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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24ClN3S.C2H6O6S2
Molecular Weight 564.138
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROCHLORPERAZINE EDISYLATE

SMILES

OS(=O)(=O)CCS(O)(=O)=O.CN1CCN(CCCN2C3=CC(Cl)=CC=C3SC4=C2C=CC=C4)CC1

InChI

InChIKey=SWOUGRBFXFILIB-UHFFFAOYSA-N
InChI=1S/C20H24ClN3S.C2H6O6S2/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;3-9(4,5)1-2-10(6,7)8/h2-3,5-8,15H,4,9-14H2,1H3;1-2H2,(H,3,4,5)(H,6,7,8)

HIDE SMILES / InChI

Molecular Formula C2H6O6S2
Molecular Weight 190.195
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
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
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
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
Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography.
2006-03-11
Antiemetics in the ED: a randomized controlled trial comparing 3 common agents.
2006-03
[Three cases of drug-induced akathisia due to antiemetics during cancer palliative care].
2006-02
Anti-gingivitis effect of a dentifrice containing bioactive glass (NovaMin) particulate.
2006-02
Ondansetron, prochlorperazine, and dexamethasone have similar effects on prevention of delayed chemotherapy-induced nausea and vomiting.
2006-02
Cetirizine-induced dystonic movements.
2006-01-10
Chronic severe dystonia after single exposure to antiemetics.
2006-01
Roles for mitochondria in pentamidine susceptibility and resistance in Leishmania donovani.
2006-01
Clinical practice guidelines on antiemetics in oncology.
2005-12
Bioavailability and metabolism of prochlorperazine administered via the buccal and oral delivery route.
2005-12
Acute hypersensitivity reaction to ferric gluconate in a premedicated patient.
2005-12
Preliminary studies on phenothiazine-mediated reversal of multidrug resistance in mouse lymphoma and COLO 320 cells.
2005-11-10
5-Hydroxytryptamine-receptor antagonists versus prochlorperazine for control of delayed nausea caused by doxorubicin: a URCC CCOP randomised controlled trial.
2005-10
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.
2005-10
Symptomatic treatment of migraine in children: a systematic review of medication trials.
2005-08
A phase I clinical trial of continual alternating etoposide and topotecan in refractory solid tumours.
2005-07-11
Prevention and treatment of postoperative nausea and vomiting.
2005-06-15
[Effects of amino acid solution and recombinant human growth hormone on growth hormone/insulin like growth factor-1 axis in rats with liver cirrhosis].
2005-06-01
The combination of naratriptan and prochlorperazine in migraine treatment.
2005-06
Prevention of delayed chemotherapy-induced nausea and vomiting after moderately high to highly emetogenic chemotherapy: comparison of ondansetron, prochlorperazine, and dexamethasone.
2005-06
Cost-effectiveness analysis of ondansetron and prochlorperazine for the prevention of postoperative nausea and vomiting.
2005-05
Quetiapine discontinuation syndrome.
2005-05
Diphenhydramine in the treatment of akathesia induced by prochlorperazine.
2005-04
Acupuncture therapy rapidly terminates intractable hiccups complicating acute myocardial infarction.
2005-03
The use of levomepromazine in Hyperemesis Gravidarum resistant to drug therapy--a case series.
2005-02-01
[Pain management for cancer patients with critical pathway on computer].
2005-02
Promethazine adverse events after implementation of a medication shortage interchange.
2005-02
In vitro activity of phenothiazine derivatives in Enterococcus faecalis and Enterococcus faecium.
2005-01
The antipsychotic and antiemetic drug prochlorperazine delays the ventricular repolarization of the in situ canine heart.
2005-01
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
Indomethacin, alone and combined with prochlorperazine and caffeine, but not sumatriptan, abolishes peripheral and central sensitization in in vivo models of migraine.
2004-10
Diamorphine for pain relief in labour : a randomised controlled trial comparing intramuscular injection and patient-controlled analgesia.
2004-10
Coloration of phenothiazines with metal-containing drugs.
2004-09
Prochlorperazine induces central antinociception mediated by the muscarinic system.
2004-09
Plasma and cerebrospinal fluid pharmacokinetics of rebeccamycin (NSC 655649) in nonhuman primates.
2004-08
Efficacy of quality criteria to identify potentially harmful information: a cross-sectional survey of complementary and alternative medicine web sites.
2004-06-29
Postmortem distribution of the novel antipsychotic drug quetiapine.
2004-06-11
Prochlorperazine more effective than ketorolac for pediatric migraine.
2004-06
Atypical laryngeal dystonia caused by an antiemetic.
2004-04-01
Diphenhydramine in the treatment of akathisia induced by prochlorperazine.
2004-04
Droperidol vs prochlorperazine for the treatment of acute headache.
2004-02
Treatment of pediatric migraine headaches: a randomized, double-blind trial of prochlorperazine versus ketorolac.
2004-02
Acute treatment of migraine. Breaking the paradigm of monotherapy.
2004-01-28
Index of suspicion.
2004-01
Feasibility of amifostine administration in conjunction with high-dose rate brachytherapy.
2003-12
Prochlorperazine-induced cholestasis in a patient with alpha-1 antitrypsin deficiency.
2003-10-24
Surgeon-led initiatives cut costs and enhance the quality of endoscopic and laparoscopic procedures.
2003-10-16
AANA journal course. Update for nurse anesthetists. Neuroleptic malignant syndrome.
2003-10
Comparison of three outpatient regimens in the management of nausea and vomiting in pregnancy.
2003-10
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 Mon Mar 31 18:09:40 GMT 2025
Edited
by admin
on Mon Mar 31 18:09:40 GMT 2025
Record UNII
PG20W5VQZS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-757299
Preferred Name English
PROCHLORPERAZINE EDISYLATE
GREEN BOOK   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)PHENOTHIAZINE 1,2-ETHANEDISULPHONATE (1:1)
Systematic Name English
PROCHLORPERAZINE EDISILATE [MART.]
Common Name English
PROCHLORPERAZINE EDISYLATE [USP MONOGRAPH]
Common Name English
PROCHLORPERAZINE EDISYLATE [VANDF]
Common Name English
Prochlorperazine edisylate [WHO-DD]
Common Name English
PROCHLORPERAZINE EDISYLATE SALT
Common Name English
10H-PHENOTHIAZINE, 2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, 1,2-ETHANEDISULFONATE (1:1)
Systematic Name English
PROCHLORPERAZINE ETHANEDISULPHONATE
Common Name English
PROCHLORPERAZINE EDISYLATE [ORANGE BOOK]
Common Name English
PHENOTHIAZINE, 2-CHLORO-10-(3-(1-METHYL-4-PIPERAZINYL)PROPYL)-, ETHANEDISULPHONATE
Systematic Name English
PROCHLORPERAZINE EDISYLATE [GREEN BOOK]
Common Name English
PROCHLORPERAZINE ETHANEDISULFONATE
Common Name English
PHENOTHIAZINE, 2-CHLORO-10-(3-(1-METHYL-4-PIPERAZINYL)PROPYL)-, ETHANEDISULFONATE
Systematic Name English
10H-PHENOTHIAZINE, 2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-, 1,2-ETHANEDISULPHONATE (1:1)
Systematic Name English
2-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine 1,2-ethanedisulfonate (1:1)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C740
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
Code System Code Type Description
SMS_ID
100000085082
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
FDA UNII
PG20W5VQZS
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
NSC
757299
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
DRUG BANK
DBSALT000999
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
PUBCHEM
91499
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
ChEMBL
CHEMBL728
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
DAILYMED
PG20W5VQZS
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
CAS
1257-78-9
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
ECHA (EC/EINECS)
215-019-1
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
RXCUI
8705
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY RxNorm
EVMPD
SUB04051MIG
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID4074483
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
NCI_THESAURUS
C48013
Created by admin on Mon Mar 31 18:09:40 GMT 2025 , Edited by admin on Mon Mar 31 18:09:40 GMT 2025
PRIMARY
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