TEFLUDAZINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H24F4N2O
Molecular Weight	408.4324
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCCN1CCN(CC1)[C@@H]2C[C@H](C3=C2C=C(C=C3)C(F)(F)F)C4=CC=C(F)C=C4

InChI

InChIKey=JSBWGXQXCRYYTG-PZJWPPBQSA-N

InChI=1S/C22H24F4N2O/c23-17-4-1-15(2-5-17)19-14-21(28-9-7-27(8-10-28)11-12-29)20-13-16(22(24,25)26)3-6-18(19)20/h1-6,13,19,21,29H,7-12,14H2/t19-,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H24F4N2O
Molecular Weight	408.4324
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2894601 | Stromgaard Kristian, Krogsgaard-Larsen Povl, Madsen Ulf, Textbook of Drug Design and Discovery, p. 304, retrieved from: https://books.google.ru/books?id=YLPMBQAAQBAJ&pg=PA304&lpg=PA304&dq=TEFLUDAZINE&source=bl&ots=TzCd5nt5s5&sig=ACfU3U2NL776eiheTbeH97vWeHJsVpvkPw&hl=ru&sa=X&ved=2ahUKEwi5oeisgaXjAhWZ7KYKHXS1Cds4ChDoATAAegQICRAB#v=onepage&q=TEFLUDAZINE&f=false

Tefludazine (Lu 18-012) is a mixed D2 and 5-HT2 receptor antagonist that was developed as a potential antipsychotic compound. It was shown that tefludazine induced a dose-dependent decrease in both nigra pars compacta (SNC) and ventral tegmental area (VTA) dopamine (DA) activity. The development of the drug was discontinued in Phase I due to toxicological findings in dogs.

Approval Year

PubMed

Title	Date	PubMed
Antihypertensive activity in a series of 1-piperazino-3-phenylindans with potent 5-HT2-antagonistic activity.	1988-12	2903929
Conformational analysis and structural comparisons of (1R,3S)-(+)- and (1S,3R)-(-)-tefludazine, (S)-(+)- and (R)-(-)-octoclothepin, and (+)-dexclamol in relation to dopamine receptor antagonism and amine-uptake inhibition.	1988-02	2892932
Differential effects after repeated treatment with haloperidol, clozapine, thioridazine and tefludazine on SNC and VTA dopamine neurones in rats.	1988	2894601
Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans.	1983-07	6134833

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:29:48 GMT 2025` Edited by `admin` on `Wed Apr 02 08:29:48 GMT 2025`
Record UNII	2XUS19W8FE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEFLUDAZINE

Official Name

English

LU-18-012

Preferred Name

English

TRANS-4-(3-(P-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)-1-INDANYL)-1-PIPERAZINEETHANOL

Common Name

English

1-PIPERAZINEETHANOL, 4-((1R,3S)-3-(4-FLUOROPHENYL)-2,3-DIHYDRO-6-(TRIFLUOROMETHYL)-1H-INDEN-1-YL)-, REL-

Systematic Name

English

1-PIPERAZINEETHANOL, 4-(3-(4-FLUOROPHENYL)-2,3-DIHYDRO-6-(TRIFLUOROMETHYL)-1H-INDEN-1-YL)-, TRANS-(±)-

Systematic Name

English

tefludazine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66883