Lopinavir

Identification

Summary

Lopinavir is an HIV-1 protease inhibitor used in combination with ritonavir to treat human immunodeficiency virus (HIV) infection.

Brand Names

Kaletra

Generic Name

Lopinavir

DrugBank Accession Number

DB01601

Background

Lopinavir is an antiretroviral protease inhibitor used in combination with other antiretrovirals in the treatment of HIV-1 infection.⁷ Lopinavir is marketed and administered exclusively in combination with ritonavir - this combination, first marketed by Abbott under the brand name Kaletra in 2000, is necessary due to lopinavir's poor oral bioavailability and extensive biotransformation. Ritonavir is a potent inhibitor of the enzymes responsible for lopinavir metabolism, and its co-administration "boosts" lopinavir exposure and improves antiviral activity.⁷ Like many other protease inhibitors (e.g. saquinavir, nelfinavir), lopinavir is a peptidomimetic molecule - it contains a hydroxyethylene scaffold that mimics the peptide linkage typically targeted by the HIV-1 protease enzyme but which itself cannot be cleaved, thus preventing the activity of the HIV-1 protease.⁵

Lopinavir was previously under investigation in combination with ritonavir for the treatment of COVID-19 caused by SARS-CoV-2.⁸

Type

Small Molecule

Groups

Approved

Structure

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Lopinavir (DB01601)

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Weight

Average: 628.8008
Monoisotopic: 628.362470666

Chemical Formula

C₃₇H₄₈N₄O₅

Synonyms

• Lopinavir

External IDs

• A-157378-0
• A-157378.0
• ABT-378

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Pharmacology

Indication

The combination product lopinavir/ritonavir, marketed under the brand name Kaletra, is indicated in combination with other antiretrovirals for the treatment of HIV-1 infection in adults and pediatric patients ≥14 days old.⁷

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to treat	Hiv-1 infection	Combination Product in combination with: Ritonavir (DB00503)	••••••••••••			••••••••• ••••••

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Pharmacodynamics

Lopinavir inhibits the activity of an enzyme critical for the HIV viral lifecycle.⁷ It has a moderate duration of action necessitating once or twice daily dosing.⁷ Lopinavir, like other protease inhibitors, has a propensity for participating in drug interactions - use caution when administering lopinavir to patients maintained on other pharmaceutical agents as pharmacodynamic and pharmacokinetic interactions are common. Fatal hepatotoxicity and pancreatitis have been noted in patients undergoing therapy with lopinavir and patients with an increased baseline risk of these events should be monitored closely throughout therapy.⁷

Mechanism of action

The HIV lifecycle is comprised of 3 distinct stages: assembly, involving creation and packaging of essential viral components; budding, wherein the viral particle crosses the host cell plasma membrane and forms a lipid envelope; and maturation, wherein the viral particle alters its structure and becomes infectious.² At the center of this lifecycle is the Gag polyprotein which, along with the products of its proteolysis, coordinate these stages and function as the major structural proteins of the virus. The HIV-1 protease enzyme, a dimeric aspartic protease, is the enzyme responsible for cleaving the Gag polyprotein and thus plays a critical role in many aspects of the HIV viral lifecycle.²

Lopinavir is an inhibitor of the HIV-1 protease enzyme.⁷ Its design is based on the "peptidomimetic" principle, wherein the molecule contains a hydroxyethylene scaffold which mimics the normal peptide linkage (cleaved by HIV protease) but which itself cannot be cleaved.⁵ By preventing HIV-1 protease activity, and thus the proteolysis of the Gag polyprotein, lopinavir results in the production of immature, non-infectious viral particles.

Target	Actions	Organism
AHuman immunodeficiency virus type 1 protease	inhibitor	Human immunodeficiency virus 1

Absorption

When administered alone, lopinavir has exceptionally low oral bioavailability (~25%) - for this reason, it is exclusively co-administered with ritonavir, which dramatically improves bioavailability, hinders drug metabolism, and allows for the attainment of therapeutic lopinavir concentrations.^3,4 Following oral administration of lopinavir/ritonavir, maximal plasma concentrations are achieved at approximately 4.4 hours (T_max), and the C_max and AUC_tau are 9.8 ± 3.7 - 11.8 ± 3.7 µg/mL and 92.6 ± 36.7 - 154.1 ± 61.4 μg•h/mL, respectively.⁷

Relative to administration in the fasted state, administration with a meal increases the AUC of the tablet formulation slightly (~19%) but dramatically increases the AUC of the oral solution formulation (~130%).⁷

Volume of distribution

The volume of distribution of lopinavir following oral administration is approximately 16.9 L.⁷

Protein binding

Lopinavir is >98% protein-bound in plasma.⁷ It binds to both alpha-1-acid glycoprotein and albumin, but exhibits a greater affinity for alpha-1-acid glycoprotein.¹⁰

Metabolism

Lopinavir undergoes extensive oxidative metabolism, almost exclusively via hepatic CYP3A isozymes.¹⁰ Co-administration with ritonavir, a potent inhibitor of CYP3A enzymes, helps to stave off lopinavir's biotransformation and increase plasma levels of active antiviral drug. Twelve metabolites have been identified in vitro, with the C-4 oxidation products M1, M3, and M4 being the predominant metabolites found in plasma.⁶ The structures of these primary metabolites have been identified, but precise structural information regarding the remaining minor metabolites has not been elucidated.

Hover over products below to view reaction partners

• Lopinavir
  • Lopinavir M2 metabolite
  • Lopinavir M3/M4 metabolite(s)
    • Lopinavir M1 metabolite

Route of elimination

Lopinavir is primarily eliminated in the feces. Following oral administration, approximately 10.4 ± 2.3% of the administered dose is excreted in the urine and 82.6 ± 2.5% is excreted in the feces.⁷ Unchanged parent drug accounted for 2.2% and 19.8% of the administered dose in urine and feces, respectively.¹⁰

Half-life

The elimination half-life of lopinavir is 6.9 ± 2.2 hours.⁷

Clearance

The estimated apparent clearance following oral administration is approximately 6-7 L/h.^3,10

Adverse Effects

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Toxicity

As lopinavir is only available in combination with ritonavir, experience with acute lopinavir overdose in isolation is limited. The risk related to overdose appears more pronounced in pediatric patients. One case report detailed a fatal cardiogenic shock in a 2.1kg infant following an approximately 10-fold overdose of Kaletra oral solution, while other reported reactions to overdose in infants include complete AV block, cardiomyopathy, lactic acidosis, and acute renal failure. The oral Kaletra solution is highly concentrated, posing a greater risk of overdose, and contains approximately 42% (v/v) ethanol, further increasing risk in children and infants.⁷

There is no antidote for lopinavir overdose. Treatment of overdose should consist largely of supportive measures and close observation of vital signs and clinical status of the affected patient. Consideration should be given to the removal of unabsorbed drug using gastric lavage or activated charcoal, if clinically indicated. Dialysis is unlikely to be of benefit as lopinavir is highly protein-bound, but may help to remove ethanol and propylene glycol from the circulation in the case of overdose with Kaletra oral solution.⁷

Pathways

Not Available

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Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Integrate drug-drug interactions in your software
1,2-Benzodiazepine	The metabolism of 1,2-Benzodiazepine can be decreased when combined with Lopinavir.
Abacavir	The serum concentration of Abacavir can be decreased when it is combined with Lopinavir.
Abametapir	The serum concentration of Lopinavir can be increased when it is combined with Abametapir.
Abatacept	The serum concentration of Abatacept can be increased when it is combined with Lopinavir.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Lopinavir.

Food Interactions

• Avoid St. John's Wort. Induction of CYP3A by co-administration with St. John's Wort may result in reduced drug plasma concentrations and therapeutic failure.
• Take with food. The oral solution formulation must be taken with food, but the tablet formulation may be taken with or without food.

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International/Other Brands

Aluviran / Koletra

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
ALUVIA (100 MG/25 MG)	Lopinavir (100 MG) + Ritonavir (25 MG)	Tablet, film coated	Oral	บริษัท ซิลลิค ฟาร์มา จำกัด	2018-05-11	Not applicable
DUOVIHR®TABLETA RECUBIERTA	Lopinavir (200 mg) + Ritonavir (50 mg)	Tablet, coated	Oral	NUTRI MACK S.A.S.	2018-06-22	Not applicable
KALETRA	Lopinavir (200 MG) + Ritonavir (50 MG)	Tablet, film coated	Oral	Abbvie Deutschland Gmbh & Co. Kg	2014-07-08	Not applicable
Kaletra	Lopinavir (200 mg/1) + Ritonavir (50 mg/1)	Tablet, film coated	Oral	AbbVie Inc.	2010-06-18	Not applicable
Kaletra	Lopinavir (200 mg/1) + Ritonavir (50 mg/1)	Tablet, film coated	Oral	AbbVie Inc.	2020-04-08	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Kaletra	Lopinavir (200 mg/1) + Ritonavir (50 mg/1)	Tablet	Oral	Remedy Repack	2010-09-27	2013-05-16

Categories

ATC Codes

J05AR10 — Lopinavir and ritonavir

• J05AR — Antivirals for treatment of HIV infections, combinations
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

Drug Categories

• Anti-HIV Agents
• Anti-Infective Agents
• Anti-Retroviral Agents
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Antivirals used in combination for the treatment of HIV infections
• BSEP/ABCB11 Inhibitors
• Cytochrome P-450 CYP1A2 Inhibitors
• Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
• Cytochrome P-450 CYP1A2 Substrates
• Cytochrome P-450 CYP2B6 Inhibitors
• Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2B6 Inhibitors (weak)
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 Inhibitors (weak)
• Cytochrome P-450 CYP2C9 Inducers
• Cytochrome P-450 CYP2C9 Inducers (strength unknown)
• Cytochrome P-450 CYP2C9 Inhibitors
• Cytochrome P-450 CYP2C9 Inhibitors (weak)
• Cytochrome P-450 CYP2D6 Substrates
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strong)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Direct Acting Antivirals
• Enzyme Inhibitors
• Experimental Unapproved Treatments for COVID-19
• HIV Protease Inhibitors
• Hyperglycemia-Associated Agents
• Nephrotoxic agents
• OATP1B1/SLCO1B1 Inhibitors
• OATP1B3 inhibitors
• Organic Anion Transporting Polypeptide 1B1 Inhibitors
• P-glycoprotein inducers
• P-glycoprotein inhibitors
• Potential QTc-Prolonging Agents
• Protease Inhibitors
• Pyrimidinones
• QTc Prolonging Agents
• Viral Protease Inhibitors

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Valine and derivatives

Alternative Parents

Amphetamines and derivatives / m-Xylenes / Phenol ethers / Phenoxy compounds / Alkyl aryl ethers / Pyrimidones / Diazinanes / N-acyl amines / Secondary carboxylic acid amides / Ureas / Secondary alcohols / Azacyclic compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Organopnictogen compounds

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Substituents

1,3-diazinane / Alcohol / Alkyl aryl ether / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxamide group / Ether / Fatty acyl / Fatty amide / Hydrocarbon derivative / M-xylene / Monocyclic benzene moiety / N-acyl-amine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenol ether / Phenoxy compound / Pyrimidine / Pyrimidone / Secondary alcohol / Secondary carboxylic acid amide / Urea / Valine or derivatives / Xylene

show 23 more

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid diamide, amphetamines (CHEBI:31781)

Affected organisms

• Human Immunodeficiency Virus
• SARS-CoV-2

Chemical Identifiers

UNII

2494G1JF75

CAS number

192725-17-0

InChI Key

KJHKTHWMRKYKJE-SUGCFTRWSA-N

InChI

InChI=1S/C37H48N4O5/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)/t30-,31-,32-,34-/m0/s1

IUPAC Name

(2S)-N-[(2S,4S,5S)-5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl]-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide

SMILES

CC(C)[C@H](N1CCCNC1=O)C(=O)N[C@H](C[C@H](O)[C@H](CC1=CC=CC=C1)NC(=O)COC1=C(C)C=CC=C1C)CC1=CC=CC=C1

References

Synthesis Reference

US5914332

General References

1. Li F, Lu J, Ma X: CYP3A4-mediated lopinavir bioactivation and its inhibition by ritonavir. Drug Metab Dispos. 2012 Jan;40(1):18-24. doi: 10.1124/dmd.111.041400. Epub 2011 Sep 27. [Article]
2. Sundquist WI, Krausslich HG: HIV-1 assembly, budding, and maturation. Cold Spring Harb Perspect Med. 2012 Jul;2(7):a006924. doi: 10.1101/cshperspect.a006924. [Article]
3. Niu WJ, Sun T, Liu L, Liu XQ, Zhang RF, Yin L, Wang JR, Jia XF, Lu HZ, Zhong MK, Jiao Z, Zhang LJ: Population pharmacokinetics and dosing regimen optimisation of lopinavir in Chinese adults infected with HIV. Basic Clin Pharmacol Toxicol. 2019 Apr;124(4):456-465. doi: 10.1111/bcpt.13154. Epub 2018 Nov 23. [Article]
4. Sham HL, Kempf DJ, Molla A, Marsh KC, Kumar GN, Chen CM, Kati W, Stewart K, Lal R, Hsu A, Betebenner D, Korneyeva M, Vasavanonda S, McDonald E, Saldivar A, Wideburg N, Chen X, Niu P, Park C, Jayanti V, Grabowski B, Granneman GR, Sun E, Japour AJ, Leonard JM, Plattner JJ, Norbeck DW: ABT-378, a highly potent inhibitor of the human immunodeficiency virus protease. Antimicrob Agents Chemother. 1998 Dec;42(12):3218-24. [Article]
5. De Clercq E: Anti-HIV drugs: 25 compounds approved within 25 years after the discovery of HIV. Int J Antimicrob Agents. 2009 Apr;33(4):307-20. doi: 10.1016/j.ijantimicag.2008.10.010. Epub 2008 Dec 23. [Article]
6. Kumar GN, Jayanti V, Lee RD, Whittern DN, Uchic J, Thomas S, Johnson P, Grabowski B, Sham H, Betebenner D, Kempf DJ, Denissen JF: In vitro metabolism of the HIV-1 protease inhibitor ABT-378: species comparison and metabolite identification. Drug Metab Dispos. 1999 Jan;27(1):86-91. [Article]
7. FDA Approved Drug Products: Kaletra (lopinavir/ritonavir) for oral use [Link]
8. Nature Biotechnology: Coronavirus puts drug repurposing on the fast track [Link]
9. CaymanChem: Lopinavir MSDS [Link]
10. Health Canada Product Monograph: Kaletra (lopinavir/ritonavir) for oral use [Link]

External Links

Human Metabolome Database

HMDB0015539

KEGG Drug

D01425

KEGG Compound

C12871

PubChem Compound

92727

PubChem Substance

46508588

ChemSpider

83706

BindingDB

50180655

RxNav

195088

ChEBI

31781

ChEMBL

CHEMBL729

ZINC

ZINC000003951740

Therapeutic Targets Database

DAP000708

PharmGKB

PA450264

PDBe Ligand

AB1

RxList

RxList Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Lopinavir

PDB Entries

1mui / 1rv7 / 2o4s / 2q5k / 2qhc / 2rkf / 2rkg / 2z54 / 3ogq / 4l1a …

show 4 more

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Human Immunodeficiency Virus (HIV) Infections / Proteinuria	1
4	Completed	Not Available	Human Immunodeficiency Virus (HIV) Infections / Tuberculosis (TB)	1
4	Completed	Basic Science	Cardiovascular Disease (CVD) / Dyslipidemia / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Metabolic Diseases / Metabolism Disorder, Glucose	1
4	Completed	Basic Science	Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Diagnostic	AIDS-Related Opportunistic Infections / Human Immunodeficiency Virus (HIV) Infections	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Capsule, liquid filled	Oral
Tablet	Oral
Tablet, film coated	Oral
Syrup	Oral	80 mg
Tablet, film coated	Oral	100 mg
Capsule	Oral
Capsule, coated	Oral
Granule	Oral
Solution	Oral
Tablet, coated	Oral

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US6703403	Yes	2004-03-09	2016-12-26
US6037157	Yes	2000-03-14	2016-12-26
US6232333	Yes	2001-05-15	2018-05-07
US7432294	Yes	2008-10-07	2020-11-22
US7141593	Yes	2006-11-28	2020-11-22
US5914332	Yes	1999-06-22	2016-06-13
US6284767	Yes	2001-09-04	2016-08-15
US7364752	Yes	2008-04-29	2021-05-10
US8309613	Yes	2012-11-13	2025-06-24
US8377952	Yes	2013-02-19	2028-04-22
US8691878	Yes	2014-04-08	2025-02-25
US8025899	Yes	2011-09-27	2028-06-14
US7148359	Yes	2006-12-12	2020-01-19
US8470347	Yes	2013-06-25	2027-03-17
US8268349	Yes	2012-09-18	2025-02-25
US8399015	Yes	2013-03-19	2025-02-25
US6458818	Yes	2002-10-01	2018-05-07
US6521651	Yes	2003-02-18	2018-05-07
US6911214	Yes	2005-06-28	2022-05-28
US8501219	No	2013-08-06	2021-11-28

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	Practically insoluble	Health Canada Monograph

Predicted Properties

Property	Value	Source
Water Solubility	0.00192 mg/mL	ALOGPS
logP	3.91	ALOGPS
logP	4.69	Chemaxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.39	Chemaxon
pKa (Strongest Basic)	-1.5	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	120 Å2	Chemaxon
Rotatable Bond Count	15	Chemaxon
Refractivity	179.36 m3·mol-1	Chemaxon
Polarizability	68.78 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.6593
Blood Brain Barrier	-	0.9916
Caco-2 permeable	+	0.8856
P-glycoprotein substrate	Substrate	0.8755
P-glycoprotein inhibitor I	Inhibitor	0.7355
P-glycoprotein inhibitor II	Inhibitor	0.5277
Renal organic cation transporter	Non-inhibitor	0.8578
CYP450 2C9 substrate	Non-substrate	0.7508
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.6732
CYP450 1A2 substrate	Non-inhibitor	0.8935
CYP450 2C9 inhibitor	Non-inhibitor	0.7326
CYP450 2D6 inhibitor	Non-inhibitor	0.9438
CYP450 2C19 inhibitor	Non-inhibitor	0.7983
CYP450 3A4 inhibitor	Non-inhibitor	0.6469
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9054
Ames test	Non AMES toxic	0.8049
Carcinogenicity	Non-carcinogens	0.7865
Biodegradation	Not ready biodegradable	0.9182
Rat acute toxicity	2.2503 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8605
hERG inhibition (predictor II)	Inhibitor	0.8475

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0feu-6925370000-713b224b442e85bb346b
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0fb9-0119005000-e99616dc321beea979ae
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0532-1900601000-f85a252f1640f27563a8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-05r0-0301933000-8f3a16a167c4e1dcc5ca
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052b-1629621000-29d1bf161f3bf8c6c738
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4j-0903625000-1a01027b2257db51cf8b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00bd-7507921000-fa6b0599d2de85168ed4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0560-2911612000-95ec2b10408ce7c1f4f5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-05fr-3901200000-9338826d2f0fd11d6df7

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	265.7032133	predicted	DarkChem Lite v0.1.0
[M-H]-	266.6366133	predicted	DarkChem Lite v0.1.0
[M-H]-	246.51648	predicted	DeepCCS 1.0 (2019)
[M+H]+	265.0788133	predicted	DarkChem Lite v0.1.0
[M+H]+	265.1285133	predicted	DarkChem Lite v0.1.0
[M+H]+	248.34137	predicted	DeepCCS 1.0 (2019)
[M+Na]+	265.4873133	predicted	DarkChem Lite v0.1.0
[M+Na]+	253.94719	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. Human immunodeficiency virus type 1 protease

Kind

Protein

Organism

Human immunodeficiency virus 1

Pharmacological action

Yes

Actions

Inhibitor

General Function

Aspartic-type endopeptidase activity

Specific Function

Not Available

Gene Name

pol

Uniprot ID

Q72874

Uniprot Name

Pol polyprotein

Molecular Weight

10778.7 Da

References

1. Garriga C, Perez-Elias MJ, Delgado R, Ruiz L, Najera R, Pumarola T, Alonso-Socas Mdel M, Garcia-Bujalance S, Menendez-Arias L: Mutational patterns and correlated amino acid substitutions in the HIV-1 protease after virological failure to nelfinavir- and lopinavir/ritonavir-based treatments. J Med Virol. 2007 Nov;79(11):1617-28. [Article]
2. Reddy GS, Ali A, Nalam MN, Anjum SG, Cao H, Nathans RS, Schiffer CA, Rana TM: Design and synthesis of HIV-1 protease inhibitors incorporating oxazolidinones as P2/P2' ligands in pseudosymmetric dipeptide isosteres. J Med Chem. 2007 Sep 6;50(18):4316-28. Epub 2007 Aug 16. [Article]
3. Wittayanarakul K, Hannongbua S, Feig M: Accurate prediction of protonation state as a prerequisite for reliable MM-PB(GB)SA binding free energy calculations of HIV-1 protease inhibitors. J Comput Chem. 2008 Apr 15;29(5):673-85. [Article]
4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
5. Authors unspecified: Lopinavir/ritonavir: a protease inhibitor combination. Med Lett Drugs Ther. 2001 Jan 8;43(1095):1-2. [Article]

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Drug created at August 29, 2007 18:45 / Updated at April 01, 2022 19:23