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Details

Stereochemistry ABSOLUTE
Molecular Formula C37H48N4O5.H2O
Molecular Weight 646.8161
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOPINAVIR MONOHYDRATE

SMILES

O.CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](CC2=CC=CC=C2)NC(=O)COC3=C(C)C=CC=C3C)CC4=CC=CC=C4

InChI

InChIKey=XLJJEFLRMQZJDB-YIUCRBITSA-N
InChI=1S/C37H48N4O5.H2O/c1-25(2)34(41-20-12-19-38-37(41)45)36(44)39-30(21-28-15-7-5-8-16-28)23-32(42)31(22-29-17-9-6-10-18-29)40-33(43)24-46-35-26(3)13-11-14-27(35)4;/h5-11,13-18,25,30-32,34,42H,12,19-24H2,1-4H3,(H,38,45)(H,39,44)(H,40,43);1H2/t30-,31-,32-,34-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C37H48N4O5
Molecular Weight 628.8008
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021226s030lbl.pdf

Lopinavir (ABT-378) is an antiretroviral of the protease inhibitor class. It is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir, under the trade names Kaletra.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.3 pM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KALETRA

Approved Use

KALETRA (lopinavir/ritonavir) is a co-formulation of lopinavir and ritonavir. Lopinavir is an inhibitor of the HIV protease. As co-formulated in KALETRA, ritonavir inhibits the CYP3Amediated metabolism of lopinavir, thereby providing increased plasma levels of lopinavir/ KALETRA is indicated in combination with other antiretroviral agents for the treatment of HIV-infection

Launch Date

2000
Primary
LOPIMUNE

Approved Use

LOPIMUNE (lopinavir/ritonavir) is a co-formulation of lopinavir and ritonavir. Lopinavir is an inhibitor of the HIV protease. As co-formulated in LOPIMUNE, ritonavir inhibits the CYP3Amediated metabolism of lopinavir, thereby providing increased plasma levels of lopinavir/ LOPIMUNEis indicated in combination with other antiretroviral agents for the treatment of HIV-infection
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6539 ng/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9.8 μg/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
11.8 μg/mL
800 mg 1 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
60328 ng × h/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
92.6 μg × h/mL
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
154.1 μg × h/mL
800 mg 1 times / day steady-state, oral
dose: 800 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.4 h
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1.5%
400 mg 2 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered: RITONAVIR
LOPINAVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: FED
PubMed

PubMed

TitleDatePubMed
Inflammatory oedema of the legs: a new side-effect of lopinavir.
2001 Apr 13
[Overcoming weaknesses in therapy. Protease inhibitors with high IQ].
2001 Apr 2
Antiviral drugs: current state of the art.
2001 Aug
The importance of sequencing in treatment options.
2001 May-Jun
Lopinavir-Ritonavir: a new protease inhibitor.
2001 Nov
DPC 681 and DPC 684: potent, selective inhibitors of human immunodeficiency virus protease active against clinically relevant mutant variants.
2001 Nov
What's new: newly approved drugs for children.
2001 Oct
Kaletra approved in Canada.
2001 Spring
Newest protease inhibitor Kaletra has a unique profile.
2001 Winter
Serious bradyarrhythmia that was possibly induced by lopinavir-ritonavir in 2 patients with acquired immunodeficiency syndrome.
2002 Aug 15
Efficacy of highly active antiretroviral therapy in HIV-1 infected children.
2002 Feb
Drug resistance test shows encouraging results.
2002 Feb
Unfavourable interaction of amprenavir and lopinavir in combination with ritonavir?
2002 Jan 25
Efavirenz-induced skin eruption and successful desensitization.
2002 Mar
Lopinavir/ritonavir (ABT-378/r).
2002 Mar
[Plasmatic dosage of antiretroviral drugs by high performance liquid chromathography ].
2002 Mar-Apr
[When nucleoside analogs cannot be tolerated. HIV therapy with booster].
2002 May 9
Delavirdine in rescue regimens.
2002 May-Jun
[Complete auriculoventricular block in a patient treatment with Lopinavir/Ritonavir].
2002 Oct
Analysis of the virological response with respect to baseline viral phenotype and genotype in protease inhibitor-experienced HIV-1-infected patients receiving lopinavir/ritonavir therapy.
2002 Sep
Rapid quantification of HIV protease inhibitors in human plasma by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry.
2003 Feb
Protease inhibitor shown to hold HIV at undetectable levels.
2003 Jan-Feb
Patents

Sample Use Guides

Kaletra (combination of lopinavir and ritonavir) capsules and oral solution should be adminstered orally with food. Dosage for therapy-naïve adult patients KALETRA 400/100 mg (3 capsules or 5.0 mL) twice-daily taken with food or KALETRA 800/200 mg (6 capsules or 10 mL) once-daily taken with food. For therapy-experienced patients KALETRA 400/100 mg (3 capsules or 5.0 mL) twice-daily taken with food.
Route of Administration: Oral
In Vitro Use Guide
MT4 cells and wild-type virus stocks were obtained through the AIDS Research and Reference Reagent Program, AIDS Program, National Institute of Allergy and Infectious Diseases. For drug susceptibility assays, viruses were propagated in CEM cells and titers were determined in MT4 cells. Inhibition of viral replication and compound cytotoxicity were determined in parallel in MT4 cells by a standard colorimetric assay. The EC50s of lopinavir in the absence and presence of 50% human serum were 17 ± 4 and 102 ± 44 nM, respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:39:01 GMT 2023
Edited
by admin
on Sat Dec 16 15:39:01 GMT 2023
Record UNII
JK38KEB9D9
Record Status Validated (UNII)
Record Version
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Name Type Language
LOPINAVIR MONOHYDRATE
Common Name English
1(2H)-PYRIMIDINEACETAMIDE, N-((1S,3S,4S)-4-((2-(2,6-DIMETHYLPHENOXY)ACETYL)AMINO)-3-HYDROXY-5-PHENYL-1-(PHENYLMETHYL)PENTYL)TETRAHYDRO-.ALPHA.-(1-METHYLETHYL)-2-OXO-, HYDRATE (1:1), (.ALPHA.S)-
Systematic Name English
LOPINAVIR HYDRATE
Common Name English
Code System Code Type Description
FDA UNII
JK38KEB9D9
Created by admin on Sat Dec 16 15:39:01 GMT 2023 , Edited by admin on Sat Dec 16 15:39:01 GMT 2023
PRIMARY
PUBCHEM
66766312
Created by admin on Sat Dec 16 15:39:01 GMT 2023 , Edited by admin on Sat Dec 16 15:39:01 GMT 2023
PRIMARY
CAS
1239071-09-0
Created by admin on Sat Dec 16 15:39:01 GMT 2023 , Edited by admin on Sat Dec 16 15:39:01 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE