NELFINAVIR CAS 159989-64-7

Introduction：Basic information about NELFINAVIR CAS 159989-64-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

NELFINAVIR Basic information

• Product Name: NELFINAVIR
• Synonyms: Nelfinavir Regeoisomer;N-tert-butyl-2-[2-hydroxy-3-[[(3-hydroxy-2-methylphenyl)-oxomethyl]amino]-4-(phenylthio)butyl]-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide;AG 1341; AG-1341; AG1341;3-isoquinolinecarboxamide,n-(1,1-dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hy;8a-beta))-a-bet;nefinavir;NELFINAVIR;(3S,4aS,8aS)-N-(1,1-Dimethylethyl)decahydro-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-(phenylthio)butyl]-3-isoquinolinecarboxamide
• CAS: 159989-64-7
• MF: C32H45N3O4S
• MW: 567.78
• EINECS: 1533716-785-6
• Product Categories: peptides
• Mol File: 159989-64-7.mol

NELFINAVIR Chemical Properties

• Melting point: 185-186 °C
• alpha: D -119.23° (c = 0.26 in methanol)
• Boiling point: 786.8±60.0 °C(Predicted)
• density: 1.22±0.1 g/cm3(Predicted)
• storage temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• solubility: ≥ 20.45mg/mL in Ethanol
• pka: pKa1 6.0; pKa2 11.06(at 25℃)
• form: Powder
• color: White to off-white
• Water Solubility: 7g/L(temperature not stated)

Safety Information

• Toxicity: rat,LD,oral,> 5gm/kg (5000mg/kg),Toxicologist. Vol. 42, Pg. 55, 1998.

NELFINAVIR Usage And Synthesis

Uses

Antiviral.

Definition

ChEBI: An aryl sulfide that is used (as its mesylate salt) for treatment of HIV and also exhibits some anticancer properties.

Indications

Nelfinavir (Viracept) is probably the most commonlyused protease inhibitor because of its low incidence ofserious adverse effects. Its most common side effectsare diarrhea and flatulence; these may resolve with continueduse. In addition to the drugs contraindicated foruse with all protease inhibitors, amiodarone, rifampin,and quinidine are contraindicated in patients takingnelfinavir.

Brand name

Viracept (Agouron).

Antimicrobial activity

Nelfinavir inhibits HIV-1 and HIV-2 proteases. Bioavailabilityis affected to only a limited degree by combination with lowdoseritonavir.

Acquired resistance

Resistance is most frequently selected through a D30N mutationin the HIV protease. An L90M mutation also confersresistance.

Pharmaceutical Applications

A synthetic chemical formulated as the mesylate for oraladministration.

Pharmacokinetics

Oral absorption: c. 70–80% (with food)
C_max 750 mg thrice daily: c. 3–4 mg/L
1250 mg twice daily: c. 4 mg/L
C_min 750 mg thrice daily: c. 1–3 mg/L
1250 mg twice daily: c. 0.7–2.2 mg/L
Plasma half-life: c. 3.5 h
Volume of distribution: c. 2–7 L/kg
Plasma protein binding: >98%
Absorption and distribution
Food improves the bioavailability and the drug should be administered with a light meal. The semen:plasma ratio is 0.07. It is distributed into breast milk.
Metabolism and excretion
One major and several minor oxidative metabolites are found in plasma. Most of an oral dose is recovered in feces as unchanged drug (22%) and metabolites (78%). The remainder is recovered in urine, mainly unchanged.
An increase in the area under the time–concentration curve (AUC) has been observed in patients with hepatic impairment, but specific dose recommendations have not been made.

Clinical Use

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

Side effects

The most common adverse effect is diarrhea of mildto moderate severity. Other side effects include nausea,fatigue, vomiting and headache. It is associated with lessdyslipidemia in comparison with ritonavir-boosted proteaseinhibitors.

Metabolism

Following oral administration, nelfinavir peak levels in plasma ranged from 0.34 mg/mL (10 mg/kg in the dog) to 1.7 mg/mL (50 mg/kg in the rat). In the dog, nelfinavir was slowly absorbed, and bioavailability was 47%. The drug appeared to be metabolized in the liver, and the major excretory route was in feces.