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Chemistry

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Also known as: 58-38-8, Prochlorperazin, Compazine, Prochlorpromazine, Chlormeprazine, Chlorperazine
Molecular Formula
C20H24ClN3S
Molecular Weight
373.9  g/mol
InChI Key
WIKYUJGCLQQFNW-UHFFFAOYSA-N
FDA UNII
YHP6YLT61T

Prochlorperazine
A phenothiazine antipsychotic used principally in the treatment of NAUSEA; VOMITING; and VERTIGO. It is more likely than CHLORPROMAZINE to cause EXTRAPYRAMIDAL DISORDERS. (From Martindale, The Extra Pharmacopoeia, 30th ed, p612)
Prochlorperazine is a Phenothiazine.
1 2D Structure

Prochlorperazine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine
2.1.2 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
2.1.3 InChI Key
WIKYUJGCLQQFNW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl
2.2 Other Identifiers
2.2.1 UNII
YHP6YLT61T
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Compazine

2. Edisylate Salt, Prochlorperazine

3. Edisylate, Prochlorperazine

4. Maleate, Prochlorperazine

5. Prochlorperazine Edisylate

6. Prochlorperazine Edisylate Salt

7. Prochlorperazine Maleate

8. Salt, Prochlorperazine Edisylate

2.3.2 Depositor-Supplied Synonyms

1. 58-38-8

2. Prochlorperazin

3. Compazine

4. Prochlorpromazine

5. Chlormeprazine

6. Chlorperazine

7. Procloperazine

8. Capazine

9. Prochlorpemazine

10. Proclorperazine

11. Meterazin

12. Meterazine

13. Stemetil

14. Tementil

15. Kronocin

16. Compro

17. Emelent

18. Nipodal

19. Temetid

20. Prochlorpermazine

21. Proclorperazina

22. Bayer A 173

23. Prochlorperazine Maleate

24. Prochloroperazine

25. Prochlorperazinum

26. 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine

27. 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine

28. Vertigon

29. 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10h-phenothiazine

30. Skf 4657

31. 6140 Rp

32. Rp 6140

33. 3-chloro-10-(3-(1-methyl-4-piperazinyl)propyl)phenothiazine

34. 10h-phenothiazine, 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]-

35. Buccastem

36. Chloperazine

37. 2-chloro-10-(3-(1-methyl-4-piperazinyl)propyl)-phenothiazine

38. 3-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine

39. Mls000028600

40. N-(gamma-(4'-methylpiperazinyl-1')propyl)-3-chlorophenothiazine

41. 2-chloro-10-(3-(4-methylpiperazin-1-yl)propyl)-10h-phenothiazine

42. 10h-phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-

43. Chloro-3 (n-methylpiperazinyl-3 Propyl)-10 Phenothiazine

44. Yhp6ylt61t

45. Prochlorperazine Base

46. Smr000058705

47. Prochlorperazine Mesylate

48. Chebi:8435

49. Compazine Suppositories

50. Phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-

51. Prochlorperazinum [inn-latin]

52. Proclorperazina [inn-spanish]

53. Proazine

54. Mls001148133

55. Compro (tn)

56. Nsc17478

57. Nsc167375

58. Hsdb 3171

59. Cas-84-02-6

60. Compazine (*maleate*)

61. Smr000653454

62. Einecs 200-379-4

63. Unii-yhp6ylt61t

64. Chloropernazine

65. Phenothiazine, 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]-

66. Prochlorperazine (jan/usp/inn)

67. 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-10h-phenothiazine

68. Chloro-3 (n-methylpiperazinyl-3 Propyl)-10 Phenothiazine [french]

69. Prochlorperazine [usp:inn:ban:jan]

70. Eskatrol (salt/mix)

71. Spectrum_000840

72. Opera_id_244

73. Prestwick0_000399

74. Prestwick1_000399

75. Prestwick2_000399

76. Prestwick3_000399

77. Spectrum2_001297

78. Spectrum3_000881

79. Spectrum4_000972

80. Spectrum5_001339

81. Lopac-p-9178

82. Chembl728

83. Probes1_000265

84. Probes2_000307

85. Lopac0_001034

86. Schembl18429

87. Bspbio_000617

88. Bspbio_002394

89. Kbiogr_001343

90. Kbiogr_002304

91. Kbioss_001320

92. Kbioss_002306

93. Prochlorperazine [mi]

94. Cid_91499

95. Mls006011830

96. Divk1c_000413

97. Prochlorperazine [inn]

98. Prochlorperazine [jan]

99. Spbio_001333

100. Spbio_002538

101. Prochlorperazine [hsdb]

102. Bpbio1_000679

103. Gtpl7279

104. Prochlorperazine [vandf]

105. Dtxsid7023514

106. Prochlorperazine [mart.]

107. Bdbm78434

108. Kbio1_000413

109. Kbio2_001320

110. Kbio2_002304

111. Kbio2_003888

112. Kbio2_004872

113. Kbio2_006456

114. Kbio2_007440

115. Kbio3_001762

116. Kbio3_002784

117. Prochlorperazine [who-dd]

118. Cmap_000013

119. Ninds_000413

120. Hms2231p21

121. Stl371212

122. Zinc19796018

123. Prochlorperazine [orange Book]

124. Akos003600762

125. Ccg-205112

126. Db00433

127. Rp-6140

128. Sdccgsbi-0051005.p005

129. Idi1_000413

130. Mrf-0000068

131. Prochlorperazine [usp Monograph]

132. Ncgc00015856-01

133. Ncgc00015856-02

134. Ncgc00015856-03

135. Ncgc00015856-04

136. Ncgc00015856-05

137. Ncgc00015856-06

138. Ncgc00015856-07

139. Ncgc00015856-16

140. Ncgc00023036-03

141. Nci60_022783

142. P77

143. Sbi-0051005.p004

144. 6140 R.p.

145. Db-053199

146. Ab00053532

147. Ft-0603243

148. C07403

149. C16030

150. D00493

151. Ab00053532_29

152. Ab00053532_30

153. 058p388

154. A831861

155. L001030

156. Q2359690

157. Brd-k19352500-070-02-5

158. Brd-k19352500-070-05-8

159. Brd-k19352500-332-03-7

160. Sr-01000000260-11

161. 2-chloro-10-(3-(1-methyl-4-piperazinyl)-propyl)-phenothiazine

162. N-(.gamma.-(4'-methylpiperazinyl-1')propyl)-3-chlorophenothiazine

163. Phenothiazine, 2-chloro-10-[3-(1-methyl-4-piperazinyl)propyl]-

164. 10h-phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl

165. 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]-10h-phenothiazine #

166. 2-chloranyl-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine;ethane-1,2-disulfonic Acid

167. 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine;ethane-1,2-disulfonic Acid

168. 2-chloro-10-[3-(4-methylpiperazino)propyl]phenothiazine;ethane-1,2-disulfonic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 373.9 g/mol
Molecular Formula C20H24ClN3S
XLogP34.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass373.1379466 g/mol
Monoisotopic Mass373.1379466 g/mol
Topological Polar Surface Area35 Ų
Heavy Atom Count25
Formal Charge0
Complexity429
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameCompro
PubMed HealthProchlorperazine
Drug ClassesAntiemetic, Antipsychotic
Drug LabelProchlorperazine is a clear, pale yellow, viscous liquid. It is sensitive to light, very slightly soluble in water, freely soluble in alcohol, in chloroform, and in ether.Each suppository, for rectal administration, contains 25 mg of prochlorperazine...
Active IngredientProchlorperazine
Dosage FormSuppository
RouteRectal
Strength25mg
Market StatusPrescription
CompanyPaddock

2 of 6  
Drug NameProchlorperazine
Drug LabelProchlorperazine edisylate, 2-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine 1,2-ethanedisulfonate (1:1), has the following structural formula:C20H24ClN3SC2H6O6S2 MW 564.14Prochlorperazine Edis...
Active IngredientProchlorperazine
Dosage FormSuppository
RouteRectal
Strength25mg
Market StatusPrescription
CompanyG And W Labs

3 of 6  
Drug NameProchlorperazine maleate
Drug LabelProchlorperazine is a phenothiazine derivative, present in prochlorperazine tablets as the maleate. Prochlorperazine maleate is designated chemically as 2-chloro-10-[3-(4-methyl-1- piperazinyl)propyl] phenothiazine maleate and has the following struc...
Active IngredientProchlorperazine maleate
Dosage FormTablet
RouteOral
Strengtheq 5mg base; eq 10mg base
Market StatusPrescription
CompanySandoz; Teva Pharms; Mylan

4 of 6  
Drug NameCompro
PubMed HealthProchlorperazine
Drug ClassesAntiemetic, Antipsychotic
Drug LabelProchlorperazine is a clear, pale yellow, viscous liquid. It is sensitive to light, very slightly soluble in water, freely soluble in alcohol, in chloroform, and in ether.Each suppository, for rectal administration, contains 25 mg of prochlorperazine...
Active IngredientProchlorperazine
Dosage FormSuppository
RouteRectal
Strength25mg
Market StatusPrescription
CompanyPaddock

5 of 6  
Drug NameProchlorperazine
Drug LabelProchlorperazine edisylate, 2-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine 1,2-ethanedisulfonate (1:1), has the following structural formula:C20H24ClN3SC2H6O6S2 MW 564.14Prochlorperazine Edis...
Active IngredientProchlorperazine
Dosage FormSuppository
RouteRectal
Strength25mg
Market StatusPrescription
CompanyG And W Labs

6 of 6  
Drug NameProchlorperazine maleate
Drug LabelProchlorperazine is a phenothiazine derivative, present in prochlorperazine tablets as the maleate. Prochlorperazine maleate is designated chemically as 2-chloro-10-[3-(4-methyl-1- piperazinyl)propyl] phenothiazine maleate and has the following struc...
Active IngredientProchlorperazine maleate
Dosage FormTablet
RouteOral
Strengtheq 5mg base; eq 10mg base
Market StatusPrescription
CompanySandoz; Teva Pharms; Mylan

4.2 Therapeutic Uses

Antiemetics; Antipsychotic Agents, Phenothiazine; Dopamine Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)


/Prochlorperazine is indicated/ for control of severe nausea and vomiting. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Prochlorperazine (prochlorperazine maleate ) tablet (September 2009). Available from, as of June 20, 2010 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15790


/Prochlorperazine is indicated/ for the treatment of schizophrenia. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Prochlorperazine (prochlorperazine maleate) tablet (September 2009). Available from, as of June 20, 2010 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15790


Prochlorperazine is effective for the short-term treatment of generalized non-psychotic anxiety. However, prochlorperazine is not the first drug to be used in therapy for most patients with non-psychotic anxiety, because certain risks associated with its use are not shared by common alternative treatments (eg, benzodiazepines). /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for Prochlorperazine (prochlorperazine maleate) tablet (September 2009). Available from, as of June 20, 2010 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15790


For more Therapeutic Uses (Complete) data for Prochlorperazine (7 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ Elderly patients with dementia-related psychosis treated with antipsychotic drugs are at an increased risk of death. Analyses of seventeen placebo-controlled trials (modal duration of 10 weeks), largely in patients taking atypical antipsychotic drugs, revealed a risk of death in drug-treated patients of between 1.6 to 1.7 times the risk of death in placebo-treated patients. Over the course of a typical 10 week controlled trial, the rate of death in drug-treated patients was about 4.5%, compared to a rate of about 2.6% in the placebo group. Although the causes of death were varied, most of the deaths appeared to be either cardiovascular (eg, heart failure, sudden death) or infectious (eg, pneumonia) in nature. Observational studies suggest that, similar to atypical antipsychotic drugs, treatment with conventional antipsychotic drugs may increase mortality. The extent to which the findings of increased mortality in observational studies may be attributed to the antipsychotic drug as opposed to some characteristic(s) of the patients is not clear. Prochlorperazine maleate is not approved for the treatment of patients with dementia-related psychosis.

US Natl Inst Health; DailyMed. Current Medication Information for Prochlorperazine (prochlorperazine maleate) tablet (September 2009). Available from, as of June 20, 2010 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15790


VET: Epinephrine may further lower, rather than elevate, blood pressures in animals on this phenothiazine derivatives.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 486


Do not use in patients with known hypersensitivity to phenothiazines.

US Natl Inst Health; DailyMed. Current Medication Information for Prochlorperazine (prochlorperazine maleate) tablet (September 2009). Available from, as of June 20, 2010 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15790


Do not use in comatose states or in the presence of large amounts of central nervous system depressants (alcohol, barbiturates, narcotics, etc.).

US Natl Inst Health; DailyMed. Current Medication Information for Prochlorperazine (prochlorperazine maleate) tablet (September 2009). Available from, as of June 20, 2010 https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15790


For more Drug Warnings (Complete) data for Prochlorperazine (53 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

Toxic dose: 100 ug/dL /From table/

Gossel, T.A., J.D. Bricker. Principles of Clinical Toxicology. 3rd ed. New York, NY: Raven Press, Ltd., 1994., p. 422


3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR LB) FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-222


4.5 Drug Indication

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


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Prochlorperazine is an antipsychotic agent that works to promote postsynaptic inhibition of dopaminergic neurons. 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. Prochlorperazine was shown to inhibit histaminergic, cholinergic and alpha-1 adrenergic receptors. The blockade of alpha-1 adrenergic receptors may result in sedation, muscle relaxation, and hypotension. It displays anti-anxiety effects as well. 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. 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.


5.2 MeSH Pharmacological Classification

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)


Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)


Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PROCHLORPERAZINE
5.3.2 FDA UNII
YHP6YLT61T
5.3.3 Pharmacological Classes
Phenothiazines [CS]; Phenothiazine [EPC]
5.4 ATC Code

N - Nervous system

N05 - Psycholeptics

N05A - Antipsychotics

N05AB - Phenothiazines with piperazine structure

N05AB04 - Prochlorperazine


5.5 Absorption, Distribution and Excretion

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. 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.


Route of Elimination

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


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. Prochlorperazine is reported to be distributed to most body tissues with high concentrations being distributed into liver and spleen. There is evidence that phenothiazines are excreted in the breast milk of nursing mothers.


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.


Phenothiazines are generally well absorbed from the GI tract and from parenteral sites; however, absorption may be erratic, particularly following oral administration. Considerable interindividual variations in peak plasma concentrations have been reported. The variability may result from genetic differences in the rate of metabolism, biodegradation of the drug in the GI lumen, and/or metabolism of the drug during absorption (in the GI mucosa) and first pass through the liver.

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2511


Phenothiazines are highly bound to plasma proteins.

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2511


Phenothiazines and their metabolites are distributed into most body tissues and fluids, with high concentrations being distributed into the brain, lungs, liver, kidneys, and spleen. /Phenothiazine General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2511


Phenothiazines readily cross the placenta. It is not known if the drugs are distributed into milk; however, the size of the molecules and their ability to readily cross the blood-brain barrier suggest that the drugs would be distributed into milk.

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2511


For more Absorption, Distribution and Excretion (Complete) data for Prochlorperazine (12 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

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


Most metabolites of phenothiazines are pharmacologically inactive; however, certain metabolites (eg, 7-hydroxychlorpromazine, mesoridazine) show moderate pharmacologic activity and may contribute to the action of the drugs. There is limited evidence to indicate that some phenothiazines (eg, chlorpromazine) may induce their own metabolism. /Phenothiazine General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2511


Metabolized primarily in liver /by/ oxidation, hydroxylation, demethylation, sulfoxide formation and conjugation with glucuronic acid; metabolic alterations in side chain may also occur.

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1970


After chronic administration of piperazine-substituted phenothiazine drugs ... to rats, tissues contained drug metabolites, in which piperazine ring fission by multiple oxidative n-dealkylation had occurred to give substituted ethylenediamine. Thus, n-[gamma-(2-chlorphenothiazinyl-10)-propyl]ethylenediamine ... from prochlorperazine ...

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 255


Yields 2-chloro-10-(3-(4-methylpiperazin-1-yl)propyl)phenothiazine-n-oxide and 2-chloro-10-(3-(4-methylpiperazin-1-yl)propyl)phenothiazine sulfoxide in rats

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-33


For more Metabolism/Metabolites (Complete) data for Prochlorperazine (7 total), please visit the HSDB record page.


5.7 Biological Half-Life

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


5.8 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 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). Prochlorperazine exerts antiemetic effects and was shown to inhibit apomorphine-induced vomiting by blocking D2 dopamine receptors in the CTZ..


The principal pharmacologic effects of prochlorperazine are similar to those of chlorpromazine. Prochlorperazine has weak anticholinergic effects, moderate sedative effects, and strong extrapyramidal effects. Prochlorperazine has strong antiemetic activity.

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2518


The development of phenothiazine derivatives as psychopharmacologic agents resulted from the observation that certain phenothiazine antihistaminic compounds produced sedation. In an attempt to enhance the sedative effects of these drugs, promethazine and chlorpromazine were synthesized. Chlorpromazine is the pharmacologic prototype of the phenothiazines. The pharmacology of phenothiazines is complex, and because of their actions on the central and autonomic nervous systems, the drugs affect many different sites in the body. Although the actions of the various phenothiazines are generally similar, these drugs differ both quantitatively and qualitatively in the extent to which they produce specific pharmacologic effects. /Phenothiazine General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2510


In the CNS, phenothiazines act principally at the subcortical levels of the reticular formation, limbic system, and hypothalamus. Phenothiazines generally do not produce substantial cortical depression; however, there is minimal information on the specific effects of phenothiazines at the cortical level. Phenothiazines also act in the basal ganglia, exhibiting extrapyramidal effects. The precise mechanism(s) of action, including antipsychotic action, of phenothiazines has not been determined, but may be principally related to antidopaminergic effects of the drugs. There is evidence to indicate that phenothiazines antagonize dopamine-mediated neurotransmission at the synapses. There is also some evidence that phenothiazines may block postsynaptic dopamine receptor sites. However, it has not been determined whether the antipsychotic effect of the drugs is causally related to their antidopaminergic effects. Phenothiazines also have peripheral and/or central antagonistic activity against alpha-adrenergic, serotonergic, histaminic (H1-receptors), and muscarinic receptors. Phenothiazines also have some adrenergic activity, since they block the reuptake of monoamines at the presynaptic neuronal membrane, which tends to enhance neurotransmission. The effects of phenothiazines on the autonomic nervous system are complex and unpredictable because the drugs exhibit varying degrees of alpha-adrenergic blocking, muscarinic blocking, and adrenergic activity. The antipsychotic activity of phenothiazines may be related to any or all of these effects, but it has been suggested that the drugs' effects on dopamine are probably most important. It has also been suggested that effects of phenothiazines on other amines (eg, gamma-aminobutyric acid [GABA]) or peptides (eg, substance P, endorphins) may contribute to their antipsychotic effect. Further study is needed to determine the role of central neuronal receptor antagonism and of effects on biochemical mediators in the antipsychotic action of the phenothiazines and other antipsychotic agents. /Phenothiazine General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2510


Although the exact mechanism(s) of action has not been conclusively determined, phenothiazines have an antiemetic effect. The antiemetic activity may be mediated via a direct effect of the drugs on the medullary chemoreceptor trigger zone (CTZ), apparently by blocking dopamine receptors in the CTZ. Phenothiazines inhibit the central and peripheral effects of apomorphine and ergot alkaloids. Phenothiazines generally do not inhibit emesis caused by the action of drugs at the nodose ganglion or by local action on the GI tract. /Phenothiazine General Statement/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2511


For more Mechanism of Action (Complete) data for Prochlorperazine (15 total), please visit the HSDB record page.


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LABORATORIES","customerCountry":"INDIA","quantity":"50.00","actualQuantity":"50","unit":"KGS","unitRateFc":"550","totalValueFC":"30310.3","currency":"EUR","unitRateINR":"50462.5","date":"18-Dec-2023","totalValueINR":"2523125","totalValueInUsd":"30310.3","indian_port":"Bombay Air","hs_no":"29349990","bill_no":"9284507","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"VIA GUIDO GUARINI MATTEUCCI, 1 20162 MILANO (MI) Milano, , ItalySDNF Italy","customerAddress":"48, KANDIVLI INDUSTRIAL ESTATE,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1705861800,"product":"PROCHLORPERAZINE EDISYLATE USP","address":"6-3-865\/1\/2, FLAT NO.201,","city":"HYDERABAD, ANDHRA PRADESH","supplier":"TRIFARMA","supplierCountry":"ITALY","foreign_port":"MILAN","customer":"GLAND PHARMA LTD","customerCountry":"INDIA","quantity":"7.68","actualQuantity":"7.68","unit":"KGS","unitRateFc":"27425","totalValueFC":"213719","currency":"USD","unitRateINR":"2312832.1","date":"22-Jan-2024","totalValueINR":"17762550.75","totalValueInUsd":"213719","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"9779598","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN","supplierAddress":"VIA GUIDO GUARINI MATTEUCCI,MILANO- ITALIASDNF ITALY","customerAddress":"6-3-865\/1\/2, FLAT NO.201,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1705861800,"product":"PROCHLORPERAZINE EDISYLATE USP","address":"6-3-865\/1\/2, FLAT NO.201,","city":"HYDERABAD, ANDHRA PRADESH","supplier":"TRIFARMA","supplierCountry":"ITALY","foreign_port":"MILAN","customer":"GLAND PHARMA LTD","customerCountry":"INDIA","quantity":"7.88","actualQuantity":"7.88","unit":"KGS","unitRateFc":"27425","totalValueFC":"219269.2","currency":"USD","unitRateINR":"2312670","date":"22-Jan-2024","totalValueINR":"18223839.25","totalValueInUsd":"219269.2","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"9779598","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN","supplierAddress":"VIA GUIDO GUARINI MATTEUCCI,MILANO- ITALIASDNF ITALY","customerAddress":"6-3-865\/1\/2, FLAT NO.201,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1709749800,"product":"PROCHLORPERAZINE EDISYLATE USP","address":"6-3-865\/1\/2, FLAT NO.201,","city":"HYDERABAD, ANDHRA PRADESH","supplier":"TRIFARMA","supplierCountry":"ITALY","foreign_port":"MILAN - MALPENSA","customer":"GLAND PHARMA LTD","customerCountry":"INDIA","quantity":"8.27","actualQuantity":"8.27","unit":"KGS","unitRateFc":"27500","totalValueFC":"229792","currency":"USD","unitRateINR":"2307250","date":"07-Mar-2024","totalValueINR":"19080957.5","totalValueInUsd":"229792","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"2471089","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"VIA GUIDO GUARINI MATTEUCCI,MILANO- ITALIASDNF ITALY","customerAddress":"6-3-865\/1\/2, FLAT NO.201,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717007400,"product":"PROCHLORPERAZINE","address":"102,HYDE PARK,SAKIVIHAR ROAD","city":"MUMBAI","supplier":"TRIFARMA","supplierCountry":"ITALY","foreign_port":"MILAN - MALPENSA","customer":"BLISS GVS PHARMA LTD","customerCountry":"INDIA","quantity":"1.05","actualQuantity":"1.05","unit":"KGS","unitRateFc":"6000","totalValueFC":"6991.3","currency":"EUR","unitRateINR":"555000","date":"30-May-2024","totalValueINR":"582750","totalValueInUsd":"6991.3","indian_port":"Bombay Air","hs_no":"29343000","bill_no":"3740352","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"VIA GUIDO GUARINI MATTEUCCI,120162 MILANO (MI)ITALIA ITALY","customerAddress":"102,HYDE PARK,SAKIVIHAR ROAD"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717957800,"product":"PROCHLORPERAZINE MALEATE","address":"B\/2 MAHALAXMI CHAMBERS","city":"MUMBAI. MAHARASHTRA","supplier":"TRIFARMA","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"GLENMARK PHARMACEUTICALS","customerCountry":"INDIA","quantity":"225.00","actualQuantity":"225","unit":"KGS","unitRateFc":"966","totalValueFC":"219486.5","currency":"USD","unitRateINR":"81433.8","date":"10-Jun-2024","totalValueINR":"18322605","totalValueInUsd":"219486.5","indian_port":"Indore-EPZ\/SEZ","hs_no":"29343000","bill_no":"1004118","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"VIA GUIDO GUARINI MATTEUCCI, 1 2016 2 MILANO- ITALIA ITALY","customerAddress":"B\/2 MAHALAXMI CHAMBERS"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722018600,"product":"PF5107 PROCHLORPERAZINE EDISYLATE USP, BATCH NO.: PROPER-ES\/198\/L","address":"1\/5, SANTOSH COMPLEX, ARMUGAM","city":"BANGALORE , KARNATAKA","supplier":"TRIFARMA","supplierCountry":"ITALY","foreign_port":"MILAN","customer":"MAIVA PHARMA PRIVATE ","customerCountry":"INDIA","quantity":"6.20","actualQuantity":"6.2","unit":"KGS","unitRateFc":"25000","totalValueFC":"156778.1","currency":"USD","unitRateINR":"2113750","date":"27-Jul-2024","totalValueINR":"13105250","totalValueInUsd":"156778.1","indian_port":"Bangalore Air","hs_no":"29349990","bill_no":"4741591","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN","supplierAddress":"VIA GUIDO GUARINI MATTEUCCI, 120162 MILANO (MI)SDNF IT","customerAddress":"1\/5, SANTOSH COMPLEX, ARMUGAM"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722623400,"product":"(Z)-BUT-2-ENEDIOIC ACID : 2-CHLORO-10-(3-(4-METHYLPIPERAZIN-1-YL)PROPYL)PHENOTHIAZINE PROCHLORPERAZINE MALEATE","address":"PLOT NOS. B5 (pt) & B6 (pt) SIPCOT INDUSTRIAL PARK, IRUNGATTUKOTTAI","city":"SRIPERUMBUDUR","supplier":"TRIFARMA","supplierCountry":"ITALY","foreign_port":"MILAN","customer":"ORBION PHARMACEUTICALS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"100.00","actualQuantity":"100","unit":"KGS","unitRateFc":"1075","totalValueFC":"118229","currency":"EUR","unitRateINR":"99168.8","date":"03-Aug-2024","totalValueINR":"9916875","totalValueInUsd":"118229","indian_port":"Madras Air","hs_no":"29349990","bill_no":"4850945","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN","supplierAddress":"VIA DELLE INDUSTRIE,620816-CERIANO LAGHETTO (MB)-ITALIASDNF IT","customerAddress":"PLOT NOS. 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04-Mar-2021
28-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

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South Africa

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BioFlorida Conference
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Virtual BoothSanofi is a pioneer in Diabetes Solutions, Human Vaccines, Innovative Drugs, Consumer Healthcare, and the new Genzyme.

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Digital Content Digital Content

Regulatory Info : Originator

Registration Country : South Africa

Prochlorperazine

Brand Name : Stemetil 1.25% m/v/1ml Injection

Dosage Form : INJ

Dosage Strength : 1.2% m/v/ml

Packaging : 1X10% m/v/ml

Approval Date :

Application Number :

Regulatory Info : Originator

Registration Country : South Africa

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Virtual BoothSanofi is a pioneer in Diabetes Solutions, Human Vaccines, Innovative Drugs, Consumer Healthcare, and the new Genzyme.

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Digital Content Digital Content

Regulatory Info : Originator

Registration Country : South Africa

Prochlorperazine

Brand Name : Stemetil 5 mg Suppositories

Dosage Form : SUP

Dosage Strength : 5mg

Packaging : 5X1mg

Approval Date :

Application Number :

Regulatory Info : Originator

Registration Country : South Africa

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BioFlorida Conference
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  • fda
  • EDQM
  • WHO-GMP

Virtual BoothSanofi is a pioneer in Diabetes Solutions, Human Vaccines, Innovative Drugs, Consumer Healthcare, and the new Genzyme.

Flag France
Digital Content Digital Content

Regulatory Info : Originator

Registration Country : South Africa

Prochlorperazine

Brand Name : Stemetil 25 mg Suppositories

Dosage Form : SUP

Dosage Strength : 25mg

Packaging : 5X1mg

Approval Date :

Application Number :

Regulatory Info : Originator

Registration Country : South Africa

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BioFlorida Conference
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Virtual BoothSanofi is a pioneer in Diabetes Solutions, Human Vaccines, Innovative Drugs, Consumer Healthcare, and the new Genzyme.

Flag France
Digital Content Digital Content

Regulatory Info : Originator

Registration Country : South Africa

Prochlorperazine

Brand Name : Stemetil

Dosage Form : TAB

Dosage Strength : 5mg

Packaging : 25X1mg

Approval Date :

Application Number :

Regulatory Info : Originator

Registration Country : South Africa

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05

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BioFlorida Conference
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  • fda
  • EDQM
  • WHO-GMP

Virtual BoothSanofi is a pioneer in Diabetes Solutions, Human Vaccines, Innovative Drugs, Consumer Healthcare, and the new Genzyme.

Flag France
Digital Content Digital Content

Regulatory Info : Originator

Registration Country : South Africa

Prochlorperazine

Brand Name : Stemetil 5 mg Tablets

Dosage Form : TAB

Dosage Strength : 5mg

Packaging : 250X1mg

Approval Date :

Application Number :

Regulatory Info : Originator

Registration Country : South Africa

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Prochlorperazine

Brand Name : Mitil

Dosage Form : TAB

Dosage Strength : 5mg

Packaging : 250X1mg

Approval Date :

Application Number :

Regulatory Info : Generic

Registration Country : South Africa

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