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Wikipedia

Metopimazine

April 14, 2024

Metopimazine (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, BANTooltip British Approved Name), sold under the brand names Vogalen and Vogalene, is an antiemetic of the phenothiazine group which is used to treat nausea and vomiting.[1][2][3][4][5][6] It is marketed in Europe, Canada, and South America.[2][5] As of August 2020, metopimazine has been repurposed and is additionally under development for use in the United States for the treatment of gastroparesis.[6][5]

Metopimazine
Clinical data
Trade namesVogalen, Vogalene
Other namesEXP-999; RP-9965; NG-101
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-(3-[2-(methylsulfonyl)-10H-phenothiazin-10-yl]propyl)piperidine-4-carboxamide
CAS Number
  • 14008-44-7 N
PubChem CID
  • 26388
DrugBank
  • DB13591 Y
ChemSpider
  • 24584 Y
UNII
  • 238S75V9AV
KEGG
  • D05010
ChEBI
  • CHEBI:135726
ChEMBL
  • ChEMBL398615 Y
CompTox Dashboard (EPA)
  • DTXSID80161224
ECHA InfoCard100.034.367
Chemical and physical data
FormulaC22H27N3O3S2
Molar mass445.60 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=S(=O)(c2cc1N(c3c(Sc1cc2)cccc3)CCCN4CCC(C(=O)N)CC4)C
  • InChI=1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26) Y
  • Key:BQDBKDMTIJBJLA-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Metopimazine has antidopaminergic, antihistamine, and anticholinergic activity.[7] However, it has also been described as a highly potent and selective dopamine D2 and D3 receptor antagonist.[5] The D2 receptor antagonism of metopimazine is thought to underlie its antiemetic and gastroprokinetic effects.[5] It is said to not readily cross the blood–brain barrier and hence to have peripheral selectivity, in contrast to metoclopramide but similarly to domperidone.[5] Unlike domperidone however, metopimazine shows no hERG inhibition and hence is expected to have a more favorable cardiovascular profile.[5] In contrast to metoclopramide, metopimazine does not interact with serotonin 5-HT3 and 5-HT4 receptors.[5]

Medical uses edit

Metopimazine is an approved prescription drug in France under the brand name Vogalene® [8] that has been used for the treatment of nausea and vomiting.[9] Vogalene® is available under different forms, including 15 mg capsules, 7.5 mg orally disintegrating tablets, 5 mg suppository, 0.1% oral liquid, and a 10 mg/mL intravenous (IV) solution approved for the prevention of chemotherapy-induced nausea and vomiting.[10] Metopimazine is also an over-the-counter medication available in pharmacies in France (Vogalib®, 7.5 mg orally disintegrating tablets).[11] The approved dose is 30 mg per day. Most adult prescriptions are for seasonal gastroenteritis or acute nausea and vomiting of various etiologies. The IV formulation is almost exclusively used to treat chemotherapy-induced nausea and vomiting in adults and children.[12]

Adverse effects edit

Generally, studies in chemotherapy-induced nausea and vomiting suggest that doses of metopimazine higher than approved for common nausea and vomiting conditions tend to be more efficacious while remaining safe and well tolerated. Numerous open-label and randomized, placebo-controlled efficacy studies involving oral administration (ranging from 7.5 mg/day for 4 days, to up to 45 mg/day for ~7–30 days, to 120 mg/day for 4 days) or IV administration (10 mg to 40 mg) of metopimazine have concluded that metopimazine is safe and well tolerated with no report of severe adverse events.[13][14][15][16][17][18][19][20][21] In a dose-ranging, open-label study in patients undergoing chemotherapy, metopimazine administered orally at 20, 30, 40, 50, or 60 mg every 4 hours (q4h) for 48 hours was used to determine its safety and tolerability. Metopimazine was determined to be safe at a dose of 30 mg administered 6 times daily (180 mg/day). The dose-limiting toxicity to metopimazine was moderate-to-severe dizziness caused by orthostatic hypotension, which was observed beginning at 40 mg every 4 hours for 48 hours. Other side effects were few and mild in severity. A single possibly drug-related extrapyramidal adverse event was observed in a patient in the 60 mg q4h or 360 mg daily dose group.[22] In a randomized, double-blind comparison of ondansetron versus ondansetron plus metopimazine as an antiemetic prophylaxis during platinum-based chemotherapy, metopimazine was administered by IV (24-hour continuous infusion) at 35 mg/m2 followed by 30 mg per orally (PO) 4 times a day (120 mg/day) for 4 days. Metopimazine plus ondansetron was more efficacious than ondansetron alone, and adverse reactions were mild and without significant differences between the two treatment groups. However, there was an asymptomatic decrease in standing blood pressure when patients received the combination antiemetic therapy.[19] In a randomized, double-blind study assessing the efficacy and safety of sublingual metopimazine compared to ondansetron in chemotherapy-induced delayed emesis, patients received either 45 mg/day of metopimazine (7.5 mg x 2 every 8 hours) or 16 mg/day of ondansetron (8 mg every 12 hours). Results showed that metopimazine was comparable in efficacy to ondansetron; however, the incidence of gastrointestinal disorders was significantly lower in the metopimazine group, particularly abdominal pain and constipation.[23]

Mechanism of action edit

Metopimazine, a phenothiazine derivative, is a potent D2/D3 dopamine receptor antagonist. Metopimazine has also shown adrenergic alpha1, histamine H1, serotonin 5HT2a antagonism.[10]

Pharmacokinetics edit

The pharmacokinetics (PK) profile of metopimazine has been reported as comparable between adults and children. The maximum plasma concentration (Cmax) of metopimazine is reached approximately 60 minutes after oral administration, and the elimination half-life is approximately two hours.[24] Metopimazine is rapidly metabolized to metopimazine acid (Tmax ~2 hours), its major metabolite in humans. Metopimazine is primarily metabolized by a liver amidase in humans and therefore present a low risk on drug-drug interaction.[25] Exposure is reduced by ~30% and 50% (area under the curve (AUC) and Cmax, respectively) when metopimazine is administered with food.[26][10]

The bioavailability of metopimazine in humans is low. A 10 mg dose of metopimazine was reported to have an absolute bioavailability under 20%.[26]

Research edit

Metopimazine mesylate (NG101), a novel formulation of metopimazine, is under clinical development for idiopathic gastroparesis in the United States.[27] Gastroparesis is a debilitating chronic gastrointestinal disorder characterized by delayed gastric emptying without evidence of mechanical obstruction. Symptoms include nausea, vomiting, early satiety, postprandial fullness, bloating, and upper abdominal pain.[28][29][30]

Synthesis edit

 
Thieme Patent:[31] Revised:[32]

For the first step, 2-Methylthiophenothiazine [7643-08-5] (1) is protected by sequential reaction with sodium amide and acetic anhydride to give 1-[2-(Methylthio)-10H-phenothiazin-10-yl]ethanone [23503-69-7] (2). Oxidation with peracid proceeds preferentially on the more electron-rich alkyl thioether to give the sulfone. Upon hydrolysis of the acetate this affords 2-(methylsulfonyl)-10h-phenothiazine [23503-68-6] (3). Alkylation with 1-Bromo-3-chloropropane (4) gives 10-(3-chloropropyl)-2-methylsulfonylphenothiazine [40051-30-7] (5). Alkylation with piperidine-4-carboxamide (Isonipecotamide) [39546-32-2] (6) affords metopimazine (7).

References edit

  1. ^ J. Elks, ed. (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 817–. ISBN 978-1-4757-2085-3. OCLC 1058412474.
  2. ^ a b Swiss Pharmaceutical Society (2000). Swiss Pharmaceutical Society (ed.). Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 683–. ISBN 978-3-88763-075-1.
  3. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 180–. ISBN 9789401144391. OCLC 1243535030.
  4. ^ Herrstedt J (September 1998). "Chemotherapy-induced nausea and vomiting with special emphasis on metopimazine". Danish Medical Bulletin. 45 (4): 412–422. PMID 9777292.
  5. ^ a b c d e f g h Heckroth M, Luckett RT, Moser C, Parajuli D, Abell TL (April 2021). "Nausea and Vomiting in 2021: A Comprehensive Update". Journal of Clinical Gastroenterology. 55 (4): 279–299. doi:10.1097/MCG.0000000000001485. PMC 7933092. PMID 33471485.
  6. ^ a b "Metopimazine - Neurogastrx - AdisInsight".
  7. ^ Bezin J, Noize P, Mansiaux Y, Jarne A, Pariente A (March 2021). "Antidopaminergic antiemetics and trauma-related hospitalization: A population-based self-controlled case series study". British Journal of Clinical Pharmacology. 87 (3): 1303–1309. doi:10.1111/bcp.14510. PMID 32737898. S2CID 220909387.
  8. ^ "Vogalene®". www.rxreasoner.com.
  9. ^ "Accueil - ANSM". ansm.sante.fr (in French). Retrieved 26 March 2023.
  10. ^ a b c Croom KF, Keating GM (March 2006). "Metopimazine". American Journal of Cancer. 5 (2): 123–136. doi:10.2165/00024669-200605020-00006. ISSN 1175-6357. S2CID 76202219.
  11. ^ "Vogalib". www.rxreasoner.com.
  12. ^ Shirley, Matt (July 2021). "Netupitant/Palonosetron: A Review in Chemotherapy-Induced Nausea and Vomiting". Drugs. 81 (11): 1331–1342. doi:10.1007/s40265-021-01558-2. ISSN 1179-1950. PMC 8463343. PMID 34292534.
  13. ^ Paradis B, Brault R (December 1967). "[A new antiemetic: vogalen (metopimazine or 9965 RP)]". Laval Medical. 38 (10): 901–907. PMID 5596819.
  14. ^ Guerin MT, Guerin RA, Salaün O (May 1969). "[Therapeutic value of metopimazine as an antiemetic in cancerology]". La Presse Médicale. 77 (24): 893. PMID 5797645.
  15. ^ Arbus L, Parente C (May 1971). "[Use of metopimazine in certain vomitings from central origin]". Therapeutique. 47 (5): 469–471. PMID 5314918.
  16. ^ Berry GH, Duncan W, Bowman CM (October 1971). "The prevention of radiation sickness. Report of a double blind random clinical trial using prochlorperazine and metopimazine". Clinical Radiology. 22 (4): 534–537. doi:10.1016/s0009-9260(71)80130-7. PMID 4944444.
  17. ^ Arnaud B, Sportouch M (January 1972). "[Value of metopimazine (Vogalene) in the prevention and treatment of postoperative vomiting in ocular surgery. (Apropos of 100 cases)]". Archives d'Ophtalmologie et Revue Generale d'Ophtalmologie. 32 (1): 63–68. PMID 4261213.
  18. ^ Rodary C, Elman A, Durand M, Cohen-Solal J, Maillard JN (1979). "[Double blind randomized trial of metopimazine: for postoperative nausea and vomiting after cholecystectomy]". Annales de l'Anesthésiologie Française. 20 (2): 118–120. PMID 38705.
  19. ^ a b Herrstedt J, Sigsgaard T, Handberg J, Schousboe BM, Hansen M, Dombernowsky P (April 1997). "Randomized, double-blind comparison of ondansetron versus ondansetron plus metopimazine as antiemetic prophylaxis during platinum-based chemotherapy in patients with cancer". Journal of Clinical Oncology. 15 (4): 1690–1696. doi:10.1200/JCO.1997.15.4.1690. PMID 9193370.
  20. ^ Lebeau B, Depierre A, Giovannini M, Rivière A, Kaluzinski L, Votan B, et al. (September 1997). "The efficacy of a combination of ondansetron, methylprednisolone and metopimazine in patients previously uncontrolled with a dual antiemetic treatment in cisplatin-based chemotherapy. The French Ondansetron Study Group". Annals of Oncology. 8 (9): 887–892. doi:10.1023/a:1008276412559. PMID 9358940.
  21. ^ Sigsgaard T, Herrstedt J, Handberg J, Kjaer M, Dombernowsky P (April 2001). "Ondansetron plus metopimazine compared with ondansetron plus metopimazine plus prednisolone as antiemetic prophylaxis in patients receiving multiple cycles of moderately emetogenic chemotherapy". Journal of Clinical Oncology. 19 (7): 2091–2097. doi:10.1200/JCO.2001.19.7.2091. PMID 11283143.
  22. ^ Herrstedt J, Sigsgaard T, Angelo HR, Kampmann JP, Hansen M (January 1997). "Dose-finding study of oral metopimazine". Supportive Care in Cancer. 5 (1): 38–43. doi:10.1007/BF01681960. PMID 9010988. S2CID 24370010.
  23. ^ Khamales S, Bethune-Volters A, Chidiac J, Bensaoula O, Delgado A, Di Palma M (February 2006). "A randomized, double-blind trial assessing the efficacy and safety of sublingual metopimazine and ondansetron in the prophylaxis of chemotherapy-induced delayed emesis". Anti-Cancer Drugs. 17 (2): 217–224. doi:10.1097/00001813-200602000-00014. PMID 16428941. S2CID 8708071.
  24. ^ Mallet E, Bounoure F, Skiba M, Saussereau E, Goullé JP, Castanet M (June 2015). "Pharmacokinetic study of metopimazine by oral route in children". Pharmacology Research & Perspectives. 3 (3): e00130. doi:10.1002/prp2.130. PMC 4492748. PMID 26171218.
  25. ^ Busby RW, Cai X, Yang S, Ramos L, Venkatarangan L, Shen H, et al. (February 2022). "Metopimazine is primarily metabolized by a liver amidase in humans". Pharmacology Research & Perspectives. 10 (1): e00903. doi:10.1002/prp2.903. PMC 8929364. PMID 34918875.
  26. ^ a b Herrstedt J, Jørgensen M, Angelo HR (August 1990). "The effect of food on serum concentrations of metopimazine". British Journal of Clinical Pharmacology. 30 (2): 237–243. doi:10.1111/j.1365-2125.1990.tb03770.x. PMC 1368223. PMID 2206785.
  27. ^ "A Phase 2 Randomized, Double-blind, Placebo-Controlled, Parallel-Group Study, of the Safety and Efficacy of NG101 Administered Orally to Patients With Gastroparesis". clinicaltrials.gov. 4 November 2022.
  28. ^ Camilleri M, Kuo B, Nguyen L, Vaughn VM, Petrey J, Greer K, et al. (August 2022). "ACG Clinical Guideline: Gastroparesis". The American Journal of Gastroenterology. 117 (8): 1197–1220. doi:10.14309/ajg.0000000000001874. PMC 9373497. PMID 35926490.
  29. ^ De Colle C, van der Hart M, Chen J, Rassoulpour A, Pasricha PJ (2016). "1079 NG101: A potent and selective dopamine D2 receptor antagonist as a potential alternative to metoclopramide and domperidone for the treatment of gastroparesis". Gastroenterology. 150 (4): S214. doi:10.1016/S0016-5085(16)30794-6.
  30. ^ Stein B, Everhart KK, Lacy BE (August 2015). "Gastroparesis: A Review of Current Diagnosis and Treatment Options". Journal of Clinical Gastroenterology. 49 (7): 550–558. doi:10.1097/MCG.0000000000000320. PMID 25874755.
  31. ^ DE 1092476, Jacob RM, Robert JG, issued 1960, assigned to Rhone Poulenc SA. 
  32. ^ Karicherla V, Phani K, Bodireddy MR, Prashanth KB, Gajula MR, Pramod K (May 2017). "A simple and commercially viable process for improved yields of metopimazine, a dopamine D2-receptor antagonist". Organic Process Research & Development. 21 (5): 720–731. doi:10.1021/acs.oprd.7b00052. S2CID 102478746.

External links edit

  • "Metopimazine". AdisInsight. Springer Nature Switzerland AG.

April 14, 2024
metopimazine, inntooltip, international, nonproprietary, name, usantooltip, united, states, adopted, name, bantooltip, british, approved, name, sold, under, brand, names, vogalen, vogalene, antiemetic, phenothiazine, group, which, used, treat, nausea, vomiting. Metopimazine INNTooltip International Nonproprietary Name USANTooltip United States Adopted Name BANTooltip British Approved Name sold under the brand names Vogalen and Vogalene is an antiemetic of the phenothiazine group which is used to treat nausea and vomiting 1 2 3 4 5 6 It is marketed in Europe Canada and South America 2 5 As of August 2020 metopimazine has been repurposed and is additionally under development for use in the United States for the treatment of gastroparesis 6 5 MetopimazineClinical dataTrade namesVogalen VogaleneOther namesEXP 999 RP 9965 NG 101AHFS Drugs comInternational Drug NamesRoutes ofadministrationOralATC codeA04AD05 WHO Legal statusLegal statusIn general Prescription only IdentifiersIUPAC name 1 3 2 methylsulfonyl 10H phenothiazin 10 yl propyl piperidine 4 carboxamideCAS Number14008 44 7 NPubChem CID26388DrugBankDB13591 YChemSpider24584 YUNII238S75V9AVKEGGD05010ChEBICHEBI 135726ChEMBLChEMBL398615 YCompTox Dashboard EPA DTXSID80161224ECHA InfoCard100 034 367Chemical and physical dataFormulaC 22H 27N 3O 3S 2Molar mass445 60 g mol 13D model JSmol Interactive imageSMILES O S O c2cc1N c3c Sc1cc2 cccc3 CCCN4CCC C O N CC4 CInChI InChI 1S C22H27N3O3S2 c1 30 27 28 17 7 8 21 19 15 17 25 18 5 2 3 6 20 18 29 21 12 4 11 24 13 9 16 10 14 24 22 23 26 h2 3 5 8 15 16H 4 9 14H2 1H3 H2 23 26 YKey BQDBKDMTIJBJLA UHFFFAOYSA N Y N Y what is this verify Metopimazine has antidopaminergic antihistamine and anticholinergic activity 7 However it has also been described as a highly potent and selective dopamine D2 and D3 receptor antagonist 5 The D2 receptor antagonism of metopimazine is thought to underlie its antiemetic and gastroprokinetic effects 5 It is said to not readily cross the blood brain barrier and hence to have peripheral selectivity in contrast to metoclopramide but similarly to domperidone 5 Unlike domperidone however metopimazine shows no hERG inhibition and hence is expected to have a more favorable cardiovascular profile 5 In contrast to metoclopramide metopimazine does not interact with serotonin 5 HT3 and 5 HT4 receptors 5 Contents 1 Medical uses 2 Adverse effects 3 Mechanism of action 4 Pharmacokinetics 5 Research 6 Synthesis 7 References 8 External linksMedical uses editMetopimazine is an approved prescription drug in France under the brand name Vogalene 8 that has been used for the treatment of nausea and vomiting 9 Vogalene is available under different forms including 15 mg capsules 7 5 mg orally disintegrating tablets 5 mg suppository 0 1 oral liquid and a 10 mg mL intravenous IV solution approved for the prevention of chemotherapy induced nausea and vomiting 10 Metopimazine is also an over the counter medication available in pharmacies in France Vogalib 7 5 mg orally disintegrating tablets 11 The approved dose is 30 mg per day Most adult prescriptions are for seasonal gastroenteritis or acute nausea and vomiting of various etiologies The IV formulation is almost exclusively used to treat chemotherapy induced nausea and vomiting in adults and children 12 Adverse effects editGenerally studies in chemotherapy induced nausea and vomiting suggest that doses of metopimazine higher than approved for common nausea and vomiting conditions tend to be more efficacious while remaining safe and well tolerated Numerous open label and randomized placebo controlled efficacy studies involving oral administration ranging from 7 5 mg day for 4 days to up to 45 mg day for 7 30 days to 120 mg day for 4 days or IV administration 10 mg to 40 mg of metopimazine have concluded that metopimazine is safe and well tolerated with no report of severe adverse events 13 14 15 16 17 18 19 20 21 In a dose ranging open label study in patients undergoing chemotherapy metopimazine administered orally at 20 30 40 50 or 60 mg every 4 hours q4h for 48 hours was used to determine its safety and tolerability Metopimazine was determined to be safe at a dose of 30 mg administered 6 times daily 180 mg day The dose limiting toxicity to metopimazine was moderate to severe dizziness caused by orthostatic hypotension which was observed beginning at 40 mg every 4 hours for 48 hours Other side effects were few and mild in severity A single possibly drug related extrapyramidal adverse event was observed in a patient in the 60 mg q4h or 360 mg daily dose group 22 In a randomized double blind comparison of ondansetron versus ondansetron plus metopimazine as an antiemetic prophylaxis during platinum based chemotherapy metopimazine was administered by IV 24 hour continuous infusion at 35 mg m2 followed by 30 mg per orally PO 4 times a day 120 mg day for 4 days Metopimazine plus ondansetron was more efficacious than ondansetron alone and adverse reactions were mild and without significant differences between the two treatment groups However there was an asymptomatic decrease in standing blood pressure when patients received the combination antiemetic therapy 19 In a randomized double blind study assessing the efficacy and safety of sublingual metopimazine compared to ondansetron in chemotherapy induced delayed emesis patients received either 45 mg day of metopimazine 7 5 mg x 2 every 8 hours or 16 mg day of ondansetron 8 mg every 12 hours Results showed that metopimazine was comparable in efficacy to ondansetron however the incidence of gastrointestinal disorders was significantly lower in the metopimazine group particularly abdominal pain and constipation 23 Mechanism of action editMetopimazine a phenothiazine derivative is a potent D2 D3 dopamine receptor antagonist Metopimazine has also shown adrenergic alpha1 histamine H1 serotonin 5HT2a antagonism 10 Pharmacokinetics editThe pharmacokinetics PK profile of metopimazine has been reported as comparable between adults and children The maximum plasma concentration Cmax of metopimazine is reached approximately 60 minutes after oral administration and the elimination half life is approximately two hours 24 Metopimazine is rapidly metabolized to metopimazine acid Tmax 2 hours its major metabolite in humans Metopimazine is primarily metabolized by a liver amidase in humans and therefore present a low risk on drug drug interaction 25 Exposure is reduced by 30 and 50 area under the curve AUC and Cmax respectively when metopimazine is administered with food 26 10 The bioavailability of metopimazine in humans is low A 10 mg dose of metopimazine was reported to have an absolute bioavailability under 20 26 Research editMetopimazine mesylate NG101 a novel formulation of metopimazine is under clinical development for idiopathic gastroparesis in the United States 27 Gastroparesis is a debilitating chronic gastrointestinal disorder characterized by delayed gastric emptying without evidence of mechanical obstruction Symptoms include nausea vomiting early satiety postprandial fullness bloating and upper abdominal pain 28 29 30 Synthesis edit nbsp Thieme Patent 31 Revised 32 For the first step 2 Methylthiophenothiazine 7643 08 5 1 is protected by sequential reaction with sodium amide and acetic anhydride to give 1 2 Methylthio 10H phenothiazin 10 yl ethanone 23503 69 7 2 Oxidation with peracid proceeds preferentially on the more electron rich alkyl thioether to give the sulfone Upon hydrolysis of the acetate this affords 2 methylsulfonyl 10h phenothiazine 23503 68 6 3 Alkylation with 1 Bromo 3 chloropropane 4 gives 10 3 chloropropyl 2 methylsulfonylphenothiazine 40051 30 7 5 Alkylation with piperidine 4 carboxamide Isonipecotamide 39546 32 2 6 affords metopimazine 7 References edit J Elks ed 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer pp 817 ISBN 978 1 4757 2085 3 OCLC 1058412474 a b Swiss Pharmaceutical Society 2000 Swiss Pharmaceutical Society ed Index Nominum 2000 International Drug Directory Taylor amp Francis pp 683 ISBN 978 3 88763 075 1 Morton IK Hall JM 6 December 2012 Concise Dictionary of Pharmacological Agents Properties and Synonyms Springer Science amp Business Media pp 180 ISBN 9789401144391 OCLC 1243535030 Herrstedt J September 1998 Chemotherapy induced nausea and vomiting with special emphasis on metopimazine Danish Medical Bulletin 45 4 412 422 PMID 9777292 a b c d e f g h Heckroth M Luckett RT Moser C Parajuli D Abell TL April 2021 Nausea and Vomiting in 2021 A Comprehensive Update Journal of Clinical Gastroenterology 55 4 279 299 doi 10 1097 MCG 0000000000001485 PMC 7933092 PMID 33471485 a b Metopimazine Neurogastrx AdisInsight Bezin J Noize P Mansiaux Y Jarne A Pariente A March 2021 Antidopaminergic antiemetics and trauma related hospitalization A population based self controlled case series study British Journal of Clinical Pharmacology 87 3 1303 1309 doi 10 1111 bcp 14510 PMID 32737898 S2CID 220909387 Vogalene www rxreasoner com Accueil ANSM ansm sante fr in French Retrieved 26 March 2023 a b c Croom KF Keating GM March 2006 Metopimazine American Journal of Cancer 5 2 123 136 doi 10 2165 00024669 200605020 00006 ISSN 1175 6357 S2CID 76202219 Vogalib www rxreasoner com Shirley Matt July 2021 Netupitant Palonosetron A Review in Chemotherapy Induced Nausea and Vomiting Drugs 81 11 1331 1342 doi 10 1007 s40265 021 01558 2 ISSN 1179 1950 PMC 8463343 PMID 34292534 Paradis B Brault R December 1967 A new antiemetic vogalen metopimazine or 9965 RP Laval Medical 38 10 901 907 PMID 5596819 Guerin MT Guerin RA Salaun O May 1969 Therapeutic value of metopimazine as an antiemetic in cancerology La Presse Medicale 77 24 893 PMID 5797645 Arbus L Parente C May 1971 Use of metopimazine in certain vomitings from central origin Therapeutique 47 5 469 471 PMID 5314918 Berry GH Duncan W Bowman CM October 1971 The prevention of radiation sickness Report of a double blind random clinical trial using prochlorperazine and metopimazine Clinical Radiology 22 4 534 537 doi 10 1016 s0009 9260 71 80130 7 PMID 4944444 Arnaud B Sportouch M January 1972 Value of metopimazine Vogalene in the prevention and treatment of postoperative vomiting in ocular surgery Apropos of 100 cases Archives d Ophtalmologie et Revue Generale d Ophtalmologie 32 1 63 68 PMID 4261213 Rodary C Elman A Durand M Cohen Solal J Maillard JN 1979 Double blind randomized trial of metopimazine for postoperative nausea and vomiting after cholecystectomy Annales de l Anesthesiologie Francaise 20 2 118 120 PMID 38705 a b Herrstedt J Sigsgaard T Handberg J Schousboe BM Hansen M Dombernowsky P April 1997 Randomized double blind comparison of ondansetron versus ondansetron plus metopimazine as antiemetic prophylaxis during platinum based chemotherapy in patients with cancer Journal of Clinical Oncology 15 4 1690 1696 doi 10 1200 JCO 1997 15 4 1690 PMID 9193370 Lebeau B Depierre A Giovannini M Riviere A Kaluzinski L Votan B et al September 1997 The efficacy of a combination of ondansetron methylprednisolone and metopimazine in patients previously uncontrolled with a dual antiemetic treatment in cisplatin based chemotherapy The French Ondansetron Study Group Annals of Oncology 8 9 887 892 doi 10 1023 a 1008276412559 PMID 9358940 Sigsgaard T Herrstedt J Handberg J Kjaer M Dombernowsky P April 2001 Ondansetron plus metopimazine compared with ondansetron plus metopimazine plus prednisolone as antiemetic prophylaxis in patients receiving multiple cycles of moderately emetogenic chemotherapy Journal of Clinical Oncology 19 7 2091 2097 doi 10 1200 JCO 2001 19 7 2091 PMID 11283143 Herrstedt J Sigsgaard T Angelo HR Kampmann JP Hansen M January 1997 Dose finding study of oral metopimazine Supportive Care in Cancer 5 1 38 43 doi 10 1007 BF01681960 PMID 9010988 S2CID 24370010 Khamales S Bethune Volters A Chidiac J Bensaoula O Delgado A Di Palma M February 2006 A randomized double blind trial assessing the efficacy and safety of sublingual metopimazine and ondansetron in the prophylaxis of chemotherapy induced delayed emesis Anti Cancer Drugs 17 2 217 224 doi 10 1097 00001813 200602000 00014 PMID 16428941 S2CID 8708071 Mallet E Bounoure F Skiba M Saussereau E Goulle JP Castanet M June 2015 Pharmacokinetic study of metopimazine by oral route in children Pharmacology Research amp Perspectives 3 3 e00130 doi 10 1002 prp2 130 PMC 4492748 PMID 26171218 Busby RW Cai X Yang S Ramos L Venkatarangan L Shen H et al February 2022 Metopimazine is primarily metabolized by a liver amidase in humans Pharmacology Research amp Perspectives 10 1 e00903 doi 10 1002 prp2 903 PMC 8929364 PMID 34918875 a b Herrstedt J Jorgensen M Angelo HR August 1990 The effect of food on serum concentrations of metopimazine British Journal of Clinical Pharmacology 30 2 237 243 doi 10 1111 j 1365 2125 1990 tb03770 x PMC 1368223 PMID 2206785 A Phase 2 Randomized Double blind Placebo Controlled Parallel Group Study of the Safety and Efficacy of NG101 Administered Orally to Patients With Gastroparesis clinicaltrials gov 4 November 2022 Camilleri M Kuo B Nguyen L Vaughn VM Petrey J Greer K et al August 2022 ACG Clinical Guideline Gastroparesis The American Journal of Gastroenterology 117 8 1197 1220 doi 10 14309 ajg 0000000000001874 PMC 9373497 PMID 35926490 De Colle C van der Hart M Chen J Rassoulpour A Pasricha PJ 2016 1079 NG101 A potent and selective dopamine D2 receptor antagonist as a potential alternative to metoclopramide and domperidone for the treatment of gastroparesis Gastroenterology 150 4 S214 doi 10 1016 S0016 5085 16 30794 6 Stein B Everhart KK Lacy BE August 2015 Gastroparesis A Review of Current Diagnosis and Treatment Options Journal of Clinical Gastroenterology 49 7 550 558 doi 10 1097 MCG 0000000000000320 PMID 25874755 DE 1092476 Jacob RM Robert JG issued 1960 assigned to Rhone Poulenc SA Karicherla V Phani K Bodireddy MR Prashanth KB Gajula MR Pramod K May 2017 A simple and commercially viable process for improved yields of metopimazine a dopamine D2 receptor antagonist Organic Process Research amp Development 21 5 720 731 doi 10 1021 acs oprd 7b00052 S2CID 102478746 External links edit Metopimazine AdisInsight Springer Nature Switzerland AG Retrieved from https en wikipedia org w index php title Metopimazine amp oldid 1211420534, wikipedia, wiki, book, books, library,

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