Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H24ClN3S |
Molecular Weight | 373.943 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CCCN2C3=C(SC4=C2C=C(Cl)C=C4)C=CC=C3)CC1
InChI
InChIKey=WIKYUJGCLQQFNW-UHFFFAOYSA-N
InChI=1S/C20H24ClN3S/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/h2-3,5-8,15H,4,9-14H2,1H3
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 |
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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 |
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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 |
---|---|---|
[Diagnostic image (17). Acute dystonia induced by prochlorperazine]. | 2000 Dec 23 |
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Anti-emetics. | 2001 |
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Sedation and analgesia for transvaginal oocyte retrieval: an audit resulting in a change of clinical practice. | 2001 |
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Ondansetron: a review of its use as an antiemetic in children. | 2001 |
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Continuous infusion prochlorperazine: pharmacokinetics, antiemetic efficacy, and feasibility of high-dose therapy. | 2001 Apr |
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Tolerability and effectiveness of prochlorperazine for intractable migraine in children. | 2001 Apr |
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[Inactivation of Trypanosoma cruzi trypanothione reductase by phenothiazine cationic free radicals]. | 2001 Jan-Mar |
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Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review. | 2001 Jul 7 |
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Headache in the emergency department. | 2001 Jun |
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Pegylated liposomal doxorubicin: tolerability and toxicity. | 2001 Jun |
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[A case report. Drugs can be administered via colostomy but the scientific support is negligible]. | 2001 May 9 |
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Amphotericin B-induced seizures in a patient with AIDS. | 2001 Sep |
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Incompatibility of prochlorperizine and ketoprofen. | 2001 Sep |
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Droperidol vs. prochlorperazine for benign headaches in the emergency department. | 2001 Sep |
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Oral mucosal drug delivery: clinical pharmacokinetics and therapeutic applications. | 2002 |
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Myeloperoxidase-generated phenothiazine cation radicals inactivate Trypanosoma cruzi dihydrolipoamide dehydrogenase. | 2002 Apr-Jun |
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Identification and characterization of 17 phenothiazine compounds by capillary high-performance liquid chromatography/fast atom bombardment mass spectrometry. | 2002 Dec |
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Upper airway obstruction resulting from an antiemetic. | 2002 Dec |
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Antimicrobial potentiality of a phenothiazine group of antipsychotic drug-prochlorperazine. | 2002 Jul |
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Medical management of Meniere's disease. | 2002 Jun |
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Akathisia: problematic but preventable. | 2002 May |
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Antiemetic use in pediatric gastroenteritis: a national survey of emergency physicians, pediatricians, and pediatric emergency physicians. | 2002 Nov-Dec |
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Efficacy and tolerability of prochlorperazine buccal tablets in treatment of acute migraine. | 2002 Oct |
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Indomethacin, caffeine and prochlorperazine alone and combined revert hyperalgesia in in vivo models of migraine. | 2002 Sep |
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The efficacy and cost-effectiveness of prophylactic 5-hydroxytryptamine3 receptor antagonists: tropisetron, ondansetron and dolasetron. | 2003 Feb |
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Akathisia can be reduced by lowering the dose of D2 receptor antagonists. | 2003 Feb |
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Serotonin syndrome induced by low-dose venlafaxine. | 2003 Feb |
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Variations among emergency departments in the treatment of benign headache. | 2003 Jan |
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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 |
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Surgeon-led initiatives cut costs and enhance the quality of endoscopic and laparoscopic procedures. | 2003 Jul-Sep |
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Intravenous sodium valproate versus prochlorperazine for the emergency department treatment of acute migraine headaches: a prospective, randomized, double-blind trial. | 2003 Jun |
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Phenothiazine radicals inactivate Trypanosoma cruzi dihydrolipoamide dehydrogenase: enzyme protection by radical scavengers. | 2003 Mar |
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Extrapyramidal reactions to ondansetron: cross-reactivity between ondansetron and prochlorperazine? | 2003 May |
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Comparison of three outpatient regimens in the management of nausea and vomiting in pregnancy. | 2003 Oct |
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Aborting a prolonged migrainous aura with intravenous prochlorperazine and magnesium sulfate. | 2003 Sep |
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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 |
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Prochlorperazine-induced cholestasis in a patient with alpha-1 antitrypsin deficiency. | 2003 Sep-Oct |
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Prochlorperazine more effective than ketorolac for pediatric migraine. | 2004 Jun |
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Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine. | 2005 |
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Clinical practice guidelines on antiemetics in oncology. | 2005 Dec |
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Bioavailability and metabolism of prochlorperazine administered via the buccal and oral delivery route. | 2005 Dec |
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Acute hypersensitivity reaction to ferric gluconate in a premedicated patient. | 2005 Dec |
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In vitro activity of phenothiazine derivatives in Enterococcus faecalis and Enterococcus faecium. | 2005 Jan |
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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 |
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Acupuncture therapy rapidly terminates intractable hiccups complicating acute myocardial infarction. | 2005 Mar |
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Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography. | 2005 Nov-Dec |
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[Three cases of drug-induced akathisia due to antiemetics during cancer palliative care]. | 2006 Feb |
|
Chronic severe dystonia after single exposure to antiemetics. | 2006 Jan |
|
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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Record UNII |
YHP6YLT61T
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Validated (UNII)
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NDF-RT |
N0000007544
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LIVERTOX |
NBK548122
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WHO-ATC |
N05AB04
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CFR |
21 CFR 520.1920
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CFR |
21 CFR 520.1921
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NDF-RT |
N0000007544
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NDF-RT |
N0000007544
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CFR |
21 CFR 522.1920
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NCI_THESAURUS |
C740
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N0000175746
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WHO-VATC |
QN05AB04
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DB00433
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SUB10059MIG
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Prochlorperazine
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ASSAY (TITRATION)
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METABOLITE -> PARENT | |||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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