Loxapine
Antipsychotic medication
Loxapine Trade names Loxitane, Adasuve AHFS /Drugs.com Monograph MedlinePlus a682311 License data
Routes of administration By mouth , inhalation , intramuscular Drug class Antipsychotic ATC code Legal status
Protein binding 96.8%[3] Metabolism Extensive Liver ; active metabolites include amoxapine and 8-hydroxyloxapine. Inhibits P-gp and is a substrate of CYP1A2 , CYP3A4 and CYP2D6 [3] Elimination half-life 4 hours (oral); 7.61 hours (inhalation)[3] Excretion Majority are excreted within 24 hours, main route through urine (conjugated metabolites), small amounts through the feces (unconjugated metabolites)
8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.016.215 Formula C 18 H 18 Cl N 3 O Molar mass 327.81 g·mol−1 3D model (JSmol ) Melting point 109 to 110 °C (228 to 230 °F)
Clc2ccc1Oc4c(/N=C(\c1c2)N3CCN(C)CC3)cccc4
InChI=1S/C18H18ClN3O/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3
Y Key:XJGVXQDUIWGIRW-UHFFFAOYSA-N
Y
N Y (what is this?) (verify)
Bottle containing loxapine capsules, a mid-potency antipsychotic.
Loxapine , sold under the brand names Loxitane and Adasuve (inhalation only) among others, is a tricyclic [4] antipsychotic medication used primarily in the treatment of schizophrenia . The medicine is a member of the dibenzoxazepine class and structurally very similar to clozapine . Several researchers have argued that loxapine, initially classified as a typical antipsychotic , behaves as an atypical antipsychotic .[5]
Loxapine may be metabolized by N -demethylation to amoxapine , a tricyclic antidepressant .[6]
Medical uses
The US Food and Drug Administration (FDA) has approved loxapine inhalation powder for the acute treatment of agitation associated with schizophrenia or bipolar I disorder in adults.[7]
A brief review of loxapine found no conclusive evidence that it was particularly effective in patients with schizophrenia .[8] A subsequent systematic review considered that the limited evidence did not indicate a clear difference in its effects from other antipsychotics.[9]
Loxapine can be taken by mouth .[10] It is also available as an intramuscular injection and as a powder for inhalation.[7] [10]
Side effects
Loxapine can cause side effects that are generally similar to that of other antipsychotic medications. These include, e.g., gastrointestinal problems (like constipation and abdominal pain), cardiovascular problems (like tachycardia), moderate likelihood of drowsiness (relative to other antipsychotics),[11] and movement problems (i.e. extrapyramidal symptoms [EPS]).[12] At lower dosages its propensity for causing EPS appears to be similar to that of atypical antipsychotics.[13] Although it is structurally similar to clozapine , it has much lower risk of agranulocytosis (which, even with clozapine, is 0.8%); however, mild and temporary fluctuations in blood leukocyte levels can occur.[14] [15] Abuse of loxapine has been reported.[16]
The inhaled formulation of loxapine carries a low risk for a type of airway adverse reaction called bronchospasm that is not thought to occur when loxapine is taken by mouth.[7]
Pharmacology
Mechanism of action
Some scientists say loxapine is a "mid-potency " typical antipsychotic.[15] However, unlike most other typical antipsychotics, it has significant potency at the 5HT2A receptor (6.6 nM), which is similar to atypical antipsychotics like clozapine (5.35 nM). The higher likelihood of EPS with loxapine, compared to clozapine, may be due to its higher affinity for the D2 receptor compared to clozapine , which has one of the lowest binding affinities at the D2 receptor of any antipsychotic.[15]
Loxapine (and metabolite)[17] [18]
Site
LOX
AMX Tooltip Amoxapine
5-HT1A
2,460
ND
5-HT1B
388
ND
5-HT1D
3,470
ND
5-HT1E
1,400
ND
5-HT2A
6.6
0.5
5-HT2C
13
2 (rat)
5-HT3
190
ND
5-HT5A
780
ND
5-HT6
31
50
5-HT7
88
40 (rat)
α1A
31
ND
α1B
53
ND
α2A
151
ND
α2B
108
ND
α2C
80
ND
β1
>10,000
ND
β2
>10,000
ND
M1
120
ND
M2
445
ND
M3
211
ND
M4
1,270
ND
M5
166
ND
D1
54
ND
D2
11
21
D3
19
21
D4
8.4
21
D5
75
ND
H1
2.2–4.9
7.9–25
H2
208
ND
H3
55,000
>100,000
H4
5,050–8,710
6,310
SERT Tooltip Serotonin transporter
>10,000
58
NET Tooltip Norepinephrine transporter
5,700
16
DAT Tooltip Dopamine transporter
>10,000
58
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.
Pharmacokinetics
Loxapine is metabolized to amoxapine , as well as its 8-hydroxy metabolite (8-hydroxyloxapine).[3] Amoxapine is further metabolized to its 8-hydroxy metabolite (8-hydroxyamoxapine ), which is also found in the blood of people taking loxapine.[19] At steady-state after taking loxapine by mouth, the relative amounts of loxapine and its metabolites in the blood is as follows: 8-hydroxyloxapine > 8-hydroxyamoxapine > loxapine.[19]
The pharmacokinetics of loxapine change depending on how it is given. Intramuscular injections of loxapine lead to higher blood levels and area under the curve of loxapine than when it is taken by mouth.[19]
Chemistry
Loxapine is a dibenzoxazepine and is structurally very similar to clozapine , an atypical antipsychotic .
Chemical structures of loxapine and clozapine, with key differences highlighted.
References
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)" . nctr-crs.fda.gov . FDA . Retrieved 22 Oct 2023 .
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16 .
^ a b c d Truven Health Analytics, Inc. DrugPoint System (Internet) [cited 2013 Sep 21]. Greenwood Village, CO: Thomsen Healthcare; 2013.
^ Popovic D, Nuss P, Vieta E (2015-04-01). "Revisiting loxapine: a systematic review" . Annals of General Psychiatry . 14 : 15. doi :10.1186/s12991-015-0053-3 . PMC 4391595 . PMID 25859275 .
^ Glazer WM (1999). "Does loxapine have "atypical" properties? Clinical evidence" . The Journal of Clinical Psychiatry . 60 (Suppl 10): 42–46. PMID 10340686 .
^ Cheung SW, Tang SW, Remington G (March 1991). "Simultaneous quantitation of loxapine, amoxapine and their 7- and 8-hydroxy metabolites in plasma by high-performance liquid chromatography". Journal of Chromatography . 564 (1): 213–221. doi :10.1016/0378-4347(91)80083-O . PMID 1860915 .
^ a b c "ADASUVE Package Insert" (PDF) . Galen US Inc.
^ "Clozapine and loxapine for schizophrenia". Drug and Therapeutics Bulletin . 29 (11): 41–42. May 1991. doi :10.1136/dtb.29.11.41 . PMID 1747161 . S2CID 27613339 .
^ Chakrabarti A, Bagnall A, Chue P, Fenton M, Palaniswamy V, Wong W, Xia J (October 2007). Chakrabarti A (ed.). "Loxapine for schizophrenia" . The Cochrane Database of Systematic Reviews . 2007 (4): CD001943. doi :10.1002/14651858.CD001943.pub2 . PMC 7017975 . PMID 17943763 .
^ a b "LOXITANE Package Insert" (PDF) . Watson Laboratories, Inc.
^ Taylor D, Paton C, Kapur S, Taylor D (2012). The Maudsley prescribing guidelines in psychiatry (11th ed.). Chichester, West Sussex: Wiley-Blackwell. ISBN 978-0-470-97948-8 .
^ Chakrabarti A, Bagnall A, Chue P, Fenton M, Palaniswamy V, Wong W, Xia J (October 2007). "Loxapine for schizophrenia" . The Cochrane Database of Systematic Reviews . 2007 (4): CD001943. doi :10.1002/14651858.CD001943.pub2 . PMC 7017975 . PMID 17943763 .
^ Nordstrom K (2012). "Inhaled loxapine for rapid treatment of agitation in schizophrenia and bipolar disorder: An update". Neuropsychiatry . 2 (3): 253–260. doi :10.2217/npy.12.23 . S2CID 39718567 .
^ DePaulo JR, Ayd FJ (March 1982). "Loxapine: fifteen years' clinical experience". Psychosomatics . 23 (3): 261–271. doi :10.1016/S0033-3182(82)73416-4 . PMID 7041162 .
^ a b c Singh AN, Barlas C, Singh S, Franks P, Mishra RK (January 1996). "A neurochemical basis for the antipsychotic activity of loxapine: interactions with dopamine D1, D2, D4 and serotonin 5-HT2 receptor subtypes" . Journal of Psychiatry & Neuroscience . 21 (1): 29–35. PMC 1188731 . PMID 8580115 .
^ Sperry L, Hudson B, Chan CH (March 1984). "Loxapine abuse". The New England Journal of Medicine . 310 (9): 598. doi :10.1056/NEJM198403013100920 . PMID 6694719 .
^ Roth BL , Driscol J. "PDSP Ki Database" . Psychoactive Drug Screening Program (PDSP) . University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 14 August 2017 .
^ Appl H, Holzammer T, Dove S, Haen E, Strasser A, Seifert R (February 2012). "Interactions of recombinant human histamine H₁R, H₂R, H₃R, and H₄R receptors with 34 antidepressants and antipsychotics". Naunyn-Schmiedeberg's Archives of Pharmacology . 385 (2): 145–170. doi :10.1007/s00210-011-0704-0 . PMID 22033803 . S2CID 14274150 .
^ a b c Simpson GM, Cooper TB, Lee JH, Young MA (March 1978). "Clinical and plasma level characteristics of intramuscular and oral loxapine". Psychopharmacology . 56 (2): 225–232. doi :10.1007/BF00431855 . PMID 417377 . S2CID 21795809 .
External links
"Loxapine" . Drug Information Portal . U.S. National Library of Medicine.
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DOx (e.g., DOB , DOC , DOI , DOM )
Efavirenz
Ergolines (e.g., 1P-LSD , ALD-52 , bromocriptine , cabergoline , ergine (LSA) , ergometrine (ergonovine) , ergotamine , lisuride , LA-SS-Az , LSB , LSD , LSD-Pip , LSH , LSP , methylergometrine (methylergonovine) , pergolide )
Flumexadol
IHCH-7113
Jimscaline
Lorcaserin
MDxx (e.g., MDA (tenamfetamine) , MDMA (midomafetamine) , MDOH , MMDA )
O-4310
Oxaflozane
PHA-57378
PNU-22394
PNU-181731
RH-34
SCHEMBL5334361
Phenethylamines (e.g., lophophine , mescaline )
Piperazines (e.g., BZP , quipazine , TFMPP )
Serotonin (5-HT)
TCB-2
TFMFly
Tryptamines (e.g., 5-BT , 5-CT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
Antagonists: 5-I-R91150
5-MeO-NBpBrT
AC-90179
Adatanserin
Altanserin
Antihistamines (e.g., cyproheptadine , hydroxyzine , ketotifen , perlapine )
AMDA
Atypical antipsychotics (e.g., amperozide , aripiprazole , asenapine , blonanserin , brexpiprazole , carpipramine , clocapramine , clorotepine , clozapine , fluperlapine , gevotroline , iloperidone , lurasidone , melperone , mosapramine , ocaperidone , olanzapine , paliperidone , quetiapine , risperidone , sertindole , zicronapine , ziprasidone , zotepine )
Chlorprothixene
Cinanserin
CSP-2503
Deramciclane
Dotarizine
Eplivanserin
Ergolines (e.g., amesergide , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
Fananserin
Flibanserin
Glemanserin
Irindalone
Ketanserin
KML-010
Landipirdine
LY-393558
mCPP
Medifoxamine
Metitepine (methiothepin)
MIN-117 (WF-516)
Naftidrofuryl
Nantenine
Nelotanserin
Opiranserin (VVZ-149)
Pelanserin
Phenoxybenzamine
Pimavanserin
Pirenperone
Pizotifen
Pruvanserin
Rauwolscine
Ritanserin
Roluperidone
S-14671
Sarpogrelate
Serotonin antagonists and reuptake inhibitors (e.g., etoperidone , hydroxynefazodone , lubazodone , mepiprazole , nefazodone , triazoledione , trazodone )
SR-46349B
TGBA01AD
Teniloxazine
Temanogrel
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
Tricyclic antidepressants (e.g., amitriptyline )
Typical antipsychotics (e.g., chlorpromazine , fluphenazine , haloperidol , loxapine , perphenazine , pimozide , pipamperone , prochlorperazine , setoperone , spiperone , spiramide , thioridazine , thiothixene , trifluoperazine )
Volinanserin
Xylamidine
Yohimbine
5-HT2B
Agonists: 4-Methylaminorex
Aminorex
Amphetamines (e.g., chlorphentermine , cloforex , dexfenfluramine , fenfluramine , levofenfluramine , norfenfluramine )
BW-723C86
DOx (e.g., DOB , DOC , DOI , DOM )
Ergolines (e.g., cabergoline , dihydroergocryptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
Lorcaserin
MDxx (e.g., MDA (tenamfetamine) , MDMA (midomafetamine) , MDOH , MMDA )
Piperazines (e.g., TFMPP )
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 )
Antagonists: Agomelatine
Atypical antipsychotics (e.g., amisulpride , aripiprazole , asenapine , brexpiprazole , cariprazine , clozapine , N-desalkylquetiapine (norquetiapine) , N-desmethylclozapine (norclozapine) , olanzapine , pipamperone , quetiapine , risperidone , ziprasidone )
Cyproheptadine
EGIS-7625
Ergolines (e.g., amesergide , bromocriptine , lisuride , LY-53857 , LY-272015 , mesulergine )
Ketanserin
LY-393558
mCPP
Metadoxine
Metitepine (methiothepin)
Pirenperone
Pizotifen
Propranolol
PRX-08066
Rauwolscine
Ritanserin
RS-127445
Sarpogrelate
SB-200646
SB-204741
SB-206553
SB-215505
SB-221284
SB-228357
SDZ SER-082
Tegaserod
Tetracyclic antidepressants (e.g., amoxapine , mianserin , mirtazapine )
Trazodone
Typical antipsychotics (e.g., chlorpromazine )
TIK-301
Yohimbine
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 (tenamfetamine) , MDMA (midomafetamine) , 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
Desmetramadol
Dotarizine
Eltoprazine
Ergolines (e.g., amesergide , bromocriptine , LY-53857 , LY-215,840 , 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
Tramadol
Trazodone
Tricyclic antidepressants (e.g., amitriptyline , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine , pimozide , pipamperone , thioridazine )
Xylamidine
5-HT3 –7
5-HT3
Agonists: Alcohols (e.g., butanol , ethanol (alcohol) , 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
Anpirtoline
Arazasetron
AS-8112
Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine )
Azasetron
Batanopride
Bemesetron (MDL-72222)
Bupropion
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
Hydroxybupropion
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 )
Hypidone
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 , ST-1936 , 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-12,233
GW-742457
Idalopirdine
Ketanserin
Landipirdine
Latrepirdine (dimebolin)
Masupirdine
Metitepine (methiothepin)
MS-245
PRX-07034
Ritanserin
Ro 04-6790
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 , brexpiprazole , clorotepine , clozapine , fluperlapine , olanzapine , risperidone , sertindole , tiospirone , ziprasidone , zotepine )
Butaclamol
DR-4485
EGIS-12,233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215,840
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