Aprepitant

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Cat Number

API170729803

CAS Number

170729-80-3

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Product Detail Description Scientific Support Customer Q&A

CAS Number

170729-80-3

EINECS

677-636-6

Storage

Store at room temperature

Synonyms

MK-869; Cinvanti; Aponvie; aprepitantum; DTXSID3049047; 1NF15YR6UY

Molecular Formula

C23H21F7N4O3

Molecular Weight

534.4

Smiles

C[C@H](C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)O[C@@H]2[C@@H](N(CCO2)CC3=NNC(=O)N3)C4=CC=C(C=C4)F

Appearance

White to off-white powder to crystal

Melting Point

249.0-253.0°C

General Description

Aprepitant is a synthetic neurokinin-1 (NK1) receptor antagonist, a morpholine derivative with a triazole group. Its chemical structure is 5-[[(2S,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,2-dihydro-1,2,4-triazol-3-one. Aprepitant is a white to off-white crystalline powder, practically insoluble in water.

Mechanism of Action

Aprepitant acts as a selective, high-affinity antagonist at the NK1 receptor, blocking the binding of substance P, a neuropeptide that is a key mediator in the emetic pathway. By inhibiting the action of substance P in the chemoreceptor trigger zone and the nucleus tractus solitarius, it prevents the initiation of the vomiting reflex, particularly in the delayed phase of chemotherapy-induced nausea.

Application

Aprepitant is indicated in combination with other antiemetic agents for the prevention of acute and delayed nausea and vomiting associated with highly emetogenic chemotherapy, including cisplatin-based regimens. It is also used for the prevention of postoperative nausea and vomiting (PONV). The drug is effective in reducing the incidence and severity of emesis.

An individual patient data meta-analysis of six studies (2,767 patients) compared NEPA (netupitant/fosnetupitant) with aprepitant/fosaprepitant for CINV prevention. Complete response and no significant nausea rates were similar during the acute phase (0-24 h), but NEPA showed significantly higher rates during the delayed phase (>24-120 h) and overall (0-120 h), particularly on days 3-5. NEPA-based regimens offer improved CINV prevention, especially for prolonged nausea and vomiting associated with newer targeted anticancer therapies.

Fig. 1 Crude pooled daily incidence of breakthrough emesis and/or use of rescue medication (all patients in the intent-to-treat population). (Navari RM, et al., 2025)

References

Navari RM, et al. Individual patient data meta-analysis of NEPA versus aprepitant-based antiemetic regimens for preventing chemotherapy-induced nausea and vomiting. Future Oncol. 2025;21(21):2823-2833.

Does Aprepitant require protection from light and moisture during storage?

Yes, it is sensitive to both light and moisture. Light causes photodegradation and moisture promotes hydrolysis of the morpholine ring. Store in light-resistant, tightly sealed containers with desiccant.

What is the recommended storage temperature for Aprepitant?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate degradation.

Is Aprepitant stable in capsule formulations with standard excipients?

Yes, when formulated with moisture-protective packaging (e.g., blisters).

How is the impurity aprepitant N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.