Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H25F2N3OS.C4H6O6 |
| Molecular Weight | 627.656 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC1=C(CCN2CCC(CC2)=C(C3=CC=C(F)C=C3)C4=CC=C(F)C=C4)C(=O)N5C=CSC5=N1
InChI
InChIKey=NJKCCYRWKDAVQS-LREBCSMRSA-N
InChI=1S/C27H25F2N3OS.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h2-9,16-17H,10-15H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
| Molecular Formula | C4H6O6 |
| Molecular Weight | 150.0868 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| 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 |
DescriptionCurator'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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL214 |
251.2 nM [Kd] | ||
Target ID: CHEMBL225 |
1.8 nM [Ki] | ||
Target ID: CHEMBL3155 |
45.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
121 ng/mL |
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 |
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
41 h |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| RS-127445: a selective, high affinity, orally bioavailable 5-HT2B receptor antagonist. | 1999 Jul |
|
| New developments in the pharmacotherapy of alcohol dependence. | 2001 |
|
| Serotonergic modulation of ventilation and upper airway stability in obese Zucker rats. | 2001 Apr |
|
| A 5-HT(7) receptor-mediated depolarization in the anterodorsal thalamus. I. Pharmacological characterization. | 2001 Apr |
|
| Human 5-HT(5) receptors: the 5-HT(5A) receptor is functional but the 5-HT(5B) receptor was lost during mammalian evolution. | 2001 Apr 27 |
|
| 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 |
|
| Serotonin localization in Phallusia mammillata larvae and effects of 5-HT antagonists during larval development. | 2001 Dec |
|
| Effects of the 5-HT(6) receptor antagonist Ro 04-6790 on learning consolidation. | 2001 Jan 8 |
|
| The antidepressant activity of inositol in the forced swim test involves 5-HT(2) receptors. | 2001 Jan 8 |
|
| An investigation of the mechanisms responsible for acute fluoxetine-induced anxiogenic-like effects in mice. | 2001 Jun |
|
| The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution. | 2001 Jun |
|
| Role of 5-HT(1A) and 5-HT(7) receptors in the facilitatory response induced by 8-OH-DPAT on learning consolidation. | 2001 Jun |
|
| Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor. | 2001 Oct |
|
| Effect of SB-243213, a selective 5-HT(2C) receptor antagonist, on the rat sleep profile: a comparison to paroxetine. | 2002 Apr |
|
| Effects of sarpogrelate, a novel 5-HT2 antagonist, on 5-HT-induced endothelium-dependent relaxations in porcine coronary artery. | 2002 Aug |
|
| Methiothepin attenuates gastric secretion and motility effects of vagal stimulants at the dorsal vagal complex. | 2002 Feb 1 |
|
| 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 |
|
| 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 |
|
| Ritanserin antagonism of m-chlorophenylpiperazine effects in neuroleptic-free schizophrenics patients: support for serotonin-2 receptor modulation of schizophrenia symptoms. | 2002 Jun |
|
| Nefazodone treatment of dysthymic disorder an open, long-term, prospective pilot study. | 2002 May |
|
| Differential regulation of hippocampal BDNF mRNA by typical and atypical antipsychotic administration. | 2002 Nov 1 |
|
| Benefits and risks of pharmacotherapy for dysthymia: a systematic appraisal of the evidence. | 2003 |
|
| 5-HT2 and 3 receptor antagonists suppress the response of rat type I slowly adapting mechanoreceptor: an in vitro study. | 2003 Apr 18 |
|
| Characterization of the 5-hydroxytryptamine receptors mediating contraction in the pig isolated intravesical ureter. | 2003 Jan |
|
| Evidence that central 5-HT2A and 5-HT2B/C receptors regulate 5-HT cell firing in the dorsal raphe nucleus of the anaesthetised rat. | 2003 Jul |
|
| Mirtazapine in L-dopa-induced dyskinesias. | 2003 Jul-Aug |
|
| Ritanserin as an adjunct to lithium and haloperidol for the treatment of medication-naive patients with acute mania: a double blind and placebo controlled trial. | 2003 Jun 19 |
Sample Use Guides
2.5 mg, 5 mg or 10 mg ritanserin given once daily over 6 months
Route of Administration:
Oral
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
Edited
Sat Dec 16 09:49:29 GMT 2023
by
admin
on
Sat Dec 16 09:49:29 GMT 2023
|
| Record UNII |
01K37QO47K
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
13519970
Created by
admin on Sat Dec 16 09:49:29 GMT 2023 , Edited by admin on Sat Dec 16 09:49:29 GMT 2023
|
PRIMARY | |||
|
93076-39-2
Created by
admin on Sat Dec 16 09:49:29 GMT 2023 , Edited by admin on Sat Dec 16 09:49:29 GMT 2023
|
PRIMARY | |||
|
m9633
Created by
admin on Sat Dec 16 09:49:29 GMT 2023 , Edited by admin on Sat Dec 16 09:49:29 GMT 2023
|
PRIMARY | Merck Index | ||
|
01K37QO47K
Created by
admin on Sat Dec 16 09:49:29 GMT 2023 , Edited by admin on Sat Dec 16 09:49:29 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
