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Drug

D0064 | Haloperidol

Molecular Formula C21H23ClFNO2
Molecular Weight 375.9
Structure
State solid
Clearance Haloperidol clearance after extravascular administration ranges from 0.9-1.5 l/h/kg, however this rate is reduced in poor metabolizers of C_YP2D6_ enzyme. Reduced CYP2D6 enzyme activity may result in increased concentrations of haloperidol. The inter-subject variability (coefficient of variation, %) in haloperidol clearance was estimated to be 44% in a population pharmacokinetic analysis in patients with schizophrenia [L2028].
Volume of distribution The apparent volume of distribution is about 20 L/kg, in concordance with the high lipophilicity of the drug [L1996], and largely depends on the subject [L2028]. Haloperidol is rapidly distributed to various tissues and organs, as indicated by the large volume of distribution (mean values 8 to 21 L/kg after intravenous dosing). Haloperidol readily crosses the blood-brain barrier. It also crosses the placenta and is excreted in breast milk [L2028].
Route of elimination Urine 40% (1% unchanged), feces 15% [L1997]
Protein binding Haloperidol circulates in the blood bound predominantly (90-94%) to plasma proteins [L1996].
Half life For the non-decanoate formulations, the haloperidol half-life is on average 24 hours after oral administration and 21 hours after intramuscular administration [L2028].
Absorption Haloperidol is well-absorbed from the gastrointestinal tract when ingested orally, however, the first-pass hepatic metabolism decreases its oral bioavailability to 40 - 75% [L1996]. Administration of haloperidol decanoate (the depot form of haloperidol for long-term treatment) in sesame oil results in slow release of the drug for long-term effects. The plasma concentrations of haloperidol gradually rise, reaching its peak concentration at about 6 days after the injection, with an apparent half-life of about 21 days. Steady-state plasma concentrations are achieved after the third or fourth dose [FDA label]. Serum concentration peaks 0.5 to 4 hours after an oral dose [L1996].
Trade names Haldol
Description D2R antagonist; first-generation (typical) antipsychotic

N

N05AD01 Haloperidol


[N05AD] Butyrophenone derivatives


[N05A] ANTIPSYCHOTICS


[N05] PSYCHOLEPTICS


[N] Nervous system

Toxicity Dose Time Species Model Method Action Positive criterion Reference
UNCOUPLING rat isolated liver mitochondria measurements of mitochondrial respiration; RST inhibition assay, RST uncoupling assay; IC 50ratio of glucose/galactose assay Negative 53
ELECTRON TRANSPORT CHAIN rat isolated liver mitochondria decrease 23
ELECTRON TRANSPORT CHAIN decrease 23
ELECTRON TRANSPORT CHAIN rat isolated liver mitochondria measurements of mitochondrial respiration; RST inhibition assay, RST uncoupling assay; IC 50ratio of glucose/galactose assay Negative 53
ELECTRON TRANSPORT CHAIN 3 μM NADH–Q-1 decrease IC50 119
ELECTRON TRANSPORT CHAIN inhibit 197
MITOCHONDRIA TRANSPORT 10 µM 2h rat Hippocampal Neurons time-lapse imaging experiments increase 216

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase rat isolated liver mitochondria inhibitor 23
NADH:ubiquinone reductase inhibitor 23
NADH:ubiquinone reductase 3 μM NADH–Q-1 inhibitor IC50 119
NADH:ubiquinone reductase 185

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 209 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 2 of 209 companies. For more detailed information, please visit ECHA C&L website


Of the 7 notification(s) provided by 207 of 209 companies with hazard statement code(s):


H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]


H315 (96.14%): Causes skin irritation [Warning Skin corrosion/irritation]


H317 (94.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]


H319 (96.14%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H335 (95.17%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure


Respiratory tract irritation]


H361 (95.17%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P261, P264, P270, P271, P272, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Warning

Aggregated GHS information provided by 41 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]


H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]


H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)
Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]


H360: May damage fertility or the unborn child [Danger Reproductive toxicity]


H362: May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]


H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]


H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


 P201, P202, P260, P263, P264, P270, P281, P301+P312, P307+P311, P308+P313, P314, P321, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • Abnormal behaviour

  • Affect lability

  • Conduct disorder

  • Disturbance in social behaviour

  • Frustration

  • Hyperkinesia

  • Mood swings

  • Psychotic disorder

  • Schizoaffective disorder

  • Schizophrenia

  • Tourette's disorder

    • .gamma.-(4-(p-Chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenone .gamma.-[4-(p-Chlorphenyl)-4-hydroxpiperidino]-p-fluorbutyrophenone 1-(3-p-Fluorobenzoylpropyl)-4-p-chlorophenyl-4-hydroxypiperidine
    1-Butanone, 4-(4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)- 1-Butanone, 4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)- 177716-59-5
    4'-Fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidinyl)butyrophenone 4'-Fluoro-4-(4-hydroxy-4-(4'-chlorophenyl)piperidino)butyrophenone 4'-Fluoro-4-(4-hydroxy-4-p-chlorophenylpiperidino)butyrophenone
    4'-Fluoro-4-[4-hydroxy-4-(4'-chlorophenyl)piperidino]butyrophenone 4-(4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl)-1-(4-fluorophenyl)-1-butanone 4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-1-(4-fluorophenyl)butan-1-one
    4-(4-(p-Chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone 4-(4-(para-Chlorophenyl)-4-hydroxypiperidino)-4'-fluorobutyrophenone 4-(4-Hydroxy-4'-chloro-4-phenylpiperidino)-4'-fluorobutyrophenone
    4-[4-(4-Chloro-phenyl)-4-hydroxy-piperidin-1-yl]-1-(4-fluoro-phenyl)-butan-1-one;propionate(HCl) 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl) -1-butanone 4-[4-(4-Chlorophenyl)-4-hydroxy-1-piperidinyl]-1-(4-fluorophenyl)-1-butanone
    4-[4-(4-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone 4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)-butan-1-one 4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidyl]-1-(4-fluorophenyl)butan-1-one
    4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one 4-[4-(4-chlorophenyl)-4-hydroxypiperidyl]-1-(4-fluorophenyl)butan-1-one 4-[4-(p-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone
    4-[4-(para-Chlorophenyl)-4-hydroxypiperidino]-4'-fluorobutyrophenone 4763-EP2269989A1 4763-EP2269990A1
    4763-EP2272537A2 4763-EP2272972A1 4763-EP2272973A1
    4763-EP2275420A1 4763-EP2277872A1 4763-EP2277876A1
    4763-EP2292614A1 4763-EP2295061A1 4763-EP2295412A1
    4763-EP2295413A1 4763-EP2295439A1 4763-EP2298731A1
    4763-EP2298776A1 4763-EP2305260A1 4763-EP2308867A2
    4763-EP2308870A2 4763-EP2311801A1 4763-EP2311803A1
    4763-EP2311824A1 4763-EP2311837A1 4763-EP2316834A1
    5-21-02-00377 (Beilstein Handbook Reference) 52-86-8 61788-97-4
    A0H334 AB00052008 AB00052008-21
    AB00052008-22 AB00052008_23 AB00052008_24
    AB2000375 AC-19691 AC250
    ACM1189986591 AKOS000280660 AOB5645
    API0002885 Aldo Aloperidin
    Aloperidol Aloperidolo Aloperidolo [DCIT]
    Aloperidolo [Italian] Aloperidon BDBM21398
    BG0211 BIDD:GT0128 BPBio1_000144
    BPBio1_001231 BRD-K67783091-001-04-8 BRD-K67783091-001-05-5
    BRD-K67783091-003-03-6 BRN 0331267 BSPBio_000130
    BSPBio_002096 Biomol-NT_000035 Bioperidolo
    Brotopon Butyrophenone, 4'-fluoro-4-(4-(p-chlorophenyl)-4-hydroxypiperidino)- Butyrophenone, 4-(4-(p-chlorophenyl)-4-hydroxypiperidino)-4'-fluoro-
    Butyrophenone, 4-[4-(p-chlorophenyl)-4-hydroxypiperidino]-4'-fluoro- C-35402 C01814
    C21H23ClFNO2 CAS-52-86-8 CC-16450
    CCG-36042 CCG-39111 CCRIS 1630
    CHEBI:5613 CHEMBL54 CS-1971
    Certified Reference Material D00136 DB00502
    DSSTox_CID_14150 DSSTox_GSID_34150 DSSTox_RID_79117
    DTXSID4034150 DivK1c_000654 Dozic
    Duraperidol EINECS 200-155-6 EU-0100583
    Einalon S Eukystol FT-0669100
    FT-0697842 Fortunan GTPL86
    Galoperidol H 1512 HMS1568G12
    HMS1920D03 HMS2089M15 HMS2091J09
    HMS2095G12 HMS2234P08 HMS3261F08
    HMS3370H11 HMS3657I13 HMS3712G12
    HMS502A16 HSDB 3093 HY-14538
    Haldol Haldol (TN) Haldol Solutab
    Halidol Halojust Halol
    Halopal Haloperidol (Haldol) Haloperidol (JP17/USP/INN)
    Haloperidol 1.0 mg/ml in Methanol Haloperidol [USAN:INN:BAN:JAN] Haloperidol [USAN:USP:INN:BAN:JAN]
    Haloperidol for peak identification, European Pharmacopoeia (EP) Reference Standard Haloperidol for system suitability, European Pharmacopoeia (EP) Reference Standard Haloperidol solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material
    Haloperidol(Haldol) Haloperidol, 1 Haloperidol, European Pharmacopoeia (EP) Reference Standard
    Haloperidol, Pharmaceutical Secondary Standard Haloperidol, United States Pharmacopeia (USP) Reference Standard Haloperidol, powder
    Haloperidolum Haloperidolum [INN-Latin] Halopidol
    Halopoidol Halosten IDI1_000654
    InChI=1/C21H23ClFNO2/c22-18-7-5-17(6-8-18)21(26)11-14-24(15-12-21)13-1-2-20(25)16-3-9-19(23)10-4-16/h3-10,26H,1-2,11-15H2 J6292F8L3D KBio1_000654
    KBio2_001341 KBio2_002390 KBio2_003909
    KBio2_004958 KBio2_006477 KBio2_007526
    KBio3_001316 KBio3_002869 KBioGR_000980
    KBioGR_002390 KBioSS_001341 KBioSS_002395
    Keselan L000288 LNEPOXFFQSENCJ-UHFFFAOYSA-
    LNEPOXFFQSENCJ-UHFFFAOYSA-N LP00583 LS-48311
    Lealgin compositum Linton Lopac-H-1512
    Lopac0_000583 MCULE-3693790133 MDMO-PPV
    MFCD00051423 MLS000028450 MLS001146904
    MRF-0000027 McM-JR-1625 McN-JR-1625
    Mixidol N1910 NCGC00015500-01
    NCGC00015500-02 NCGC00015500-03 NCGC00015500-04
    NCGC00015500-05 NCGC00015500-06 NCGC00015500-07
    NCGC00015500-08 NCGC00015500-09 NCGC00015500-10
    NCGC00015500-11 NCGC00015500-12 NCGC00015500-13
    NCGC00015500-14 NCGC00015500-15 NCGC00015500-16
    NCGC00015500-17 NCGC00015500-19 NCGC00016234-01
    NCGC00023875-02 NCGC00023875-04 NCGC00023875-05
    NCGC00023875-06 NCGC00023875-07 NCGC00023875-08
    NCGC00023875-09 NCGC00254503-01 NCGC00261268-01
    NINDS_000654 NSC 170973 NSC 615296
    NSC-170973 NSC-615296 NSC-757054
    NSC170973 NSC615296 NSC757054
    Opera_ID_446 Oprea1_509923 Pekuces
    Peluces Pernox Pharmakon1600-01500325
    Picroside-III Poly[2-methoxy-5-(3,7-dimethyoctyoxyl)-1,4-phenylenevinylene] Prestwick0_000115
    Prestwick1_000115 Prestwick2_000115 Prestwick3_000115
    Prestwick_250 Probes1_000255 Probes2_000296
    Q251347 QTL1_000042 R 1625
    R-1625 S1920 SBI-0050565.P004
    SC 170973 SC-81035 SCHEMBL8264
    SMR000058303 SPBio_001236 SPBio_002069
    SPECTRUM1500325 SR-01000003076 SR-01000003076-11
    SR-01000003076-2 SR-01000003076-8 ST50319916
    STL417208 SW196557-4 Serenace
    Serenase Serenelfi Sernas
    Sernel Sigaperidol Spectrum2_001268
    Spectrum3_000448 Spectrum4_000570 Spectrum5_000788
    Spectrum_000861 TR-018722 Tocris-0931
    Tox21_110162 Tox21_110162_1 Tox21_300475
    Tox21_500583 UNII-J6292F8L3D Ulcolind
    Uliolind VU0239704-10 Vesalium
    W-105791 W0039 WLN: T6NTJ A3VR DF& DQ DR DG
    ZINC537822 cMAP_000037 gamma-(4-(p-Chlorophenyl)-4-hydroxpiperidino)-p-fluorbutyrophenone
    gamma-(4-(p-Chlorophenyl)-4-hydroxypiperidino)-p-fluorbutyrophenone gamma-(4-(p-Chlorophenyl)-4-hydroxypiperidino)-p-fluorobutyrophenone gamma-[4-(p-chlorophenyl)-4-hydroxypiperidino]-p-fluorobutyrophenone
    haloperidol

    DrugBank Name Haloperidol
    DrugBank DB00502
    CAS Number 1189986-59-1, 1511-16-6, 177716-59-5, 52-86-8, 61788-97-4, 64461-95-6
    PubChem Compound 3559
    KEGG Compound ID C01814
    KEGG Drug D00136
    PubChem.Substance 46508794
    ChEBI 5613
    PharmGKB PA449841
    ChemSpider 3438
    BindingDB 21398.0
    TTD DAP000313
    Wikipedia Haloperidol
    HET GMJ
    DPD 10146|1903

    1. Chan et al. (2005)
    2. Vuda et al. (2016)