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Lopinavir

Product Name
Lopinavir
CAS No.
192725-17-0
Chemical Name
Lopinavir
Synonyms
CS-546;134368;Koletr;Koletra;ABT 378;Aluvia);Aluviran;LOPINAVIR;A 157378.0;Lopinavir CRS
CBNumber
CB3663640
Molecular Formula
C37H48N4O5
Formula Weight
628.81
MOL File
192725-17-0.mol
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Lopinavir Property

Melting point:
255.2-260.6 °F (124—127°C)
Boiling point:
924.1±65.0 °C(Predicted)
Density 
1.163±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble20mg/mL, clear
form 
powder
pka
13.89±0.46(Predicted)
color 
white to beige
optical activity
[α]/D -20 to -27°, c = 0.4 in methanol
Stability:
Hygroscopic
CAS DataBase Reference
192725-17-0(CAS DataBase Reference)
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Safety

RIDADR 
3077
HS Code 
29335990
Hazardous Substances Data
192725-17-0(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML1222
Product name
Lopinavir
Purity
≥98% (HPLC)
Packaging
10mg
Price
$24.5
Updated
2021/12/16
Sigma-Aldrich
Product number
Y0001505
Product name
Lopinavir for system suitability
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/12/16
Sigma-Aldrich
Product number
Y0001506
Product name
Lopinavir for peak identification
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/12/16
Sigma-Aldrich
Product number
Y0001498
Product name
Lopinavir
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/12/16
Sigma-Aldrich
Product number
1370101
Product name
Lopinavir
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
350mg
Price
$1300
Updated
2021/12/16
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Lopinavir Chemical Properties,Usage,Production

Description

Lopinavir, the sixth HIV protease inhibitor in the “navir” class, was launched in coformulation with ritonavir, another HIV protease inhibitor already marketed (Abbott, 1996); this original formulation was introduced as Kaletra for use in combination with either nucleoside or non-nucleoside reverse transcriptase inhibitors for the treatment of AIDS in adults and children. Lopinavir is a peptidomimetic compound with a structural core identical to that of ritonavir, on which terminal groups, particularly a modified valine, were introduced by peptide coupling procedures. Lopinavir is a potent competitive inhibitor of HIV-I protease exhibiting high potential against ritonavir-resistant mutations. In several animal species, pharmacokinetic studies with the lopinavirlritonavir association showed that the modest properties of lopinavir were significantly improved in presence of ritonavir, in terms of Cmax and duration of action. Ritonavir inhibits the P450 isoenzyme CYP3A4 and the human liver microsomal metabolism of lopinavir, so strongly amplifying plasma levels of this latter component. In AIDS patients, the plasma HIV RNA level was considerably reduced and the CD4+ T-cell counts increased after administration of lopinavir combined with relatively small doses of ritonavir. Kaletra is intended to be used jointly with other antiretroviral agents.

Chemical Properties

White Crystalline Solid

Originator

Abbott (US)

Uses

Lopinavir has been used as a ZMPSTE24 and human immunodeficiency virus protease inhibitor.

Uses

A selective HIV protease inhibitor. An analogue of Ritonavir. Antiviral.

Uses

Lopinavir is a potent HIV protease inhibitor with Ki of 1.3 pM

Definition

ChEBI: A dicarboxylic acid amide in which a parent structure of amphetamine is substituted on nitrogen by a (2,6-dimethylphenoxy)acetyl group and on the carbon alpha to nitrogen by a (1S,3S)-1-hydroxy-3-{[(2S)-3- ethyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)butanoyl]amino}-4-phenylbutyl group. An antiretroviral of the protease inhibitor class. It is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir.

Indications

Lopinavir is available in the United States only as a fixed-dose combination with ritonavir (Kaletra). In this regimen, a low dose of ritonavir is used to inhibit the rapid inactivation of lopinavir by CYP3A4.

Manufacturing Process

Manufacturing process for Lopinavir includes these steps as follows: Synthesis of 2,6-dimethylphenoxyacetic acid; 2,6- dimethylphenoxyacetyl chloride as an oil; synthesis of (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-(tbutyloxycarbonylamino)-1,6-diphenylhexane; (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5- amino-1,6-diphenylhexane as a white needles; synthesis of N-carbonylbenzyloxy-3- aminopropanol;synthesis of N-carbonylbenzyloxy-3-aminopropanal solution; N-(N- (benzyloxycarbonyl-3-amino)-propyl)valine methyl ester, oil state; synthesis of 2S-(1-tetrahydro-pyrimid-2-onyl)-3- methyl butanoic acid methyl ester;synthesis of 2S-(1- tetrahydro-pyrimid-2-onyl)-3-methyl butanoic acid methyl ester. The mixture of (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5- amino-1,6-diphenylhexane (100 g, 0.22 mol), 2S-(1-tetrahydro-pyrimid-2- onyl)-3-methyl butanoic acid methyl ester (44.8 g, 0.22 mol) and 750 ml DMF was cooled in an ice/water bath. N-Hydroxybenzotriazole (90.9 g, 0.67 mol), 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide (86 g, 0.45 mol) and triethylamine (62.5 ml, 0.45 mol) were added and the ice bath was removed, allowing the reaction mixture to stir with warming to room temperature for 5 hours. The mixture was diluted with 1000 ml of IPAC and quenched with 1000 ml of water. The mixture was shaken and separated, the aq. layer was extracted IPAC, the organics were washed with 10% HCl, solution of NaHCO3 with 100 ml hexanes, then washed 500 ml water, and brine, dried over MgSO4, filtered and concentrated to provide. (2S,3S,5S)-2-(2,6- dimethylphenoxyacetyl)amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)- 3-methylbutanoyl)amino-1,6-diphenylhexane as a white foam.

brand name

Kaletra

Therapeutic Function

Antiviral

Antimicrobial activity

Lopinavir is active against HIV-1 and HIV-2.

Acquired resistance

Significant resistance to the antiretroviral efficacy of ritonavirbooted lopinavir occurs as a result of amino acid substitutions at positions 32, 47 and 82 in the protease region. Protease inhibitor resistance is uncommon in patients identified with early failure of combination therapy with ritonavir boostedlopinavir and nucleotide reverse transcriptase inhibitors.

General Description

Lopinavir is a protease inhibitor that has been approved foruse in combination with ritonavir for patients with HIV whohave not responded to other treatment modalities. Lopinaviris used in excess over ritonavir. Ritonavir at amounts givenhas no antiretroviral activity, Ritonavir inhibits lopinavir’smetabolism by CYP3A4, causing a higher level of lopinavirin the system. The combination is the first protease inhibitorapproved for patients as young as 6 months of age.

Pharmaceutical Applications

A synthetic compound, co-formulated with ritonavir for oral administration. In this formulation, ritonavir functions to inhibit the metabolic clearance of lopinavir, and does not contribute to the antiretroviral activity.

Biochem/physiol Actions

Lopinavir is an antiviral HIV Protease Inhibitor. Lopinavir has insufficient bioavailability alone, so it is used in therapy in combination with Ritonavir, a HIV protease inhibitor, which inhibits cytochrome P450-3A4 (CYP3A4), a liver enzyme that normally metabolizes protease inhibitors. Lopinavir also has an ability to inhibit ZMPSTE24 (zinc metallopeptidase STE24).

Pharmacokinetics

Oral absorption: Not known/available
Cmax 400 mg + ritonavir 100 mg twice daily: c. 9.6 mg/L
Cmin 400 mg + ritonavir 100 mg twice daily: c. 5.5 mg/L
Plasma half-life: c. 5–6 h
Volume of distribution: Not known/available
Plasma protein binding: c. 98–99%
Absorption and distribution
The absorption of lopinavir–ritonavir in capsule or liquid form is favorably affected by the presence of food, particularly if high in fat. The CNS penetration is good. It has a semen:plasma ratio of 0.07. It is distributed into breast milk.
Metabolism
Lopinavir is extensively metabolized by the CYP3A4 system, but this is inhibited by ritonavir.
Excretion
Over an 8-day period after single dosing with the combined formulation, around 10% and 83% of the administered dose is recovered in urine and feces, respectively. Less than 3% of the dose is recovered as unchanged drug in urine and 20% in feces. In mild to moderate hepatic impairment, an increase in exposure of approximately 30% is observed, but is probably not clinically relevant. It should be avoided in severe hepatic impairment.

Clinical Use

Treatment of HIV infection (in combination with ritonavir and other antiretroviral agents)

Side effects

The most common adverse events seen in trials of complex antiretroviral regimens were diarrhea, nausea, headache, fatigue, vomiting and rash. Ritonavir-boosted lopinavir is associated with a dyslipidemia profile characteristic of those treated with other protease inhibitors boosted with 200 mg of ritonavir.

Side effects

Side effects, which are generally mild, include diarrhea, nausea, asthenia, and headache. Pancreatitis occurs rarely. Ritonavir is a potent inhibitor of CYP3A4 and also inhibits CYP2D6. In addition to the drugs contraindicated for all protease inhibitors, flecainide, propafenone, pimozide, and rifampin should not be given with lopinavir–ritonavir combination therapy.

Lopinavir Preparation Products And Raw materials

Raw materials

Preparation Products

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Lopinavir Suppliers

Wisdom Drugs Co., Ltd.
Tel
Email
527536256@qq.com
Country
China
ProdList
95
Advantage
58
Taizhou Crene Biotechnology Co. Ltd.
Tel
0576-88813233-
Email
sales@pharm-intermediates.com
Country
China
ProdList
1963
Advantage
58
Shenzhen Shengda Pharmaceutical co Limited
Tel
0755-85269922-
Fax
QQ:1799060443
Email
sales@shengdapharm.com
Country
China
ProdList
376
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2926
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15877
Advantage
69
Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5947
Advantage
61
ShangHai DEMO Chemical Co.,Ltd
Tel
400-021-7337 qq:2355568890
Fax
0086-21-50182339
Email
sales@demochem.com; export1@demochem.com
Country
China
ProdList
2582
Advantage
57
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028-
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12270
Advantage
60
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
9917
Advantage
62
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View Lastest Price from Lopinavir manufacturers

Handan Tongyi New Material Technology Co., Ltd
Product
Lopinavir 192725-17-0
Price
US $1.00/KG
Min. Order
1KG
Purity
99.9%
Supply Ability
800kgs/month
Release date
2021-03-01
Baoji Guokang Bio-Technology Co., Ltd.
Product
Lopinavir 192725-17-0
Price
US $1556.00/Kg/Bag
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2021-06-03
Hebei Yirun Sega Biological Technology Co. Ltd
Product
Lopinavir 192725-17-0
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
200000pcs
Release date
2021-03-17

192725-17-0, LopinavirRelated Search:


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