Home Halogens bis((2Z)-but-2-enedioic acid); 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine

bis((2Z)-but-2-enedioic acid); 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine

CAS No.:
84-02-6
Catalog Number:
AG00G2BI
Molecular Formula:
C28H32ClN3O8S
Molecular Weight:
606.0870
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
95%
In Stock USA
United States
$38
- +
5g
95%
In Stock USA
United States
$107
- +
25g
95%
In Stock USA
United States
$438
- +
Product Description
Catalog Number:
AG00G2BI
Chemical Name:
bis((2Z)-but-2-enedioic acid); 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
CAS Number:
84-02-6
Molecular Formula:
C28H32ClN3O8S
Molecular Weight:
606.0870
MDL Number:
MFCD00069330
IUPAC Name:
(Z)-but-2-enedioic acid;2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine
InChI:
InChI=1S/C20H24ClN3S.2C4H4O4/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24;2*5-3(6)1-2-4(7)8/h2-3,5-8,15H,4,9-14H2,1H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-
InChI Key:
DSKIOWHQLUWFLG-SPIKMXEPSA-N
SMILES:
CN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(Cl)cc2.OC(=O)/C=C\C(=O)O.OC(=O)/C=C\C(=O)O
EC Number:
201-511-3
UNII:
I1T8O1JTL6
RTECS Number:
SO3150000
Properties
Complexity:
548  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
3  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
2  
Exact Mass:
605.16g/mol
Formal Charge:
0
Heavy Atom Count:
41  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
606.087g/mol
Monoisotopic Mass:
605.16g/mol
Rotatable Bond Count:
8  
Topological Polar Surface Area:
184A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
Prevention of delayed nausea: a University of Rochester Cancer Center Community Clinical Oncology Program study of patients receiving chemotherapy. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20120920
Simultaneous determination of prochlorperazine and its metabolites in human plasma using isocratic liquid chromatography tandem mass spectrometry. Biomedical chromatography : BMC 20120601
Microneedle assisted iontophoretic transdermal delivery of prochlorperazine edisylate. Drug development and industrial pharmacy 20120501
Evolving treatment paradigms for chemotherapy-induced nausea and vomiting. Cancer control : journal of the Moffitt Cancer Center 20120401
Prochlorperazine in children with migraine: a look at its effectiveness and rate of akathisia. The American journal of emergency medicine 20120301
Once daily controlled release matrix tablet of Prochlorperazine maleate: influence of Ethocel® and/or Methocel® on in vitro drug release and bioavailability. Drug development and industrial pharmacy 20120201
Neuroleptic malignant syndrome associated with the use of prochlorperazine in a patient with a recent history of antipsychotic-induced neuroleptic malignant syndrome. The Annals of pharmacotherapy 20111101
Buccal prochlorperazine causing perioral fixed drug eruption. Clinical and experimental dermatology 20110801
Amitriptyline and prochlorperazine inhibit proinflammatory mediator release from human mast cells: possible relevance to chronic fatigue syndrome. Journal of clinical psychopharmacology 20110601
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 20110401
Prochlorperazine-induced tardive dystonia and its worsening with clozapine in a non-mentally ill patient with migraine. The Annals of pharmacotherapy 20110401
Treatment and assessment of emergency department nausea and vomiting in Australasia: a survey of anti-emetic management. Emergency medicine Australasia : EMA 20110401
An integrated bioinformatics approach identifies elevated cyclin E2 expression and E2F activity as distinct features of tamoxifen resistant breast tumors. PloS one 20110101
Antiemetic efficacy of metoclopramide and diphenhydramine added to patient-controlled morphine analgesia: a randomised controlled trial. European journal of anaesthesiology 20101201
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
TIAs - management in general practice. Australian family physician 20101101
Antiemetic therapy for nausea and vomiting in the emergency department. The Journal of emergency medicine 20100901
Increased risk of hip fracture in the elderly associated with prochlorperazine: is a prescribing cascade contributing? Pharmacoepidemiology and drug safety 20100901
Clinical outcomes of children treated with intravenous prochlorperazine for migraine in a pediatric emergency department. The Journal of emergency medicine 20100801
Insight in the prediction of chemotherapy-induced nausea. Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer 20100701
A prospective, randomized trial of intravenous prochlorperazine versus subcutaneous sumatriptan in acute migraine therapy in the emergency department. Annals of emergency medicine 20100701
[Antiemetic-induced extrapyramidal symptoms seen by our palliative care team]. Masui. The Japanese journal of anesthesiology 20100501
Acute vomiting in cats: rational treatment selection. Journal of feline medicine and surgery 20100301
Suicide associated with corticosteroid use during chemotherapy: case report. Japanese journal of clinical oncology 20100201
Feasibility of transdermal delivery of prochlorperazine. Biological & pharmaceutical bulletin 20100101
The central analgesia induced by antimigraine drugs is independent from Gi proteins: superiority of a fixed combination of indomethacin, prochlorperazine and caffeine, compared to sumatriptan, in an in vivo model. The journal of headache and pain 20091201
Quantification of prochlorperazine maleate in human plasma by liquid chromatography-mass spectrometry: Application to a bioequivalence study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091001
Prochlorperazine tablets repackaged into dose administration aids: can the patient be assured of quality? Journal of clinical pharmacy and therapeutics 20090401
Prochlorperazine--treatment for acute confusional migraine. Headache 20090301
Neuroleptics and migraine. Central nervous system agents in medicinal chemistry 20090301
In vitro and in vivo characteristics of prochlorperazine oral disintegrating film. International journal of pharmaceutics 20090223
Randomized evaluation of octreotide vs prochlorperazine for ED treatment of migraine headache. The American journal of emergency medicine 20090201
The pharmacokinetics and bioavailability of prochlorperazine delivered as a thermally generated aerosol in a single breath to volunteers. Clinical pharmacology and therapeutics 20090101
Suppression of dopamine-related side effects of morphine by aripiprazole, a dopamine system stabilizer. European journal of pharmacology 20081214
Emergency pretreatment for contrast allergy before direct percutaneous coronary intervention for ST-elevation myocardial infarction. The American journal of cardiology 20081201
Patient-controlled analgesia combined with either ondansetron or ondansetron plus prochlorperazine for control of pain and nausea and vomiting in patients undergoing abdominal surgery. Journal of clinical anesthesia 20081201
A randomized controlled trial of prochlorperazine versus metoclopramide for treatment of acute migraine. Annals of emergency medicine 20081001
Psychotropic drugs interfere with the tight coupling of polyphosphoinositide cycle metabolites in human platelets: a result of receptor-independent drug intercalation in the plasma membrane? Biochimica et biophysica acta 20081001
Prochlorperazine vs. promethazine for headache treatment in the emergency department: a randomized controlled trial. The Journal of emergency medicine 20081001
Management of Ménière's disease in general practice: adherence to the UK National Health Service 'Prodigy' guidelines. The Journal of laryngology and otology 20080801
Acute migraine therapy: recent evidence from randomized comparative trials. Current opinion in neurology 20080601
Maternal use of antipsychotics in early pregnancy and delivery outcome. Journal of clinical psychopharmacology 20080601
A case of respiratory akathisia in a cancer patient: a case report. Palliative & supportive care 20080301
Unexpectedly high prevalence of akathisia in cancer patients. Palliative & supportive care 20071201
Efficacy of dosing and re-dosing of two oral fixed combinations of indomethacin, prochlorperazine and caffeine compared with oral sumatriptan in the acute treatment of multiple migraine attacks: a double-blind, double-dummy, randomised, parallel group, multicentre study. International journal of clinical practice 20070801
Acute dystonic reaction secondary to prochlorperazine use in the treatment of hyperemesis gravidarum. Irish journal of medical science 20070301
Recirculatory pharmacokinetic model of the uptake, distribution, and bioavailability of prochlorperazine administered as a thermally generated aerosol in a single breath to dogs. Drug metabolism and disposition: the biological fate of chemicals 20070201
Hypogycaemia without coma. Journal of the Indian Medical Association 20070201
Ultra-fast absorption of amorphous pure drug aerosols via deep lung inhalation. Journal of pharmaceutical sciences 20061101
A preliminary ecotoxicity study of pharmaceuticals in the marine environment. Journal of toxicology and environmental health. Part A 20061101
Antiemetics in the ED: a randomized controlled trial comparing 3 common agents. The American journal of emergency medicine 20060901
Blockade of HERG human K+ channel and IKr of guinea pig cardiomyocytes by prochlorperazine. European journal of pharmacology 20060821
Effect of overuse of the antimigraine combination of indomethacin, prochlorperazine and caffeine (IPC) on the disposition of its components in chronic headache patients. Pharmacological research 20060801
Development of a simplified instrument for the diagnosis and grading of akathisia in a cohort of patients receiving prochlorperazine. The Journal of emergency medicine 20060801
Prevention of nausea and vomiting following breast surgery. American journal of surgery 20060601
Antiemetic-related dystonic reaction unmasked by removal of a scopolamine transdermal patch. The Journal of emergency medicine 20060401
Antiemetics in the ED: a randomized controlled trial comparing 3 common agents. The American journal of emergency medicine 20060301
Are newer, more expensive pharmacotherapy options associated with superior symptom control compared to less costly agents used in a collaborative practice setting? The American journal of hospice & palliative care 20060101
Acute hypersensitivity reaction to ferric gluconate in a premedicated patient. The Annals of pharmacotherapy 20051201
Bioavailability and metabolism of prochlorperazine administered via the buccal and oral delivery route. Journal of clinical pharmacology 20051201
Efficacy of a fixed combination of indomethacin, prochlorperazine, and caffeine in the treatment of episodic tension-type headache: a double-blind, randomized, nimesulide-controlled, parallel group, multicentre trial. European journal of neurology 20051001
5-Hydroxytryptamine-receptor antagonists versus prochlorperazine for control of delayed nausea caused by doxorubicin: a URCC CCOP randomised controlled trial. The Lancet. Oncology 20051001
Cyanide trapping of iminium ion reactive intermediates followed by detection and structure identification using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Chemical research in toxicology 20051001
Symptomatic treatment of migraine in children: a systematic review of medication trials. Pediatrics 20050801
Prevention of delayed chemotherapy-induced nausea and vomiting after moderately high to highly emetogenic chemotherapy: comparison of ondansetron, prochlorperazine, and dexamethasone. American journal of clinical oncology 20050601
The combination of naratriptan and prochlorperazine in migraine treatment. Headache 20050601
Quetiapine discontinuation syndrome. The American journal of psychiatry 20050501
Cost-effectiveness analysis of ondansetron and prochlorperazine for the prevention of postoperative nausea and vomiting. Journal of managed care pharmacy : JMCP 20050501
Diphenhydramine in the treatment of akathesia induced by prochlorperazine. The Journal of emergency medicine 20050401
The antipsychotic and antiemetic drug prochlorperazine delays the ventricular repolarization of the in situ canine heart. Journal of pharmacological sciences 20050101
Increasing throughput and information content for in vitro drug metabolism experiments using ultra-performance liquid chromatography coupled to a quadrupole time-of-flight mass spectrometer. Rapid communications in mass spectrometry : RCM 20050101
Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine. Microbiological research 20050101
Preliminary studies on phenothiazine-mediated reversal of multidrug resistance in mouse lymphoma and COLO 320 cells. In vivo (Athens, Greece) 20050101
Comparison of metoclopramide, prochlorperazine and placebo in prevention of postoperative nausea and vomiting (PONV) following tonsillectomy in young adults. Journal of Ayub Medical College, Abbottabad : JAMC 20050101
Indomethacin, alone and combined with prochlorperazine and caffeine, but not sumatriptan, abolishes peripheral and central sensitization in in vivo models of migraine. The journal of pain : official journal of the American Pain Society 20041001
Prochlorperazine induces central antinociception mediated by the muscarinic system. Pharmacological research 20040901
Diphenhydramine in the treatment of akathisia induced by prochlorperazine. The Journal of emergency medicine 20040401
Atypical laryngeal dystonia caused by an antiemetic. American family physician 20040401
Treatment of pediatric migraine headaches: a randomized, double-blind trial of prochlorperazine versus ketorolac. Annals of emergency medicine 20040201
Droperidol vs prochlorperazine for the treatment of acute headache. The Journal of emergency medicine 20040201
Index of suspicion. Pediatrics in review 20040101
Comparison of three outpatient regimens in the management of nausea and vomiting in pregnancy. Journal of perinatology : official journal of the California Perinatal Association 20031001
Efficacy of a fixed combination of indomethacin, prochlorperazine, and caffeine versus sumatriptan in acute treatment of multiple migraine attacks: a multicenter, randomized, crossover trial. Headache 20030901
Aborting a prolonged migrainous aura with intravenous prochlorperazine and magnesium sulfate. Headache 20030901
Intravenous sodium valproate versus prochlorperazine for the emergency department treatment of acute migraine headaches: a prospective, randomized, double-blind trial. Annals of emergency medicine 20030601
Extrapyramidal reactions to ondansetron: cross-reactivity between ondansetron and prochlorperazine? Anesthesia and analgesia 20030501
Akathisia can be reduced by lowering the dose of D2 receptor antagonists. Annals of emergency medicine 20030201
Variations among emergency departments in the treatment of benign headache. Annals of emergency medicine 20030101
The effectiveness of combined naloxone/lofexidine in opiate detoxification: results from a double-blind randomized and placebo-controlled trial. The American journal on addictions 20030101
Prochlorperazine-induced cholestasis in a patient with alpha-1 antitrypsin deficiency. Hepato-gastroenterology 20030101
Upper airway obstruction resulting from an antiemetic. International journal of clinical practice 20021201
Efficacy and tolerability of prochlorperazine buccal tablets in treatment of acute migraine. Headache 20021001
Indomethacin, caffeine and prochlorperazine alone and combined revert hyperalgesia in in vivo models of migraine. Pharmacological research 20020901
Antimicrobial potentiality of a phenothiazine group of antipsychotic drug-prochlorperazine. Indian journal of experimental biology 20020701
Medical management of Meniere's disease. Otolaryngologic clinics of North America 20020601
Akathisia: problematic but preventable. Annals of emergency medicine 20020501
Intravenous administration of prochlorperazine by 15-minute infusion versus 2-minute bolus does not affect the incidence of akathisia: a prospective, randomized, controlled trial. Annals of emergency medicine 20011101
Droperidol vs. prochlorperazine for benign headaches in the emergency department. Academic emergency medicine : official journal of the Society for Academic Emergency Medicine 20010901
Incompatibility of prochlorperizine and ketoprofen. Anaesthesia 20010901
Pegylated liposomal doxorubicin: tolerability and toxicity. Pharmacotherapy 20010601
Headache in the emergency department. Headache 20010601
[A case report. Drugs can be administered via colostomy but the scientific support is negligible]. Lakartidningen 20010509
Tolerability and effectiveness of prochlorperazine for intractable migraine in children. Pediatrics 20010401
Continuous infusion prochlorperazine: pharmacokinetics, antiemetic efficacy, and feasibility of high-dose therapy. Cancer chemotherapy and pharmacology 20010401
Frequency of adverse reactions to prochlorperazine in the ED: a response. The American journal of emergency medicine 20010301
Diphenhydramine for the prevention of akathisia induced by prochlorperazine: a randomized, controlled trial. Annals of emergency medicine 20010201
Slow infusion for the prevention of akathisia induced by prochlorperazine: a randomized controlled trial. The Journal of emergency medicine 20010201
Photosensitivity associated with fluorouracil, prochlorperazine, and topical tretinoin. Pharmacotherapy 20010201
Sedation and analgesia for transvaginal oocyte retrieval: an audit resulting in a change of clinical practice. Human fertility (Cambridge, England) 20010101
Anti-emetics. Current medical research and opinion 20010101
[Diagnostic image (17). Acute dystonia induced by prochlorperazine]. Nederlands tijdschrift voor geneeskunde 20001223
Frequency of adverse reactions to prochlorperazine in the ED. The American journal of emergency medicine 20000901
Images in cardiovascular medicine. Labile repolarization from 'cell to bedside'. Circulation 20000815
Prochlorperazine-induced extrapyramidal effects mimicking meningitis in a child. Southern medical journal 20000601
Emergency! Prochlorperazine-induced dystonia. The American journal of nursing 19991101
The prophylactic antiemetic efficacy of prochlorperazine and ondansetron in nasal septal surgery: a randomized double-blind comparison. Anaesthesia and intensive care 19961001
A comparison of ondansetron and prochlorperazine for the prevention of nausea and vomiting after tympanoplasty. Canadian journal of anaesthesia = Journal canadien d'anesthesie 19960901
Unrecognized drug reaction. Nursing 19960701
Comparison of ondansetron and prochlorperazine for the prevention of nausea and vomiting after adenotonsillectomy. British journal of anaesthesia 19960301
Syndrome of inappropriate antidiuresis seen twice in eight years. Endocrine journal 19950401
A randomized, double-blind, cross-over study comparing a levosulpiride-based and a metoclopramide-based combination in the prevention of ProMECE-CytaBOM-induced emesis. Haematologica 19950101
Drug-induced dystonia in a patient with C4 quadriplegia. Case report. American journal of physical medicine & rehabilitation 19930401
Persistent extrapyramidal syndrome with dystonia and rigidity caused by combined metoclopramide and prochlorperazine therapy. Southern medical journal 19910501
Acute oculogyric crisis after administration of prochlorperazine. Southern medical journal 19910301
Extrapyramidal reactions to metoclopramide and prochlorperazine. The Quarterly journal of medicine 19890401
Acute upper airway obstruction due to supraglottic dystonia induced by a neuroleptic. BMJ (Clinical research ed.) 19881015
Prochlorperazine-induced chronic cholestasis. Journal of hepatology 19880601
A randomized trial of oral nabilone and prochlorperazine compared to intravenous metoclopramide and dexamethasone in the treatment of nausea and vomiting induced by chemotherapy regimens containing cisplatin or cisplatin analogues. European journal of cancer & clinical oncology 19880401
Psychological misinterpretations in the diagnosis of acute dystonia. Psychosomatics 19880101
Severe parkinsonism in two AIDS patients taking prochlorperazine. Lancet (London, England) 19870808
Preliminary studies of the pharmacokinetics and pharmacodynamics of prochlorperazine in healthy volunteers. British journal of clinical pharmacology 19870201
Extrapyramidal reactions to prochlorperazine and haloperidol in the United Kingdom. The Quarterly journal of medicine 19860601
A cross-over comparison of nabilone and prochlorperazine for emesis induced by cancer chemotherapy. American journal of clinical oncology 19850801
Cerebral and ocular toxicity induced by desferrioxamine. The Quarterly journal of medicine 19850701
Hypertension and intravenous antidopaminergic drugs. The New England journal of medicine 19850425
Drug-induced parkinsonism in the elderly. Lancet (London, England) 19841110
Acute dystonic reactions to neuroleptic drugs. Anesthesia progress 19840101
Pharmacological evaluation of minaprine dihydrochloride, a new psychotropic drug. Arzneimittel-Forschung 19820101
Compazine complications: a review. Journal of the National Medical Association 19810501
Nabilone: an effective antiemetic in patients receiving cancer chemotherapy. Journal of clinical pharmacology 19810101
Superiority of nabilone over prochlorperazine as an antiemetic in patients receiving cancer chemotherapy. The New England journal of medicine 19790607
Turning in MFB-lesioned rats and antagonism of neuroleptic-induced catalepsy after lisuride and LSD. Life sciences 19780508
Dystonic syndrome after Compazine therapy. Southern medical journal 19780501
Prochlorperazine in childhood: side-effects. Clinical neurology and neurosurgery 19770101
Tardive dyskinesia treated with pimozide. Journal of the neurological sciences 19750401
Tissue metabolites of trifluorperazine, fluphenazine, prochlorperazine, and perphenazine. Kinetics in chronic treatment. Drug metabolism and disposition: the biological fate of chemicals 19750101
Neuroleptic-induced tardiave dyskinesias in nonpsychotic patients. Archives of neurology 19740401
Interaction between piperazine and chlorpromazine. British journal of pharmacology 19740101
Drug-induced extrapyramidal symptoms. A cooperative study. JAMA 19730507
Neuroleptics and neurologic reactions. Southern medical journal 19730301
Drug-induced convulsions. Report from Boston Collaborative Drug Surveillance Program. Lancet (London, England) 19720930
Acute reactions to phenothiazine derivatives. British journal of anaesthesia 19720501
Drug-induced dyskinesia treated with intravenous diazepam. The Journal of the Florida Medical Association 19720101
Sudden death in phenothiazine therapy. (A clinicopathologic study of 12 cases). The Psychiatric quarterly 19700101
Reaction to prochlorperazine? Lancet (London, England) 19690412
Oculogyric crises due to phenothiazines. British medical journal 19670722
Drug-induced extrapyramidal symptoms: their incidence and treatment. The American journal of psychiatry 19670101
Dystonic reactions to prochlorperazine in hypoparathyroidism. The New England journal of medicine 19661103
Dystonic reactions to phenothiazine derivatives. Archives of disease in childhood 19661001
[ANTIEMETIC ACTION OF METOCLOPRAMIDE WITH RESPECT TO APOMORPHINE AND HYDERGINE]. Comptes rendus des seances de la Societe de biologie et de ses filiales 19640101
Properties