Identification

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Name
Prochlorperazine
Accession Number
DB00433  (APRD00624)
Type
Small Molecule
Groups
Approved, Vet approved
Description

Prochlorperazine, also known as compazine, is a piperazine phenothiazine and first-generation antipsychotic drug that is used for the treatment of severe nausea and vomiting, as well as short-term management of psychotic disorders such as generalized non-psychotic anxiety and schizophrenia.Label It mainly works by depressing the chemoreceptor trigger zone and blocking D2 dopamine receptors in the brain. It was shown to also block histaminergic, cholinergic and noradrenergic receptors.9 Prochlorperazine was first developed in the 1950s 11 and was first approved by the FDA in 1956. Although newer antiemetic agents such as 5-HT3 antagonists are more heavily promoted, prochlorperazine is still widely used in nausea and vomiting.10

Structure
Thumb
Synonyms
  • 2-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)-phenothiazine
  • 2-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine
  • 3-Chloro-10-(3-(1-methyl-4-piperazinyl)propyl)phenothiazine
  • 3-Chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine
  • Capazine
  • Chlormeprazine
  • Chloro-3 (N-methylpiperazinyl-3 propyl)-10 phenothiazine
  • Chloropernazine
  • N-(gamma-(4'-Methylpiperazinyl-1')propyl)-3-chlorophenothiazine
  • Prochlorperazin
  • Prochlorpérazine
  • Prochlorperazine
  • Prochlorperazinum
  • Prochlorpermazine
  • Prochlorpromazine
  • Procloperazine
  • Proclorperazina
External IDs
Bayer A 173 / RP 6140 / SKF 4657
Product Ingredients
IngredientUNIICASInChI Key
Prochlorperazine edisylatePG20W5VQZS1257-78-9SWOUGRBFXFILIB-UHFFFAOYSA-N
Prochlorperazine maleateI1T8O1JTL684-02-6DSKIOWHQLUWFLG-SPIKMXEPSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CompazineSyrup5 mg/5mLOralGlaxoSmithKline2006-05-112006-05-11Us
CompazineInjection, solution5 mg/1mmIntramuscular; IntravenousGlaxoSmithKline2006-05-112006-05-11Us
CompazineTablet, coated5 mg/1OralPhysicians Total Care, Inc.1956-10-232004-12-31Us
CompazineSuppository25 mg/1RectalGlaxoSmithKline2006-05-112006-05-11Us
CompazineCapsule, extended release15 mg/1OralGlaxoSmithKline2006-05-112006-05-11Us
CompazineSuppository25 mg/1RectalPhysicians Total Care, Inc.1993-06-222011-05-31Us
CompazineSuppository5 mg/1RectalGlaxoSmithKline2006-05-112006-05-11Us
CompazineTablet, coated10 mg/1OralGlaxoSmithKline2006-05-112006-05-11Us
CompazineTablet, coated5 mg/1OralGlaxosmithkline Inc2006-02-022011-02-11Us
CompazineSuppository2.5 mg/1RectalGlaxoSmithKline2006-05-112006-05-11Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CompazineTablet, film coated5 mg/1OralPbm Pharmaceuticals Inc.2014-04-012015-12-31Us
CompazineSuppository25 mg/1RectalPbm Pharmaceuticals Inc.2013-07-01Not applicableUs
CompazineTablet, film coated10 mg/1OralPbm Pharmaceuticals Inc.2014-04-012016-01-31Us
ComproSuppository25 mg/1RectalPD-Rx Pharmaceuticals, Inc.2000-09-01Not applicableUs
ComproSuppository25 mg/1RectalPaddock Laboratories, LLC2000-09-01Not applicableUs
ComproSuppository25 mg/1RectalA-S Medication Solutions2000-09-01Not applicableUs
Nu-prochlor Tab 10mgTabletOralNu Pharm Inc1992-12-312012-09-04Canada
Nu-prochlor Tab 5mgTabletOralNu Pharm Inc1992-12-312012-09-04Canada
PMS Prochlorperazine Inj 5mg/mlSolutionIntramuscular; IntravenousPharmascience Inc1989-12-31Not applicableCanada
PMS-prochlorperazine Suppositoires 10mgSuppositoryRectalPharmascience Inc1989-12-31Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Buccastem (Reckitt Benckiser) / Emetiral (Zentiva) / Stemzine (Sanofi-Aventis) / Volimin (Chin Teng)
Categories
UNII
YHP6YLT61T
CAS number
58-38-8
Weight
Average: 373.943
Monoisotopic: 373.13794618
Chemical Formula
C20H24ClN3S
InChI Key
WIKYUJGCLQQFNW-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
SMILES
CN1CCN(CCCN2C3=CC=CC=C3SC3=C2C=C(Cl)C=C3)CC1

Pharmacology

Indication

Indicated for the symptomatic treatment of severe nausea and vomiting.Label

Indicated for the management of manifestations of psychotic disorders, such as schizophrenia and generalized non-psychotic anxiety. The use of prochlorperazine for the management of generalized non-psychotic anxiety is typically not a first-line therapy and should be limited to doses of less than 20 mg per day or for shorter than 12 weeks.Label,8

Off-label uses include use in emergency settings for adult and pediatric migraines. The American Headache Society recommends the use of prochlorperazine as the first-line medication in this setting. In pediatric migraines, a non-steroidal anti-inflammatory agent is often used in combination with dopamine antagonist.9

Associated Conditions
Pharmacodynamics

Prochlorperazine is an antipsychotic agent that works to promote postsynaptic inhibition of dopaminergic neurons.10 It also exerts its anti-emetic actions via anti-dopaminergic effects, where it displays similar efficacy as ondansteron, a 5HT-3 receptor antagonist and anti-emetic, in preventing delayed nausea and vomiting.3 Prochlorperazine was shown to inhibit histaminergic, cholinergic and alpha-1 adrenergic receptors.1,9 The blockade of alpha-1 adrenergic receptors may result in sedation, muscle relaxation, and hypotension. It displays anti-anxiety effects as well.10 Compared to other phenothiazine derivatives, prochlorperazine is less sedating and has a weak propensity for causing hypotension or potentiating the effects of CNS depressants and anesthetics.12 Other than its primary action on D2 receptors, one study showed that prochlorperazine may inhibit the P2X7 receptor in human macrophages, leading to inhibition of calcium ion influx.9

Mechanism of action

The mechanism of action of prochlorperazine has not been fully determined, but may be primarily related to its anti-dopaminergic effects. Prochlorperazine blocks the D2 dopamine receptors in the brain, which are somatodendritic autoreceptors. Inhibition of D2 receptor signaling results in the blockade of postsynaptic dopamine receptors in the mesolimbic system 11 and an increased dopamine turnover. Nausea and vomiting are proposed to arise from peripheral or central stimulation of serotonin type 3 (5-HT3) and dopamine type 2 receptors, the predominant receptors expressed at the chemoreceptor trigger zone (CTZ).6,11 Prochlorperazine exerts antiemetic effects and was shown to inhibit apomorphine-induced vomiting by blocking D2 dopamine receptors in the CTZ.3.

TargetActionsOrganism
ADopamine D2 receptor
antagonist
Humans
UHistamine H1 receptor
antagonist
Humans
UAlpha-1 adrenergic receptors
antagonist
Humans
NAlpha-2 adrenergic receptors
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Following oral administration, prochlorperazine is reported to be well absorbed from the gastrointestinal tract. The onset of pharmacological action is about 30 to 40 minutes following oral administration and 10 to 20 minutes following intramuscular administration. The duration of action for all routes is about 3 to 4 hours.12 Following oral administration in healthy volunteers, the mean oral bioavailability was about 12.5%. In these patients, the time to reach the peak plasma concentrations was about 5 hours. Repeated oral dosing resulted in an accumulation of prochlorperazine and its metabolite. Following multiple twice daily dosing, the steady state of prochlorperazine was reached by 7 days.1

Volume of distribution

In a preliminary pharmacokinetic study involving healthy volunteers, the mean apparent volume of distribution following intravenous administration of 6.25 mg and 12.5 mg prochlorperazine were approximately 1401 L and 1548 L, respectively.4 Prochlorperazine is reported to be distributed to most body tissues with high concentrations being distributed into liver and spleen.12 There is evidence that phenothiazines are excreted in the breast milk of nursing mothers.Label

Protein binding

There is limited data on protein binding of prochlorperazine.

Metabolism

Prochlorperazine undergoes hepatic metabolism involving oxidation, hydroxylation, demethylation, sulfoxide formation and conjugation with glucuronic acid.13 The oxidation reaction is mediated by CYP2D6.3 N-desmethyl prochlorperazine was detected in the plasma1, as well as prochlorperazine sulfoxide, prochlorperazine 7-hydroxide and prochlorperazine sulfoxide 4'-N-oxide, following oral and buccal administration.5 Prochlorperazine may enter the enterohepatic circulation.12

Route of elimination

Prochlorperazine is reported to be mainly excreted via the feces and bile.12 Low quantities of unchanged prochlorperazine and its metabolite were detectable in the urine.1

Half life

Following intravenous and single oral dose administration, the terminal elimination half live were 9 and 8 hours, respectively.1

Clearance

The mean plasma clearance (CL) of prochlorperazine following intravenous administration in healthy volunteers was approximately 0.98L/h x kg. The mean renal clearance was about 23.6 mL/h.1

Toxicity

LD50 and Overdose

Oral LD50 in rats is 750 mg/kg. Intraperitoneal and subcutaneous LD50 in mice are 191 mg/kg and 320 mg/kg, respectively.MSDS In placebo-controlled trials, there were increased incidences of mortality in elderly patients with dementia-related psychosis receiving antipsychotic medications. The risk of death in drug-treated patients was about 1.6 to 1.7 times that of placebo-treated patients. Deaths were largely resulting from cardiovascular, such as heart failure and sudden death, or infectious, such as pneumonia, conditions.Label Due to its antagonist action on dopamine receptors, prochlorperazine is associated with a risk for developing extrapyramidal symptoms such as tardive dyskinesia, which is a syndrome consisting of potentially irreversible, involuntary, dyskinetic movements. This risk is also conferred on other antipsychotic agents that block dopamine receptors. It is proposed that increased duration of the drug treatment is likely thus increased total cumulative dose of antipsychotic drugs administered to the patient leads to increased risk for developing the syndrome and the likelihood that it will become irreversible. As with other antipsychotic agents, prochlorperazine is associated with a risk for causing neuroleptic malignant syndrome (NMS), which is a potentially fatal symptom complex, which is manifested as hyperpyrexia, muscle rigidity, altered mental status and evidence of autonomic instability.

There is no known antidote for prochlorperazine thus overdose treatment should be supportive and symptomatic. Overdose of prochlorperazine may produce dystonic reactions that involve extrapyramidal mechanism. To reduce these symptoms, antiparkinsonism drugs, barbiturates, or diphenhydramine may be used. Symptoms of central nervous system depression, such as somnolence or coma, may also be observed. Amphetamine, destroamphetamine, or caffeine and sodium benzoate may be used to induce stimulatory effects. In contrast, agitation and restlessness may also be seen in case of overdose. Other possible manifestations include convulsions, EKG changes and cardiac arrhythmias, fever, and autonomic reactions such as hypotension, dry mouth and ileus. Hypotension can be responded with the standard measures for managing circulatory shock.Label

Nonclinical Toxicology

In a rat developmental or reproductive toxicity study, abnormalities in both the reproductive measures and neurobehavioral testing were observed following administration of 25 mg/kg of prochlorperazine.13

Use in specific populations

As the use of antipsychotic agents during the third trimester of pregnancy is associated with a risk for extrapyramidal and/or withdrawal symptoms following delivery, the use of prochlorperazine in pregnant patients is generally not recommended and it should be limited after careful consideration of the potential benefit of drug therapy justifying the potential risk to the fetus. Caution should be exercised when prochlorperazine is administered to a nursing mother. While lower doses of prochlorperazine is reported to be safe for elderly patients, caution is still advised, especially those with higher susceptibility to hypotension and neuromuscular reactions.Label

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Prochlorperazine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Prochlorperazine.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Prochlorperazine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
2,5-Dimethoxy-4-ethylamphetamineProchlorperazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineProchlorperazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Prochlorperazine.
3,5-DinitrocatecholThe therapeutic efficacy of 3,5-Dinitrocatechol can be decreased when used in combination with Prochlorperazine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Prochlorperazine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Prochlorperazine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Prochlorperazine is combined with 4-Methoxyamphetamine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Avoid alcohol.
  • Take with a full glass of water Avoid excessive quantities of coffee or tea (Caffeine).
  • Take with food.

References

Synthesis Reference
US2902484
General References
  1. Isah AO, Rawlins MD, Bateman DN: Clinical pharmacology of prochlorperazine in healthy young males. Br J Clin Pharmacol. 1991 Dec;32(6):677-84. [PubMed:1768559]
  2. Isah AO, Rawlins MD, Bateman DN: The pharmacokinetics and effects of prochlorperazine in elderly female volunteers. Age Ageing. 1992 Jan;21(1):27-31. doi: 10.1093/ageing/21.1.27. [PubMed:1553856]
  3. Perwitasari DA, Gelderblom H, Atthobari J, Mustofa M, Dwiprahasto I, Nortier JW, Guchelaar HJ: Anti-emetic drugs in oncology: pharmacology and individualization by pharmacogenetics. Int J Clin Pharm. 2011 Feb;33(1):33-43. doi: 10.1007/s11096-010-9454-1. Epub 2011 Jan 28. [PubMed:21365391]
  4. Taylor WB, Bateman DN: Preliminary studies of the pharmacokinetics and pharmacodynamics of prochlorperazine in healthy volunteers. Br J Clin Pharmacol. 1987 Feb;23(2):137-42. doi: 10.1111/j.1365-2125.1987.tb03021.x. [PubMed:3828192]
  5. Finn A, Collins J, Voyksner R, Lindley C: Bioavailability and metabolism of prochlorperazine administered via the buccal and oral delivery route. J Clin Pharmacol. 2005 Dec;45(12):1383-90. doi: 10.1177/0091270005281044. [PubMed:16291713]
  6. O'Brien C: Nausea and vomiting. Can Fam Physician. 2008 Jun;54(6):861-3. [PubMed:18556493]
  7. Prochlorperazine Tablets BP 5mg - Summary of Product Characteristics [Link]
  8. Prochlorperazine - FDA Approval Package [Link]
  9. Prochlorperazine - StatPearls - NCBI Bookshelf [Link]
  10. Prochlorperazine - LiverTox - NIH [Link]
  11. Prochlorperazine — the forgotten antiemetic - UF Health [Link]
  12. Prochlorperazine Prescribing Information - AA Pharma [Link]
  13. Prochlorperazine - National Library of Medicine HSDB Database [Link]
External Links
Human Metabolome Database
HMDB0014577
KEGG Drug
D00493
KEGG Compound
C07403
PubChem Compound
4917
PubChem Substance
46509018
ChemSpider
4748
BindingDB
78434
ChEBI
8435
ChEMBL
CHEMBL728
Therapeutic Targets Database
DAP000373
PharmGKB
PA451114
HET
P77
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Prochlorperazine
ATC Codes
N05AB04 — Prochlorperazine
AHFS Codes
  • 56:22.08 — Antihistamines
  • 28:16.08.24 — Phenothiazines
PDB Entries
3m0w
FDA label
Download (294 KB)
MSDS
Download (24 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCardiotoxicity / Migraine1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentMigraine1
2CompletedTreatmentMigraine Headache, With or Without Aura1
2CompletedTreatmentNausea and vomiting1
2TerminatedTreatmentBenign Headache1
3Active Not RecruitingTreatmentMigraine Disorders1
3CompletedSupportive CareNausea1
3CompletedSupportive CareNausea and vomiting / Unspecified Adult Solid Tumor, Protocol Specific1
3RecruitingSupportive CareCarcinoma, Breast1
3RecruitingTreatmentMigraine in Adolescence / Migraine in Children / Sphenopalatine neuralgia1
3TerminatedTreatmentHeadaches1
4CompletedTreatmentHeadaches1
4CompletedTreatmentMigraine2
4RecruitingPreventionLaparoscopic Sleeve Gastrectomy / Post-Operative Nausea and Vomiting (PONV)1
4RecruitingTreatmentHeadaches1
4TerminatedTreatmentMigraine1
Not AvailableCompletedNot AvailableSchizophrenic Disorders1
Not AvailableCompletedTreatmentAcute Migraine1
Not AvailableUnknown StatusSupportive CareNon-Hodgkin's Lymphoma (NHL)1

Pharmacoeconomics

Manufacturers
  • Glaxosmithkline
  • Paddock laboratories inc
  • Able laboratories inc
  • G and w laboratories inc
  • Alpharma us pharmaceuticals division
  • Morton grove pharmaceuticals inc
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Marsam pharmaceuticals llc
  • Smith and nephew solopak div smith and nephew
  • Teva parenteral medicines inc
  • Watson laboratories inc
  • Wyeth ayerst laboratories
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Cadista pharmaceuticals inc
Packagers
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bryant Ranch Prepack
  • Cadista Pharmaceuticals Inc.
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • G & W Labs
  • General Injectables and Vaccines Inc.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Hospira Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Liberty Pharmaceuticals
  • Medisca Inc.
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharma Pac LLC
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
Capsule, extended releaseOral10 mg/1
Capsule, extended releaseOral15 mg/1
Injection, solutionIntramuscular; Intravenous5 mg/1mm
SuppositoryRectal2.5 mg/1
SuppositoryRectal5 mg/1
SyrupOral5 mg/5mL
Tablet, coatedOral10 mg/1
Tablet, coatedOral5 mg/1
SuppositoryRectal
TabletOral
SuppositoryRectal25 mg/1
InjectionIntramuscular5 mg/1mL
InjectionIntramuscular; Intravenous5 mg/1mL
Injection, solutionIntramuscular; Intravenous5 mg/1mL
TabletOral10 mg/1
TabletOral5 mg/1
TabletOral5 mg/61
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
LiquidIntramuscular; Intravenous
SolutionIntramuscular; Intravenous
SyrupOral
Prices
Unit descriptionCostUnit
Prochlorperazine mal powder4.77USD g
Compazine 25 mg suppository4.25USD suppository
Prochlorperazine 25 mg suppository3.13USD suppository
Compro 25 mg suppository3.05USD suppository
Compazine 5 mg tablet1.82USD tablet
Compazine 10 mg tablet1.8USD tablet
Prochlorperazine 5 mg/ml vial1.22USD ml
Prochlorperazine 5 mg/ml0.91USD ml
Prochlorperazine Maleate 10 mg tablet0.88USD tablet
Sandoz Prochlorperazine 10 mg Suppository0.87USD suppository
Prochlorperazine 10 mg tablet0.85USD tablet
Prochlorperazine Maleate 5 mg tablet0.59USD tablet
Prochlorperazine 5 mg tablet0.57USD tablet
Apo-Prochlorazine 10 mg Tablet0.21USD tablet
Apo-Prochlorazine 5 mg Tablet0.17USD tablet
Novamine 15% iv solution0.09USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)228 °CPhysProp
water solubility15 mg/L (at 24 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.88HANSCH,C ET AL. (1995)
logS-4.4ADME Research, USCD
pKa8.1SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.011 mg/mLALOGPS
logP4.67ALOGPS
logP4.38ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.72 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.81 m3·mol-1ChemAxon
Polarizability41.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9821
Blood Brain Barrier+0.9781
Caco-2 permeable+0.7729
P-glycoprotein substrateSubstrate0.8537
P-glycoprotein inhibitor IInhibitor0.817
P-glycoprotein inhibitor IIInhibitor0.8577
Renal organic cation transporterInhibitor0.7615
CYP450 2C9 substrateNon-substrate0.7702
CYP450 2D6 substrateNon-substrate0.5179
CYP450 3A4 substrateNon-substrate0.5346
CYP450 1A2 substrateInhibitor0.9376
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.9723
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.7676
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8557
Ames testNon AMES toxic0.8999
CarcinogenicityNon-carcinogens0.9456
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3496 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8165
hERG inhibition (predictor II)Inhibitor0.786
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.4 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-01vo-9853000000-ba88fedd94e150c34e1a
GC-MS Spectrum - EI-BGC-MSsplash10-0229-7933000000-4e14a9a9728c361941d3
Mass Spectrum (Electron Ionization)MSsplash10-022c-9752000000-533ac31876b44d82f2aa
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00fr-0219000000-abf2f9a1f6a1efb497b8

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Phenothiazines
Direct Parent
Phenothiazines
Alternative Parents
Alkyldiarylamines / Diarylthioethers / N-methylpiperazines / Benzenoids / Aryl chlorides / 1,4-thiazines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides
show 1 more
Substituents
Phenothiazine / Alkyldiarylamine / Diarylthioether / Aryl thioether / Tertiary aliphatic/aromatic amine / N-alkylpiperazine / N-methylpiperazine / Para-thiazine / Aryl chloride / Aryl halide
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines, organochlorine compound, N-alkylpiperazine, N-methylpiperazine (CHEBI:8435)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Roberge RJ: Antiemetic-related dystonic reaction unmasked by removal of a scopolamine transdermal patch. J Emerg Med. 2006 Apr;30(3):299-302. [PubMed:16677982]
  3. Hamik A, Peroutka SJ: Differential interactions of traditional and novel antiemetics with dopamine D2 and 5-hydroxytryptamine3 receptors. Cancer Chemother Pharmacol. 1989;24(5):307-10. [PubMed:2527092]
  4. Vinson DR: Development of a simplified instrument for the diagnosis and grading of akathisia in a cohort of patients receiving prochlorperazine. J Emerg Med. 2006 Aug;31(2):139-45. [PubMed:17044574]
  5. Callan JE, Kostic MA, Bachrach EA, Rieg TS: Prochlorperazine vs. promethazine for headache treatment in the emergency department: a randomized controlled trial. J Emerg Med. 2008 Oct;35(3):247-53. doi: 10.1016/j.jemermed.2007.09.047. Epub 2008 Jun 5. [PubMed:18534808]
  6. Narita M, Takei D, Shiokawa M, Tsurukawa Y, Matsushima Y, Nakamura A, Takagi S, Asato M, Ikegami D, Narita M, Amano T, Niikura K, Hashimoto K, Kuzumaki N, Suzuki T: Suppression of dopamine-related side effects of morphine by aripiprazole, a dopamine system stabilizer. Eur J Pharmacol. 2008 Dec 14;600(1-3):105-9. doi: 10.1016/j.ejphar.2008.10.030. Epub 2008 Oct 21. [PubMed:18955042]
  7. Golembiewski J, Tokumaru S: Pharmacological prophylaxis and management of adult postoperative/postdischarge nausea and vomiting. J Perianesth Nurs. 2006 Dec;21(6):385-97. [PubMed:17169748]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
This binding interaction is theoretical based on the actions of the phenothiazine drug class and requires further investigation.
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Isah AO, Rawlins MD, Bateman DN: Clinical pharmacology of prochlorperazine in healthy young males. Br J Clin Pharmacol. 1991 Dec;32(6):677-84. [PubMed:1768559]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
This binding interaction is theoretical based on the actions of the phenothiazine drug class and requires further investigation.
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:
References
  1. Isah AO, Rawlins MD, Bateman DN: Clinical pharmacology of prochlorperazine in healthy young males. Br J Clin Pharmacol. 1991 Dec;32(6):677-84. [PubMed:1768559]
Kind
Protein group
Organism
Humans
Pharmacological action
No
Actions
Antagonist
Curator comments
This binding interaction is theoretical based on the actions of the phenothiazine drug class and requires further investigation.
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...

Components:
References
  1. Isah AO, Rawlins MD, Bateman DN: Clinical pharmacology of prochlorperazine in healthy young males. Br J Clin Pharmacol. 1991 Dec;32(6):677-84. [PubMed:1768559]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Davies SJ, Eayrs S, Pratt P, Lennard MS: Potential for drug interactions involving cytochromes P450 2D6 and 3A4 on general adult psychiatric and functional elderly psychiatric wards. Br J Clin Pharmacol. 2004 Apr;57(4):464-72. doi: 10.1111/j.1365-2125.2003.02040.x. [PubMed:15025745]

Drug created on June 13, 2005 07:24 / Updated on September 23, 2019 04:11