RITANSERIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H25F2N3OS
Molecular Weight	477.569
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(CCN2CCC(CC2)=C(C3=CC=C(F)C=C3)C4=CC=C(F)C=C4)C(=O)N5C=CSC5=N1

InChI

InChIKey=JUQLTPCYUFPYKE-UHFFFAOYSA-N

InChI=1S/C27H25F2N3OS/c1-18-24(26(33)32-16-17-34-27(32)30-18)12-15-31-13-10-21(11-14-31)25(19-2-6-22(28)7-3-19)20-4-8-23(29)9-5-20/h2-9,16-17H,10-15H2,1H3

HIDE SMILES / InChI

Molecular Formula	C27H25F2N3OS
Molecular Weight	477.569
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10069551
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8974378 | https://www.ncbi.nlm.nih.gov/pubmed/3109453 | http://onlinelibrary.wiley.com/doi/10.1002/ddr.430250106/pdf | https://www.ncbi.nlm.nih.gov/pubmed/11141696 | https://www.ncbi.nlm.nih.gov/pubmed/18801405

Ritanserin (INN, USAN, BAN) is a serotonin receptor antagonist which was never marketed for clinical use but has been used in scientific research. In humans, ritanserin increases deep slow-wave sleep, improved liveliness in a variety of psychiatric disorders and facilitated participation in behaviour therapy. During clinical trials, unexpected observations indicated that ritanserin may be of value in treating obsessive-compulsive disorder, acute mania, negative symptoms of schizophrenia, drug addicts, etc. Clinical observations confirmed the efficacy of ritanserin in the chronic withdrawal phase after detoxification from ethanol. Ritanserin had been in phase III clinical trials by Janssen L.P. for the treatment of anxiety disorder and major depressive disorder. However, the clinical development of ritanserin was discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19754201	Antagonist 2778	251.2 nM [Kd]
Serotonin 2c (5-HT2c) receptor 124 Target ID: CHEMBL225 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18282705	Antagonist 2778	1.8 nM [Ki]
Serotonin 7 (5-HT7) receptor 31 Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12825922	Antagonist 2778	45.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Cushing’s disease 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11141696	Primary	Not Provided 504	Unknown Approved Use Unknown
Negative symptoms of schizophrenia 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18801405	Primary	Not Provided 504	Unknown Approved Use Unknown
Acute mania 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12816549	Primary	Not Provided 504	Unknown Approved Use Unknown
Cocaine-related disorders 19 Sources: https://clinicaltrials.gov/ct2/show/NCT00000187	Primary	Phase II 1132	Unknown Approved Use Unknown
Narcolepsy 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12905101	Primary	Not Provided 504	Unknown Approved Use Unknown
Alcohol addiction 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10069551	Primary	Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
121 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/1910052	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		RITANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
73.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1910052	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		RITANSERIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
3867 ng × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/1910052	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		RITANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2031 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1910052	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		RITANSERIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
41 h REVIEW https://pubmed.ncbi.nlm.nih.gov/1910052	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		RITANSERIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
39.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1910052	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		RITANSERIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY115039	https://www.001chemical.com/chem/search?q=DY115039
1PlusChem LLC	1P008E6B	https://www.1pchem.com/search?query=1P008E6B
AK Scientific	3726AC	https://aksci.com/item_detail.php?cat=3726AC
ApexBio Technology	B6898	https://www.apexbt.com/catalogsearch/result/?q=B6898
AstaTech	55492	http://astatechinc.com/CPSResult.php?CRNO=55492
BLD Pharm	BD150457	http://www.bldpharm.com/search/Search.html?keyword=BD150457
BOC Sciences	87051-43-2	http://www.bocsci.com/description.asp?cas=87051-43-2
Cayman Chemical	21374	http://www.caymanchem.com/app/template/Product.vm/catalog/21374
Chem Scene	CS-0002823	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0002823
ChemShuttle	105099	https://www.chemshuttle.com/catalogsearch/result/?q=105099
Matrix Scientific	98269	http://www.matrixscientific.com/098269.html
MedChem Express	HY-10791	https://www.medchemexpress.com/search.html?q=HY-10791&ft=&fa=&fp=
MolPort	MolPort-003-666-486	https://www.molport.com/shop/molecule-link/MolPort-003-666-486
Molcore	MC115039	http://www.molcore.com/CatMC115039.html
MuseChem	R049212	https://www.musechem.com/product/R049212.html
ShangHai Biochempartner	BCP13728	http://www.biochempartner.com/search_BCP13728
Tetrahedron	TS72361	http://www.thsci.com/search.do?q=TS72361
Tocris	1955	https://www.tocris.com/search.php?Type=QuickSearch&Value=1955
eMolecules	594025	https://orderbb.emolecules.com/search/#?query=594025
eNovation Chemicals	D381321	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D381321&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1911638043	https://mcule.com/MCULE-1911638043/
mcule	MCULE-9424377828	https://mcule.com/MCULE-9424377828/

PubMed

Title	Date	PubMed
The effect of Psilocybe cubensis extract on hippocampal neurons in vitro.	2001	11962085
Serotonergic modulation of ventilation and upper airway stability in obese Zucker rats.	2001 Apr	11316658
Fenfluramine-induced pulmonary vasoconstriction: role of serotonin receptors and potassium channels.	2001 Aug	11457791
Serotonin 2A receptor regulation of striatal neuropeptide gene expression is selective for tachykinin, but not enkephalin neurons following dopamine depletion.	2001 Aug 15	11483243
m-CPP hypolocomotion is selectively antagonized by compounds with high affinity for 5-HT(2C) receptors but not 5-HT(2A) or 5-HT(2B) receptors.	2001 Dec	11856898
A randomized, double-blind, placebo-controlled study of ritanserin pharmacotherapy for cocaine dependence.	2001 Jan 1	11137283
Potent serotonin (5-HT)(2A) receptor antagonists completely prevent the development of hyperthermia in an animal model of the 5-HT syndrome.	2001 Jan 26	11164765
The antidepressant activity of inositol in the forced swim test involves 5-HT(2) receptors.	2001 Jan 8	11163636
Serotonin-based pharmacotherapy for acute neuroleptic-induced akathisia: a new approach to an old problem.	2001 Jul	11435260
On the mechanism of tolerance to morphine-induced Straub tail reaction in mice.	2001 Jul-Aug	11509199
Affinity of serotonin receptor antagonists and agonists to recombinant and native alpha1-adrenoceptor subtypes.	2001 Jun	11459121
Role of 5-HT(1A) and 5-HT(7) receptors in the facilitatory response induced by 8-OH-DPAT on learning consolidation.	2001 Jun	11275281
The GR127935-sensitive 5-HT(1) receptors mediating canine internal carotid vasoconstriction: resemblance to the 5-HT(1B), but not to the 5-HT(1D) or 5-ht(1F), receptor subtype.	2001 Mar	11226129
Evidence for 5-HT(1B/1D) and 5-HT(2A) receptors mediating constriction of the canine internal carotid circulation.	2001 Mar	11226128
Embryonic cocaine exposure and corticosterone: serotonin(2) receptor mediation.	2001 May-Jun	11420070
Assessment of affinity and dissociation ability of a newly synthesized 5-HT2 antagonist, AT-1015: comparison with other 5-HT2 antagonists.	2001 Nov	11885967
5-HT(2A/2C) receptor-mediated hypopnea in the newborn rat: relationship to Fos immunoreactivity.	2001 Nov	11641454
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.	2001 Oct	11561066
Effect of 5-HT1A and 5-HT2A/2C receptor modulation on neuroleptic-induced vacuous chewing movements.	2001 Sep 28	11779040
Effect of SB-243213, a selective 5-HT(2C) receptor antagonist, on the rat sleep profile: a comparison to paroxetine.	2002 Apr	11888551
Functional cooperation between neurosteroids and D2 dopamine antagonists on KCl-evoked [3H]noradrenaline release: modulation by calcium channel blockers.	2002 Dec	12472876
Smooth muscle 5-HT2A receptors mediating contraction of porcine isolated proximal stomach strips.	2002 Dec	12466231
5-HT(1B) but not 5-HT(6) or 5-HT(7) receptors mediate depression of spinal nociceptive reflexes in vitro.	2002 Feb	11861321
Methiothepin attenuates gastric secretion and motility effects of vagal stimulants at the dorsal vagal complex.	2002 Feb 1	11834248
Calcium-antagonistic activity of sumatriptan in the rat anococcygeus muscle.	2002 Jan	11731721
Acute and long-term effects of the 5-HT2 receptor antagonist ritanserin on EEG power spectra, motor activity, and sleep: changes at the light-dark phase shift.	2002 Jul 5	12088844
Erratum to "CNS drugs in Cushing's disease: pathophysiological and therapeutic implications for mood disorders" [Prog. Neuro-Psycol. Biol. Psychiatry, 26, 763 (2002)].	2002 Jun	12369251
Ritanserin antagonism of m-chlorophenylpiperazine effects in neuroleptic-free schizophrenics patients: support for serotonin-2 receptor modulation of schizophrenia symptoms.	2002 Jun	12107618
The human 5-HT7 serotonin receptor splice variants: constitutive activity and inverse agonist effects.	2002 Mar	11906971
The atypical 5-HT2 receptor mediating tachycardia in pithed rats: pharmacological correlation with the 5-HT2A receptor subtype.	2002 Mar	11906967
Effect of a 5-HT(2C) serotonin agonist, dexnorfenfluramine, on amyloid precursor protein metabolism in guinea pigs.	2002 Sep 27	12231467
Anxiolytic effect of ting-chih-wan in mouse behavior models of anxiety.	2003	12723754
5-HT2 and 3 receptor antagonists suppress the response of rat type I slowly adapting mechanoreceptor: an in vitro study.	2003 Apr 18	12676383
Localization of serotonin and its possible role in early embryos of Tritonia diomedea(Mollusca: Nudibranchia).	2003 Feb	12596045
Characterization of the 5-hydroxytryptamine receptors mediating contraction in the pig isolated intravesical ureter.	2003 Jan	12522083

Patents

Sample Use Guides

In Vivo Use Guide

2.5 mg, 5 mg or 10 mg ritanserin given once daily over 6 months

Route of Administration: Oral

In Vitro Use Guide

HeLa and human glioblastoma cells, U87 and U251, were treated as follows: 4 and 40 mkM of R59022 and ritanserin, 40 mkM ketanserin, and 100 nM PMA for 30 min with and without pretreatment with 500 nM bisindolylmaleimide II for 1 h. For additional PKC activation experiments, HeLa cells were treated with 10 mkM TCB-2 for 6 h with and without co-treatment with 40 mkM ketanserin, 40 mkM ketanserin alone, and 500 nM bisindolylmaleimide II for 1 h. The cells were lysed in IPBB, 20 mM Tris-HCl pH 7.5, 150 mM NaCl, 1% Triton X-100 and protease inhibitors and the cell lysate was cleared by centrifugation at 16,000g for 10 min.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:21:31 UTC 2023` Edited by `admin` on `Sat Dec 16 16:21:31 UTC 2023`
Record UNII	145TFV465S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RITANSERIN

Official Name

English

ritanserin [INN]

Common Name

English

5H-THIAZOLO(3,2-A)PYRIMIDIN-5-ONE, 6-(2-(4-BIS(4-FLUOROPHENYL)METHYLENE)-1-PIPERIDINYL)ETHYL)-7-METHYL-

Common Name

English

TISERTON

Brand Name

English

Ritanserin [WHO-DD]

Common Name

English

RITANSERIN [MART.]

Common Name

English

R-55667

Code

English

NSC-758470

Code

English

RITANSERIN [USAN]

Common Name

English

RITANSERIN [VANDF]

Common Name

English

6-(2-(4-(BIS(P-FLUOROPHENYL)METHYLENE)-PIPERIDINO)ETHYL)-7-METHYL-5H-THIAZOLO-(3,2-A)PYRIMIDIN-5-ONE

Common Name

English

R 55,667

Code

English

RITANSERIN [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66885