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Details

Stereochemistry ACHIRAL
Molecular Formula C20H24ClN3S.2CH4O3S
Molecular Weight 566.154
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROCHLORPERAZINE DIMETHANESULFONATE

SMILES

CS(O)(=O)=O.CS(O)(=O)=O.CN1CCN(CCCN2C3=C(SC4=C2C=C(Cl)C=C4)C=CC=C3)CC1

InChI

InChIKey=BTOOUKJFDLARFG-UHFFFAOYSA-N
InChI=1S/C20H24ClN3S.2CH4O3S/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*1-5(2,3)4/h2-3,5-8,15H,4,9-14H2,1H3;2*1H3,(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
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

-3.44995201E11
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

-3.44995201E11
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

-3.44995201E11
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

-3.44995201E11
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
Feasibility of amifostine administration in conjunction with high-dose rate brachytherapy.
2003 Dec
Surgeon-led initiatives cut costs and enhance the quality of endoscopic and laparoscopic procedures.
2003 Jul-Sep
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
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
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
Diphenhydramine in the treatment of akathesia induced by prochlorperazine.
2005 Apr
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
Promethazine adverse events after implementation of a medication shortage interchange.
2005 Feb
In vitro activity of phenothiazine derivatives in Enterococcus faecalis and Enterococcus faecium.
2005 Jan
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
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
Prevention and treatment of postoperative nausea and vomiting.
2005 Jun 15
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
The use of levomepromazine in Hyperemesis Gravidarum resistant to drug therapy--a case series.
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
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
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
Chronic severe dystonia after single exposure to antiemetics.
2006 Jan
Roles for mitochondria in pentamidine susceptibility and resistance in Leishmania donovani.
2006 Jan
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 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 15:24:33 UTC 2023
Edited
by admin
on Fri Dec 15 15:24:33 UTC 2023
Record UNII
531SH87H9N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROCHLORPERAZINE DIMETHANESULFONATE
MI  
Common Name English
2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-10H-PHENOTHIAZINE DIMETHANESULFONATE
Systematic Name English
2-CHLORO-10-(3-(4-METHYL-1-PIPERAZINYL)PROPYL)-10H-PHENOTHIAZINE DIMETHANESULPHONATE
Systematic Name English
PROCHLORPERAZINE MESILATE
JAN   MART.   WHO-DD  
Common Name English
Prochlorperazine mesilate [WHO-DD]
Common Name English
PROCHLORPERAZINE DIMETHANESULPHONATE
Common Name English
PROCHLORPERAZINE MESILATE [MART.]
Common Name English
PROCHLORPERAZINE MESILATE [JAN]
Common Name English
PROCHLORPERAZINE MESYLATE
Common Name English
PROCHLORPERAZINE DIMETHANESULFONATE [MI]
Common Name English
Code System Code Type Description
SMS_ID
100000085083
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
MERCK INDEX
m9149
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY Merck Index
RXCUI
235739
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY RxNorm
CAS
51888-09-6
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
CAS
40222-89-7
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
SUPERSEDED
CAS
5132-55-8
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
SUPERSEDED
ChEMBL
CHEMBL728
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
CAS
39530-87-5
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
SUPERSEDED
PUBCHEM
125791
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
CHEBI
34932
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
EVMPD
SUB04053MIG
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
FDA UNII
531SH87H9N
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
257-495-3
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID20199844
Created by admin on Fri Dec 15 15:24:33 UTC 2023 , Edited by admin on Fri Dec 15 15:24:33 UTC 2023
PRIMARY
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