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

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
Emergency! Prochlorperazine-induced dystonia.
1999 Nov
Images in cardiovascular medicine. Labile repolarization from "cell to bedside".
2000 Aug 15
[Diagnostic image (17). Acute dystonia induced by prochlorperazine].
2000 Dec 23
Photosensitivity associated with fluorouracil, prochlorperazine, and topical tretinoin.
2001 Feb
Slow infusion for the prevention of akathisia induced by prochlorperazine: a randomized controlled trial.
2001 Feb
Oral mucosal drug delivery: clinical pharmacokinetics and therapeutic applications.
2002
Medical management of Meniere's disease.
2002 Jun
Options for the prevention and management of acute chemotherapy-induced nausea and vomiting in children.
2003
Serotonin syndrome induced by low-dose venlafaxine.
2003 Feb
Surgeon-led initiatives cut costs and enhance the quality of endoscopic and laparoscopic procedures.
2003 Jul-Sep
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
Efficacy of quality criteria to identify potentially harmful information: a cross-sectional survey of complementary and alternative medicine web sites.
2004 Jun 29
Diamorphine for pain relief in labour : a randomised controlled trial comparing intramuscular injection and patient-controlled analgesia.
2004 Oct
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
In vitro activity of phenothiazine derivatives in Enterococcus faecalis and Enterococcus faecium.
2005 Jan
Cost-effectiveness analysis of ondansetron and prochlorperazine for the prevention of postoperative nausea and vomiting.
2005 May
Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography.
2005 Nov-Dec
Cetirizine-induced dystonic movements.
2006 Jan 10
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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