Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H28N4O |
Molecular Weight | 340.4625 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C[C@@H](CN2C)NC(=O)N(CC)CC
InChI
InChIKey=JOAHPSVPXZTVEP-YXJHDRRASA-N
InChI=1S/C20H28N4O/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14/h6-8,11,14,16,18,21H,4-5,9-10,12H2,1-3H3,(H,22,25)/t14-,16+,18+/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22049464Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/terguride.html | https://www.ncbi.nlm.nih.gov/pubmed/2571729 | https://www.ncbi.nlm.nih.gov/pubmed/11520375 | https://www.ncbi.nlm.nih.gov/pubmed/3127243
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22049464
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/terguride.html | https://www.ncbi.nlm.nih.gov/pubmed/2571729 | https://www.ncbi.nlm.nih.gov/pubmed/11520375 | https://www.ncbi.nlm.nih.gov/pubmed/3127243
Terguride (INN), also known as trans-dihydrolisuride, is a serotonin receptor antagonist and dopamine receptor agonist of the ergoline family. Terguride is approved for and used in the treatment of hyperprolactinemia. Terguride is an oral, potent antagonist of 5-HT2B and 5-HT2A (serotonin) receptors. Serotonin stimulates the proliferation of pulmonary artery smooth muscle cells and induces fibrosis in the wall of pulmonary arteries. Together, this causes vascular remodeling and narrowing of the pulmonary arteries. These changes result in increased vascular resistance and PAH. Due to the potential anti-proliferative and anti-fibrotic activity of terguride, this potential medicine could offer the hope of achieving reversal of pulmonary artery vascular remodeling and attenuation of disease progression. In May 2008, terguride was granted orphan drug status for the treatment of pulmonary arterial hypertension. In May 2010 Pfizer purchased worldwide rights for the drug.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2571729 |
25.0 nM [IC50] | ||
Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2571729 |
4.0 nM [IC50] | ||
Target ID: CHEMBL265 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2571729 |
69.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Teluron Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Behavioural profile of partial D2 dopamine receptor agonists. 1. Atypical inhibition of d-amphetamine-induced locomotor hyperactivity and stereotypy. | 1991 |
|
Antagonist effect of terguride in Parkinson's disease. | 1991 Oct |
|
Effect of D1 and D2 agonists and antagonists on dyskinesia produced by L-dopa in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated monkeys. | 1991 Oct |
|
Terguride attenuates prolactin levels and ameliorates insulin sensitivity and insulin binding in obese spontaneously hypertensive rats. | 2001 |
|
A dopamine partial agonist and antagonist block amphetamine self-administration in a progressive ratio schedule. | 2001 Apr |
|
Effects of dopamine d2 receptor agonists in a pituitary transplantation-induced hyperprolactinaemia/anovulation model in rats. | 2001 Aug |
|
Dopamine partial agonist reverses amphetamine withdrawal in rats. | 2001 Nov |
|
[Results of treatment for male prolactinomas]. | 2002 Dec |
|
Terguride treatment attenuated prolactin release and enhanced insulin receptor affinity and GLUT 4 content in obese spontaneously hypertensive female, but not male rats. | 2002 Jun |
|
Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. III. Agonist and antagonist properties at serotonin, 5-HT(1) and 5-HT(2), receptor subtypes. | 2002 Nov |
|
[Pharmacokinetic/pharmacodynamic analysis of anti-hyperprolactinemic effect of terguride based on dopamine D2 receptor occupancy]. | 2003 Apr |
|
Effects of a partial dopamine D2-like agonist on the cocaine-induced behavioral sensitization of preweanling rats. | 2003 Aug |
|
Suppression of cocaine- and food-maintained behavior by the D2-like receptor partial agonist terguride in squirrel monkeys. | 2003 Mar |
|
Management of restless legs syndrome by the partial D2-agonist terguride. | 2003 Sep |
|
Influence of steric hindrance on enantioseparation of Dns-amino acids and pesticides on terguride based chiral selectors in capillary electrophoresis. | 2005 May |
|
Aripiprazole's low intrinsic activities at human dopamine D2L and D2S receptors render it a unique antipsychotic. | 2005 May 16 |
|
Effects of a partial D2-like receptor agonist on striatal dopamine autoreceptor functioning in preweanling rats. | 2006 Feb 16 |
|
Effects of terguride, ropinirole, and acetyl-L-carnitine on methamphetamine withdrawal in the rat. | 2006 Mar |
|
The partial dopamine D2-like receptor agonist terguride functions as an agonist in preweanling rats after a 5-day reserpine regimen. | 2006 Mar |
|
Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer. | 2008 Dec |
|
Recruitment of beta-arrestin2 to the dopamine D2 receptor: insights into anti-psychotic and anti-parkinsonian drug receptor signaling. | 2008 Jun |
|
Characterization of aripiprazole partial agonist activity at human dopamine D3 receptors. | 2008 Nov 12 |
|
Co-administration of the partial dopamine D2 agonist terguride with L-dopa attenuates L-dopa-induced locomotor sensitization in hemiparkinsonian mice. | 2009 Sep 14 |
|
Development and application of an LC-MS/MS method for measuring the effect of (partial) agonists on cAMP accumulation in vitro. | 2010 Apr 30 |
|
The dopamine D(2) partial agonist and antagonist terguride decreases heroin self-administration on fixed- and progressive-ratio schedules. | 2010 Dec |
|
Evaluation of the efficacy and safety of terguride in patients with fibromyalgia syndrome: results of a twelve-week, multicenter, randomized, double-blind, placebo-controlled, parallel-group study. | 2010 Jan |
|
Increased expression of 5-hydroxytryptamine2A/B receptors in idiopathic pulmonary fibrosis: a rationale for therapeutic intervention. | 2010 Nov |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3127243
Terguride was given orally in doses of 0.25 mg, 0.5 mg, and 1 mg.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22049464
Collagen synthesis activity was assessed by measuring the incorporation of [3H]proline as follows: 3 x 104 cells were seeded in 24-well plates and grown overnight in DMEM/F12 medium supplemented with 10% dialyzed fetal calf serum and penicillin/streptomycin. The medium was replaced with a low serum concentration of 0.5%. After 48 h the cells were incubated in DMEM/F12 supplemented with 10 mkM phenelzine (a nonselective monoamine oxidase inhibitor) and 0.6 mM ascorbic acid. 5-HT (in the absence and presence of terguride) and terguride alone were added. Terguride was added 30 min before 5-HT. Cells were then incubated for 48 h in the presence of 1 mkCi/ml [3H]proline. Cells were washed twice with ice-cold PBS before precipitation with ice-cold 10% trichloroacetic acid for 1 h at 4°C. The precipitates were solubilized in 0.3 N NaOH/0.1% SDS solution at 37°C under gentle agitation, mixed with scintillation cocktail, and measured in a beta-scintillation counter. Experiments were performed in triplicate or quadruplicate. Results are presented as fold-changes compared with untreated control cells.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
G02CB06
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
||
|
FDA ORPHAN DRUG |
380512
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
||
|
FDA ORPHAN DRUG |
255007
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
||
|
NCI_THESAURUS |
C47794
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
||
|
EU-Orphan Drug |
EU/3/13/1104
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
||
|
WHO-VATC |
QG02CB06
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
||
|
NCI_THESAURUS |
C66884
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000091952
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
2601
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
56
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
253-624-2
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
5437
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
Terguride
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
SUB10923MIG
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
CHEMBL73151
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
C006208
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
37686-84-3
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
443951
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
m10577
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | Merck Index | ||
|
DB13399
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
C152567
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
DTXSID3045809
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY | |||
|
21OJT43Q88
Created by
admin on Fri Dec 15 15:58:45 UTC 2023 , Edited by admin on Fri Dec 15 15:58:45 UTC 2023
|
PRIMARY |
ACTIVE MOIETY