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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/25147603

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P41146
Gene ID: 4987.0
Gene Symbol: OPRL1
Target Organism: Homo sapiens (Human)
13.0 nM [EC50]
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
1.2 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
891 pg/mL
1200 μg 1 times / day steady-state, oral
dose: 1200 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEBRANOPADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1119 pg/mL
1600 μg 1 times / day steady-state, oral
dose: 1600 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEBRANOPADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
255 pg/mL
400 μg 1 times / day steady-state, oral
dose: 400 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEBRANOPADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14474 pg × h/mL
1200 μg 1 times / day steady-state, oral
dose: 1200 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEBRANOPADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
18785 pg × h/mL
1600 μg 1 times / day steady-state, oral
dose: 1600 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEBRANOPADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4260 pg × h/mL
400 μg 1 times / day steady-state, oral
dose: 400 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CEBRANOPADOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Discovery of a Potent Analgesic NOP and Opioid Receptor Agonist: Cebranopadol.
2014 Aug 14
Cebranopadol: a novel potent analgesic nociceptin/orphanin FQ peptide and opioid receptor agonist.
2014 Jun
Cebranopadol : a first-in-class potent analgesic agent with agonistic activity at nociceptin/orphanin FQ and opioid receptors.
2015 Jun
Simultaneous targeting of multiple opioid receptor types.
2015 Jun
Cebranopadol: a first in-class example of a nociceptin/orphanin FQ receptor and opioid receptor agonist.
2015 Mar
Cebranopadol: novel dual opioid/NOP receptor agonist analgesic.
2017 Feb
Patents

Patents

Sample Use Guides

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
Created
by admin
on Thu Jul 06 01:26:26 UTC 2023
Edited
by admin
on Thu Jul 06 01:26:26 UTC 2023
Record UNII
7GDW9S3GN3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEBRANOPADOL
INN   USAN  
USAN   INN  
Official Name English
CEBRANOPADOL [USAN]
Common Name English
GRT6005
Code English
cebranopadol [INN]
Common Name English
GRT-6005
Code English
TRANS-6'-FLUORO-N,N-DIMETHYL-4-PHENYL-4',9''-DIHYDRO-3'H-SPIRO(CYCLOHEXANE-1,1'-PYRANO(3,4-B)INDOL)-4-AMINE
Common Name English
SPIRO(CYCLOHEXANE-1,1'(3'H)-PYRANO(3,4-B)INDOL)-4-AMINE, 6'-FLUORO-4',9'-DIHYDRO-N,N-DIMETHYL-4-PHENYL-, TRANS-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
Code System Code Type Description
USAN
ZZ-140
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
NCI_THESAURUS
C112002
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
CAS
863513-91-1
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID001031965
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
PUBCHEM
11848225
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
DRUG BANK
DB12830
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
FDA UNII
7GDW9S3GN3
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
SMS_ID
300000034106
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
INN
9631
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
ChEMBL
CHEMBL2364605
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
WIKIPEDIA
Cebranopadol
Created by admin on Thu Jul 06 01:26:26 UTC 2023 , Edited by admin on Thu Jul 06 01:26:26 UTC 2023
PRIMARY
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