Dinalbuphine sebacate

Dinalbuphine sebacate
Clinical data
Other namesDNS; Nalbuphine sebacate; Sebacoyldinalbuphine; SDN; Sebacoyl dinalbuphine ester; SDE; LT-1001
Routes of
administration		Intramuscular injection
Drug classOpioid analgesic
Pharmacokinetic data
Bioavailability• IMTooltip Intramuscular injection: 85.4% (relative to nalbuphine)
MetabolismHydrolysis
MetabolitesNalbuphine
Elimination half-life• DNS: 83.2 hours (mean absorption time: 145.2 hours)
• Nalbuphine: 4.0 hours
Identifiers
  • Bis[(4R,4aS,7S,7aR,12bS)-3-(cyclobutylmethyl)-4a,7-dihydroxy-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-9-yl] decanedioate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC52H68N2O10
Molar mass881.120 g·mol−1
3D model (JSmol)
  • C1CC(C1)CN2CC[C@]34[C@@H]5[C@H](CC[C@]3([C@H]2CC6=C4C(=C(C=C6)OC(=O)CCCCCCCCC(=O)OC7=C8C9=C(C[C@@H]1[C@]2([C@]9(CCN1CC1CCC1)[C@@H](O8)[C@H](CC2)O)O)C=C7)O5)O)O
  • InChI=1S/C52H68N2O10/c55-35-19-21-51(59)39-27-33-15-17-37(45-43(33)49(51,47(35)63-45)23-25-53(39)29-31-9-7-10-31)61-41(57)13-5-3-1-2-4-6-14-42(58)62-38-18-16-34-28-40-52(60)22-20-36(56)48-50(52,44(34)46(38)64-48)24-26-54(40)30-32-11-8-12-32/h15-18,31-32,35-36,39-40,47-48,55-56,59-60H,1-14,19-30H2/t35-,36-,39+,40+,47-,48-,49-,50-,51+,52+/m0/s1
  • Key:ALOIOAGKUOQNID-ITCIXCFHSA-N

Dinalbuphine sebacate (DNS), also known as nalbuphine sebacate or as sebacoyl dinalbuphine ester (SDE) and sold under the brand name Naldebain, is a non-controlled opioid analgesic which is used as a 7-day long-acting injection in the treatment of moderate to severe postoperative pain.

The compound is a diester of nalbuphine (Nubain) joined via a sebacic acid linker, and acts as a long-lasting prodrug of nalbuphine via slow hydrolysis. It was developed to extend the duration of action of nalbuphine, which has a short duration and requires frequent injections. Whereas nalbuphine must be injected every 4 to 6 hours, a single injection of DNS lasts for up to 7 to 10 days.

It was invented by Professor Oliver Yoa-Pu Hu (National Defense Medical Center) and codeveloped with Lumosa Therapeutics. Naldebain received market approvals from Taiwan FDA in March 2017, Health Sciences Authority of Singapore in December 2020, the Ministry of Public Health of Thailand in December 2021, the Drug Control Authority of Malaysia in 2022, State Service of Ukraine on Medicines and Drugs Control and Brunei Darussalam Medicines Control Authority (BDMCA) in 2023. Development is ongoing in the United States, China, Korea, and the Philippines.

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