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Saquinavir

Saquinavir
Saquinavir structure
CAS No.
127779-20-8
Chemical Name:
Saquinavir
Synonyms
FLUNIXIN;FLUNIXINE;Sch 52852;SAQUINAVIR;SAGUINAVIR;Ro 31-8959/000;Ro-31-8959/003:Invirase;Saquinavir Solution, 100ppm;Saquinavir & Saquinavir Mesylate;SAQUINAVIRMESYLATE(SUBJECTTOPATENTFREE)
CBNumber:
CB2161048
Molecular Formula:
C38H50N6O5
Formula Weight:
670.84
MOL File:
127779-20-8.mol

Saquinavir Properties

alpha 
D20 -55.9° (c = 0.5 in methanol)
CAS DataBase Reference
127779-20-8(CAS DataBase Reference)

Saquinavir Chemical Properties,Uses,Production

Description

Saquinavir mesylate, the first HIV protease inhibitor to reach the market, was launched in the U.S.A.. It is indicated for use in combination with approved nucleoside analogs for the treatment of advanced HIV infection. Saquinavir, a transition state analog of Phe-Pro, is a very potent and competitive inhibitor of HIV-1 and HIV-2 proteases with high specificity. Saquinavir inhibits the last stage in the replication process of HIV and prevents virion maturation in both acute and chronically infected cells. Combination of saquinavir with the nucleoside analogs such as zidovudine (AZT) or/and zalcitabine which inhibit the enzyme reverse transcriptase and target at an earlier stage in the HIV replication process, shows a greater than additive effect in increase in CD4 cell counts and reduction in viral load, with the combination delaying the onset of resistance to either drug alone. Saquinavir is well tolerated alone and in combination with A n .

Originator

Roche (Switzerland)

Uses

Antiviral (HIV protease inhibitor).

Definition

ChEBI: An aspartic acid derivative obtained by formal condensation of the primary amino group of (2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin- (1H)-yl]-3-hydroxy-1-phenylbutan-2-ylamine with the carboxy group of N2(-quinolin-2-ylcarbonyl)-L-asparagine. An inhibitor of HIV-1 protease.

Indications

Saquinavir is a potent inhibitor of HIV-1 and HIV-2 protease. Fortovase, a soft gel preparation of saquinavir, has largely replaced saquinavir mesylate capsules (Invirase) because it has improved bioavailability. Saquinavir is usually well tolerated and most frequently produces mild gastrointestinal side effects.

brand name

Fortovase (Roche).

Acquired resistance

Resistance is associated with an amino acid substitution at position 48 in the HIV protease (G48V). An L90M mutation also confers resistance, as it does for most protease inhibitors. Saquinavir-resistant isolates from patients on long-term therapy often show cross-resistance to other protease inhibitors.

General Description

Saquinavir (Invirase) is well tolerated following oral administration.Absorption of saquinavir is poor but is increasedwith a fatty meal. The drug does not distribute intothe CSF, and it is approximately 98% bound to plasma proteins.Saquinavir is extensively metabolized by the firstpasseffect. Bioavailability is 4% from a hard capsule and12% to 15% from a soft capsule. Saquinavir lowers p24antigen levels in HIV-infected patients, elevates CD4+counts, and exerts a synergistic antiviral effect when combinedwith RT inhibitors such as AZT and ddC.Although HIV-1 resistance to saquinavir and other HIVPIs occurs in vivo, it is believed to be less stringent andless frequent than resistance to the RT inhibitors.Nevertheless,cross-resistance between different HIV PIsappears to be common and additive,suggesting thatusing combinations of inhibitors from this class would notconstitute rational prescribing. The drug should be used incombination with at least two other antiretroviral drugs tominimize resistance. Dosage forms are Invirase (hard capsule)and Fortovase (soft capsule).

Pharmaceutical Applications

A peptidomimetic protease inhibitor formulated as the mesylate for oral use.

Pharmacokinetics

Oral absorption: c. 4%
Cmax 1200 mg thrice daily: c. 1–2.2 mg/L
Cmin 1200 mg thrice daily: c. 0.1–0.22 mg/L
Plasma half-life: c. 7–12 h
Volume of distribution: c. 700 L
Plasma protein binding: c. 98%
Absorption and distribution
It is poorly absorbed and penetrates poorly into the CNS. The semen:plasma ratio is 0.04. It is not known if it is distributed into human breast milk.
Metabolism and excretion
It is metabolized via CYP3A4, principally to mono- and dihydroxylated derivatives. Around 88% of the dose is excreted in feces and 1% in urine. Caution should be exercised in severe renal impairment and moderate hepatic impairment; use in decompensated hepatic impairment is contraindicated.

Clinical Use

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

Side effects

The most frequently reported adverse effects include abdominal discomfort, diarrhea and nausea. Ritonavir-boosted saquinavir is associated with a dyslipidemic profile characteristic of those treated with a boosted protease inhibitor requiring 200 mg of the ritonavir ‘booster’.

Saquinavir Preparation Products And Raw materials

Raw materials

Preparation Products


Saquinavir Suppliers

Global( 100)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Alpha Biopharmaceuticals Co., Ltd
0086-411-39042497
0086-411-39042693 sales@alphabiopharm.com China 920 58
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32447 55
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23978 58
BOC Sciences
1-631-619-7922
1-631-614-7828 inquiry@bocsci.com United States 20115 58
Shanghai Witofly Chemical Co.,Ltd
sales@witofly.com China 2870 52
Shanghai Boyle Chemical Co., Ltd.
86-21-57758967 sales@boylechem.com China 2926 55
Alabiochem Tech.Co., Ltd. 0086-512-58900862; 400-0707-518; 0086-512-56727736
0086-512-56765862 sales@alabiochem.com China 990 59
Chemfun Medical Technology(Shanghai) Co., Ltd. 021-67220633 & 021-37212706
+86-21-67220638 chemfun@chemfun.net China 21812 59
LGM Pharma 1-(800)-881-8210
615-250-9817 inquiries@lgmpharma.com United States 1940 70
Hangzhou Yuhao Chemical Technology Co., Ltd 0571-82693216
+86-571-82880190 info@yuhaochemical.com China 9406 52

127779-20-8(Saquinavir)Related Search:


  • Ro-31-8959/003:Invirase
  • Saquinavir Solution, 100ppm
  • (3S)-N-tert-Butyl-2-[(2R,3S)-3-[N-(2-quinolinylcarbonyl)-3-carbamoylalanylamino]-2-hydroxy-4-phenylbutyl]-1,2,3,4,4aβ,5,6,7,8,8aβ-decahydroisoquinoline-3α-carboxamide
  • (4aS,8aβ)-N-tert-Butyldecahydro-2-[(2R,3S)-2-hydroxy-4-phenyl-3-[[(2S)-3-carbamoyl-2-(2-quinolinylcarbonylamino)propanoyl]amino]butyl]isoquinoline-3α-carboxamide
  • Saquinavir & Saquinavir Mesylate
  • ButanediaMide,N1-[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-diMethylethyl)aMino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylMethyl)propyl]-2-[(2-quinolinylcarbonyl)aMino]-,(2S)-
  • n1-[(1s,2r)-3-[(3s,4as,8as)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1h)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-butanediamide
  • SAGUINAVIR
  • SAQUINAVIR
  • 2-[[2-METHYL-3-(TRIFLUOROMETHYL)PHENYL]AMINO]PYRIDINE-3-CARBOXYLIC ACID
  • (2S)-N-[(2S,3R)-4-[(3S,4AS,8AS)-3-(TERT-BUTYLCARBAMOYL)-3,4,4A,5,6,7,8,8A-OCTAHYDRO-1H-ISOQUINOLIN-2-YL]-3-HYDROXY-1-PHENYL-BUTAN-2-YL]-2-(QUINOLINE-2-CARBONYLAMINO)BUTANEDIAMIDE
  • FLUNIXIN
  • FLUNIXINE
  • SAQUINAVIRMESYLATE(SUBJECTTOPATENTFREE)
  • (S)-N-[(aS)-a-[(1R)-2-[(3S,4aS,8aS)-3-(tert-Butylcarbamoyl)octahydro-2(1H)-isoquinolyl]-1-hydroxyethyl]phenethyl]-2-quinaldamidosuccinamide
  • Butanediamide, N1-[(1S,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-, (2S)- (9CI)
  • Butanediamide, N1-[3-[3-[[(1,1-dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-, [3S-[2[1R*(R*),2S*],3a,4ab,8ab]]-
  • Ro 31-8959/000
  • Sch 52852
  • 127779-20-8
  • 12779-20-8
  • C38H50N6O5
  • Saquinavir
  • peptides
  • API
  • Active Pharmaceutical Ingredients
  • -
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