Dezocine

Dezocine
Clinical data
Trade names	Dalgan
Other names	WY-16225
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Intravenous infusion, intramuscular injection
ATC code	N02AX03 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	2.2 hours
Identifiers
	IUPAC name (5R,11S,13R)-13-Amino-5-methyl-5,6,7,8,9,10,11,12-octahydro-5,11-methanobenzo[10]annulen-3-ol;
CAS Number	53648-55-8 ;
PubChem CID	3033053;
DrugBank	DB01209 ;
ChemSpider	2297867 ;
UNII	VHX8K5SV4X;
KEGG	D00838 ;
ChEBI	CHEBI:4474 ;
ChEMBL	ChEMBL1685 ;
CompTox Dashboard (EPA)	DTXSID2022911 ;
Chemical and physical data
Formula	C16H23NO
Molar mass	245.366 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc1ccc2c(c1)[C@@]3(C)CCCCC[C@@H](C2)[C@H]3N;
	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 ; Key:VTMVHDZWSFQSQP-VBNZEHGJSA-N ;
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Dezocine, sold under the brand name Dalgan, is an atypical opioid analgesic which is used in the treatment of pain.^[1]^[2] It is used by intravenous infusion and intramuscular injection.^[1]^[2]

Dezocine is an opioid receptor modulator, acting as a partial agonist of the μ- and κ-opioid receptors.^[2] It has a similar profile of effects to related opioids acting at the μ-opioid receptor, including analgesia and euphoria.^[2]^[3] Unlike other opioids acting at the κ-opioid receptor however, dezocine does not produce side effects such as dysphoria or hallucinations at any therapeutically used dose.^[4]

Dezocine was first synthesized in 1970.^[5] It was introduced for medical use in the United States in 1986 but was not marketed in other countries.^[2]^[6] Dezocine was discontinued in the United States in 2011 with no official reason given.^[2] However, it has become one of the most widely used analgesics in China.^[2] In light of the opioid epidemic, dezocine has seen a resurgence in use and interest.^[2]

^ ^a ^b ^c O'Brien JJ, Benfield P (August 1989). "Dezocine. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy". Drugs. 38 (2): 226–48. doi:10.2165/00003495-198938020-00005. PMID 2670517. S2CID 195697572.
^ ^a ^b ^c ^d ^e ^f ^g ^h Childers WE, Abou-Gharbia MA (June 2021). ""I'll Be Back": The Resurrection of Dezocine". ACS Med Chem Lett. 12 (6): 961–968. doi:10.1021/acsmedchemlett.1c00233. PMC 8201756. PMID 34141081.
^ Zacny JP, Lichtor JL, de Wit H (April 1992). "Subjective, behavioral, and physiologic responses to intravenous dezocine in healthy volunteers". Anesthesia and Analgesia. 74 (4): 523–30. doi:10.1213/00000539-199204000-00010. PMID 1348168. S2CID 34394471.
^ Westmoreland C (August 1991). "Opioid agonist-antagonists". Current Opinion in Anesthesiology. 4 (4): 556–562. doi:10.1097/00001503-199108000-00017.
^ "Espacenet". Espacenet Patent Search.
^ Cite error: The named reference SwissPharmaceuticalSociety2000 was invoked but never defined (see the help page).

[pmid2670517-1] O'Brien JJ, Benfield P (August 1989). "Dezocine. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy". Drugs. 38 (2): 226–48. doi:10.2165/00003495-198938020-00005. PMID 2670517. S2CID 195697572.

[pmid34141081-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h Childers WE, Abou-Gharbia MA (June 2021). ""I'll Be Back": The Resurrection of Dezocine". ACS Med Chem Lett. 12 (6): 961–968. doi:10.1021/acsmedchemlett.1c00233. PMC 8201756. PMID 34141081.

[pmid1348168-3] Zacny JP, Lichtor JL, de Wit H (April 1992). "Subjective, behavioral, and physiologic responses to intravenous dezocine in healthy volunteers". Anesthesia and Analgesia. 74 (4): 523–30. doi:10.1213/00000539-199204000-00010. PMID 1348168. S2CID 34394471.

[Westmoreland1991-4] Westmoreland C (August 1991). "Opioid agonist-antagonists". Current Opinion in Anesthesiology. 4 (4): 556–562. doi:10.1097/00001503-199108000-00017.

[5] "Espacenet". Espacenet Patent Search.

[SwissPharmaceuticalSociety2000-6] Cite error: The named reference SwissPharmaceuticalSociety2000 was invoked but never defined (see the help page).

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