Fosaprepitant

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 416448532

| image = Fosaprepitant.svg

| alt = Skeletal formula of fosaprepitant

| width = 255

| image2 = Fosaprepitant-3D-spacefill.png

| alt2 = Space-filling model of the fosaprepitant molecule

| tradename = Emend, Ivemend

| Drugs.com = {{drugs.com|cons|fosaprepitant}}

| MedlinePlus = a604003

| licence_EU = yes

| DailyMedID = Fosaprepitant

| licence_US = Fosaprepitant

| pregnancy_AU = B2

| pregnancy_AU_comment = {{cite web | title=Prescribing medicines in pregnancy database | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/products/medicines/find-information-about-medicine/prescribing-medicines-pregnancy-database | access-date=28 April 2023 | archive-date=2 March 2023 | archive-url=https://web.archive.org/web/20230302112837/https://www.tga.gov.au/products/medicines/find-information-about-medicine/prescribing-medicines-pregnancy-database | url-status=live }}

| pregnancy_category =

| routes_of_administration = Intravenous

| ATC_prefix = A04

| ATC_suffix = AD12

| legal_AU = S4

| legal_AU_comment = {{cite web | title=Emend IV fosaprepitant 150mg (as fosaprepitant dimeglumine) powder for injection vial (167061) | website=Therapeutic Goods Administration (TGA) | date=27 May 2022 | url=https://www.tga.gov.au/resources/artg/167061 | access-date=28 April 2023}}{{cite web | title=Fosaprepitant MSN (Accelagen Pty Ltd) | website=Therapeutic Goods Administration (TGA) | date=11 November 2022 | url=https://www.tga.gov.au/resources/prescription-medicines-registrations/fosaprepitant-msn-accelagen-pty-ltd | access-date=28 April 2023 | archive-date=18 March 2023 | archive-url=https://web.archive.org/web/20230318050818/https://www.tga.gov.au/resources/prescription-medicines-registrations/fosaprepitant-msn-accelagen-pty-ltd | url-status=live }}

| legal_CA =

| legal_UK = POM

| legal_US = Rx-only

| legal_US_comment = {{cite web | title=Emend- fosaprepitant dimeglumine injection, powder, lyophilized, for solution | website=DailyMed | date=2 May 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8d66803a-6811-4c29-9c57-e16acfa87f21 | access-date=27 September 2022 | archive-date=1 December 2021 | archive-url=https://web.archive.org/web/20211201165415/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8d66803a-6811-4c29-9c57-e16acfa87f21 | url-status=live }}

| legal_EU = Rx-only

| legal_EU_comment =

| bioavailability = n/a

| protein_bound = >95% (aprepitant)

| metabolism = To aprepitant

| elimination_half-life = 9 to 13 hours (aprepitant)

| excretion =

| IUPHAR_ligand = 7623

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 172673-20-0

| CAS_supplemental =
{{CAS|265121-04-8}} (dimeglumine)

| PubChem = 219090

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB06717

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 6L8OF9XRDC

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D06597

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1199324

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 64321

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 189912

| IUPAC_name = [3-{[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl] ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl}-5-oxo- 2H-1,2,4-triazol-1-yl]phosphonic acid

| C=23 | H=22 | F=7 | N=4 | O=6 | P=1

| smiles = C[C@H](c1cc(cc(c1)C(F)(F)F)C(F)(F)F)O[C@@H]2[C@@H](N(CCO2)Cc3[nH]c(=O)n(n3)P(=O)(O)O)c4ccc(cc4)F

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C23H22F7N4O6P/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)40-20-19(13-2-4-17(24)5-3-13)33(6-7-39-20)11-18-31-21(35)34(32-18)41(36,37)38/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H,31,32,35)(H2,36,37,38)/t12-,19+,20-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = BARDROPHSZEBKC-OITMNORJSA-N

}}

Fosaprepitant, sold under the brand names Emend (US) and Ivemend (EU) among others, is an antiemetic medication,{{cite journal | vauthors = Garnock-Jones KP | title = Fosaprepitant Dimeglumine: A Review in the Prevention of Nausea and Vomiting Associated with Chemotherapy | journal = Drugs | volume = 76 | issue = 14 | pages = 1365–72 | date = September 2016 | pmid = 27510503 | doi = 10.1007/s40265-016-0627-7 | s2cid = 30018182 }} administered intravenously. It is a prodrug of aprepitant.

Fosaprepitant was developed by Merck & Co. and was approved for medical use in the United States,{{cite web |url=https://www.drugs.com/newdrugs/fda-approves-emend-fosaprepitant-dimeglumine-merck-s-new-intravenous-therapy-combination-other-833.html |title=Drugs.com, FDA Approves Emend (fosaprepitant dimeglumine) for Injection, Merck's New Intravenous Therapy, for Use in Combination with Other Antiemetics for Prevention of Nausea and Vomiting Caused by Chemotherapy |access-date=2008-03-15 |archive-date=2008-04-09 |archive-url=https://web.archive.org/web/20080409192526/http://www.drugs.com/newdrugs/fda-approves-emend-fosaprepitant-dimeglumine-merck-s-new-intravenous-therapy-combination-other-833.html |url-status=live }} and in the European Union in January 2008.{{cite web | title=Ivemend EPAR | website=European Medicines Agency | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/ivemend | access-date=27 September 2022 | archive-date=31 December 2021 | archive-url=https://web.archive.org/web/20211231185908/https://www.ema.europa.eu/en/medicines/human/EPAR/ivemend | url-status=live }}