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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24ClN3S.2C4H4O4
Molecular Weight 606.087
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PROCHLORPERAZINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CN1CCN(CCCN2C3=C(SC4=C2C=C(Cl)C=C4)C=CC=C3)CC1

InChI

InChIKey=DSKIOWHQLUWFLG-SPIKMXEPSA-N
InChI=1S/C20H24ClN3S.2C4H4O4/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;2*5-3(6)1-2-4(7)8/h2-3,5-8,15H,4,9-14H2,1H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

Molecular Formula C20H24ClN3S
Molecular Weight 373.943
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://apm.amegroups.com/article/view/1039/1266

Prochlorperazine is a piperazine phenothiazine antipsychotic which block postsynaptic mesolimbic dopaminergic receptors in the brain and has antiemetic effects by its antagonist actions in the D2 dopamine receptors in the chemoreceptor trigger zone. It also exhibits alpha-adrenergic blocking effect on α1 receptros and may depress the release of hypothalamic and hypophyseal hormones. Prochlorperazine is used for the control of severe nausea and vomiting, for the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety. 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

1959
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

1959
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

1959
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

1959
Primary
Unknown

Approved Use

Unknown
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
Co-administed with::
doxorubicin, i.v.(60 mg/m2; q.d.)
Sources: Page: p.380
unhealthy, 38-77
n = 4
Health Status: unhealthy
Condition: Cancer
Age Group: 38-77
Sex: M+F
Population Size: 4
Sources: Page: p.380
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: Page: p.380
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: Page: p.1469
unhealthy
n = 3
Health Status: unhealthy
Condition: Nausea|Vomiting
Sex: M+F
Population Size: 3
Sources: Page: p.1469
DLT: Hypotension, Restlessness...
Dose limiting toxicities:
Hypotension (33.3%)
Restlessness (100%)
Sources: Page: p.1469
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
Co-administed with::
doxorubicin, i.v.(60 mg/m2; q.d.)
Sources: Page: p.380
unhealthy, 38-77
n = 4
Health Status: unhealthy
Condition: Cancer
Age Group: 38-77
Sex: M+F
Population Size: 4
Sources: Page: p.380
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
Co-administed with::
doxorubicin, i.v.(60 mg/m2; q.d.)
Sources: Page: p.380
unhealthy, 38-77
n = 4
Health Status: unhealthy
Condition: Cancer
Age Group: 38-77
Sex: M+F
Population Size: 4
Sources: Page: p.380
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
Co-administed with::
doxorubicin, i.v.(60 mg/m2; q.d.)
Sources: Page: p.380
unhealthy, 38-77
n = 4
Health Status: unhealthy
Condition: Cancer
Age Group: 38-77
Sex: M+F
Population Size: 4
Sources: Page: p.380
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: Page: p.1469
unhealthy
n = 3
Health Status: unhealthy
Condition: Nausea|Vomiting
Sex: M+F
Population Size: 3
Sources: Page: p.1469
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: Page: p.1469
unhealthy
n = 3
Health Status: unhealthy
Condition: Nausea|Vomiting
Sex: M+F
Population Size: 3
Sources: Page: p.1469
PubMed

PubMed

TitleDatePubMed
Identification and characterization of 17 phenothiazine compounds by capillary high-performance liquid chromatography/fast atom bombardment mass spectrometry.
2002 Dec
Antimicrobial potentiality of a phenothiazine group of antipsychotic drug-prochlorperazine.
2002 Jul
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
The efficacy and cost-effectiveness of prophylactic 5-hydroxytryptamine3 receptor antagonists: tropisetron, ondansetron and dolasetron.
2003 Feb
Akathisia can be reduced by lowering the dose of D2 receptor antagonists.
2003 Feb
Serotonin syndrome induced by low-dose venlafaxine.
2003 Feb
Variations among emergency departments in the treatment of benign headache.
2003 Jan
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
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
Diamorphine for pain relief in labour : a randomised controlled trial comparing intramuscular injection and patient-controlled analgesia.
2004 Oct
Coloration of phenothiazines with metal-containing drugs.
2004 Sep
Prochlorperazine induces central antinociception mediated by the muscarinic system.
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
Symptomatic treatment of migraine in children: a systematic review of medication trials.
2005 Aug
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
The antipsychotic and antiemetic drug prochlorperazine delays the ventricular repolarization of the in situ canine heart.
2005 Jan
A phase I clinical trial of continual alternating etoposide and topotecan in refractory solid tumours.
2005 Jul 11
The combination of naratriptan and prochlorperazine in migraine treatment.
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
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
The use of levomepromazine in Hyperemesis Gravidarum resistant to drug therapy--a case series.
2005 Nov-Dec
Efficacy of a fixed combination of indomethacin, prochlorperazine, and caffeine in the treatment of episodic tension-type headache: a double-blind, randomized, nimesulide-controlled, parallel group, multicentre trial.
2005 Oct
[Three cases of drug-induced akathisia due to antiemetics during cancer palliative care].
2006 Feb
Ondansetron, prochlorperazine, and dexamethasone have similar effects on prevention of delayed chemotherapy-induced nausea and vomiting.
2006 Feb
Chronic severe dystonia after single exposure to antiemetics.
2006 Jan
Roles for mitochondria in pentamidine susceptibility and resistance in Leishmania donovani.
2006 Jan
Patents

Sample Use Guides

DOSAGE AND ADMINISTRATION–ADULTS 1. To Control Severe Nausea and Vomiting: Adjust dosage to the response of the individual. Begin with the lowest recommended dosage. Oral Dosage–Tablets: Usually one 5 mg or 10 mg tablet 3 or 4 times daily. Daily dosages above 40 mg should be used only in resistant cases. Spansule capsules: Initially, usually one 15 mg capsule on arising or one 10 mg capsule q12h. Daily doses above 40 mg should be used only in resistant cases. 11 Rectal Dosage: 25 mg twice daily. I.M. Dosage: Initially 5 to 10 mg (1 to 2 mL) injected deeply into the upper outer quadrant of the buttock. If necessary, repeat every 3 or 4 hours. Total I.M. dosage should not exceed 40 mg per day. I.V. Dosage: 2½ to 10 mg (½ to 2 mL) by slow I.V. injection or infusion at a rate not to exceed 5 mg per minute. Compazine Injection may be administered either undiluted or diluted in isotonic solution. A single dose of the drug should not exceed 10 mg; total I.V. dosage should not exceed 40 mg per day. When administered I.V., do not use bolus injection. Hypotension is a possibility if the drug is given by I.V. injection or infusion. 2. Adult Surgery (for severe nausea and vomiting): Total parenteral dosage should not exceed 40 mg per day. Hypotension is a possibility if the drug is given by I.V. injection or infusion. I.M. Dosage: 5 to 10 mg (1 to 2 mL) 1 to 2 hours before induction of anesthesia (repeat once in 30 minutes, if necessary), or to control acute symptoms during and after surgery (repeat once if necessary). I.V. Dosage: 5 to 10 mg (1 to 2 mL) as a slow I.V. injection or infusion 15 to 30 minutes before induction of anesthesia, or to control acute symptoms during or after surgery. Repeat once if necessary. Compazine (prochlorperazine) may be administered either undiluted or diluted in isotonic solution, but a single dose of the drug should not exceed 10 mg. The rate of administration should not exceed 5 mg per minute. When administered I.V., do not use bolus injection. 3. In Adult Psychiatric Disorders: Adjust dosage to the response of the individual and according to the severity of the condition. Begin with the lowest recommended dose. Although response ordinarily is seen within a day or 2, longer treatment is usually required before maximal improvement is seen. Oral Dosage: Non-Psychotic Anxiety–Usual dosage is 5 mg 3 or 4 times daily; by Spansule capsule, usually one 15 mg capsule on arising or one 10 mg capsule q12h. Do not administer in doses of more than 20 mg per day or for longer than 12 weeks. Psychotic Disorders including Schizophrenia–In relatively mild conditions, as seen in private psychiatric practice or in outpatient clinics, dosage is 5 or 10 mg 3 or 4 times daily. In moderate to severe conditions, for hospitalized or adequately supervised patients, usual starting dosage is 10 mg 3 or 4 times daily. Increase dosage gradually until symptoms are controlled or side effects become bothersome. When dosage is increased by small increments every 2 or 3 days, side effects either do not occur or are easily controlled. Some patients respond satisfactorily on 50 to 75 mg daily. In more severe disturbances, optimum dosage is usually 100 to 150 mg daily. I.M. Dosage: For immediate control of adult schizophrenic patients with severe symptomatology, inject an initial dose of 10 to 20 mg (2 to 4 mL) deeply into the upper outer quadrant of the buttock. Many patients respond shortly after the first injection. If necessary, however, repeat the initial dose every 2 to 4 hours (or, in resistant cases, every hour) to gain control of the patient. More than three or four doses are seldom necessary. After control is achieved, switch patient to an oral form of the drug at the same dosage level or higher. If, in rare cases, parenteral therapy is needed for a prolonged period, give 10 to 20 mg (2 to 4 mL) every 4 to 6 hours. Pain and irritation at the site of injection have seldom occurred. Subcutaneous administration is not advisable because of local irritation.
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:40 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:40 GMT 2023
Record UNII
I1T8O1JTL6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROCHLORPERAZINE MALEATE
EP   GREEN BOOK   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
PROCHLORPERAZINE MALEATE [MART.]
Common Name English
2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)PHENOTHIAZINE MALEATE (1:2).
Common Name English
PROCHLORPERAZINE MALEATE [GREEN BOOK]
Common Name English
PROCHLORPERAZINE MALEATE [USP MONOGRAPH]
Common Name English
PROCHLORPERAZINE MALEATE [USP IMPURITY]
Common Name English
PROCHLORPERAZINE MALEATE [EP MONOGRAPH]
Common Name English
PROCHLORPERAZINE MALEATE [VANDF]
Common Name English
PROCHLORPERAZINE DIMALEATE [MI]
Common Name English
10H-PHENOTHIAZINE, 2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, (Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
PROCHLORPERAZINE DIMALEATE [GREEN BOOK]
Common Name English
Prochlorperazine maleate [WHO-DD]
Common Name English
PROCHLORPERAZINE DIMALEATE
GREEN BOOK   MI  
Common Name English
PROCHLORPERAZINE MALEATE [JAN]
Common Name English
PROCHLORPERAZINE MALEATE [USP-RS]
Common Name English
PROCHLORPERAZINE MALEATE [ORANGE BOOK]
Common Name English
10H-PHENOTHIAZINE, 2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, (2Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C740
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
Code System Code Type Description
PUBCHEM
5281032
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
MERCK INDEX
m9149
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
201-511-3
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
CAS
84-02-6
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
SMS_ID
100000085101
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
RS_ITEM_NUM
1566001
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
DRUG BANK
DBSALT000998
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
WIKIPEDIA
Prochlorperazine maleate
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
DAILYMED
I1T8O1JTL6
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
CHEBI
8436
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL728
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
FDA UNII
I1T8O1JTL6
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
RXCUI
8706
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY RxNorm
EVMPD
SUB04052MIG
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID1049015
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
NCI_THESAURUS
C775
Created by admin on Fri Dec 15 15:03:41 GMT 2023 , Edited by admin on Fri Dec 15 15:03:41 GMT 2023
PRIMARY
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