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MedKoo Cat#: 596693 | Name: Fosaprepitant free acid
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Description:

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

Fosaprepitant, also known as MK0517, is an antiemetic drug, administered intravenously. It is a prodrug of aprepitant. Fosaprepitant was developed by Merck & Co. and was approved. It is a prodrug of Aprepitant. It aids in the prevention of acute and delayed nausea and vomiting associated with chemotherapy treatment. Fosaprepitant is a weak inhibitor of CYP3A4, and aprepitant, the active moiety, is a substrate, inhibitor, and inducer of CYP3A4

Chemical Structure

Fosaprepitant free acid
Fosaprepitant free acid
CAS#172673-20-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 596693

Name: Fosaprepitant free acid

CAS#: 172673-20-0 (free acid)

Chemical Formula: C23H22F7N4O6P

Exact Mass: 614.1165

Molecular Weight: 614.41

Elemental Analysis: C, 44.96; H, 3.61; F, 21.64; N, 9.12; O, 15.62; P, 5.04

Price and Availability

Size Price Availability Quantity
25mg USD 150.00 2 Weeks
50mg USD 250.00 2 Weeks
100mg USD 450.00 2 Weeks
200mg USD 750.00 2 Weeks
500mg USD 1,650.00 2 Weeks
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Related CAS #
265121-04-8 (dimeglumine) 172673-20-0 (free acid)
Synonym
Fosaprepitant; L-758298; L 758298; L758298; MK0517; MK 0517; MK-0517;
IUPAC/Chemical Name
(3-(((2R,3S)-2-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholino)methyl)-5-oxo-2,5-dihydro-1H-1,2,4-triazol-1-yl)phosphonic acid
InChi Key
BARDROPHSZEBKC-OITMNORJSA-N
InChi Code
InChI=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
SMILES Code
O=C1N=C(CN2[C@@H](C3=CC=C(F)C=C3)[C@@H](O[C@@H](C4=CC(C(F)(F)F)=CC(C(F)(F)F)=C4)C)OCC2)NN1P(O)(O)=O
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
>2 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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Fosaprepitant is a neurokinin-1 receptor antagonist, which is development for the prevention of chemotherapy-induced nausea and vomiting (CINV).
In vitro activity:
Fosaprepitant is likely to be combined and stored in the same intravenous (IV) bag with 5-HT3 antagonists and corticosteroids, therefore the in vitro compatibility of fosaprepitant with these agents and other IV diluents was assessed. Fosaprepitant (1 mg/mL in 0.9 % sodium chloride injection solution) was combined in binary or tertiary fashion with therapeutic-dose preparations of a 5-HT3 antagonist (ondansetron, granisetron, palonosetron, or tropisetron) and/or a corticosteroid (dexamethasone sodium phosphate or methylprednisolone sodium succinate). For diluent compatibility assessment, fosaprepitant was also prepared 1 mg/mL in 0.9 % sodium chloride injection solution, water for injection, or 5 % dextrose injection solution. Fosaprepitant demonstrated compatibility when combined in the same IV infusion bag with common 5-HT3 antagonists and corticosteroids for storage and IV coadministration, with the exception of palonosetron (incompatible under all experimental conditions) and tropisetron (incompatible unless combined with a corticosteroid). No incompatibility was observed between fosaprepitant and any of the 3 diluents tested. Use of fosaprepitant in combination with other antiemetics may provide a flexible option for administration of antiemetics to patients receiving moderately or highly emetogenic chemotherapy. Reference: Cancer Chemother Pharmacol. 2013 Sep;72(3):509-13. https://pubmed.ncbi.nlm.nih.gov/23860958/
In vivo activity:
The aim of this study was to test the efficacy of Neurokinin-1 Receptor (NK-1R) antagonist -Fosaprepitant- in inducing regression of established corneal neovascularization (CNV). Twenty C57BL/6 mice underwent alkali burn. Seven days later, when corneal neovessels had developed, they received Fosaprepitant 10 mg/ml, administered topically six times a day in the right eye for 10 days. In parallel, a group of 20 causticated mice was treated with normal saline, as control. A second independent experiment was also performed (n = 10/group). Finally, ten healthy mice received the same topical treatment for 10 days to evaluate Fosaprepitant safety. Topical Fosaprepitant administration induced a significant reduction of (i) CD31+ blood corneal neovessels (-27%, p = 0.0132), (ii) LYVE1+ lymphatic corneal neovessels (-31%, p = 0.0118) and (iii) CD45+ leucocyte infiltration (-36%; p = 0.0237). The second independent experiment confirmed these data. Moreover, Fosaprepitant-treated corneas showed a reduction in opacity, no impairment in corneal fluorescein staining and decreased infiltration of neutrophils (-72%, p < 0.05) and macrophages (-75%, p < 0.01). Finally, topical Fosaprepitant was not toxic to the ocular surface: no signs of conjunctivitis, opacity, perforations or corneal fluorescein staining were detected. Similarly, corneal TUJ1+ nerve density was not affected. The data suggests that NK-1R antagonists, such as Fosaprepitant, could be a new, promising therapeutic tool to inhibit CNV after this has been established. Reference: Acta Ophthalmol. 2017 Nov;95(7):e641-e648. https://onlinelibrary.wiley.com/doi/full/10.1111/aos.13304

Preparing Stock Solutions

The following data is based on the product molecular weight 614.41 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
Formulation protocol:
1. Sun S, Schaller J, Placek J, Duersch B. Compatibility of intravenous fosaprepitant with intravenous 5-HT3 antagonists and corticosteroids. Cancer Chemother Pharmacol. 2013 Sep;72(3):509-13. doi: 10.1007/s00280-013-2201-2. Epub 2013 Jul 17. PMID: 23860958. 2. Bignami F, Lorusso A, Rama P, Ferrari G. Growth inhibition of formed corneal neovascularization following Fosaprepitant treatment. Acta Ophthalmol. 2017 Nov;95(7):e641-e648. doi: 10.1111/aos.13304. Epub 2017 Feb 15. PMID: 28205389. 3. Prasoon P, Gupta S, Kumar R, Gautam M, Kaler S, Ray SB. Role of fosaprepitant, a neurokinin Type 1 receptor antagonist, in morphine-induced antinociception in rats. Indian J Pharmacol. 2016 Jul-Aug;48(4):394-398. doi: 10.4103/0253-7613.186198. PMID: 27756950; PMCID: PMC4980927.
In vitro protocol:
1. Sun S, Schaller J, Placek J, Duersch B. Compatibility of intravenous fosaprepitant with intravenous 5-HT3 antagonists and corticosteroids. Cancer Chemother Pharmacol. 2013 Sep;72(3):509-13. doi: 10.1007/s00280-013-2201-2. Epub 2013 Jul 17. PMID: 23860958.
In vivo protocol:
1. Bignami F, Lorusso A, Rama P, Ferrari G. Growth inhibition of formed corneal neovascularization following Fosaprepitant treatment. Acta Ophthalmol. 2017 Nov;95(7):e641-e648. doi: 10.1111/aos.13304. Epub 2017 Feb 15. PMID: 28205389. 2. Prasoon P, Gupta S, Kumar R, Gautam M, Kaler S, Ray SB. Role of fosaprepitant, a neurokinin Type 1 receptor antagonist, in morphine-induced antinociception in rats. Indian J Pharmacol. 2016 Jul-Aug;48(4):394-398. doi: 10.4103/0253-7613.186198. PMID: 27756950; PMCID: PMC4980927.
1: Weinstein C, Jordan K, Green SA, Camacho E, Khanani S, Beckford-Brathwaite E, Pong A, Noga SJ, Rapoport BL. Evaluation of factors contributing to the response to fosaprepitant in a heterogeneous, moderately emetogenic chemotherapy population: an exploratory analysis of a randomized phase III trial. Support Care Cancer. 2018 May 28. doi: 10.1007/s00520-018-4242-x. [Epub ahead of print] PubMed PMID: 29808377. 2: Schwartzberg LS, Navari RM. Safety of Polysorbate 80 in the Oncology Setting. Adv Ther. 2018 May 23. doi: 10.1007/s12325-018-0707-z. [Epub ahead of print] Review. PubMed PMID: 29796927. 3: Timaeus S, Elder J, Franco K. Evaluation of the Use of Fosaprepitant for the Prevention of Chemotherapy-induced Nausea and Vomiting in Pediatric Patients. J Pediatr Hematol Oncol. 2018 May 22. doi: 10.1097/MPH.0000000000001213. [Epub ahead of print] PubMed PMID: 29794645. 4: Molinos-Quintana A, Trujillo-Hacha P, Piruat JI, Bejarano-García JA, García-Guerrero E, Pérez-Simón JA, Muñoz M. Human acute myeloid leukemia cells express Neurokinin-1 receptor, which is involved in the antileukemic effect of Neurokinin-1 receptor antagonists. Invest New Drugs. 2018 May 2. doi: 10.1007/s10637-018-0607-8. [Epub ahead of print] PubMed PMID: 29721755. 5: Chau E, Lundberg J, Phillips G, Berger M, Wesolowski R. Updated report on incidence of infusion-site reactions associated with peripheral intravenous administration of fosaprepitant. J Oncol Pharm Pract. 2018 Jan 1:1078155218769347. doi: 10.1177/1078155218769347. [Epub ahead of print] PubMed PMID: 29651918. 6: Di Maio M, Baratelli C, Bironzo P, Vignani F, Bria E, Sperti E, Marcato M, Roila F. Efficacy of neurokinin-1 receptor antagonists in the prevention of chemotherapy-induced nausea and vomiting in patients receiving carboplatin-based chemotherapy: A systematic review and meta-analysis. Crit Rev Oncol Hematol. 2018 Apr;124:21-28. doi: 10.1016/j.critrevonc.2018.02.001. Epub 2018 Feb 7. Review. PubMed PMID: 29548482. 7: Ottoboni T, Keller MR, Cravets M, Clendeninn N, Quart B. Bioequivalence of HTX-019 (aprepitant IV) and fosaprepitant in healthy subjects: a Phase I, open-label, randomized, two-way crossover evaluation. Drug Des Devel Ther. 2018 Mar 1;12:429-435. doi: 10.2147/DDDT.S155875. eCollection 2018. PubMed PMID: 29535504; PubMed Central PMCID: PMC5837372. 8: O'Sullivan CC, Van Houten HK, Sangaralingham LR, Leal AD, Shinde S, Liu H, Ettinger D, Loprinzi CL, Ruddy KJ. Ten-Year Trends in Antiemetic Prescribing in Patients Receiving Highly Emetogenic Chemotherapy. J Natl Compr Canc Netw. 2018 Mar;16(3):294-299. doi: 10.6004/jnccn.2017.7043. PubMed PMID: 29523668. 9: Murakami C, Kakuta N, Kume K, Sakai Y, Kasai A, Oyama T, Tanaka K, Tsutsumi YM. A Comparison of Fosaprepitant and Ondansetron for Preventing Postoperative Nausea and Vomiting in Moderate to High Risk Patients: A Retrospective Database Analysis. Biomed Res Int. 2017;2017:5703528. doi: 10.1155/2017/5703528. Epub 2017 Dec 19. PubMed PMID: 29410964; PubMed Central PMCID: PMC5749222. 10: Yamamoto K, Yamatodani A. Strain differences in the development of cisplatin-induced pica behavior in mice. J Pharmacol Toxicol Methods. 2018 May - Jun;91:66-71. doi: 10.1016/j.vascn.2018.01.559. Epub 2018 Jan 31. PubMed PMID: 29407728. 11: Zhang Z, Zhang Y, Chen G, Hong S, Yang Y, Fang W, Luo F, Chen X, Ma Y, Zhao Y, Zhan J, Xue C, Hou X, Zhou T, Ma S, Gao F, Huang Y, Chen L, Zhou N, Zhao H, Zhang L. Olanzapine-Based Triple Regimens Versus Neurokinin-1 Receptor Antagonist-Based Triple Regimens in Preventing Chemotherapy-Induced Nausea and Vomiting Associated with Highly Emetogenic Chemotherapy: A Network Meta-Analysis. Oncologist. 2018 May;23(5):603-616. doi: 10.1634/theoncologist.2017-0378. Epub 2018 Jan 12. PubMed PMID: 29330211; PubMed Central PMCID: PMC5947448. 12: Patel P, Leeder JS, Piquette-Miller M, Dupuis LL. Response to 'Aprepitant and fosaprepitant decrease the effectiveness of hormonal contraceptives'. Br J Clin Pharmacol. 2018 Mar;84(3):604. doi: 10.1111/bcp.13487. Epub 2018 Jan 6. PubMed PMID: 29315725; PubMed Central PMCID: PMC5809359. 13: Bailard N, Rebello E. Aprepitant and fosaprepitant decrease the effectiveness of hormonal contraceptives. Br J Clin Pharmacol. 2018 Mar;84(3):602-603. doi: 10.1111/bcp.13472. Epub 2017 Dec 19. PubMed PMID: 29266364; PubMed Central PMCID: PMC5809356. 14: Rapoport BL, Jordan K, Weinstein C. Neurokinin 1 receptor antagonists in the prevention of chemotherapy-induced nausea and vomiting: focus on fosaprepitant. Future Oncol. 2018 Jan;14(1):77-92. doi: 10.2217/fon-2017-0377. Epub 2017 Nov 13. PubMed PMID: 29130344. 15: Gonçalves SC, Sanches SM, Bueno CT, Villela de Castro DL, Damascena A, Santos GRC. Incidence of Infusion Site Reactions in Peripheral Fosaprepitant Infusions. J Infus Nurs. 2017 Nov/Dec;40(6):380-383. doi: 10.1097/NAN.0000000000000252. PubMed PMID: 29112587. 16: Uchiyama K, Yamada M, Shiiba Y, Kasazaki S, Suga K, Iwabuchi H, Asoda S, Uehara K. [Determination of the Effect of Aprepitant and Fosaprepitant for Nausea in Patients with Oral Cancer Receiving Combination Chemotherapy with TPF]. Gan To Kagaku Ryoho. 2017 Jul;44(7):585-589. Japanese. PubMed PMID: 28790262. 17: Dulin JD, Coyne PJ, Bohm NM, Adler M. Fosaprepitant for the Management of Refractory Pain in a Patient with Cancer-Related Dermatomyositis. J Palliat Med. 2017 Dec;20(12):1415-1419. doi: 10.1089/jpm.2017.0075. Epub 2017 Aug 7. PubMed PMID: 28783481. 18: Restelli U, Saibene G, Nardulli P, Di Turi R, Bonizzoni E, Scolari F, Perrone T, Croce D, Celio L. Cost-utility and budget impact analyses of the use of NEPA for chemotherapy-induced nausea and vomiting prophylaxis in Italy. BMJ Open. 2017 Aug 1;7(7):e015645. doi: 10.1136/bmjopen-2016-015645. Erratum in: BMJ Open. 2017 Dec 22;7(12 ):e015645corr1. PubMed PMID: 28765126; PubMed Central PMCID: PMC5642784. 19: Trifilio S, Welles C, Seeger K, Mehta S, Fishman M, McGowan K, Strejcek K, Eiten E, Pirotte C, Lucier E, DeFrates S, Mehta J. Olanzapine Reduces Chemotherapy-induced Nausea and Vomiting Compared With Aprepitant in Myeloma Patients Receiving High-dose Melphalan Before Stem Cell Transplantation: A Retrospective Study. Clin Lymphoma Myeloma Leuk. 2017 Sep;17(9):584-589. doi: 10.1016/j.clml.2017.06.012. Epub 2017 Jun 20. PubMed PMID: 28694084. 20: Morrey ME, Sanchez-Sotelo J, Lewallen EA, An KN, Grill DE, Steinmann SP, Yao JJ, Salib CG, Trousdale WH, Reina N, Kremers HM, Lewallen DG, van Wijnen AJ, Abdel MP. Intra-articular injection of a substance P inhibitor affects gene expression in a joint contracture model. J Cell Biochem. 2018 Feb;119(2):1326-1336. doi: 10.1002/jcb.26256. Epub 2017 Nov 20. PubMed PMID: 28671282.

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