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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
Structure of JDTIC

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

HIDE SMILES / InChI
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

Description
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

Unknown
127998
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2737
 0.3 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Pharmacological properties of JDTic: a novel kappa-opioid receptor antagonist.
2004 Oct 6
Differential effects of the novel kappa opioid receptor antagonist, JDTic, on reinstatement of cocaine-seeking induced by footshock stressors vs cocaine primes and its antidepressant-like effects in rats.
2005 Nov
Effects of JDTic, a selective kappa-opioid receptor antagonist, on the development and expression of physical dependence on morphine using a rat continuous-infusion model.
2005 Nov 7
Patents

Patents

06974824
2
20020132828
2

Sample Use Guides

In Vivo Use Guide
Single dose: 1 mg, 3 mg, or 10 mg
Route of Administration: Oral
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 Sat Dec 17 12:55:08 UTC 2022
Edited
by admin
on Sat Dec 17 12:55:08 UTC 2022
Record UNII
3C6FZ6UXC8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
JDTIC
Common Name English
RTI-JDTIC
Common Name English
(3R)-7-HYDROXY-N-((2S)-1-((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYLPIPERIDIN-1-YL)-3-METHYLBUTAN-2-YL)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXAMIDE
Systematic Name English
3-ISOQUINOLINECARBOXAMIDE, 1,2,3,4-TETRAHYDRO-7-HYDROXY-N-((1S)-1-(((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYL-1-PIPERIDINYL)METHYL)-2-METHYLPROPYL)-, (3R)-
Systematic Name English
Code System Code Type Description
CAS
361444-66-8
Created by admin on Sat Dec 17 12:55:08 UTC 2022 , Edited by admin on Sat Dec 17 12:55:08 UTC 2022
PRIMARY
CLINICAL_TRIALS.GOV
JDTIC
Created by admin on Sat Dec 17 12:55:08 UTC 2022 , Edited by admin on Sat Dec 17 12:55:08 UTC 2022
PRIMARY This study has been terminated.(No further subjects will be enrolled due to adverse events.)
FDA UNII
3C6FZ6UXC8
Created by admin on Sat Dec 17 12:55:08 UTC 2022 , Edited by admin on Sat Dec 17 12:55:08 UTC 2022
PRIMARY
EPA CompTox
DTXSID70433301
Created by admin on Sat Dec 17 12:55:08 UTC 2022 , Edited by admin on Sat Dec 17 12:55:08 UTC 2022
PRIMARY
PUBCHEM
9956146
Created by admin on Sat Dec 17 12:55:08 UTC 2022 , Edited by admin on Sat Dec 17 12:55:08 UTC 2022
PRIMARY
WIKIPEDIA
JDTIC
Created by admin on Sat Dec 17 12:55:08 UTC 2022 , Edited by admin on Sat Dec 17 12:55:08 UTC 2022
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.
MANUFACTURER PRODUCT INFORMATION
JDTIC
Created by admin on Sat Dec 17 12:55:08 UTC 2022 , Edited by admin on Sat Dec 17 12:55:08 UTC 2022
PRIMARY Kappa Antagonist JDTic in Phase 1 Clinical Trial
Related Record Type Details
KAPPA-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
Related Record Type Details
Structure of JDTIC
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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