U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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.

CNS Activity

Originator

Approval Year

Unknown
127998
Targets

Targets

Primary TargetPharmacologyConditionPotency
Nociceptin receptor
14
Target ID: P41146
Gene ID: 4987.0
Gene Symbol: OPRL1
Target Organism: Homo sapiens (Human)
Agonist
2637
 13.0 nM [EC50]
Mu-type opioid receptor
61
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
Agonist
2637
 1.2 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Phase III
651
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
891 pg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28623508
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28623508
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28623508
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28623508
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28623508
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28623508
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
1PlusChem LLC
1P00GUJ3
https://www.1pchem.com/search?query=1P00GUJ3
AChemBlock
I-9462
http://www.achemblock.com/catalogsearch/result/?q=I-9462
Angene
AGN-PC-0V4DMB
http://www.angenechemical.com/productshow/AGN-PC-0V4DMB.html
AstaTech
42183
http://astatechinc.com/CPSResult.php?CRNO=42183
Chem Scene
CS-1323
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1323
Chem Scene
CS-6129
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6129
ChemShuttle
157283
https://www.chemshuttle.com/catalogsearch/result/?q=157283
Combi-Blocks
QJ-6161
http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-6161
Excenen
EX-A1095
http://www.excenen.com/searchresultlist.php?id=EX-A1095
KeyOrganics
AS-35183
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35183
Lab Network
LN01342690
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342690
MedChem Express
HY-15536
https://www.medchemexpress.com/search.html?q=HY-15536A&ft=&fa=&fp=
MedChem Express
HY-15536A
https://www.medchemexpress.com/search.html?q=HY-15536A&ft=&fa=&fp=
MolPort
MolPort-039-063-422
https://www.molport.com/shop/molecule-link/MolPort-039-063-422
MolPort
MolPort-046-417-064
https://www.molport.com/shop/molecule-link/MolPort-046-417-064
Molnova
M16252
https://www.molnova.com/en/serch-list.html?keywords=M16252
MuseChem
I005180
https://www.musechem.com/product/I005180.html
MuseChem
I005181
https://www.musechem.com/product/I005181.html
ShangHai Biochempartner
BCP001152
http://www.biochempartner.com/search_BCP001152
ShangHai Biochempartner
BCP09612
http://www.biochempartner.com/search_BCP09612
Toronto Research Chemicals
C228810
https://www.trc-canada.com/product-detail/?CatNum=C228810
eMolecules
194972304
https://orderbb.emolecules.com/search/#?query=194972304
eMolecules
301142128
https://orderbb.emolecules.com/search/#?query=301142128
eMolecules
313127473
https://orderbb.emolecules.com/search/#?query=313127473
eNovation Chemicals
D497609
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D497609&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals
D621132
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D621132&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals
D621209
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D621209&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals
D621211
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D621211&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-3938014218
https://mcule.com/MCULE-3938014218/
PubMed

PubMed

TitleDatePubMed
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
Patents

Patents

20060004034
3

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
Created
by admin
on Fri Dec 16 23:54:37 UTC 2022
Edited
by admin
on Fri Dec 16 23:54:37 UTC 2022
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 Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
Code System Code Type Description
USAN
ZZ-140
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
NCI_THESAURUS
C112002
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
CAS
863513-91-1
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
EPA CompTox
DTXSID001031965
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
PUBCHEM
11848225
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
DRUG BANK
DB12830
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
FDA UNII
7GDW9S3GN3
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
INN
9631
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
ChEMBL
CHEMBL2364605
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
WIKIPEDIA
Cebranopadol
Created by admin on Fri Dec 16 23:54:37 UTC 2022 , Edited by admin on Fri Dec 16 23:54:37 UTC 2022
PRIMARY
Related Record Type Details
KAPPA-TYPE OPIOID RECEPTOR
AGONIST -> TARGET
DELTA-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
BINDING
Ki
KAPPA-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
BINDING
Ki
MU-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
BINDING
Ki
NOCICEPTIN RECEPTOR
TARGET -> AGONIST
BINDING
Ki
Related Record Type Details
Structure of CEBRANOPADOL
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966