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 UNSPECIFIED
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=CC(Cl)=CC=C3SC4=C2C=CC=C4)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 C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C20H24ClN3S
Molecular Weight 373.943
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
22.6 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Images in cardiovascular medicine. Labile repolarization from "cell to bedside".
2000 Aug 15
Ondansetron: a review of its use as an antiemetic in children.
2001
Continuous infusion prochlorperazine: pharmacokinetics, antiemetic efficacy, and feasibility of high-dose therapy.
2001 Apr
Tolerability and effectiveness of prochlorperazine for intractable migraine in children.
2001 Apr
Slow infusion for the prevention of akathisia induced by prochlorperazine: a randomized controlled trial.
2001 Feb
Diphenhydramine for the prevention of akathisia induced by prochlorperazine: a randomized, controlled trial.
2001 Feb
[Inactivation of Trypanosoma cruzi trypanothione reductase by phenothiazine cationic free radicals].
2001 Jan-Mar
Headache in the emergency department.
2001 Jun
Pegylated liposomal doxorubicin: tolerability and toxicity.
2001 Jun
Frequency of adverse reactions to prochlorperazine in the ED: a response.
2001 Mar
Droperidol vs. prochlorperazine for benign headaches in the emergency department.
2001 Sep
Antimicrobial potentiality of a phenothiazine group of antipsychotic drug-prochlorperazine.
2002 Jul
Treatment patterns of isolated benign headache in US emergency departments.
2002 Mar
Antiemetic use in pediatric gastroenteritis: a national survey of emergency physicians, pediatricians, and pediatric emergency physicians.
2002 Nov-Dec
Efficacy and tolerability of prochlorperazine buccal tablets in treatment of acute migraine.
2002 Oct
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
In vitro human plasma leucine(5)-enkephalin degradation is inhibited by a select number of drugs with the phenothiazine molecule in their chemical structure.
2003 Jan
An evaluation of protein assays for quantitative determination of drugs.
2003 Jul 31
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
Impact of nausea and vomiting on quality of life in cancer patients during chemotherapy.
2003 Sep 17
Treatment of pediatric migraine headaches: a randomized, double-blind trial of prochlorperazine versus ketorolac.
2004 Feb
Acute treatment of migraine. Breaking the paradigm of monotherapy.
2004 Jan 28
Prochlorperazine more effective than ketorolac for pediatric migraine.
2004 Jun
Postmortem distribution of the novel antipsychotic drug quetiapine.
2004 May-Jun
Diamorphine for pain relief in labour : a randomised controlled trial comparing intramuscular injection and patient-controlled analgesia.
2004 Oct
Prochlorperazine induces central antinociception mediated by the muscarinic system.
2004 Sep
Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine.
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
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
Prevention and treatment of postoperative nausea and vomiting.
2005 Jun 15
Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography.
2005 Nov-Dec
The use of levomepromazine in Hyperemesis Gravidarum resistant to drug therapy--a case series.
2005 Nov-Dec
Antiemetics in the ED: a randomized controlled trial comparing 3 common agents.
2006 Mar
Patents

Sample Use Guides

In Vivo Use Guide
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: rectal, oral, parenteral
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 Tue Oct 22 00:47:39 UTC 2019
Edited
by admin
on Tue Oct 22 00:47:39 UTC 2019
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 [WHO-DD]
Common Name English
PROCHLORPERAZINE MALEATE [GREEN BOOK]
Common Name English
PROCHLORPERAZINE MALEATE [USP]
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 [EP]
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 Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
Code System Code Type Description
PUBCHEM
5281032
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY
MERCK INDEX
M9149
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
201-511-3
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY
CAS
84-02-6
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY
WIKIPEDIA
Prochlorperazine maleate
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY
ChEMBL
CHEMBL728
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY
RXCUI
8706
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY RxNorm
EVMPD
SUB04052MIG
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY
EPA CompTox
84-02-6
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY
NCI_THESAURUS
C775
Created by admin on Tue Oct 22 00:47:39 UTC 2019 , Edited by admin on Tue Oct 22 00:47:39 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Related Record Type Details
ACTIVE MOIETY