Chlorprothixene (Cloxan , Taractan , Truxal ) is a typical antipsychotic drug of the thioxanthene class and was the first of the series to be synthesized.[1] It was introduced in 1959 by Lundbeck .[2]
Chlorprothixene is not approved for use in the United States.
Pharmacology [ edit ]
Chlorprothixene exerts strong antagonism at the following receptors :
5-HT2 : antipsychotic effects, anxiolysis, weight gain
D1 , D2 , D3 : antipsychotic effects, sedation, extrapyramidal side effects, prolactin increase, depression, apathy/anhedonia, weight gain
H1 : sedation, weight gain
mACh : anticholinergic effects, inhibition of extrapyramidal side effects
α1 -adrenergic : hypotension, tachycardia
Chlorprothixene does also act as FIASMA (functional inhibitor of acid sphingomyelinase ).[3]
One metabolite of chlorprothixene is N -desmethylchlorprothixene.
Structure of
N -desmethylchlorprothixene
Indications [ edit ]
Chlorprothixene's principal indications are the treatment of psychotic disorders (e.g. schizophrenia ) and of acute mania occurring as part of bipolar disorders .
Other uses are pre- and postoperative states with anxiety and insomnia, severe nausea / emesis (in hospitalized patients), the amelioration of anxiety and agitation due to use of selective serotonin reuptake inhibitors for depression and, off-label, the amelioration of alcohol and opioid withdrawal. It may also be used cautiously to treat nonpsychotic irritability, aggression, and insomnia in pediatric patients.
An intrinsic antidepressant effect of chlorprothixene has been discussed, but not proven yet. Likewise, it is unclear, if chlorprothixene has genuine (intrinsic) analgesic effects. However, chlorprothixene can be used as comedication in severe chronic pain. Also, like most antipsychotics, chlorprothixene has antiemetic effects.
Side effects [ edit ]
Chlorprothixene has a strong sedative activity with a high incidence of anticholinergic side effects. The types of side effects encountered (dry mouth, massive hypotension and tachycardia , hyperhidrosis , substantial weight gain etc.) normally do not allow a full effective dose for the remission of psychotic disorders to be given. So cotreatment with another, more potent, antipsychotic agent is needed.
Chlorprothixene is structurally related to chlorpromazine , with which it shares, in principle, all side effects. Allergic side effects and liver damage seem to appear with an appreciable lower frequency. The elderly are particularly sensitive to anticholinergic side effects of chlorprothixene (precipitation of narrow angle glaucoma , severe obstipation, difficulties in urinating, confusional and delirant states). In patients >60 years the doses should be particularly low.
Early and late extrapyramidal side effects may occur but have been noted with a low frequency (one study with a great number of participants has delivered a total number of only 1%).
Overdosage [ edit ]
Overdose symptoms can be confusion, hypotension, and tachycardia, and several fatalities have been reported with concentrations in postmortem blood ranging from 0.1 to 7.0 mg/L compared to non-toxic levels in postmortem blood which can extend to 0.4 mg/kg.[4]
The initial doses of chlorprothixene should always be as low as possible (e.g. 30 mg at bedtime, 15 mg morning dose) and be increased gradually. Patients receiving 90 mg daily (and more) of the drug should be hospitalized, particularly during the initial phase of treatment. The theoretical maximum is 800 mg daily which can usually not be given due to side effects as stated above. Elderly and pediatric patients should be treated with particular low initial doses. Dose increments should be done slowly. If chlorprothixene is to be withdrawn, it should not be stopped abruptly, but the dose should be decreased steadily.
Interactions [ edit ]
Chlorprothixene may increase the plasma-level of concomitantly given lithium . In order to avoid lithium intoxication, lithium plasma levels should be monitored closely.
If chlorprothixene is given concomitantly with opioids , the opioid dose should be reduced (by approx. 50%), because chlorprothixene amplifies the therapeutic actions and side effects of opioids considerably.
Avoid the concomitant use of chlorprothixene and tramadol (Ultram). Seizures may be encountered with this combination.
Consider additive sedative effects and confusional states to emerge, if chlorprothixene is given with benzodiazepines or barbiturates . Choose particular low doses of these drugs.
Exert particular caution in combining chlorprothixene with other anticholinergic drugs (tricyclic antidepressants and antiparkinsonian agents): Particularly the elderly may develop delirium, high fever, severe obstipation , even ileus and glaucoma .
Synthesis [ edit ]
Chlorprothixene (2-chloro-9[(1-dimethylamino)-3-propyliden]thioxanthene) is made starting from 2-Chlorothioxanthone . 2-Chlorothioxantone, in turn, is prepared from 2-mercaptobenzoic acid (1 ), the reaction of which with 1-bromo-4-chlorobenzene (2 ) forms 2-(4-chlorophenylthio)benzoic acid 5 , which upon reaction with phosphorus pentachloride transforms into acid chloride (6 ), and further undergoes intramolecular cyclization with the use of aluminum chloride to give 2-chlorthioxantone (6 ).[5]
An alternative way of making 2-chlorthioxantone (7 ) is by making 2-(4-chlorophenylthio)benzoic acid (5 ) by reacting 2-iodobenzoic acid (3 ) with 4-chlorothiophenol (4 ).[6]
The resulting 2-chlorothioxantone is reacted as a carbonyl component with either 3-dimethylaminopropylmagnesiumbromide (see Engelhardt above), or with allylmagnesiumbromide, giving the corresponding tertiary alcohols 8 , and 9 .
Dehydration of the tertiary (8 ) is accomplished by acylation of the tertiary hydroxyl group using acetyl chloride and the subsequent pyrolysis of the formed acetate, which leads to the desired chlorprothixene. In the second case, dehydration of the tertiary alcohol (9 ) is accomplished by chlorination of the tertiary alcohol group by thionyl chloride , forming the diene 2-chloro-9-(3-propen-1-iliden)thioxanthene (10 ), the addition to which of dimethylamine at high temperature forms the desired chlorprothixene (11 ).
See also [ edit ]
References [ edit ]
^ Healy, David (1997). The antidepressant era . Cambridge: Harvard University Press. p. 182. ISBN 0-674-03958-0 .
^ Sneader, Walter (2005). Drug discovery: a history . New York: Wiley. p. 410. ISBN 0-471-89980-1 .
^ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P (2011). "Identification of novel functional inhibitors of acid sphingomyelinase" . PLoS ONE . 6 (8): e23852. doi :10.1371/journal.pone.0023852 . PMC 3166082 . PMID 21909365 .
^ Skov L, Johansen SS, Linnet K (Jan 2015). "Postmortem Femoral Blood Reference Concentrations of Aripiprazole, Chlorprothixene, and Quetiapine". Journal of Analytical Toxicology . 39 (1): 41–44. doi :10.1093/jat/bku121 . PMID 25342720 .
^ H. Spiegelberg, K. Doeben, DE 1044103 (1957).
^ E.L. Engelhardt, J.M. Sprague, U.S. Patent 2,951,082 (1960).
α1
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Trihexyphenidyl
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Non-generational: Atypical antipsychotics (e.g., aripiprazole , asenapine , clozapine , iloperidone , olanzapine , paliperidone , quetiapine , risperidone , ziprasidone , zotepine )
Tetracyclic antidepressants (e.g., amoxapine , loxapine , maprotiline , mianserin , mirtazapine , oxaprotiline )
Tricyclic antidepressants (e.g., amitriptyline , butriptyline , clomipramine , desipramine , dosulepin (dothiepin) , doxepin , imipramine , iprindole , lofepramine , nortriptyline , protriptyline , trimipramine )
Typical antipsychotics (e.g., chlorpromazine , flupenthixol , fluphenazine , loxapine , perphenazine , prochlorperazine , thioridazine , thiothixene )
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TGBA01AD
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2C-B-FLY
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AL-34662
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Antagonists: 5-I-R91150
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AC-90179
Adatanserin
Altanserin
AMDA
APD-215
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Deramciclane
Dotarizine
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Etoperidone
Fananserin
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Glemanserin
Irindalone
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KML-010
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LY-393558
Medifoxamine
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MIN-101
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S-14671
Sarpogrelate
Setoperone
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SR-46349B
TGBA01AD
Teniloxazine
Temanogrel
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
Trazodone
Tricyclic antidepressants (e.g., amitriptyline )
Typical antipsychotics (e.g., chlorpromazine , fluphenazine , haloperidol , loxapine , perphenazine , pimozide , pipamperone , prochlorperazine , thioridazine , thiothixene , trifluoperazine )
Volinanserin
Xylamidine
Yohimbine
5-HT2B
Agonists: 4-Methylaminorex
Aminorex
Amphetamines (eg., chlorphentermine , cloforex , dexfenfluramine , fenfluramine , levofenfluramine , norfenfluramine )
BW-723C86
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Ergolines (e.g., cabergoline , dihydroergocryptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
MDxx (e.g., MDA , MDMA , MDOH , MMDA )
Piperazines (e.g., mCPP )
PNU-22394
Ro60-0175
Serotonin (5-HT)
Tryptamines (e.g., 5-BT , 5-CT , 5-MT , α-Me-5-HT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
5-HT2C
Agonists: 2Cs (e.g., 2C-B , 2C-E , 2C-I , 2C-T-2 , 2C-T-7 , 2C-T-21 )
5-Methoxytryptamines (5-MeO-DET , 5-MeO-DiPT , 5-MeO-DMT , 5-MeO-DPT , 5-MT )
α-Alkyltryptamines (e.g., 5-Cl-αMT , 5-Fl-αMT , 5-MeO-αET , 5-MeO-αMT , α-Me-5-HT , αET , αMT )
A-372159
AL-38022A
Alstonine
CP-809101
Dimemebfe
DOx (e.g., DOB , DOC , DOI , DOM )
Ergolines (e.g., ALD-52 , cabergoline , dihydroergotamine , ergine (LSA) , ergotamine , lisuride , LA-SS-Az , LSB , LSD , LSD-Pip , LSH , LSP , pergolide )
Flumexadol
Lorcaserin
MDxx (e.g., MDA , MDMA , MDOH , MMDA )
MK-212
Org 12962
Org 37684
Oxaflozane
PHA-57378
Phenethylamines (e.g., lophophine , mescaline )
Piperazines (e.g., aripiprazole , BZP , mCPP , quipazine , TFMPP )
PNU-22394
PNU-181731
Ro60-0175
Ro60-0213
Serotonin (5-HT)
Tryptamines (e.g., 5-BT , 5-CT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
Vabicaserin
WAY-629
WAY-161503
YM-348
Antagonists: Adatanserin
Agomelatine
Atypical antipsychotics (e.g., asenapine , clorotepine , clozapine , fluperlapine , iloperidone , melperone , olanzapine , paliperidone , quetiapine , risperidone , sertindole , ziprasidone , zotepine )
Captodiame
CEPC
Cinanserin
Cyproheptadine
Deramciclane
Dotarizine
Eltoprazine
Ergolines (e.g., amesergide , bromocriptine , LY-53857 , LY-215840 , mesulergine , metergoline , methysergide , sergolexole )
Etoperidone
Fluoxetine
FR-260010
Irindalone
Ketanserin
Ketotifen
Latrepirdine (dimebolin)
Medifoxamine
Metitepine (methiothepin)
Nefazodone
Pirenperone
Pizotifen
Propranolol
Ritanserin
RS-102221
S-14671
SB-200646
SB-206553
SB-221284
SB-228357
SB-242084
SB-243213
SDZ SER-082
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
TIK-301
Trazodone
Tricyclic antidepressants (e.g., amitriptyline , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine , pimozide , pipamperone , thioridazine )
Xylamidine
5-HT3
Agonists: Alcohols (e.g., butanol , ethanol , trichloroethanol )
m-CPBG
Phenylbiguanide
Piperazines (e.g., BZP , mCPP , quipazine )
RS-56812
Serotonin (5-HT)
SR-57227
SR-57227A
Tryptamines (e.g., 2-Me-5-HT , 5-CT , bufotenidine (5-HTQ) )
Volatiles/gases (e.g., halothane , isoflurane , toluene , trichloroethane )
YM-31636
Antagonists: Alosetron
AS-8112
Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine )
Azasetron
Batanopride
Bemesetron (MDL-72222)
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
ICS-205930
Lerisetron
Memantine
Ondansetron
Palonosetron
Ramosetron
Renzapride
Ricasetron
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine , mianserin , mirtazapine )
Thujone
Tropanserin
Tropisetron
Typical antipsychotics (e.g., loxapine )
Volatiles/gases (e.g., nitrous oxide , sevoflurane , xenon )
Vortioxetine
Zacopride
Zatosetron
5-HT4
5-HT5A
5-HT6
Agonists: Ergolines (e.g., dihydroergocryptine , dihydroergotamine , ergotamine , lisuride , LSD , mesulergine , metergoline , methysergide )
Serotonin (5-HT)
Tryptamines (e.g., 2-Me-5-HT , 5-BT , 5-CT , 5-MT , Bufotenin , E-6801 , E-6837 , EMD-386088 , EMDT , LY-586713 , N-Me-5-HT , tryptamine )
WAY-181187
WAY-208466
Antagonists: ABT-354
Atypical antipsychotics (e.g., aripiprazole , asenapine , clorotepine , clozapine , fluperlapine , iloperidone , olanzapine , tiospirone )
AVN-101
AVN-211
AVN-322
AVN-397
BGC20-760
BVT-5182
BVT-74316
Cerlapirdine
EGIS-12233
GW-742457
Idalopirdine
Ketanserin
Latrepirdine (dimebolin)
Metitepine (methiothepin)
MS-245
PRX-07034
Ritanserin
Ro04-6790
Ro 63-0563
SB-258585
SB-271046
SB-357134
SB-399885
SB-742457
Tetracyclic antidepressants (e.g., amoxapine , mianserin )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine )
5-HT7
Antagonists: Atypical antipsychotics (e.g., amisulpride , aripiprazole , asenapine , clorotepine , clozapine , fluperlapine , olanzapine , risperidone , sertindole , tiospirone , ziprasidone , zotepine )
Butaclamol
DR-4485
EGIS-12233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857 , LY-215840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215840
Metitepine (methiothepin)
Ritanserin
SB-258719
SB-258741
SB-269970
SB-656104
SB-656104A
SB-691673
SLV-313
SLV-314
Spiperone
SSR-181507
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , imipramine )
Typical antipsychotics (e.g., acetophenazine , chlorpromazine , chlorprothixene , fluphenazine , loxapine , pimozide )
Vortioxetine