AMPRENAVIR

Product Name: AMPRENAVIR
CAS No.: 161814-49-9
Chemical Name: AMPRENAVIR
Synonyms: VX 478;PROZEI;141W94;KVX-478;CS-1052;AGENERASE;AMPRENAVIR;Angenerase;Amprenavir 13C6;5-Bromo-5-nitro-1
CBNumber: CB4186139
Molecular Formula: C25H35N3O6S
Formula Weight: 505.63
MOL File: 161814-49-9.mol

More

Less

AMPRENAVIR Property

Melting point:: 72-74°C
Density: 1.30±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: DMSO: soluble20mg/mL, clear
pka: 11.54±0.46(Predicted)
form: powder
color: white to beige
optical activity: [α]/D +8 to +12°, c = 0.5 in methanol
BCS Class: 2
InChIKey: YMARZQAQMVYCKC-OEMFJLHTSA-N

More

Less

Safety

RIDADR: 3077
WGK Germany: 3
HS Code: 29350090
Hazardous Substances Data: 161814-49-9(Hazardous Substances Data)

More

Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More

Less

N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0685
Product name: Amprenavir
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $119
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0685
Product name: Amprenavir
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $482
Updated: 2024/03/01

Cayman Chemical

Product number: 15369
Product name: Amprenavir
Purity: ≥95%
Packaging: 5mg
Price: $93
Updated: 2024/03/01

Cayman Chemical

Product number: 15369
Product name: Amprenavir
Purity: ≥95%
Packaging: 25mg
Price: $388
Updated: 2024/03/01

Cayman Chemical

Product number: 15369
Product name: Amprenavir
Purity: ≥95%
Packaging: 50mg
Price: $728
Updated: 2024/03/01

More

Less

AMPRENAVIR Chemical Properties,Usage,Production

Description

Amprenavir was launched as Agenerase in the US for the treatment of AIDS patients in combination with approved agent antiretroviral nucleoside analogs. It is the fifth non-peptidic inhibitor of HIV-1 protease to be marketed in this indication after the last approved Neflinavir. Amprenavir, designed via a structure-based process, is the smallest molecule in the 《navir》 class and exhibits a reduced peptidic character. An improved process for preparation comprising four steps from a (1S, 2R)-2-hydroxy-3-aminopropylcarbamate has been developed. Amprenavir is a potent inhibitor of HIV-1 aspartyl protease (Ki = 0.6nM), an enzyme required by the virus to cleave pro-form polyproteins to structural proteins during the last stage in the replication process. The compound displays good oral bioavailability in humans and penetrates the CNS, which is an important advantage in long-term treatment. Its plasma half-life is approximately 10h. Treatment with Amprenavir in combination with nucleoside analog reverse transcriptase inhibitors considerably decreases viral load and restores CD4+ T-cell counts in patients with HIV infection.

Description

Amprenavir is an inhibitor of HIV protease (K_i = 0.04 nM). It inhibits the cytopathic effects of HIV-1 in MT-4 cells (IC₅₀ = 150 nM). Formulations containing amprenavir have been used in combination with other antiretroviral agents in the treatment of HIV-1 infection.

Chemical Properties

Off-White to Pale Yellow

Originator

Vertex Pharm (US)

Uses

A selective HIV protease inhibitor. An analogue of Ritonavir

Uses

Protease inhibitor, anti-HIV agent

Indications

Amprenavir (Agenerase) is administered twice daily, providing the patient with an advantage over other protease inhibitors that must be taken more frequently (e.g., indinavir, saquinavir). Common side effects of am-prenavir include nausea, vomiting, diarrhea, and perioral paraesthesias. Rash occurs in approximately 20 to 30% of patients and can be mild or severe (Stevens- Johnson syndrome).

Definition

ChEBI: Amprenavir is a tetrahydrofuryl ester, a sulfonamide and a carbamate ester. It has a role as a HIV protease inhibitor and an antiviral drug.

Manufacturing Process

(1-Oxiranyl-2-phenylethyl)-carbamic acid t-butyl ester may be synthesized from available starting materials (see B. E. Evans et al., J. Org. Chem., 50, p.4615 (1985)). The amprenavir may be preparated with the next steps.
1. (1-Benzyl-3-isobutylaminopropyl)-carbamic acid t-butylester. A solution of 4.1 g of epoxide (1-oxiranyl-2-phenylethyl)-carbamic acid t-butyl ester in 30 ml of ethanol was treated with 22.4 ml of isobutylamine and heated under reflux for 1 h. The mixture was concentrated to yield the title compound as a white solid which was used without subsequent purification.
2. To a solution of the above compound (2.5 g, 7.43 mmol) in CH2Cl2 (50 ml) was added triethylamine (2.1 ml, 14.9 mmol) followed by addition of benzyl chloroformate (1.2 ml, 8.1 mmol). The mixture was allowed to stir at ambient temperature for 6 h. The solution was diluted with 1 L of CH2Cl2 and washed with water. The organics were dried over anhydrous MgSO4, concentrated under reduced pressure, then purified via silica gel chromatography. Gradient solvent system: CH2Cl2 followed by 3:97 methanol/CH2Cl2. (3-t- Butoxycabonylamino-4-phenylbutyl)-isobutylcarbamic acid benzyl ester (2.97 g) was obtained as a colorless oil. TLC: Rf= 0.14, 3:97 methanol/CH2Cl2. 3. BOC - protecting group was removed as followed: to a solution of 1.5 g (3.187 mmol) of the above compound of in ethyl acetate (25 ml) at - 20°C was bubbled anhydrous HCl gas for 10 min. The ice bath was removed and after an additional 15 min the reaction mixture was sparged with nitrogen, then concentrated in vacuo to provide 1.29 g of deprotected product as a white solid which was used directly for the next reaction TLC: Rf= 0.14, 10% methanol/CH2Cl2.
4. Isobutyl[4-phenyl-(S)-3-tetrahydrofuran-3-yl-oxycarbonylamino)-butyl]- carbamic acid benzyl ester. To a solution of 1.077 g of the above resultant crude compound (2.647 mmol) in acetonitrile (10 ml) was added sequentially at ambient temperature under an atmosphere of nitrogen, 1.61 ml (9.263 mmol) of diisopropylethylamine and 910 mg (3.97 mmol) of the Nsuccinimidyl-( S)-3-tetrahydrocfuryl carbonate. The last one was prepared from phosgene and (S)-(+)-3-hydroxytetrahydrofuran by usual procedure. After stirring for 3 h, an additional 223 mg (0.973 mmol) of the N-succinimidyl-(S)- 3-tetrahydrocfuryl carbonate was added. The mixture was stirred for 16 h and then concentrated in vacuo. The residue was taken up in ethyl acetate and washed with water, 0.5 N HCl, saturated sodium bicarbonate, saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by low pressure silica gel column chromatography using a gradient 10% to 25% ethyl acetate in CH2Cl2 eluent to yield 1.025 g of the title product as a white solid. TLC: Rf= 0.10, 10% ethyl acetate/CH2Cl2.
5. A solution of 872 mg (1.799 mmol) isobutyl[4-phenyl-(S)-3- tetrahydrofuran-3-yl-oxycarbonylamino)-butyl]-carbamic acid benzyl ester in (10 ml) of ethyl alcohol was added, at ambient temperature under a nitrogen atmosphere, to a slurry of 87 mg (10% by weight) of 10% palladium on carbon in (5 ml) ethyl alcohol and hydrogenated for 16 h under a slight positive pressure of hydrogen. The mixture was filtered and concentrated in vacuo to yield 553.2 mg of the carbamic acid as a colorless glass which was used directly for ensuing reaction. TLC: Rf = 0.46, 10% methanol/CH2Cl2.
6. A solution of 102 mg of the resultant compound of a step 5 in 4:1 CH2Cl2/saturated aqueous NaHCO3 was treated sequentially, at ambient temperature under an atmosphere of nitrogen, with 65 mg of pnitrobenzenesulfonyl chloride and 51 mg of sodium bicarbonate. The mixture was stirred for 14 h, diluted with CH2Cl2, washed with saturated NaCl, then dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by low pressure silica gel chromatography using 20% diethyl ether/CH2Cl2 as eluent to provide 124 mg of the 1-benzyl-3-[isobutyl-(4- nitrobenzenesylfonyl)-amino]-propylcarbamic acid tetrahydrofuran-3(S)-yl] ester as a white solid. TLC: Rf = 0.36, 20% diethyl ether/CH2Cl2, HPLC: Rt = 15.15 min. (1H)-NMR (CDCl3) consist with structure.
7. A solution of 124 mg of the resultant compound of the step 6 in ethyl acetate was treated, at ambient temperature, with 13 mg of 10% palladium on carbon. The mixture was stirred for 14 h under an atmosphere of hydrogen, filtered through a pad of celite filter agent, and concentrated in vacuo. The residue was subjected to preparative HPLC to yield 82 mg of the ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1- (phenylmethyl)propyl)-, (3S)-tetrahydro-3-furanyl carbamic ester a white solid. TLC: Rf= 0.10, 20% ether/CH2Cl2, HPLC: Rt= 13.16 min. (1H)-NMR (CDCl3) consistent with structure.

brand name

Agenerase (GlaxoSmithKline).

Therapeutic Function

Antiviral

Acquired resistance

Mutations at position 50, 76 and 84 of the protease enzyme gene are associated with significantly reduced susceptibility.

General Description

Amprenavir is a second-generation drug derived from hydroxyethylamine sulfonamide.

Pharmaceutical Applications

A synthetic compound formulated as the calcium salt of the oral prodrug fosamprenavir.

Biochem/physiol Actions

Protease inhibition results in inactive and immature virus.

Pharmacokinetics

Oral absorption: Not known/available
C_max 700 mg + ritonavir 100 mg:c. 6.08 mg/L
twice daily
C_min 700 mg + ritonavir 100 mg:c. 2.12 mg/L
twice daily
Plasma half-life: c. 7.7 h
Volume of distribution: c. 430 L
Plasma protein binding: c. 90%
Absorption
Fosamprenavir is rapidly and almost completely hydrolyzed to amprenavir and inorganic phosphate by cellular phosphatases in the gut epithelium as it is absorbed. Absolute bioavailability has not been established. It can be taken without regard to food.
Distribution
It penetrates moderately well into the CNS. The semen:plasma ratio is negligible. It is not known if it is distributed into breast milk.
Metabolism and excretion
It is extensively metabolized by the cytochrome P₄₅₀ (CYP) 3A4 enzyme system. Two major metabolites have been identified that appear to result from the oxidation of the tetrahydrofuran and aniline moieties. Around 14% of a dose is eliminated in the urine and 75% in feces, <3% as unchanged drug. Metabolites account for >90% of administered drug found in fecal samples. It should be used with caution and at reduced doses in adults with mild or moderate hepatic impairment; it is contraindicated in patients with severe hepatic impairment.

Clinical Use

Treatment of HIV infection (in combination with other antiretroviral drugs)

Side effects

The most common adverse events in patients receiving boosted fosamprenavir were diarrhea, nausea, headache, fatigue, vomiting and rash. Ritonavir-boosted fosamprenavir is associated with a dyslipidemia profile characteristic of those treated with other protease inhibitors boosted with 200 mg of ritonavir.

target

HIV Protease

AMPRENAVIR Preparation Products And Raw materials

Raw materials

Preparation Products

More

Less

AMPRENAVIR Suppliers

Canada 1 China 149 Europe 2 Germany 1 India 6 South Korea 1 United Kingdom 5 United States 37 Global 202

LGM Pharma

Tel: 1-(800)-881-8210
Fax: 615-250-9817
Email: inquiries@lgmpharma.com
Country: United States
ProdList: 2123
Advantage: 70

BOC Sciences

Tel: 1-631-485-4226; 16314854226
Email: info@bocsci.com
Country: United States
ProdList: 14055
Advantage: 65

MedChemexpress LLC

Tel: 021-58955995
Fax: 609-228-5909
Email: sales@medchemexpress.cn
Country: United States
ProdList: 4861
Advantage: 58

AdooQ BioScience, LLC

Tel: +1 (866) 930-6790
Fax: +1 (866) 333-9607
Email: info@adooq.com
Country: United States
ProdList: 2782
Advantage: 58

ApexBio Technology LLC

Tel: +1-832-696-8203
Fax: +1-832-641-3177
Email: info@apexbt.com
Country: United States
ProdList: 477
Advantage: 60

Alfa Chemistry

Tel: 1-516-6625404
Fax: 1-516-927-0118
Email: support@alfa-chemistry.com
Country: United States
ProdList: 9171
Advantage: 60

BOC Sciences

Tel: 16314854226
Email: info@bocsci.com
Country: United States
ProdList: 9923
Advantage: 65

Target molecule Corp.

Tel: 857-239-0968
Fax: 857-239-8801
Email: service1@targetmol.com
Country: United States
ProdList: 2559
Advantage: 60

Alabiotech Inc.

Tel: 001-619-354-5251
Fax: 001-855-855-6087
Email: sales@alabiotech-e.com
Country: United States
ProdList: 972
Advantage: 60

Musechem

Tel: +1-800-259-7612
Fax: +1-800-259-7612
Email: info@musechem.com
Country: United States
ProdList: 4660
Advantage: 60

TargetMol Chemicals Inc.

Tel: +1-781-999-5354 +1-00000000000
Email: marketing@targetmol.com
Country: United States
ProdList: 32165
Advantage: 58

InvivoChem

Tel: +1-708-310-1919 +1-13798911105
Fax: 708-557-7486
Email: sales@invivochem.cn
Country: United States
ProdList: 6391
Advantage: 58

Cckinase, Inc.

Tel: +1 (732)236-3202
Email: sales@cckinase.com
Country: United States
ProdList: 2738
Advantage: 58

Alchem Pharmtech,Inc.

Tel: 8485655694
Email: sales@alchempharmtech.com
Country: United States
ProdList: 63687
Advantage: 58

Aladdin Scientific

Tel: +1-+1(833)-552-7181
Email: sales@aladdinsci.com
Country: United States
ProdList: 57505
Advantage: 58

TargetMol Chemicals Inc.

Tel
Email: support@targetmol.com
Country: United States
ProdList: 38632
Advantage: 58

ApexBio Technology

Tel: --
Fax: --
Email: sales@apexbt.com
Country: United States
ProdList: 6251
Advantage: 58

CarboMer, Inc.

Tel: --
Fax: --
Email: sales@carbomer.com
Country: United States
ProdList: 4026
Advantage: 67

Olinax Inc.

Tel: --
Fax: --
Email: info@olinax.com
Country: United States
ProdList: 404
Advantage: 50

Cayman Chemical Company

Tel: --
Fax: --
Email: cayman@caymanchem.com
Country: United States
ProdList: 6213
Advantage: 81

Creative Enzymes

Tel: --
Fax: --
Email: info@creative-enzymes.com
Country: United States
ProdList: 6057
Advantage: 58

MedChemExpress

Tel: --
Fax: --
Email: sales@medchemexpress.com
Country: United States
ProdList: 6398
Advantage: 58

Riedel-de Haen AG

Tel: --
Fax: --
Country: United States
ProdList: 6773
Advantage: 87

Matrix Scientific

Tel: --
Fax: --
Email: sales@matrixscientific.com
Country: United States
ProdList: 6632
Advantage: 80

3B Scientific Corporation

Tel: --
Fax: --
Email: sales@3bsc.com
Country: United States
ProdList: 6962
Advantage: 56

Santa Cruz Biotechnology, Inc.

Tel: --
Fax: --
Email: scbt@scbt.com
Country: United States
ProdList: 3597
Advantage: 60

Waterstone Technology, LLC

Tel: --
Fax: --
Email: sales@waterstonetech.com
Country: United States
ProdList: 6786
Advantage: 30

AlliChem, LLC

Tel: --
Fax: --
Email: sales@allichemllc.com
Country: United States
ProdList: 6516
Advantage: 60

Medical Isotopes

Tel: --
Fax: --
Email: stohler@medicalisotopes.com
Country: United States
ProdList: 6181
Advantage: 68

HONEST JOY HOLDINGS LIMITED

Tel: --
Fax: --
Email: sales@honestjoy.cn
Country: United States
ProdList: 6675
Advantage: 54

2A PharmaChem USA

Tel: --
Fax: --
Email: sales@2apharmachem.com
Country: United States
ProdList: 6137
Advantage: 39

3B Scientific Corporation

Tel: --
Fax: --
Email: sales@3bsc.com
Country: United States
ProdList: 6718
Advantage: 47

APAC Pharmaceutical, LLC

Tel: --
Fax: --
Email: sales@apacpharma.com
Country: United States
ProdList: 6322
Advantage: 38

BOSCHE SCIENTIFIC, LLC

Tel: --
Fax: --
Email: Sales@BoscheSci.com
Country: United States
ProdList: 6477
Advantage: 55

ChemPacific Corporation

Tel: --
Fax: --
Email: sales@chempacific.com
Country: United States
ProdList: 6891
Advantage: 51

American Radiolabeled Chemicals, Inc.

Tel: --
Fax: --
Email: arcinc@arc-inc.com
Country: United States
ProdList: 2608
Advantage: 60

Moravek Biochemicals, Inc.

Tel: --
Fax: --
Email: moravek@worldnet.att.net
Country: United States
ProdList: 1227
Advantage: 69

More

Less

View Lastest Price from AMPRENAVIR manufacturers

Hebei Ningnan Trade Co. LTD

Product: AMPRENAVIR 161814-49-9
Price: US $10.00-200.00/G
Min. Order: 100G
Purity: 99.99%
Supply Ability: 20MT
Release date: 2022-11-04

Honest Joy Holdings Limited

Product: Amprenavir 161814-49-9
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98.1%
Supply Ability: 100 tons
Release date: 2022-02-08

Zhuozhou Wenxi import and Export Co., Ltd

Product: Amprenavir 161814-49-9
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

161814-49-9, AMPRENAVIRRelated Search:

Fosamprenavir-d4 Fosamprenavir Impurity 2 (S)-4-Chloro-1,3-butanediol Raltegravir Daclatasvir Lopinavir Darunavir ethanolate Elvitegravir Ritonavir Fosamprenavir calcium AMPRENAVIR (3S)-TETRAHYDRO-3-FURANYL ESTER AMPRENAVIR [3H(G)] AMPRENAVIR-D4 Fosamprenavir-D4 Calcium Salt Fosamprenavir AMPRENAVIR, [3H]- AKOS 92102

KVX-478

AGENERASE

AMPRENAVIR

141W94

PROZEI

141W94, KVX-478, Agenerase, Prozei,

Carbamic acid, (1S,2R)-3-(4-aminophenyl)sulfonyl(2-methylpropyl)amino-2-hydroxy-1-(phenylmethyl)propyl-, (3S)-tetrahydro-3-furanyl ester

Angenerase

Carbamic acid, [3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, tetrahydro-3-furanyl ester, [3S-[3R*(1R*,2S*)]]-

VX 478

AMPRENAVIR (VX-478)

CS-1052

(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)(4-aminobenzene)sulfonamido]-1-phenylbutan-2-yl]carbamate

[(3S)-Oxolan-3-yl] N-[(2S,3R)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate

N-[(1S,2R)-3-[[(4-AMinophenyl)sulfonyl](2-Methylpropyl)aMino]-2-hydroxy-1-(phenylMethyl)propyl]carbaMic Acid (3S)-Tetrahydro-3-furanyl Ester

AMprenavir(agenerase)

Amprenavir(KVX-478)

Carbamic acid, N-[(1S,2R)-3-[[(4-aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-, (3S)-tetrahydro-3-furanyl ester

AMPRENAVIR USP/EP/BP

Amprenavir 13C6

AmprenavirQ: What is Amprenavir Q: What is the CAS Number of Amprenavir Q: What is the storage condition of Amprenavir Q: What are the applications of Amprenavir

5-Bromo-5-nitro-1

(S)-Tetrahydrofuran-3-yl ((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate

161814-49-9

C25H35N3O6S

Inhibitor

peptides

API

Anti-viral Compounds

Anti-virals

Inhibitors

Intermediates & Fine Chemicals

Non-nucleoside Reverse Transcriptase

Pharmaceuticals