Fluphenazine

Structural formula
General
Non-proprietary name	Fluphenazine
other names	4- [3- (2-trifluoromethylphenothiazin-10-yl) propyl] -1-piperazineethanol
Molecular formula	C 22 H 26 F 3 N 3 OS (fluphenazine) ; C 22 H 26 F 3 N 3 OS 2HCl (fluphenazine di hydrochloride ) ; C 32 H 44 F 3 N 3 O 2 S (fluphenazine decanoate) ;
Brief description	white solid (dihydrochloride)
External identifiers / databases
EC number	200-702-9
ECHA InfoCard	100,000,639
PubChem	3372
ChemSpider	3255
DrugBank	DB00623
Wikidata	Q58376
Drug information
ATC code	N05 AB02
Drug class	Neuroleptic
properties
Molar mass	437.52 g mol −1 (fluphenazine) ; 510.44 g mol −1 (fluphenazine dihydrochloride) ; 591.77 g mol −1 (fluphenazine decanoate) ;
Physical state	firmly
Melting point	235–237 ° C or 224.5–226 ° C (fluphenazine dihydrochloride)
boiling point	269-274 ° C (66.5 Pa)
pK s value	8.05
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 301-360
	P: 201-301 + 310-308 + 313
Toxicological data	220 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fluphenazine is a drug from the phenothiazine group that is used as a neuroleptic . It was the active ingredient in the first depot neuroleptic, which was introduced in the United States in 1967 as Prolixin .

Clinical information

Application areas (indications)

Fluphenazine is a neuroleptic that is commercially available for oral and parenteral administration. It is used:

as a long-term therapeutic agent for symptom suppression in chronic schizophrenic psychoses and for relapse prophylaxis in phasic schizophrenic psychoses
in acute psychotic syndromes with delusions , hallucinations, thought disorders , thought experience and ego disorders
at catatonic schizophrenia
in chronic endogenous psychoses (symptom suppression and relapse prophylaxis)
for the therapy of psychomotor agitation

Other Information

Chemical and pharmaceutical information

Fluphenazine is produced in a multi-step synthesis starting from 1- (3-hydroxypropyl) piperazine. The active ingredient is used as a dihydrochloride .

history

Fluphenazine was first patented by Squibb in 1956 ; In 1961 it was introduced in the FRG in tablet form under the trade names Omca and Lyogen. In 1968 the ester of fluphenazine with decanoic acid was brought onto the market under the trade name Dapotum D as the first depot neuroleptic . Fluphenazine is now commercially available as a generic .

doping

Fluphenazine is used in veterinary medicine as a sedative, in addition to the preparation for anesthesia z. B. to rest animals during transport. The use of fluphenazine to calm horses in dressage competitions is, however, prohibited as doping .

Side effects

The undesirable side effects include the so-called extrapyramidal syndrome , which has strong similarities to motor changes that occur in Parkinson's disease , such as muscle stiffness , tremors , slow motor skills and restlessness. Some of these symptoms resolve after stopping the drug. However, persistent and sometimes permanent motor disorders can also occur. As with other neuroleptics, other undesirable effects relate to anticholinergic effects.

Trade names

Monopreparations

Lyogen (D) and a generic (D)

literature

Florian Holsboer; Gerhard founder; Otto Benkert: Manual of psychopharmacotherapy: with 155 tables . Springer, Heidelberg 2008, ISBN 978-3-540-20475-6

Individual evidence

↑ ^a ^b ^c data sheet Fluphenazine dihydrochloride from Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).
^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, pp. 716-717, ISBN 978-0-911910-00-1 .
↑ ^a ^b ^c ^d ^e Entry on Fluphenazine. In: Römpp Online . Georg Thieme Verlag, accessed on July 2, 2019.
↑ Entry on fluphenazine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , 4th edition (2000) 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.
↑ Mutschler, drug effects, 9th edition, Wissenschaftliche Verlagsgesellschaft Stuttgart, 2008 ISBN 978-3-8047-1952-1
↑ epsy.de: Psychopharmaka Zeittafel .
^ Robert M. Julien: Drugs and Psychotropic Drugs. Spektrum Akademischer Verlag, 1997, ISBN 3-8274-0044-9 . P. 292.
↑ Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt. Volume 116, Issue 29 f. (July 22) 2019, pp. 508-517, p. 511.

[sigma-1] ta sheet Fluphenazine dihydrochloride from Sigma-Aldrich , accessed on April 2, 2011 ( PDF ).

[Merckedex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, pp. 716-717, ISBN 978-0-911910-00-1 .

[römpp-3] Entry on Fluphenazine. In: Römpp Online . Georg Thieme Verlag, accessed on July 2, 2019.

[ChemIDplus-4] Entry on fluphenazine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Kleemann-5] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , 4th edition (2000) 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.

[6] Mutschler, drug effects, 9th edition, Wissenschaftliche Verlagsgesellschaft Stuttgart, 2008 ISBN 978-3-8047-1952-1

[7] sy.de: Psychopharmaka Zeittafel .

[8] Robert M. Julien: Drugs and Psychotropic Drugs. Spektrum Akademischer Verlag, 1997, ISBN 3-8274-0044-9 . P. 292.

[9] Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt. Volume 116, Issue 29 f. (July 22) 2019, pp. 508-517, p. 511.