NELFINAVIR Chemical Properties

Melting point:

185-186 °C

Boiling point:

786.8±60.0 °C(Predicted)

alpha 

D -119.23° (c = 0.26 in methanol)

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

form 

Powder

pka

pKa1 6.0; pKa2 11.06(at 25℃)

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 commonly used protease inhibitor because of its low incidence of serious adverse effects. Its most common side effects are diarrhea and flatulence; these may resolve with continued use. In addition to the drugs contraindicated for use with all protease inhibitors, amiodarone, rifampin, and quinidine are contraindicated in patients taking nelfinavir.

brand name

Viracept (Agouron).

Antimicrobial activity

Nelfinavir inhibits HIV-1 and HIV-2 proteases. Bioavailability is affected to only a limited degree by combination with lowdose ritonavir.

Acquired resistance

Resistance is most frequently selected through a D30N mutation in the HIV protease. An L90M mutation also confers resistance.

Pharmaceutical Applications

A synthetic chemical formulated as the mesylate for oral administration.

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 mild to moderate severity. Other side effects include nausea, fatigue, vomiting and headache. It is associated with less dyslipidemia in comparison with ritonavir-boosted protease inhibitors.

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.

NELFINAVIR(159989-64-7)Related Product Information

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• Nelfinavir Related Compound A (15 mg) ((3S,4aS,8aS)-N-tert-Butyl-2-[(2R,3R)-2-hydroxy-3-(3-hydroxy-2-methylbenzamido)-4-(phenylsulfinyl)butyl]decahydroisoquinoline-3-carboxamide)
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