Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C28H39N3O3 |
| Molecular Weight | 465.6276 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@@H](CN1CC[C@](C)([C@@H](C)C1)C2=CC(O)=CC=C2)NC(=O)[C@H]3CC4=C(CN3)C=C(O)C=C4
InChI
InChIKey=ZLVXBBHTMQJRSX-VMGNSXQWSA-N
InChI=1S/C28H39N3O3/c1-18(2)26(30-27(34)25-13-20-8-9-24(33)12-21(20)15-29-25)17-31-11-10-28(4,19(3)16-31)22-6-5-7-23(32)14-22/h5-9,12,14,18-19,25-26,29,32-33H,10-11,13,15-17H2,1-4H3,(H,30,34)/t19-,25+,26+,28+/m0/s1
| Molecular Formula | C28H39N3O3 |
| Molecular Weight | 465.6276 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT01431586?term=JDTIC&rank=1
Curator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT01431586?term=JDTIC&rank=1
JDTic demonstrated high affinity for the kappa opioid receptor in the binding assay and highly potent and selective kappa antagonism in the [(35)S]GTP-gamma-S assay. This drug was in phase I of clinical trials for the treatment of cocaine abuse, but development was stopped because of incidence of non-sustained ventricular tachycardia.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Identification of (3R)-7-hydroxy-N-((1S)-1-[[(3R,4R)-4-(3-hydroxyphenyl)- 3,4-dimethyl-1-piperidinyl]methyl]-2-methylpropyl)-1,2,3,4-tetrahydro- 3-isoquinolinecarboxamide as a novel potent and selective opioid kappa receptor antagonist. | 2003 Jul 3 |
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| Pharmacological properties of JDTic: a novel kappa-opioid receptor antagonist. | 2004 Oct 6 |
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| Synthesis and in vitro opioid receptor functional antagonism of methyl-substituted analogues of (3R)-7-hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). | 2009 Dec 10 |
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| Analogues of (3R)-7-hydroxy-N-[(1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic). Synthesis and in vitro and in vivo opioid receptor antagonist activity. | 2010 Jul 22 |
|
| Effectiveness of analogs of the kappa opioid receptor antagonist (3R)-7-hydroxy-N-((1S)-1-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl}-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide (JDTic) to reduce U50,488-induced diuresis and stress-induced cocaine reinstatement in rats. | 2010 Jun |
Patents
Sample Use Guides
In Vitro Use Guide
Curator's Comment: JDTic demonstrated high affinity for the κ receptor in the binding assay and highly potent and selective κ antagonism in the [35S]GTP-γ-S assay. In the [35S]GTP-γ-S functional assay, JDTic demonstrated a 3.4-fold increase in κ antagonist potency relative to the functional assay utilizing guinea pig membranes.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:49:12 UTC 2023
by
admin
on
Sat Dec 16 01:49:12 UTC 2023
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| Record UNII |
3C6FZ6UXC8
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| Record Status |
Validated (UNII)
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| Record Version |
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361444-66-8
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JDTIC
Created by
admin on Sat Dec 16 01:49:12 UTC 2023 , Edited by admin on Sat Dec 16 01:49:12 UTC 2023
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PRIMARY | This study has been terminated.(No further subjects will be enrolled due to adverse events.) | ||
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3C6FZ6UXC8
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DTXSID70433301
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9956146
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admin on Sat Dec 16 01:49:12 UTC 2023 , Edited by admin on Sat Dec 16 01:49:12 UTC 2023
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JDTIC
Created by
admin on Sat Dec 16 01:49:12 UTC 2023 , Edited by admin on Sat Dec 16 01:49:12 UTC 2023
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PRIMARY | JDTic is a selective, long-acting ("inactivating") antagonist of the .KAPPA.-opioid receptor (KOR). JDTic is a 4-phenylpiperidine derivative, distantly related structurally to analgesics such as pethidine and ketobemidone, and more closely to the MOR antagonist alvimopan. In addition, it is structurally distinct from other KOR antagonists such as norbinaltorphimine. | ||
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JDTIC
Created by
admin on Sat Dec 16 01:49:12 UTC 2023 , Edited by admin on Sat Dec 16 01:49:12 UTC 2023
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PRIMARY | Kappa Antagonist JDTic in Phase 1 Clinical Trial |
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TARGET -> AGONIST |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
When JDTic was administered either s.c. or p.o. 24 h before the selective KOP (kappa)-opioid receptor agonist, enadoline, AD(50s) of 4.1 and 27.3, respectively, were obtained. A time-course study of JDTic versus enadoline indicated significant antagonist p.o. activity up to 28 days.
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