Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H28N4O.C4H4O4 |
Molecular Weight | 456.5347 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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=SORAZNWVQFKAFD-IBIFCFAISA-N
InChI=1S/C20H28N4O.C4H4O4/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)/b;2-1-/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 |
---|---|---|
Partial dopamine agonist therapy of levodopa-induced dyskinesias. | 1992 Jun |
|
Effects of terguride, a partial D2 agonist, on MPTP-lesioned parkinsonian cynomolgus monkeys. | 1993 May |
|
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 |
|
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 |
|
Agonism at 5-HT2B receptors is not a class effect of the ergolines. | 2005 Apr 25 |
|
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 |
|
Pharmacological properties of a wide array of ergolines at functional alpha(1)-adrenoceptor subtypes. | 2008 Jan |
|
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
37686-85-4
Created by
admin on Sat Dec 16 18:48:14 GMT 2023 , Edited by admin on Sat Dec 16 18:48:14 GMT 2023
|
PRIMARY | |||
|
m10577
Created by
admin on Sat Dec 16 18:48:14 GMT 2023 , Edited by admin on Sat Dec 16 18:48:14 GMT 2023
|
PRIMARY | Merck Index | ||
|
20839521
Created by
admin on Sat Dec 16 18:48:14 GMT 2023 , Edited by admin on Sat Dec 16 18:48:14 GMT 2023
|
PRIMARY | |||
|
253-625-8
Created by
admin on Sat Dec 16 18:48:14 GMT 2023 , Edited by admin on Sat Dec 16 18:48:14 GMT 2023
|
PRIMARY | |||
|
SUB04725MIG
Created by
admin on Sat Dec 16 18:48:14 GMT 2023 , Edited by admin on Sat Dec 16 18:48:14 GMT 2023
|
PRIMARY | |||
|
100000084813
Created by
admin on Sat Dec 16 18:48:14 GMT 2023 , Edited by admin on Sat Dec 16 18:48:14 GMT 2023
|
PRIMARY | |||
|
U5WJP6R7AH
Created by
admin on Sat Dec 16 18:48:14 GMT 2023 , Edited by admin on Sat Dec 16 18:48:14 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD