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MedKoo Cat#: 584523 | Name: Prochlorperazine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Prochlorperazine is discontinued (DEA controlled substance). It is a phenothiazine antipsychotic used principally in the treatment of nausea, vomiting, and vertigo.

Chemical Structure

Prochlorperazine
CAS#58-38-8 (free base)

Theoretical Analysis

MedKoo Cat#: 584523

Name: Prochlorperazine

CAS#: 58-38-8 (free base)

Chemical Formula: C20H24ClN3S

Exact Mass: 373.1379

Molecular Weight: 373.94

Elemental Analysis: C, 64.24; H, 6.47; Cl, 9.48; N, 11.24; S, 8.57

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
84-02-6 (dimaleate) 58-38-8 (free base) 3450-05-3 (maleate) 3111-70-4 (mesylate) 51888-09-6 (dimesylate)
Synonym
6140 RP; RP 6140; Meterazine; SKF 4657; Stemetil
IUPAC/Chemical Name
10H-Phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-
InChi Key
WIKYUJGCLQQFNW-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CN1CCN(CCCN2C3=C(C=CC=C3)SC4=CC=C(Cl)C=C24)CC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 373.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: BET 1: Metoclopramide or prochlorperazine for headache in acute migraine? Emerg Med J. 2013 Jul;30(7):595-6. doi: 10.1136/emermed-2013-202853.1. Review. PubMed PMID: 23765765. 2: Trottier ED, Bailey B, Lucas N, Lortie A. Prochlorperazine in children with migraine: a look at its effectiveness and rate of akathisia. Am J Emerg Med. 2012 Mar;30(3):456-63. doi: 10.1016/j.ajem.2010.12.020. Epub 2011 Feb 5. PubMed PMID: 21296523. 3: Tashiro M, Naito T, Ohnishi K, Kagawa Y, Kawakami J. Impact of genetic and non-genetic factors on clinical responses to prochlorperazine in oxycodone-treated cancer patients. Clin Chim Acta. 2014 Feb 15;429:175-80. doi: 10.1016/j.cca.2013.12.011. Epub 2013 Dec 17. PubMed PMID: 24360851. 4: Hoy SM, Scott LJ. Indomethacin/prochlorperazine/caffeine: a review of its use in the acute treatment of migraine and in the treatment of episodic tension-type headache. CNS Drugs. 2011 Apr;25(4):343-58. doi: 10.2165/11206740-000000000-00000. Review. PubMed PMID: 21425885. 5: Yomiya K, Takei D, Kurosawa H, Kono B. [A study on the antiemetic effect and extrapyramidal symptoms of prochlorperazine versus perospirone for the control of nausea and vomiting due to opioid introduction]. Gan To Kagaku Ryoho. 2013 Aug;40(8):1037-41. Japanese. PubMed PMID: 23986047. 6: Badshah A, Subhan F, Shah NH, Bukhari NI, Saeed M, Shah KU. Once daily controlled release matrix tablet of Prochlorperazine maleate: influence of Ethocel® and/or Methocel® on in vitro drug release and bioavailability. Drug Dev Ind Pharm. 2012 Feb;38(2):190-9. doi: 10.3109/03639045.2011.595416. Epub 2011 Jul 13. PubMed PMID: 21749268. 7: Coralic Z, Kim AS, Vinson DR. Prochlorperazine-Induced Hemidystonia Mimicking Acute Stroke. West J Emerg Med. 2015 Jul;16(4):572-4. doi: 10.5811/westjem.2015.4.26003. Epub 2015 Jul 2. PubMed PMID: 26265971; PubMed Central PMCID: PMC4530917. 8: Tashiro M, Naito T, Kagawa Y, Kawakami J. Simultaneous determination of prochlorperazine and its metabolites in human plasma using isocratic liquid chromatography tandem mass spectrometry. Biomed Chromatogr. 2012 Jun;26(6):754-60. doi: 10.1002/bmc.1725. Epub 2011 Oct 12. PubMed PMID: 21990013. 9: Caughey GE, Roughead EE, Pratt N, Shakib S, Vitry AI, Gilbert AL. Increased risk of hip fracture in the elderly associated with prochlorperazine: is a prescribing cascade contributing? Pharmacoepidemiol Drug Saf. 2010 Sep;19(9):977-82. doi: 10.1002/pds.2009. PubMed PMID: 20623516. 10: Kostic MA, Gutierrez FJ, Rieg TS, Moore TS, Gendron RT. A prospective, randomized trial of intravenous prochlorperazine versus subcutaneous sumatriptan in acute migraine therapy in the emergency department. Ann Emerg Med. 2010 Jul;56(1):1-6. doi: 10.1016/j.annemergmed.2009.11.020. Epub 2010 Jan 4. PubMed PMID: 20045576. 11: Lau Moon Lin M, Robinson PD, Flank J, Sung L, Dupuis LL. The Safety of Prochlorperazine in Children: A Systematic Review and Meta-Analysis. Drug Saf. 2016 Jun;39(6):509-16. doi: 10.1007/s40264-016-0398-9. Review. PubMed PMID: 26884326. 12: Miller MA, Levsky ME, Enslow W, Rosin A. Randomized evaluation of octreotide vs prochlorperazine for ED treatment of migraine headache. Am J Emerg Med. 2009 Feb;27(2):160-4. doi: 10.1016/j.ajem.2008.01.015. PubMed PMID: 19371522. 13: Clayton M, Ramamoorthy A. Physical incompatibility between prochlorperazine, diclofenac and Injekt® syringe. Anaesthesia. 2013 Jul;68(7):781-2. doi: 10.1111/anae.12307. PubMed PMID: 24044397. 14: Lane M, Smith FE, Sullivan RA, Plasse TF. Dronabinol and prochlorperazine alone and in combination as antiemetic agents for cancer chemotherapy. Am J Clin Oncol. 1990 Dec;13(6):480-4. PubMed PMID: 2173391. 15: Patanwala AE, Amini R, Hays DP, Rosen P. Antiemetic therapy for nausea and vomiting in the emergency department. J Emerg Med. 2010 Sep;39(3):330-6. doi: 10.1016/j.jemermed.2009.08.060. Epub 2009 Dec 21. Review. PubMed PMID: 20022195. 16: Roché H, Hyman G, Nahas G, Stoopler M, Ellison R, Desjardins R. Comparative effects of intravenously administered alizapride and prochlorperazine in cisplatin-induced emesis. Cancer Invest. 1987;5(2):89-93. PubMed PMID: 3607576. 17: Obata Y, Otake Y, Takayama K. Feasibility of transdermal delivery of prochlorperazine. Biol Pharm Bull. 2010;33(8):1454-7. PubMed PMID: 20686248. 18: Bond CM. Comparison of buccal and oral prochlorperazine in the treatment of dizziness associated with nausea and/or vomiting. Curr Med Res Opin. 1998;14(4):203-12. PubMed PMID: 9891192. 19: Tokola RA. The effect of metoclopramide and prochlorperazine on the absorption of effervescent paracetamol in migraine. Cephalalgia. 1988 Sep;8(3):139-47. PubMed PMID: 3197094. 20: Lane M, Vogel CL, Ferguson J, Krasnow S, Saiers JL, Hamm J, Salva K, Wiernik PH, Holroyde CP, Hammill S, et al. Dronabinol and prochlorperazine in combination for treatment of cancer chemotherapy-induced nausea and vomiting. J Pain Symptom Manage. 1991 Aug;6(6):352-9. PubMed PMID: 1652611.