BUPRENORPHINE

Search structure
Synonyms:
Status: Approved (1981)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N02AE01
UNII: 40D3SCR4GZ

Structure
InChI Key RMRJXGBAOAMLHD-CTAPUXPBSA-N
Smile CO[C@@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1Cc4ccc(O)c5c4[C@@]3(CCN1CC1CC1)[C@H]2O5
InChI
InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H41NO4
Molecular Weight 467.65
AlogP 4.41
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 62.16
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 34.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Kappa opioid receptor agonist
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 7585.78-7943.28 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Opioid receptor
0.11-14.8 0.41-0.59 - 0.09-1.585 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Opioid-Related Disorders 4 D009293 ClinicalTrials
Substance-Related Disorders 4 D019966 ClinicalTrials
Heroin Dependence 3 D006556 ClinicalTrials
Neonatal Abstinence Syndrome 3 D009357 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Cocaine-Related Disorders 3 D019970 ClinicalTrials
Morphine Dependence 3 D009021 ClinicalTrials
Substance Withdrawal Syndrome 3 D013375 ClinicalTrials
Back Pain 3 D001416 ClinicalTrials
Neuralgia 3 D009437 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Intervertebral Disc Degeneration 3 D055959 ClinicalTrials
Depressive Disorder, Major 3 D003865 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Stress Disorders, Post-Traumatic 2 D013313 ClinicalTrials
Rotator Cuff Injuries 2 D000070636 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Toothache 2 D014098 ClinicalTrials
Amphetamine-Related Disorders 2 D019969 ClinicalTrials
Schizophrenia 2 D012559 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials

Related Entries

Scaffolds

Cross References

Resources Reference
ChEMBL CHEMBL511142
FDA SRS 40D3SCR4GZ
PubChem 9848990
SureChEMBL SCHEMBL15820
ZINC ZINC000100373348
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