,8,9,10,11.ALPHA.,12-OCTAHYDRO-5.ALPHA.-METHYL-5,11-METHANOBENZOCYCLODECEN-3-OL

Common Name

English

Dezocine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413