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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
Structure of RITANSERIN TARTRATE

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

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency
251.2 nM [Kd]
1.8 nM [Ki]
45.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
121 ng/mL
10 mg single, oral
RITANSERIN plasma
Homo sapiens
73.6 ng/mL
10 mg single, oral
RITANSERIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3867 ng × h/mL
10 mg single, oral
RITANSERIN plasma
Homo sapiens
2031 ng × h/mL
10 mg single, oral
RITANSERIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
41 h
10 mg single, oral
RITANSERIN plasma
Homo sapiens
39.2 h
10 mg single, oral
RITANSERIN plasma
Homo sapiens

PubMed

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.