Lopinavir | CAS#192725-17-0 | HIV Protease Inhibitor

MedKoo Cat#: 318161 | Name: Lopinavir

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lopinavir is an HIV protease inhibitor used in a fixed-dose combination with Ritonavir. It is used against HIV infections as a fixed-dose combination with another protease inhibitor, ritonavir, under the trade names Kaletra and Aluvia. It was first approved by the FDA on 15 September 2000.

Chemical Structure

Lopinavir

CAS#192725-17-0

Theoretical Analysis

MedKoo Cat#: 318161

Name: Lopinavir

CAS#: 192725-17-0

Chemical Formula: C37H48N4O5

Exact Mass: 628.3625

Molecular Weight: 628.80

Elemental Analysis: C, 70.67; H, 7.69; N, 8.91; O, 12.72

Price and Availability

Size	Price	Availability
200mg	USD 90.00	Ready to ship
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 450.00	Ready to ship
5g	USD 950.00	Ready to ship
10g	USD 1,650.00	Ready to shipr
20g	USD 2,950.00	Ready to ship

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Related CAS #

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Synonym

Lopinavir; ABT-378; Aluviran; Koletra; ABT 378; A 157378.0; A-157378.0; A157378.0; ABT 378; ABT-378; ABT378;

IUPAC/Chemical Name

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

InChi Key

KJHKTHWMRKYKJE-SUGCFTRWSA-N

InChi Code

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

SMILES Code

CC1=C(C(=CC=C1)C)OCC(=O)N[C@@H](CC2=CC=CC=C2)[C@H](C[C@H](CC3=CC=CC=C3)NC(=O)[C@H](C(C)C)N4CCCNC4=O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T20D08P19

QC Data

View QC data: current batch, Lot#T20D08P19

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Lopinavir (ABT-378) is a highly potent, selective peptidomimetic inhibitor of the HIV-1 protease, with Kis of 1.3 to 3.6 pM for wildtype and mutant HIV protease as well as a SARS-CoV 3CLpro inhibitor with an IC50 of 14.2 μM.

In vitro activity:

Finally, replacement of the P2’ (thiazolyl)methoxycarbonyl moiety with the known P2’ dimethylphenoxyacetyl group produced ABT378, which inhibited 93% of wild-type HIV protease activity at 0.5 nM and bound with a Ki of 1.3 pM. A high (>105-fold) specificity for HIV protease over those of the mammalian aspartic proteinases renin, cathepsin D, and cathepsin E was observed (data not shown). In MT4 cells, the EC50s of ABT-378 in the absence and presence of 50% HS were 17 ± 4 and 102 ± 44 nM, respectively (mean ± standard deviation of 10 triplicate determinations). In a direct comparison, the EC50s of ritonavir were 58 ± 14 and 1,044 ± 306 nM, respectively. Thus, in the presence of 50% HS, the anti-HIV activity of ABT-378 was 10-fold greater than that of ritonavir. ABT-378 was also highly potent against primary HIV cultured in peripheral blood mononuclear cells (in the absence of HS), with an EC50 of 6.5 nM (mean for six isolates; range, 4 to 11 nM). Reference: Antimicrob Agents Chemother. 1998 Dec; 42(12): 3218–3224. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC106025/

In vivo activity:

Based on all the in vitro beneficial effects caused by lopinavir on C. albicans cells, it was decided to evaluate its efficacy on in vivo infection by using a well-established murine model. Firstly, immunocompetent BALB/c mice were intravenously infected with C. albicans yeasts, and 1 h after the inoculation, the animals were treated with PBS (positive control of infection), fluconazole (a classical antifungal used to treat candidiasis, including in this animal model) and lopinavir (the test drug). No animals died after 5 days postinfection; therefore, the infection was evaluated by counting the number of CFUs in three target organs: kidneys, spleen and liver. Lopinavir significantly diminished the infection in the kidney in a dose-dependent fashion. The infection in the liver was controlled by both fluconazole and lopinavir at both employed concentrations (10 or 15 mg/mL). Spleen infection was significantly reduced only when using fluconazole or lopinavir at the highest concentration (Figure 10). Conclusively, the exposed results highlight that lopinavir may be used as a promising repurposing drug against C. albicans infection as well as may be used as a lead compound for the development of novel antifungal drugs. Reference: J Fungi (Basel). 2021 Jun; 7(6): 424. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8229492/

	Solvent	mg/mL	mM
Solubility
	DMSO	130.0	206.74
	Ethanol	73.0	116.09

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 628.80 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. 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. doi: 10.1128/AAC.42.12.3218. PMID: 9835517; PMCID: PMC106025. 2. Carrillo A, Stewart KD, Sham HL, Norbeck DW, Kohlbrenner WE, Leonard JM, Kempf DJ, Molla A. In vitro selection and characterization of human immunodeficiency virus type 1 variants with increased resistance to ABT-378, a novel protease inhibitor. J Virol. 1998 Sep;72(9):7532-41. doi: 10.1128/JVI.72.9.7532-7541.1998. PMID: 9696850; PMCID: PMC109995. 3. Santos ALS, Braga-Silva LA, Gonçalves DS, Ramos LS, Oliveira SSC, Souza LOP, Oliveira VS, Lins RD, Pinto MR, Muñoz JE, Taborda CP, Branquinha MH. Repositioning Lopinavir, an HIV Protease Inhibitor, as a Promising Antifungal Drug: Lessons Learned from Candida albicans-In Silico, In Vitro and In Vivo Approaches. J Fungi (Basel). 2021 May 28;7(6):424. doi: 10.3390/jof7060424. PMID: 34071195; PMCID: PMC8229492. 4. Ansari H, Singh P. Formulation and in-vivo Evaluation of Novel Topical Gel of Lopinavir for Targeting HIV. Curr HIV Res. 2018;16(4):270-279. doi: 10.2174/1570162X16666180924101650. PMID: 30246641; PMCID: PMC6416462.

In vitro protocol:

In vivo protocol:

1. Santos ALS, Braga-Silva LA, Gonçalves DS, Ramos LS, Oliveira SSC, Souza LOP, Oliveira VS, Lins RD, Pinto MR, Muñoz JE, Taborda CP, Branquinha MH. Repositioning Lopinavir, an HIV Protease Inhibitor, as a Promising Antifungal Drug: Lessons Learned from Candida albicans-In Silico, In Vitro and In Vivo Approaches. J Fungi (Basel). 2021 May 28;7(6):424. doi: 10.3390/jof7060424. PMID: 34071195; PMCID: PMC8229492. 2. Ansari H, Singh P. Formulation and in-vivo Evaluation of Novel Topical Gel of Lopinavir for Targeting HIV. Curr HIV Res. 2018;16(4):270-279. doi: 10.2174/1570162X16666180924101650. PMID: 30246641; PMCID: PMC6416462.

1: Aline F, Aurélie R, Matthias C, Olivier B, Thierry B, Paule SM, Chantal C. Comparison of population pharmacokinetics based on steady-state assumption versus electronically monitored adherence to lopinavir, atazanavir, efavirenz, and etravirine: A retrospective study. Ther Drug Monit. 2016 Mar 1. [Epub ahead of print] PubMed PMID: 26937748. 2: Pandie M, Wiesner L, McIlleron H, Hughes J, Siwendu S, Conradie F, Variava E, Maartens G. Drug-drug interactions between bedaquiline and the antiretrovirals lopinavir/ritonavir and nevirapine in HIV-infected patients with drug-resistant TB. J Antimicrob Chemother. 2016 Apr;71(4):1037-40. doi: 10.1093/jac/dkv447. Epub 2016 Jan 7. PubMed PMID: 26747099. 3: Raposo LM, Arruda MB, de Brindeiro RM, Nobre FF. Lopinavir Resistance Classification with Imbalanced Data Using Probabilistic Neural Networks. J Med Syst. 2016 Mar;40(3):69. doi: 10.1007/s10916-015-0428-7. Epub 2016 Jan 6. PubMed PMID: 26733278. 4: Srinivas NR. Prediction of area under the concentration-time curve for lopinavir from peak or trough lopinavir concentrations in patients receiving lopinavir-ritonavir therapy. Am J Health Syst Pharm. 2016 Mar 15;73(6):376-85. doi: 10.2146/ajhp150417. PubMed PMID: 26953282. 5: Patel G, Shelat P, Lalwani A. Statistical modeling, optimization and characterization of solid self-nanoemulsifying drug delivery system of lopinavir using design of experiment. Drug Deliv. 2016 Feb 16:1-16. [Epub ahead of print] PubMed PMID: 26882014. 6: Santos JR, Llibre JM, Bravo I, García-Rosado D, Cañadas MP, Pérez-Álvarez N, Paredes R, Clotet B, Moltó J. Efficacy and Safety of Treatment Simplification to Lopinavir/Ritonavir or Darunavir/Ritonavir Monotherapy: A Randomized Clinical Trial. AIDS Res Hum Retroviruses. 2016 Feb 11. [Epub ahead of print] PubMed PMID: 26781004. 7: Garg B, Katare OP, Beg S, Lohan S, Singh B. Systematic development of solid self-nanoemulsifying oily formulations (S-SNEOFs) for enhancing the oral bioavailability and intestinal lymphatic uptake of lopinavir. Colloids Surf B Biointerfaces. 2016 Feb 8;141:611-622. doi: 10.1016/j.colsurfb.2016.02.012. [Epub ahead of print] PubMed PMID: 26916320. 8: Abiodun OO, Gbimadee N, Gbotosho GO. Lopinavir/ritonavir enhanced the antimalarial activity of amodiaquine and artesunate in a mouse model of Plasmodium berghei. J Chemother. 2016 Feb 22:1-5. [Epub ahead of print] PubMed PMID: 26900802. 9: Pham K, Li D, Guo S, Penzak S, Dong X. Development and in vivo evaluation of child-friendly lopinavir/ritonavir pediatric granules utilizing novel in situ self-assembly nanoparticles. J Control Release. 2016 Feb 2;226:88-97. doi: 10.1016/j.jconrel.2016.02.001. [Epub ahead of print] PubMed PMID: 26849919. 10: Tookey PA, Thorne C, van Wyk J, Norton M. Maternal and foetal outcomes among 4118 women with HIV infection treated with lopinavir/ritonavir during pregnancy: analysis of population-based surveillance data from the national study of HIV in pregnancy and childhood in the United Kingdom and Ireland. BMC Infect Dis. 2016 Feb 4;16(1):65. doi: 10.1186/s12879-016-1400-y. PubMed PMID: 26847625; PubMed Central PMCID: PMC4743413. 11: Nagot N, Kankasa C, Tumwine JK, Meda N, Hofmeyr GJ, Vallo R, Mwiya M, Kwagala M, Traore H, Sunday A, Singata M, Siuluta C, Some E, Rutagwera D, Neboua D, Ndeezi G, Jackson D, Maréchal V, Neveu D, Engebretsen IM, Lombard C, Blanche S, Sommerfelt H, Rekacewicz C, Tylleskär T, Van de Perre P; ANRS 12174 Trial Group. Extended pre-exposure prophylaxis with lopinavir-ritonavir versus lamivudine to prevent HIV-1 transmission through breastfeeding up to 50 weeks in infants in Africa (ANRS 12174): a randomised controlled trial. Lancet. 2016 Feb 6;387(10018):566-73. doi: 10.1016/S0140-6736(15)00984-8. Epub 2015 Nov 19. PubMed PMID: 26603917. 12: Hampson L, Maranga IO, Masinde MS, Oliver AW, Batman G, He X, Desai M, Okemwa PM, Stringfellow H, Martin-Hirsch P, Mwaniki AM, Gichangi P, Hampson IN. A Single-Arm, Proof-Of-Concept Trial of Lopimune (Lopinavir/Ritonavir) as a Treatment for HPV-Related Pre-Invasive Cervical Disease. PLoS One. 2016 Jan 29;11(1):e0147917. doi: 10.1371/journal.pone.0147917. eCollection 2016. PubMed PMID: 26824902; PubMed Central PMCID: PMC4732739. 13: Kredo T, Mauff K, Workman L, Van der Walt JS, Wiesner L, Smith PJ, Maartens G, Cohen K, Barnes KI. The interaction between artemether-lumefantrine and lopinavir/ritonavir-based antiretroviral therapy in HIV-1 infected patients. BMC Infect Dis. 2016 Jan 27;16(1):30. doi: 10.1186/s12879-016-1345-1. PubMed PMID: 26818566; PubMed Central PMCID: PMC4728832. 14: Cooper DA, Cordery DV, Zajdenverg R, Ruxrungtham K, Arastéh K, Bergmann F, Neto JL, Scherer J, Chaves RL, Robinson P; study team. Tipranavir/Ritonavir (500/200 mg and 500/100 mg) Was Virologically Non-Inferior to Lopinavir/Ritonavir (400/100 mg) at Week 48 in Treatment-Naïve HIV-1-Infected Patients: A Randomized, Multinational, Multicenter Trial. PLoS One. 2016 Jan 5;11(1):e0144917. doi: 10.1371/journal.pone.0144917. eCollection 2016. PubMed PMID: 26730818; PubMed Central PMCID: PMC4701182. 15: Perry M, Taylor GP, Sabin CA, Conway K, Flanagan S, Dwyer E, Stevenson J, Mulka L, McKendry A, Williams E, Barbour A, Dermont S, Roedling S, Shah R, Anderson J, Rodgers M, Wood C, Sarner L, Hay P, Hawkins D, deRuiter A. Lopinavir and atazanavir in pregnancy: comparable infant outcomes, virological efficacies and preterm delivery rates. HIV Med. 2016 Jan;17(1):28-35. doi: 10.1111/hiv.12277. Epub 2015 Jul 22. PubMed PMID: 26200570. 16: Gordon LA, Malati CY, Hadigan C, McLaughlin M, Alfaro RM, Calderón MM, Kovacs JA, Penzak SR. Lack of an Effect of Ritonavir Alone and Lopinavir-Ritonavir on the Pharmacokinetics of Fenofibric Acid in Healthy Volunteers. Pharmacotherapy. 2016 Jan;36(1):49-56. doi: 10.1002/phar.1682. PubMed PMID: 26799348. 17: Rattanapunya S, Cressey TR, Rueangweerayut R, Tawon Y, Kongjam P, Na-Bangchang K. Pharmacokinetic Interactions Between Quinine and Lopinavir/Ritonavir in Healthy Thai Adults. Am J Trop Med Hyg. 2015 Dec 9;93(6):1383-90. doi: 10.4269/ajtmh.15-0453. Epub 2015 Sep 28. PubMed PMID: 26416104; PubMed Central PMCID: PMC4674263. 18: Chan JF, Yao Y, Yeung ML, Deng W, Bao L, Jia L, Li F, Xiao C, Gao H, Yu P, Cai JP, Chu H, Zhou J, Chen H, Qin C, Yuen KY. Treatment With Lopinavir/Ritonavir or Interferon-β1b Improves Outcome of MERS-CoV Infection in a Nonhuman Primate Model of Common Marmoset. J Infect Dis. 2015 Dec 15;212(12):1904-13. doi: 10.1093/infdis/jiv392. Epub 2015 Jul 21. PubMed PMID: 26198719. 19: Tiraboschi JM, Knobel H, Imaz A, Villar J, Ferrer E, Saumoy M, González A, Rozas N, Vila A, Niubó J, Curto J, Podzamczer D. Cerebrospinal fluid and plasma lopinavir concentrations and viral response in virologically suppressed patients switching to lopinavir/ritonavir monotherapy once daily. Antivir Ther. 2015 Dec 14. doi: 10.3851/IMP3015. [Epub ahead of print] PubMed PMID: 26656921. 20: Dumond JB, Rigdon J, Mollan K, Tierney C, Kashuba AD, Aweeka F, Collier AC. Brief Report: Significant Decreases in Both Total and Unbound Lopinavir and Amprenavir Exposures During Coadministration: ACTG Protocol A5143/A5147s Results. J Acquir Immune Defic Syndr. 2015 Dec 15;70(5):510-4. doi: 10.1097/QAI.0000000000000777. PubMed PMID: 26230332; PubMed Central PMCID: PMC4648657.