U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H24ClN3S
Molecular Weight 373.9444
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROCHLORPERAZINE

SMILES

CN1CCN(CCCN2c3ccccc3Sc4ccc(cc42)Cl)CC1

InChI

InChIKey=WIKYUJGCLQQFNW-UHFFFAOYSA-N
InChI=1S/C20H24ClN3S/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24/h2-3,5-8,15H,4,9-14H2,1H3

HIDE SMILES / InChI

Description
Curator's Comment:: http://apm.amegroups.com/article/view/1039/1266

Prochlorperazine may be an effective treatment of acute headaches and refractory chronic daily headache.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
COMPAZINE

Approved Use

To control severe nausea and vomiting. For the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety.

Launch Date

-344995200000
Primary
COMPAZINE

Approved Use

To control severe nausea and vomiting. For the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety.

Launch Date

-344995200000
Primary
COMPAZINE

Approved Use

To control severe nausea and vomiting. For the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety.

Launch Date

-344995200000
Primary
COMPAZINE

Approved Use

To control severe nausea and vomiting. For the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety.

Launch Date

-344995200000
Primary
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.9 ng/mL
25 mg 2 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PROCHLORPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROCHLORPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
32.3 ng × h/mL
25 mg 2 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PROCHLORPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18.1 h
25 mg 2 times / day multiple, oral
dose: 25 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
PROCHLORPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROCHLORPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
9 h
12.5 mg/kg single, intravenous
dose: 12.5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PROCHLORPERAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
180 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 180 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 180 mg/m2, 1 times / day
Sources:
unhealthy, 38-77
Health Status: unhealthy
Age Group: 38-77
Sex: M+F
Sources:
DLT: Sedation, Hypotension...
Disc. AE: Akathisia...
Dose limiting toxicities:
Sedation (grade 3, 25%)
Hypotension (grade 3, 25%)
AEs leading to
discontinuation/dose reduction:
Akathisia (50%)
Sources:
1.2 mg/kg 1 times / day multiple, intravenous
MTD
Dose: 1.2 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1.2 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
DLT: Hypotension, Restlessness...
Dose limiting toxicities:
Hypotension (33.3%)
Restlessness (100%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Akathisia 50%
Disc. AE
180 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 180 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 180 mg/m2, 1 times / day
Sources:
unhealthy, 38-77
Health Status: unhealthy
Age Group: 38-77
Sex: M+F
Sources:
Hypotension grade 3, 25%
DLT
180 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 180 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 180 mg/m2, 1 times / day
Sources:
unhealthy, 38-77
Health Status: unhealthy
Age Group: 38-77
Sex: M+F
Sources:
Sedation grade 3, 25%
DLT
180 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 180 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 180 mg/m2, 1 times / day
Sources:
unhealthy, 38-77
Health Status: unhealthy
Age Group: 38-77
Sex: M+F
Sources:
Restlessness 100%
DLT
1.2 mg/kg 1 times / day multiple, intravenous
MTD
Dose: 1.2 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1.2 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Hypotension 33.3%
DLT
1.2 mg/kg 1 times / day multiple, intravenous
MTD
Dose: 1.2 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1.2 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
PubMed

PubMed

TitleDatePubMed
Identification and characterization of 17 phenothiazine compounds by capillary high-performance liquid chromatography/fast atom bombardment mass spectrometry.
2002 Dec
Options for the prevention and management of acute chemotherapy-induced nausea and vomiting in children.
2003
Feasibility of amifostine administration in conjunction with high-dose rate brachytherapy.
2003 Dec
An evaluation of protein assays for quantitative determination of drugs.
2003 Jul 31
Surgeon-led initiatives cut costs and enhance the quality of endoscopic and laparoscopic procedures.
2003 Jul-Sep
The effectiveness of combined naloxone/lofexidine in opiate detoxification: results from a double-blind randomized and placebo-controlled trial.
2003 Jul-Sep
Analgesic effects of parecoxib following total abdominal hysterectomy.
2003 Jun
Intravenous sodium valproate versus prochlorperazine for the emergency department treatment of acute migraine headaches: a prospective, randomized, double-blind trial.
2003 Jun
Phenothiazine radicals inactivate Trypanosoma cruzi dihydrolipoamide dehydrogenase: enzyme protection by radical scavengers.
2003 Mar
Extrapyramidal reactions to ondansetron: cross-reactivity between ondansetron and prochlorperazine?
2003 May
AANA journal course. Update for nurse anesthetists. Neuroleptic malignant syndrome.
2003 Oct
Comparison of three outpatient regimens in the management of nausea and vomiting in pregnancy.
2003 Oct
Aborting a prolonged migrainous aura with intravenous prochlorperazine and magnesium sulfate.
2003 Sep
Efficacy of a fixed combination of indomethacin, prochlorperazine, and caffeine versus sumatriptan in acute treatment of multiple migraine attacks: a multicenter, randomized, crossover trial.
2003 Sep
Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy.
2003 Sep 17
Prochlorperazine-induced cholestasis in a patient with alpha-1 antitrypsin deficiency.
2003 Sep-Oct
Diphenhydramine in the treatment of akathisia induced by prochlorperazine.
2004 Apr
Atypical laryngeal dystonia caused by an antiemetic.
2004 Apr 1
Plasma and cerebrospinal fluid pharmacokinetics of rebeccamycin (NSC 655649) in nonhuman primates.
2004 Aug
Droperidol vs prochlorperazine for the treatment of acute headache.
2004 Feb
Treatment of pediatric migraine headaches: a randomized, double-blind trial of prochlorperazine versus ketorolac.
2004 Feb
Index of suspicion.
2004 Jan
Acute treatment of migraine. Breaking the paradigm of monotherapy.
2004 Jan 28
Prochlorperazine more effective than ketorolac for pediatric migraine.
2004 Jun
Efficacy of quality criteria to identify potentially harmful information: a cross-sectional survey of complementary and alternative medicine web sites.
2004 Jun 29
Postmortem distribution of the novel antipsychotic drug quetiapine.
2004 May-Jun
Indomethacin, alone and combined with prochlorperazine and caffeine, but not sumatriptan, abolishes peripheral and central sensitization in in vivo models of migraine.
2004 Oct
Coloration of phenothiazines with metal-containing drugs.
2004 Sep
Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine.
2005
Increasing throughput and information content for in vitro drug metabolism experiments using ultra-performance liquid chromatography coupled to a quadrupole time-of-flight mass spectrometer.
2005
Diphenhydramine in the treatment of akathesia induced by prochlorperazine.
2005 Apr
Clinical practice guidelines on antiemetics in oncology.
2005 Dec
Bioavailability and metabolism of prochlorperazine administered via the buccal and oral delivery route.
2005 Dec
Acute hypersensitivity reaction to ferric gluconate in a premedicated patient.
2005 Dec
[Pain management for cancer patients with critical pathway on computer].
2005 Feb
In vitro activity of phenothiazine derivatives in Enterococcus faecalis and Enterococcus faecium.
2005 Jan
The combination of naratriptan and prochlorperazine in migraine treatment.
2005 Jun
Prevention of delayed chemotherapy-induced nausea and vomiting after moderately high to highly emetogenic chemotherapy: comparison of ondansetron, prochlorperazine, and dexamethasone.
2005 Jun
[Effects of amino acid solution and recombinant human growth hormone on growth hormone/insulin like growth factor-1 axis in rats with liver cirrhosis].
2005 Jun 1
Acupuncture therapy rapidly terminates intractable hiccups complicating acute myocardial infarction.
2005 Mar
Cost-effectiveness analysis of ondansetron and prochlorperazine for the prevention of postoperative nausea and vomiting.
2005 May
Quetiapine discontinuation syndrome.
2005 May
Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography.
2005 Nov-Dec
Preliminary studies on phenothiazine-mediated reversal of multidrug resistance in mouse lymphoma and COLO 320 cells.
2005 Nov-Dec
5-Hydroxytryptamine-receptor antagonists versus prochlorperazine for control of delayed nausea caused by doxorubicin: a URCC CCOP randomised controlled trial.
2005 Oct
[Three cases of drug-induced akathisia due to antiemetics during cancer palliative care].
2006 Feb
Anti-gingivitis effect of a dentifrice containing bioactive glass (NovaMin) particulate.
2006 Feb
Ondansetron, prochlorperazine, and dexamethasone have similar effects on prevention of delayed chemotherapy-induced nausea and vomiting.
2006 Feb
Cetirizine-induced dystonic movements.
2006 Jan 10
Antiemetics in the ED: a randomized controlled trial comparing 3 common agents.
2006 Mar
Patents

Sample Use Guides

DOSAGE AND ADMINISTRATION–ADULTS
Route of Administration: Other
In Vitro Use Guide
We have studied the effects of prochlorperazine on the activities of UDP-glucuronosyltransferase and glucose-6-phosphatase (glucose-6-P'ase) in rat liver microsomes. The activity of UDP-glucuronosyltransferase was increased in a graded fashion by addition of prochlorperazine. Maximal stimulation occurred at 1 mg prochlorperazine to 2 mg microsomal protein, which resulted in a 6-fold increase in activity.
Name Type Language
PROCHLORPERAZINE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
Official Name English
PROCHLORPERAZINE [HSDB]
Common Name English
10H-PHENOTHIAZINE, 2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL
Common Name English
COMPRO
Brand Name English
PROCHLORPERAZINE [MART.]
Common Name English
PROCHLORPERAZINE [INN]
Common Name English
PROCHLORPERAZINE [JAN]
Common Name English
COMPAZINE
Brand Name English
PROCHLORPERAZINE [WHO-DD]
Common Name English
PROCHLORPERAZINE [MI]
Common Name English
2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)PHENOTHIAZINE
Systematic Name English
PROCHLORPERAZINE [ORANGE BOOK]
Common Name English
2-CHLORO-10-(3-(4-METHYLPIPERAZIN-1-YL)PROPYL)-10H-PHENOTHIAZINE
Systematic Name English
PROCHLORPERAZINE [USP MONOGRAPH]
Common Name English
PROCHLORPERAZINE [VANDF]
Common Name English
Classification Tree Code System Code
NDF-RT N0000007544
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
LIVERTOX 802
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
WHO-ATC N05AB04
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
CFR 21 CFR 520.1920
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
CFR 21 CFR 520.1921
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
NDF-RT N0000007544
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
NDF-RT N0000007544
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
CFR 21 CFR 522.1920
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
NCI_THESAURUS C740
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
NDF-RT N0000175746
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
WHO-VATC QN05AB04
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
Code System Code Type Description
IUPHAR
7279
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
PRIMARY
DRUG BANK
DB00433
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
PRIMARY
HSDB
3171
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PRIMARY
NCI_THESAURUS
C774
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PRIMARY
EVMPD
SUB10059MIG
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
PRIMARY
LACTMED
Prochlorperazine
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PRIMARY
MERCK INDEX
M9149
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PRIMARY Merck Index
EPA CompTox
58-38-8
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PRIMARY
ECHA (EC/EINECS)
200-379-4
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PRIMARY
CAS
58-38-8
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
PRIMARY
DRUG CENTRAL
2274
Created by admin on Fri Jun 25 20:59:04 UTC 2021 , Edited by admin on Fri Jun 25 20:59:04 UTC 2021
PRIMARY
PUBCHEM
4917
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PRIMARY
ChEMBL
CHEMBL728
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PRIMARY
MESH
D011346
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PRIMARY
FDA UNII
YHP6YLT61T
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PRIMARY
INN
699
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PRIMARY
RXCUI
8704
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PRIMARY RxNorm