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 |
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Primary | Teluron Approved UseUnknown |
PubMed
Title | Date | PubMed |
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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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Dopamine partial agonist reverses amphetamine withdrawal in rats. | 2001 Nov |
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[Results of treatment for male prolactinomas]. | 2002 Dec |
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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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In vitro antiplasmodial activities of semisynthetic N,N'-spacer-linked oligomeric ergolines. | 2004 Feb 15 |
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Effects of aripiprazole and terguride on dopamine synthesis in the dorsal striatum and medial prefrontal cortex of preweanling rats. | 2008 |
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Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer. | 2008 Dec |
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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 |
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Dopamine receptor subtypes contribution to Homer1a induction: insights into antipsychotic molecular action. | 2009 Aug 1 |
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 GMT 2023
by
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on
Fri Dec 15 15:58:45 GMT 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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