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
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)
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 |
DescriptionCurator's Comment: Description was created based on several sources, including
http://apm.amegroups.com/article/view/1039/1266
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4805 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23954492 |
|||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16860311 |
22.6 µM [IC50] | ||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | COMPAZINE Approved UseTo control severe nausea and vomiting. For the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety. Launch Date1959 |
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Primary | COMPAZINE Approved UseTo control severe nausea and vomiting. For the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety. Launch Date1959 |
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Primary | COMPAZINE Approved UseTo control severe nausea and vomiting. For the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety. Launch Date1959 |
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Primary | COMPAZINE Approved UseTo control severe nausea and vomiting. For the treatment of schizophrenia. Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety. Launch Date1959 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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%) AEs leading toHypotension (grade 3, 25%) 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%) Sources: Page: p.1469Restlessness (100%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
Anti-emetics. | 2001 |
|
Sedation and analgesia for transvaginal oocyte retrieval: an audit resulting in a change of clinical practice. | 2001 |
|
Continuous infusion prochlorperazine: pharmacokinetics, antiemetic efficacy, and feasibility of high-dose therapy. | 2001 Apr |
|
Intranasal lidocaine for the treatment of migraine headache: a randomized, controlled trial. | 2001 Apr |
|
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 |
|
Diphenhydramine for the prevention of akathisia induced by prochlorperazine: a randomized, controlled trial. | 2001 Feb |
|
Pegylated liposomal doxorubicin: tolerability and toxicity. | 2001 Jun |
|
Frequency of adverse reactions to prochlorperazine in the ED: a response. | 2001 Mar |
|
Identification and characterization of 17 phenothiazine compounds by capillary high-performance liquid chromatography/fast atom bombardment mass spectrometry. | 2002 Dec |
|
Upper airway obstruction resulting from an antiemetic. | 2002 Dec |
|
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 |
|
Indomethacin, caffeine and prochlorperazine alone and combined revert hyperalgesia in in vivo models of migraine. | 2002 Sep |
|
Variations among emergency departments in the treatment of benign headache. | 2003 Jan |
|
AANA journal course. Update for nurse anesthetists. Neuroleptic malignant syndrome. | 2003 Oct |
|
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 |
|
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 |
|
Acute treatment of migraine. Breaking the paradigm of monotherapy. | 2004 Jan 28 |
|
Prochlorperazine more effective than ketorolac for pediatric migraine. | 2004 Jun |
|
Coloration of phenothiazines with metal-containing drugs. | 2004 Sep |
|
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 |
|
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 |
|
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 |
|
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2833274
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
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admin
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Edited
Fri Dec 15 15:24:33 GMT 2023
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Record UNII |
531SH87H9N
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Record Status |
Validated (UNII)
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Record Version |
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100000085083
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m9149
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235739
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51888-09-6
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40222-89-7
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5132-55-8
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CHEMBL728
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39530-87-5
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125791
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34932
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SUB04053MIG
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531SH87H9N
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257-495-3
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DTXSID20199844
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