Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H28N4O.C4H4O4.H2O |
Molecular Weight | 474.55 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OC(=O)\C=C/C(O)=O.[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C[C@@H](CN2C)NC(=O)N(CC)CC
InChI
InChIKey=FFZZPXNWIVRTAW-UWRDHRKBSA-N
InChI=1S/C20H28N4O.C4H4O4.H2O/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;5-3(6)1-2-4(7)8;/h6-8,11,14,16,18,21H,4-5,9-10,12H2,1-3H3,(H,22,25);1-2H,(H,5,6)(H,7,8);1H2/b;2-1-;/t14-,16+,18+;;/m0../s1
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
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 |
---|---|---|
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 |
|
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 |
|
Effects of several partial dopamine D2 receptor agonists in Cebus apella monkeys previously treated with haloperidol. | 1993 Jun 24 |
|
Terguride attenuates prolactin levels and ameliorates insulin sensitivity and insulin binding in obese spontaneously hypertensive rats. | 2001 |
|
Clinical features and medical treatment of male prolactinomas. | 2001 |
|
A dopamine partial agonist and antagonist block amphetamine self-administration in a progressive ratio schedule. | 2001 Apr |
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Effects of dopamine d2 receptor agonists in a pituitary transplantation-induced hyperprolactinaemia/anovulation model in rats. | 2001 Aug |
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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 |
|
[Results of treatment for male prolactinomas]. | 2002 Dec |
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Clustered ergot alkaloids modulate cell-mediated cytotoxicity. | 2002 Feb |
|
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 |
|
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 |
|
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 |
|
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 |
|
Effects of a partial dopamine D2-like agonist on the cocaine-induced behavioral sensitization of preweanling rats. | 2003 Aug |
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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 |
|
Pergolide, terguride and N,N'-spacer-linked oligomers of both interact with 5-HT2A receptors of rat tail artery. | 2004 |
|
In vitro antiplasmodial activities of semisynthetic N,N'-spacer-linked oligomeric ergolines. | 2004 Feb 15 |
|
Buprenorphine and a CRF1 antagonist block the acquisition of opiate withdrawal-induced conditioned place aversion in rats. | 2005 Jan |
|
Aripiprazole's low intrinsic activities at human dopamine D2L and D2S receptors render it a unique antipsychotic. | 2005 May 16 |
|
In vitro characterization of SLV308 (7-[4-methyl-1-piperazinyl]-2(3H)-benzoxazolone, monohydrochloride): a novel partial dopamine D2 and D3 receptor agonist and serotonin 5-HT1A receptor agonist. | 2006 Dec 15 |
|
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 |
|
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 |
|
Effects of aripiprazole and terguride on dopamine synthesis in the dorsal striatum and medial prefrontal cortex of preweanling rats. | 2008 |
|
Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. | 2008 Jan |
|
Recruitment of beta-arrestin2 to the dopamine D2 receptor: insights into anti-psychotic and anti-parkinsonian drug receptor signaling. | 2008 Jun |
|
Dopamine receptor subtypes contribution to Homer1a induction: insights into antipsychotic molecular action. | 2009 Aug 1 |
|
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 |
|
LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor. | 2010 Feb |
|
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.
Substance Class |
Chemical
Created
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Edited
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Record UNII |
MVI7KL5PLQ
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Record Status |
Validated (UNII)
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Record Version |
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ANHYDROUS->SOLVATE |