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
Molecular Formula | C20H28N4O |
Molecular Weight | 340.4625 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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Behavioural profile of partial D2 dopamine receptor agonists. 1. Atypical inhibition of d-amphetamine-induced locomotor hyperactivity and stereotypy. | 1991 |
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Antagonist effect of terguride in Parkinson's disease. | 1991 Oct |
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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 |
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Partial dopamine agonist therapy of levodopa-induced dyskinesias. | 1992 Jun |
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Effects of several partial dopamine D2 receptor agonists in Cebus apella monkeys previously treated with haloperidol. | 1993 Jun 24 |
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Effects of terguride, a partial D2 agonist, on MPTP-lesioned parkinsonian cynomolgus monkeys. | 1993 May |
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Effects of terguride on anterior pituitary function in parkinsonian patients treated with L-dopa: a double-blind study versus placebo. | 1996 Feb |
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Clinical features and medical treatment of male prolactinomas. | 2001 |
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A dopamine partial agonist and antagonist block amphetamine self-administration in a progressive ratio schedule. | 2001 Apr |
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Dopamine partial agonist reverses amphetamine withdrawal in rats. | 2001 Nov |
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Reinforcing effects of D2 dopamine receptor agonists and partial agonists in rhesus monkeys. | 2001 Oct 1 |
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[Results of treatment for male prolactinomas]. | 2002 Dec |
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Clustered ergot alkaloids modulate cell-mediated cytotoxicity. | 2002 Feb |
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Atypical kinetics for a series of putative dopamine antagonists to reverse the low-magnitude Ca2+ phase in the dopamine-bound D2short receptor state. | 2002 Jan |
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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 |
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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 |
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Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. II. Agonist and antagonist properties at subtypes of dopamine D(2)-like receptor and alpha(1)/alpha(2)-adrenoceptor. | 2002 Nov |
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Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes. | 2002 Nov |
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[Pharmacokinetic/pharmacodynamic analysis of anti-hyperprolactinemic effect of terguride based on dopamine D2 receptor occupancy]. | 2003 Apr |
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Effects of a partial dopamine D2-like agonist on the cocaine-induced behavioral sensitization of preweanling rats. | 2003 Aug |
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[Arrest of lactation after 2nd trimester abortion with a single dose of cabergoline in comparison with 10-day administration of teguride]. | 2003 Jan |
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Suppression of cocaine- and food-maintained behavior by the D2-like receptor partial agonist terguride in squirrel monkeys. | 2003 Mar |
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Management of restless legs syndrome by the partial D2-agonist terguride. | 2003 Sep |
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Effects of terguride treatment on glucose abnormalities induced by ischemic brain damage in SHR/N-cp lean Koletsky strain and in rats of Wistar strain. | 2004 |
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Pergolide, terguride and N,N'-spacer-linked oligomers of both interact with 5-HT2A receptors of rat tail artery. | 2004 |
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In vitro antiplasmodial activities of semisynthetic N,N'-spacer-linked oligomeric ergolines. | 2004 Feb 15 |
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The partial D2-like dopamine receptor agonist terguride acts as a functional antagonist in states of high and low dopaminergic tone: evidence from preweanling rats. | 2005 Apr |
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Agonism at 5-HT2B receptors is not a class effect of the ergolines. | 2005 Apr 25 |
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Buprenorphine and a CRF1 antagonist block the acquisition of opiate withdrawal-induced conditioned place aversion in rats. | 2005 Jan |
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Influence of steric hindrance on enantioseparation of Dns-amino acids and pesticides on terguride based chiral selectors in capillary electrophoresis. | 2005 May |
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Aripiprazole's low intrinsic activities at human dopamine D2L and D2S receptors render it a unique antipsychotic. | 2005 May 16 |
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Pre- and postsynaptic actions of a partial D2 receptor agonist in reserpinized young rats: longevity of agonistic effects. | 2006 Dec 8 |
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Effects of a partial D2-like receptor agonist on striatal dopamine autoreceptor functioning in preweanling rats. | 2006 Feb 16 |
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Effects of terguride, ropinirole, and acetyl-L-carnitine on methamphetamine withdrawal in the rat. | 2006 Mar |
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The partial dopamine D2-like receptor agonist terguride functions as an agonist in preweanling rats after a 5-day reserpine regimen. | 2006 Mar |
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[A case of ruptured internal carotid artery aneurysm mimicking pituitary apoplexy]. | 2007 Dec |
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Long-term serotonin effects in the rat are prevented by terguride. | 2007 Oct 4 |
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Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. | 2008 Jan |
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Recruitment of beta-arrestin2 to the dopamine D2 receptor: insights into anti-psychotic and anti-parkinsonian drug receptor signaling. | 2008 Jun |
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The effect of terguride in carbon tetrachloride-induced liver fibrosis in rat. | 2008 Nov |
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Characterization of aripiprazole partial agonist activity at human dopamine D3 receptors. | 2008 Nov 12 |
|
Dopamine receptor subtypes contribution to Homer1a induction: insights into antipsychotic molecular action. | 2009 Aug 1 |
|
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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:58:45 UTC 2023
by
admin
on
Fri Dec 15 15:58:45 UTC 2023
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Record UNII |
21OJT43Q88
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
G02CB06
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FDA ORPHAN DRUG |
380512
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FDA ORPHAN DRUG |
255007
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NCI_THESAURUS |
C47794
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EU-Orphan Drug |
EU/3/13/1104
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WHO-VATC |
QG02CB06
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NCI_THESAURUS |
C66884
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100000091952
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2601
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56
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253-624-2
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5437
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Terguride
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SUB10923MIG
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CHEMBL73151
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C006208
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37686-84-3
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443951
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m10577
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DB13399
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C152567
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DTXSID3045809
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21OJT43Q88
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Related Record | Type | Details | ||
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TARGET->PARTIAL AGONIST |
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TARGET->PARTIAL AGONIST |
Ki
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TARGET->PARTIAL AGONIST |
Emax = 90%
EC50
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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