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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
Structure of TERGURIDE HYDROGEN MALEATE

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

HIDE SMILES / InChI

Description
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.

Originator

Sources: Collection of Czechoslovak Chemical Communications Volume 25, Pages 1922-8, Journal, 1960

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
25.0 nM [IC50]
4.0 nM [IC50]
69.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Teluron

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

Terguride was given orally in doses of 0.25 mg, 0.5 mg, and 1 mg.
Route of Administration: Oral
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
TERGURIDE HYDROGEN MALEATE
MI  
Common Name English
SH-406
Code English
VUFB-6638
Code English
MYSALFON
Brand Name English
TERGURIDE HYDROGEN MALEATE [MI]
Common Name English
N,N-DIETHYL-N'-(D-6-METHYL-10.ALPHA.-ISOERGOLIN-8-YL)UREA HYDROGEN MALEATE
Common Name English
DIRONYL
Brand Name English
TERGURIDE HYDROGENMALEATE
WHO-DD  
Common Name English
ZK-31224
Code English
UREA, N,N-DIETHYL-N'-((8.ALPHA.)-6-METHYLERGOLIN-8-YL)-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Terguride hydrogenmaleate [WHO-DD]
Common Name English
Code System Code Type Description
CAS
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
MERCK INDEX
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
PUBCHEM
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
ECHA (EC/EINECS)
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
EVMPD
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
SMS_ID
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
FDA UNII
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