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Aprepitant structure
Aprepitant structure

Aprepitant

Iupac Name:3-[[(2R,3S)-2-[(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholin-4-yl]methyl]-1,4-dihydro-1,2,4-triazol-5-one
CAS No.: 170729-80-3
Molecular Weight:534.426662
Modify Date.: 2022-11-22 16:09
Introduction: Aprepitant is an antiemetic chemical compound that belongs to “substance P” antagonists (SPA) with its effect being blocking the neurokinin 1(Nk1) receptor. It is used for the prevention of acute and delayedchemotherapy-induced nausea and vomiting(CINV) and for prevention ofpostoperative nausea and vomiting. It can also be used for the treatment of cyclic vomiting syndrome and late-stage chemotherapy induced vomiting occurring during cancer treatment. Aprepitant alleviates the case of vomiting in patients through balking the signals released by Nk1 receptors. Nk1 is a G-protein-coupled receptor with its ligand being substance P (SP). The high concentration of SP is required for the vomiting reflex. Aprepitant blocks the process of SP-NK1 signaling in activating the vomiting reflex. View more+
1. Names and Identifiers
1.1 Name
Aprepitant
1.2 Synonyms

[3H]-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- 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- 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]-2,4-dihydro- 3H-1,2,4-Triazol-3-one, 5-[[2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-, [2R-[2α(R*),3α]]- 3H-1,2,4-Triazol-3-one,5-[[2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-,[2R-[2a(R*),3a]]- 5-[[(2R,3S)-2-[(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)-4-morpholinyl]methyl]-1,2-dihydro-3H-1, 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 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, Emend 5-[[(2R,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 5-[{(2R,3S)-2-((1R)-1-3,5-bis(trifluoro-methyl)phenylethoxy)-3-(4-fluorophenyl)-4-morpholinyl}methyl]-1,2-dihydro-3H-1,2,4-triazol-3-one 5-{[(2R,3S)-2-{(1R)-1-[3,5-Bis(trifluormethyl)phenyl]ethoxy}-3-(4-fluorphenyl)morpholin-4-yl]methyl}-1,2-dihydro-3H-1,2,4-triazol-3-on 5-{[(2R,3S)-2-{(1R)-1-[3,5-bis(trifluorométhyl)phényl]éthoxy}-3-(4-fluorophényl)morpholin-4-yl]méthyl}-1,2-dihydro-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-3H-1,2,4-triazol-3-one 5-{[(2R,3S)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)morpholin-4-yl]methyl}-1,2-dihydro-3H-1,2,4-triazol-3-one 5-{[(2R,3S)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)morpholin-4-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one Aprepitant (MK-0869, L-754030) Aprepitant(MK-0869) CS-274 Emend Emend (TN) Fosaprepitant Impurity 8 L 754030 L-754030 MK 0869 MK 869 MK-0869 MK-869 ONO 7436 ONO7436 S1189_Selleck

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1.3 CAS No.
170729-80-3
1.4 CID
135413536
1.5 EINECS(EC#)
1806241-263-5
1.6 Molecular Formula
C23H21F7N4O3 (isomer)
1.7 Inchi
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
1.8 InChIkey
ATALOFNDEOCMKK-OITMNORJSA-N
1.9 Canonical Smiles
CC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)OC2C(N(CCO2)CC3=NNC(=O)N3)C4=CC=C(C=C4)F
1.10 Isomers 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
2. Properties
2.1 Density
1.51
2.1 Melting point
244-246°C
2.1 Refractive index
1.564
2.1 Precise Quality
534.15000
2.1 PSA
83.24000
2.1 logP
4.89000
2.1 Appearance
Solid
2.2 Storage
-20°C Freezer
2.3 Chemical Properties
Off-White to Light Yellow Cyrstalline Solid
2.4 Color/Form
white to beige
2.5 pKa
8.06±0.20(Predicted)
2.6 Water Solubility
Practically insoluble in water
2.7 StorageTemp
Sealed in dry,2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A morpholine-based antiemetic, which is or the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/eurokinin 1 (NK1) receptors.
3.2 Usage
Antineoplastic drug.
4. Safety and Handling
4.1 Symbol
GHS07
4.1 Hazard Codes
Xn; Xi
4.1 Signal Word
Warning
4.1 Risk Statements
S26-S36
4.1 Safety Statements
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . R36/37/38:Irritating to eyes, respiratory system and skin .
4.1 Hazard Declaration
H319
4.1 RIDADR
NONH for all modes of transport
4.1 Caution Statement
P305 + P351 + P338
4.1 WGK Germany
3
4.1 Specification

?Aprepitant , its CAS NO. is 170729-80-3, the synonyms are 3-(((2R,3S)-3-(p-Fluorophenyl)-2-(((alphaR)-alpha-methyl-
3,5-bis(trifluoromethyl)benzyl)oxy)morpholino)methyl)-delta(sup 2)-1,2,4-triazolin-5-one ; 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- ; Emend .

4.2 Toxicity

?Aprepitant (CAS NO.170729-80-3) ?should not be used concurrently with pimozide, terfenadine, astemizole, or cisapride. Dose-dependent inhibition of CYP3A4 by aprepitant could result in elevated plasma concentrations of these drugs, potentially causing serious or life-threatening reactions.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Specific target organ toxicity \u2013 repeated exposure, Category 2

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H373 May cause damage to organs through prolonged or repeated exposure

H410 Very toxic to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P273 Avoid release to the environment.

Response

P314 Get medical advice/attention if you feel unwell.

P391 Collect spillage.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Anti-Vomiting drug during chemotherapy
Aprepitant is a neurokinin-1 (NK-1) receptor antagonist and belongs to the treating agents of vomiting during chemotherapy of cancer. It was first successfully developed by Merck Company (German). In March 2003, the US Food and Drug Administration approved it for being used in the treatment of chemotherapy vomiting. This product has a high selective affinity to human beings while has a low affinity to serotonin, dopamine and glucocorticoid receptor affinity. Aprepitant, when combined with 5-HT3 receptor inhibitors (such as ondansetron hydrochloride) and the corticosteroid dexamethasone, can further alleviate the cisplatin-induced acute and (or) delayed emesis. Applying this drug alone can have some preventive effect.
Substance P, a kind of tachykinin (neurokinin), is mainly distributed in the neurons of central and peripheral nervous system. It is related with a lot of features such as vomiting, depression, inflammatory pain and other inflammatory diseases. The role of substance P is mediated by NK-1 receptor which is a kind of G protein receptor coupled with phosphoinositide signaling pathway. The drug has blocking effect on the NK-1 receptor through direct binding to this receptor, thus further obtaining the treatment of substance P-mediated diseases.
Aprepitant can selectively prevent the binding of substance P with NK-1 receptor in the central nervous system to take antiemetic effect. Therefore, it can be used for treating the nausea and vomiting caused by the moderately and highly emetogenic chemotherapy.
View all
9.1 Side effects
Gastrointestinal reaction: when used for the prevention of chemotherapy-induced emesis, aprepitant may cause diarrhea, but clear relationship is still lacking.
Central nervous system: the drug can cause drowsiness and weakness (or lack thereof), but statistical significance was not obvious.
Genitourinary system: when aprepitant is applied for the treatment of severe depression, sexual dysfunction can occur.
Respiratory system: the drug is used for the prevention of chemotherapy-induced emesis, can also cause hiccups. But the clinical significance is not clear.
Skin: occasionally History-Johnson syndrome, urticaria and angioedema can occur.
Liver: when aprepitant is used for the prevention of chemotherapy-induced emesis, it can cause the increase of serum aminotransferase, but the clinical significance is unclear. No cases of liver toxicity had been reported.
9.2 Uses
Antineoplastic drug.
9.3 Chemical Properties
Off-White to Light Yellow Cyrstalline Solid
9.4 Uses
A novel selective neurokinin-1 (NK-1) receptor antagonist. In vitro studies using human liver microsomes indicate that Aprepitant is metabolised primarily by CYP3A4 with minor metabolism by CYP1A2 and CYP2C19, and no metabolism by CYP2D6, CYP2C9, or CYP2E1. Antiemetic.
9.5 Uses
anticholinergic
9.6 Definition
ChEBI: A morpholine-based antiemetic, which is or the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy. Aprepitant is a selective high-affinity antagonist of human substance P/ eurokinin 1 (NK1) receptors.
9.7 Brand name
Emend (Merck).
9.8 References
Curran, Monique P., and D. M. Robinson. "Aprepitant."Drugs69.13(2009):1853-1878.
Sant P. Chawla M.D. ? ?, et al. "Establishing the dose of the oral NK 1, antagonist aprepitant for the prevention of chemotherapy-induced nausea and vomiting." Cancer 97.9(2003):2290-2300.
Warr, D. G., et al. "Efficacy and tolerability of aprepitant for the prevention of chemotherapy-induced nausea and vomiting in patients with breast cancer after moderately emetogenic chemotherapy." Journal of Clinical Oncology Official Journal of the American Society of Clinical Oncology23.12(2005):2822-30.
https://en.wikipedia.org/wiki/Aprepitant
9.9 Originator
Merck (US)
9.10 Clinical Use
Aprepitant, a substance P (neurokinin-1 [NK-1]) receptor antagonist used for the treatment of chemotherapy-induced nausea and vomiting, was launched in the US and was later approved in the European Union. It is a non-peptide analog having a trisubstituted morpholine with three chiral centers. Two syntheses have been described. In six steps p-fluorophenylacetic acid is converted to 4-benzyl-3-pfluorophenyl- 2-oxomorpholine with a resolution step setting the S-stereochemistry. This intermediate is converted in six steps to aprepitant, with two of the steps utilizing a chiral induction strategy to set the new centers based upon the chiral 2- oxomorpholine intermediate. SAR efforts leading to aprepitant included engineering in potency for NK-1, decreasing affinity for L-type calcium ion channels, most importantly by decreasing the basicity of the core heterocycle. In vitro, it binds with very high affinity (90 pM) to the hNK1 in transfected CHO cells. It is described as an inverse agonist of hNK-1 receptor, with slow dissociation rate under some conditions. In ferrets dosed orally or intravenously prior to emetogen challenge (cisplatin, apomorphine or morphine), retching and vomiting was reduced. Its antiemetic effect is enhanced with the dosing of dexamethasone and it is effective against both the acute and delayed phase of cisplatin-induced emesis. Cisplatin-induced emesis clinical studies showed that aprepitant (125 mg p.o.) in combination with ondansetron (32 mg i.v.) and dexamethasone (20 mg p.o.) therapeutically followed by repeat dosing (days 2–5) of aprepitant (80 mg) dexamethasone (20 mg) provided acute (8 h) and delayed phase (days 2–7) no vomiting rates of 83 and 70%, respectively. L-758298, a prodrug of aprepitant, was not as effective as ondansetron (32 mg i.v.) in reducing acute phase vomiting, but was superior in reducing vomiting in the delayed phase. The terminal half-life range of aprepitant is 9–13 h and the bioavailability is about 65%. It is highly protein bound (95%) and has a Vdss of 70 L. It is a moderate CYP3A4 inhibitor, thus several drugs cleared by CYP3A4 should not be used concurrently. It is also an inducer of CYP2C9 thus potentially modulating the PK of drugs cleared by CYP2C9. Most side effects were mild to moderate, with fatigue, asthenia, diarrhea, and hiccups.
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9.11 Chemical Synthesis
Several variations to the synthesis of aprepitant (II) have been published by the Merck group. The latest optimized synthesis utilizing a novel crystallization-induced diastereoselective synthesis of aprepitant is highlighted in the Scheme. The synthetic approach entailed (1) the synthesis and coupling of the key pieces, N-benzyl lactam lactol 13 and sec-phenethyl alcohol 7, to provide lactam acetal 14, (2) stereoselective elaboration to the key intermediate 14, and (3) conversion to the final compound via either intramolecular cyclization or intermolecular coupling with triazolinone chloride 24. The intermediate secphenethyl alcohol 7 was synthesized in 97% yield and 95% e.e. (improved to 99% e.e. after recrystallization) via the enantioselective borane reduction of ketone 6 in the presence of 2 mol % of (S)-oxazaborolidine catalyst 8. The optimized conditions involved the slow addition of ketone 6 to a solution containing catalyst 8 and BH3·PhNEt2 complex in MTBE at –10 to 0°C. The synthesis of lactam 12 was done by reacting N-benzylethanolamine (9) with slight excess of aqueous glyoxylic acid (10, 2.3 equivalent of 50% aqueous solution) in refluxing THF. Adjustment of the solvent composition from predominantly THF to predominantly water resulted in the crystallization of lactam 12 directly from 11 in the reaction mixture in 76% yield. Lactam 12 was treated with trifluoroacetic anhydride (1 equiv) to give trifluoroacetate 13, which was reacted in situ with chiral alcohol 7 in the presence of BF3·OEt2 to give, after workup, a 55:45 mixture of the acetals 14 and 15 in 95-98% overall yield. To obtain the desired diastereomer from the 55:45 mixture of 14 and 15, an optimized crystallization sequence was developed. To a solution of the crude mixture in heptane, 3,7-dimethyl-3-octanol (17) (0.9 equiv) was added, cooled to –10 to –5°C and, after seeding the mixture with pure 14, potassium salt of 3,7-dimethyl-3-octanol (16) (0.3 equiv) was added to initiate the crystallization-induced epimerization of 15 to 14. After 5 hr, the mixture was transformed into a 96:4 mixture from which 14 was isolated in 83-85% yield and >99% e.e. Under an optimized condition, the lactam 1 4 was reacted with 4- fluorophenylmagnesium bromide (18) (1.3 equiv) in THF at ambient temperature followed by methanol quench and addition of p-toluenesulfonic acid (1.8-2.2 equiv). Immediate hydrogenation of this mixture in the presence of 5% Pd/C gave the addition product 19, which was isolated as hydrochloride salt in 91% yield. Under these conditions, no cleavage of the benzylic ether group was seen, even after extended hydrogenation periods. Elaboration to aprepitant (II) was done by the initial alkylation of 19 in the presence of a base with amidrazone chloride 20, which was prepared from chloroacetonitrile, to give the intermediate 21. Thermolysis of 21 in toluene provided aprepitant (II) in 85% overall yield. Alternatively, the hydrochloride salt 19 has also been alkylated directly with the triazolinone chloride 24 to give aprepitant (II).
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9.12 Drug interactions
Potentially hazardous interactions with other drugs
Antidepressants: avoid with St John’s wort.
Antipsychotics: avoid with pimozide.
Avanafil: possibly increases avanafil concentration.
Cytotoxics: possibly increases bosutinib concentration - avoid or reduce bosutinib dose; possibly increases ibrutinib concentration - reduce ibrutinib dose.
Oestrogens and progestogens: may cause contraceptive failure.
Ulipristal: possibly reduces contraceptive effect - avoid.
9.13 Metabolism
Aprepitant undergoes extensive metabolism. Following a single IV 100mg dose of [14C]fosaprepitant, a prodrug for aprepitant, aprepitant accounts for approximately 19% of the radioactivity in plasma over 72 hours. 12 metabolites of aprepitant have been identified in human plasma. The metabolism of aprepitant, primarily by CYP3A4 and potentially with minor contribution by CYP1A2 and CYP2C19, occurs largely via oxidation at the morpholine ring and its side chains and the resultant metabolites were only weakly active.
Aprepitant is not excreted unchanged in urine. Metabolites are excreted in urine (57%) and via biliary excretion in faeces (45%).
9.14 References
Curran, Monique P., and D. M. Robinson. "Aprepitant."Drugs69.13(2009):1853-1878.
Sant P. Chawla M.D. ? ?, et al. "Establishing the dose of the oral NK 1, antagonist aprepitant for the prevention of chemotherapy-induced nausea and vomiting." Cancer 97.9(2003):2290-2300.
Warr, D. G., et al. "Efficacy and tolerability of aprepitant for the prevention of chemotherapy-induced nausea and vomiting in patients with breast cancer after moderately emetogenic chemotherapy." Journal of Clinical Oncology Official Journal of the American Society of Clinical Oncology23.12(2005):2822-30.
https://en.wikipedia.org/wiki/Aprepitant
9.15 Livertox Summary
Aprepitant is an orally available antiemetic agent that is used to prevent postoperative or cancer chemotherapy related nausea and vomiting. Aprepitant is associated with a low rate of serum enzyme elevations during therapy, but has not been clearly linked to cases of clinically apparent liver injury with jaundice.|Rolapitant is an orally available antiemetic agent that is used to prevent cancer chemotherapy related nausea and vomiting. Rolapitant therapy has not been associated with serum enzyme elevations or with instances of clinically apparent liver injury with jaundice.
9.16 Mesh
Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)|Compounds that inhibit or block the activity of NEUROKININ-1 RECEPTORS. (See all compounds classified as Neurokinin-1 Receptor Antagonists.)
9.17 Absorption
The mean absolute oral bioavailability of aprepitant is approximately 60 to 65%.|Aprepitant is eliminated primarily by metabolism; aprepitant is not renally excreted. Aprepitant is excreted in the milk of rats. It is not known whether this drug is excreted in human milk.|70 L|Apparent plasma cl=62-90 mL/min
9.18 Metabolism
Aprepitant primarily undergoes CYP3A4-mediated metabolism, as well as minor metabolism mediated by CYP1A2 and CYP2C19. About seven metabolites of aprepitant have been identified in human plasma, which all retain weak pharmacological activity.|Aprepitant has known human metabolites that include (2R,3S)-2-((R)-1-(3,5-Bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)morpholine, 1-[3,5-bis(trifluoromethyl)phenyl]ethanone, 5-oxo-1,4-dihydro-1,2,4-triazole-3-carbaldehyde, and 5-{[(2S,3S)-3-(4-fluorophenyl)-2-hydroxymorpholin-4-yl]methyl}-2,4-dihydro-1,2,4-triazol-3-one.
9.19 Biological Half Life
9-13 hours
9.20 Mesh Entry Terms
(1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(fluoro)phenyl-4-(3-oxo-1,2,4-triazol-5-yl)methylmorpholine
9.21 Use Classification
Human drugs -> Emend -> EMA Drug Category|Antiemetics and antinauseants -> Human pharmacotherapeutic group|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
10. Computational chemical data
  • Molecular Weight: 534.426662g/mol
  • Molecular Formula: C23H21F7N4O3
  • Compound Is Canonicalized: True
  • XLogP3-AA: 4.2
  • Exact Mass: 534.15018768
  • Monoisotopic Mass: 534.15018768
  • Complexity: 810
  • Rotatable Bond Count: 6
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 12
  • Topological Polar Surface Area: 75.2
  • Heavy Atom Count: 37
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceB7scAAAAAAAAAAAAAAAAAAAQAAAAA8YIAAAAAAAAABQAAAHwAYAAAADDzxmB8zCIPiBACoAiJiMACSAAAgAAAPiAAYDIiaZiKAsRm3MAh03AOcqAeQwOAOAAACAAAAAAAAAAQAAAAAAAAAAAAAAA==
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13. Realated Product Infomation