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SML2215

Sigma-Aldrich

Aprepitant

≥98% (HPLC)

Synonym(s):

Aprepitant, 3H-1,2,4-Triazol-3-one, 5-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro, 5-[[(2R,3S)-2-[(1R)-1-[3,5bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3one, Emend, L-754030, MK 869, MK-0869, ONO 7436, 3-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholino]methyl]-1H-1,2,4-triazol-5(4H)-one, 5-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one

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About This Item

Empirical Formula (Hill Notation):
C23H21F7N4O3
CAS Number:
170729-80-3
Molecular Weight:
534.43
MDL number:
MFCD12912491
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +61 to +71°, c = 1.0 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

FC1=CC=C([C@@H]([C@@H](O[C@H](C)C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)OCC3)N3CC4=NNC(N4)=O)C=C1

InChI

1S/C23H21F7N4O3/c1-12(14-8-15(22(25,26)27)10-16(9-14)23(28,29)30)37-20-19(13-2-4-17(24)5-3-13)34(6-7-36-20)11-18-31-21(35)33-32-18/h2-5,8-10,12,19-20H,6-7,11H2,1H3,(H2,31,32,33,35)/t12-,19-,20+/m1/s1

InChI key

ATALOFNDEOCMKK-BYYRLHKVSA-N

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Application

Aprepitant has been used as neurokinin 1 (NK1) receptor antagonist in dorsal root ganglion (DRG) derived cells and bone marrow mesenchymal stem cells (BMSCs) coculture.

Biochem/physiol Actions

Aprepitant is an antiemetic drug. It is a moderate cytochrome P450 3A4 (CYP3A4) inhibitor. It is capable of crossing the blood brain barrier in humans. In animals, aprepitant can cross the placental barrier. Aprepitant is a potent and selective antagonist of human substance P/neurokinin 1 (NK1) receptors used clinically to treat chemotherapy-induced or post-operative nausea and vomiting, and being investigated for other activity including possible treatment for depression and pruritis.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The role of neurokinin-1 (substance P) antagonists in the prevention of postoperative nausea and vomiting
Okafor D, et al.
Journal of Anaesthesiology, Clinical Pharmacology, 33(4), 441-441 (2017)
Dorsal Root Ganglion Maintains Stemness of Bone Marrow Mesenchymal Stem Cells by Enhancing Autophagy through the AMPK/mTOR Pathway in a Coculture System
Zhang S, et al.
Stem Cells International (2018)
Aprepitant and fosaprepitant drug interactions: a systematic review
Patel P, et al.
British Journal of Clinical Pharmacology, 83(10), 2148-2148 (2017)
Deepti Jacob et al.
American journal of physiology. Gastrointestinal and liver physiology, 313(5), G505-G510 (2017-08-18)
Aprepitant, an NK1 receptor antagonist, is approved for the treatment of chemotherapy-induced or postoperative emesis by blocking NK1 receptors in the brain stem vomiting center. The effects of NK1 receptors on gastric functions and postprandial symptoms in humans are unclear;
Sergei Spitsin et al.
JCI insight, 2(19) (2017-10-06)
HIV-infected individuals, even well controlled with combined antiretroviral therapy (cART), have systemic inflammation and comorbidities. Substance P (SP) is an undecapeptide, which mediates neurotransmission and inflammation through its cognate neurokinin 1 receptor (NK1R). Plasma SP levels are elevated in HIV-infected
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