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Details

Stereochemistry ACHIRAL
Molecular Formula C24H27FN2O
Molecular Weight 378.4824
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEBRANOPADOL

SMILES

CN(C)[C@]1(CC[C@@]2(CC1)OCCC3=C2NC4=CC=C(F)C=C34)C5=CC=CC=C5

InChI

InChIKey=CSMVOZKEWSOFER-RQNOJGIXSA-N
InChI=1S/C24H27FN2O/c1-27(2)23(17-6-4-3-5-7-17)11-13-24(14-12-23)22-19(10-15-28-24)20-16-18(25)8-9-21(20)26-22/h3-9,16,26H,10-15H2,1-2H3/t23-,24-

HIDE SMILES / InChI

Molecular Formula C24H27FN2O
Molecular Weight 378.4824
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cebranopadol is a novel analgesic nociceptin/orphanin FQ peptide (NOP) and opioid receptor agonist. Cebranopadol, by its combination of agonism at NOP and opioid receptors, affords highly potent and efficacious analgesia in various pain models with a favorable side effect profile. Cebranopadol displays analgesic, antiallodynic and antihyperalgesic properties in several rat models of acute nociceptive, inflammatory, cancer and neuropathic pain. Unlike morphine, cebranopadol did not disrupt motor coordination and respiration at doses within and exceeding the analgesic dose range possessing a broader therapeutic window than classical opioids. It is currently in clinical development for the treatment of severe chronic nociceptive and neuropathic pain.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
13.0 nM [EC50]
1.2 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
891 pg/mL
1200 μg 1 times / day steady-state, oral
CEBRANOPADOL plasma
Homo sapiens
1119 pg/mL
1600 μg 1 times / day steady-state, oral
CEBRANOPADOL plasma
Homo sapiens
255 pg/mL
400 μg 1 times / day steady-state, oral
CEBRANOPADOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
14474 pg × h/mL
1200 μg 1 times / day steady-state, oral
CEBRANOPADOL plasma
Homo sapiens
18785 pg × h/mL
1600 μg 1 times / day steady-state, oral
CEBRANOPADOL plasma
Homo sapiens
4260 pg × h/mL
400 μg 1 times / day steady-state, oral
CEBRANOPADOL plasma
Homo sapiens

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Cebranopadol 200 ug to 1000 ug per day taken once a day in the morning for 26 weeks in patients suffering from cancer-related pain
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
7GDW9S3GN3
Record Status Validated (UNII)
Record Version