Indinavir sulfate | CAS#157810-81-6 | HIV protease inhibitor

MedKoo Cat#: 540220 | Name: Indinavir sulfate

Description:

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

Indinavir sulfate is an inhibitor of HIV protease, GLUT4, and calpain used to treat HIV infection. It also decreases phosphorylation of the insulin receptor β subunit, inhibits adenocarcinoma tumor growth, and may induce SOCS1 signaling.

Chemical Structure

Indinavir sulfate

CAS#157810-81-6 (sulfate)

Theoretical Analysis

MedKoo Cat#: 540220

Name: Indinavir sulfate

CAS#: 157810-81-6 (sulfate)

Chemical Formula: C36H49N5O8S

Exact Mass: 0.0000

Molecular Weight: 711.87

Elemental Analysis: C, 60.74; H, 6.94; N, 9.84; O, 17.98; S, 4.50

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 350.00	Ready to ship
5g	USD 650.00	2 Weeks

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Related CAS #

150378-17-9 (free base) 157810-81-6 (sulfate) 180683-37-8 (hydrate)

Synonym

Indinavir Sulfate; Crixivan; Indinavir, Crixivan, L 735524; L-735524; L735524; MK-639; MK 639; MK639; DRG-0233; DRG 0233; DRG0233;

IUPAC/Chemical Name

(S)-1-((2S,4R)-4-benzyl-2-hydroxy-5-(((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)amino)-5-oxopentyl)-N-(tert-butyl)-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide sulfate

InChi Key

NUBQKPWHXMGDLP-BDEHJDMKSA-N

InChi Code

InChI=1S/C36H47N5O4.H2O4S/c1-36(2,3)39-35(45)31-24-40(22-26-12-9-15-37-21-26)16-17-41(31)23-29(42)19-28(18-25-10-5-4-6-11-25)34(44)38-33-30-14-8-7-13-27(30)20-32(33)43;1-5(2,3)4/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45);(H2,1,2,3,4)/t28-,29+,31+,32-,33+;/m1./s1

SMILES Code

O=C([C@H]1N(C[C@@H](O)C[C@@H](CC2=CC=CC=C2)C(N[C@@H]3[C@H](O)CC4=C3C=CC=C4)=O)CCN(CC5=CC=CN=C5)C1)NC(C)(C)C.O=S(O)(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

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#C20M08C11

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Indinavir sulfate (MK-639 sulfate; L735524 sulfate) is a potent and specific HIV protease inhibitor and a SARS-CoV 3CLpro inhibitor with an IC50 of 1.71 μM.

In vitro activity:

The treatment with indinavir for 24 h, added to the culture at the same time as the sporulated oocysts at concentrations of 10 and 20 μM, reduced the number of C. parvum-infected cells by 40 and 64%, respectively (Figs. 1C,D). At a concentration of 50 μM indinavir (Fig. 1E), the parasites were not able to infect the cells; in fact, the peak channel of cells treated with 50 μM of indinavir was the same as that of non-infected cells (Figs. 1A,E). At a concentration of indinavir lower than 10 μM, no effect on the growth of C. parvum in HCT-8 cells was observed (data not shown). When indinavir was added to C. parvum-infected cells, the extent to which the infection decreased depended on the duration of treatment (Fig. 2). Up to 48 h of indinavir treatment, no variation was observed in the percentage of infected cells (data not shown). Treatment for 48 h resulted in a 40.1% reduction in infected cells (from 90 to 53%) (Figs. 2E,F). After 72 h of treatment, the percentage of infected cells did not substantially differ from that observed after 48 h (data not shown). Treatment for 96 h resulted in a 57.8% reduction (from 90 to 38%) (Figs. 2G,H). Reference: J Parasitol. 2003 Jul;33(7):757-64. https://linkinghub.elsevier.com/retrieve/pii/S0020751903000936

In vivo activity:

The number of oocysts in the intestinal contents decreased by 93%, and the number of intracellular parasites in the ileum homogenate decreased by 91%. The oocyst gate and the gate of intracellular parasites were defined by dot plot of FSC-H versus FL1-H (anti-C. parvum IgG FITC) (Figs. 3A,B). The mean number (±SD) of oocysts in faecal specimens and of intracellular parasites for the 15 non-treated infected mice and the 15 infected mice treated with indinavir (Group A) is shown in Table 1. The mean number of oocysts in faecal specimens and of intracellular parasites for non-treated and indinavir-treated infected mice at 7, 10 and 13 days p.i. (Group B) is shown in Fig. 4. At 7 days p.i. (i.e. after 4 days of indinavir treatment), no statistically significant difference was observed when comparing the treated mice to the controls. At 10 days p.i. (i.e. after 7 days of treatment), the number of both oocysts and intracellular parasites was significantly lower in the treated mice, compared to controls. At 11 days p.i. (data not shown in the figure), the difference between the treated mice and the controls was the same as that observed at day 10, whereas at 13 days p.i. (i.e. after 10 days of treatment), in the treated mice the number of oocysts and intracellular parasites was, respectively, 51 and 71% lower than that in the controls. Reference: J Parasitol. 2003 Jul;33(7):757-64. https://linkinghub.elsevier.com/retrieve/pii/S0020751903000936

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	140.48
	Water	50.0	70.24

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 711.87 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:

In vitro protocol:

In vivo protocol:

1. Mele R, Gomez Morales MA, Tosini F, Pozio E. Indinavir reduces Cryptosporidium parvum infection in both in vitro and in vivo models. Int J Parasitol. 2003 Jul;33(7):757-64. doi: 10.1016/s0020-7519(03)00093-6. PMID: 12814654. 2. Pereira de Oliveira M, Venisse N, Couet W, Olivier JC. LC-MS/MS determination of the HIV-1 protease inhibitor indinavir in brain and testis of mice. J Pharm Biomed Anal. 2006 Feb 13;40(2):353-9. doi: 10.1016/j.jpba.2005.07.008. Epub 2005 Aug 19. PMID: 16112534.

1: Rao RN, Vali RM, Raju SS. Liquid chromatography tandem mass spectrometric studies of indinavir sulphate and its forced degradation products. J Pharm Biomed Anal. 2013 Feb 23;74:101-10. doi: 10.1016/j.jpba.2012.10.025. Epub 2012 Oct 29. PubMed PMID: 23245240. 2: Huynh J, Hever A, Tom T, Sim JJ. Indinavir-induced nephrolithiasis three and one-half years after cessation of indinavir therapy. Int Urol Nephrol. 2011 Jun;43(2):571-3. doi: 10.1007/s11255-010-9751-6. Epub 2010 May 11. PubMed PMID: 20458537; PubMed Central PMCID: PMC3094655. 3: Jann MW, Spratlin V, Momary K, Zhang H, Turner D, Penzak SR, Wright A, VanDenBerg C. Lack of a pharmacokinetic drug-drug interaction with venlafaxine extended-release/indinavir and desvenlafaxine extended-release/indinavir. Eur J Clin Pharmacol. 2012 May;68(5):715-21. doi: 10.1007/s00228-011-1180-7. Epub 2011 Dec 16. PubMed PMID: 22173281. 4: Cressey TR, Best BM, Achalapong J, Stek A, Wang J, Chotivanich N, Yuthavisuthi P, Suriyachai P, Prommas S, Shapiro DE, Watts DH, Smith E, Capparelli E, Kreitchmann R, Mirochnick M; IMPAACT P1026s team. Reduced indinavir exposure during pregnancy. Br J Clin Pharmacol. 2013 Sep;76(3):475-83. doi: 10.1111/bcp.12078. PubMed PMID: 23305215; PubMed Central PMCID: PMC3769674. 5: Barrail-Tran A, Taburet AM, Poirier JM; Groupe Suivi Therapeutique Pharmacologique de la Societe Francaise de Pharmacologie et de Therapeutique. [Evidence-based therapeutic drug monitoring for indinavir]. Therapie. 2011 May-Jun;66(3):239-46. doi: 10.2515/therapie/2011035. Epub 2011 Aug 9. Review. French. PubMed PMID: 21819808. 6: Ascher DP, Lucy MD. Indinavir sulfate renal toxicity in a pediatric hemophiliac with HIV infection. Ann Pharmacother. 1997 Oct;31(10):1146-9. PubMed PMID: 9337438. 7: Holmstock N, De Bruyn T, Bevernage J, Annaert P, Mols R, Tack J, Augustijns P. Exploring food effects on indinavir absorption with human intestinal fluids in the mouse intestine. Eur J Pharm Sci. 2013 Apr 11;49(1):27-32. doi: 10.1016/j.ejps.2013.01.012. Epub 2013 Feb 9. PubMed PMID: 23402972. 8: Sangeda RZ, Theys K, Beheydt G, Rhee SY, Deforche K, Vercauteren J, Libin P, Imbrechts S, Grossman Z, Camacho RJ, Van Laethem K, Pironti A, Zazzi M, Sönnerborg A, Incardona F, De Luca A, Torti C, Ruiz L, Van de Vijver DA, Shafer RW, Bruzzone B, Van Wijngaerden E, Vandamme AM; Virolab and EuResist Projects. HIV-1 fitness landscape models for indinavir treatment pressure using observed evolution in longitudinal sequence data are predictive for treatment failure. Infect Genet Evol. 2013 Oct;19:349-60. doi: 10.1016/j.meegid.2013.03.014. Epub 2013 Mar 21. PubMed PMID: 23523594. 9: Kharasch ED, Bedynek PS, Hoffer C, Walker A, Whittington D. Lack of indinavir effects on methadone disposition despite inhibition of hepatic and intestinal cytochrome P4503A (CYP3A). Anesthesiology. 2012 Feb;116(2):432-47. doi: 10.1097/ALN.0b013e3182423478. PubMed PMID: 22273859; PubMed Central PMCID: PMC3586934. 10: Kuhnert M, Steuber H, Diederich WE. Structural basis for HTLV-1 protease inhibition by the HIV-1 protease inhibitor indinavir. J Med Chem. 2014 Jul 24;57(14):6266-72. doi: 10.1021/jm500402c. Epub 2014 Jul 9. PubMed PMID: 25006983. 11: Endsley AN, Ho RJ. Enhanced anti-HIV efficacy of indinavir after inclusion in CD4-targeted lipid nanoparticles. J Acquir Immune Defic Syndr. 2012 Dec 1;61(4):417-24. doi: 10.1097/QAI.0b013e3182653c1f. PubMed PMID: 22743598; PubMed Central PMCID: PMC3551348. 12: Yang JM, Ip SP, Xian Y, Zhao M, Lin ZX, Yeung JH, Chan RC, Lee SS, Che CT. Impact of the herbal medicine Sophora flavescens on the oral pharmacokinetics of indinavir in rats: the involvement of CYP3A and P-glycoprotein. PLoS One. 2012;7(2):e31312. doi: 10.1371/journal.pone.0031312. Epub 2012 Feb 16. PubMed PMID: 22359586; PubMed Central PMCID: PMC3281083. 13: Rubbens J, Brouwers J, Tack J, Augustijns P. Gastrointestinal dissolution, supersaturation and precipitation of the weak base indinavir in healthy volunteers. Eur J Pharm Biopharm. 2016 Dec;109:122-129. doi: 10.1016/j.ejpb.2016.09.014. Epub 2016 Sep 28. PubMed PMID: 27693678. 14: Lehman HP, Benson JO, Beninger PR, Anderson CA, Blumenthal SJ, Sharrar RG. A five-year evaluation of reports of overdose with indinavir sulfate. Pharmacoepidemiol Drug Saf. 2003 Sep;12(6):449-57. PubMed PMID: 14513658. 15: Prasanna SJ, Sharma HK, Mukkanti K, Sivakumaran M, Pavan Kumar KS, Kumar VJ. Validation of a sensitive ion chromatography method for determination of monoethylsulfate in Indinavir sulfate drug substance. J Pharm Biomed Anal. 2009 Dec 5;50(5):1065-9. doi: 10.1016/j.jpba.2009.06.041. Epub 2009 Jun 27. PubMed PMID: 19616913. 16: Cressey TR, Urien S, Hirt D, Halue G, Techapornroong M, Bowonwatanuwong C, Leenasirimakul P, Treluyer JM, Jourdain G, Lallemant M; PHPT-3 Team. Influence of body weight on achieving indinavir concentrations within its therapeutic window in HIV-infected Thai patients receiving indinavir boosted with ritonavir. Ther Drug Monit. 2011 Feb;33(1):25-31. doi: 10.1097/FTD.0b013e3182057f6f. PubMed PMID: 21233689; PubMed Central PMCID: PMC3058116. 17: Bollam S, Kandadi P, Apte SS, Veerabrahma K. Development of indinavir submicron lipid emulsions loaded with lipoamino acids-in vivo pharmacokinetics and brain-specific delivery. AAPS PharmSciTech. 2011 Mar;12(1):422-30. doi: 10.1208/s12249-011-9604-3. Epub 2011 Mar 1. PubMed PMID: 21360313; PubMed Central PMCID: PMC3066383. 18: Sturgill MG, Seibold JR, Boruchoff SE, Yeh KC, Haddix H, Deutsch P. Trimethoprim/sulfamethoxazole does not affect the steady-state disposition of indinavir. J Clin Pharmacol. 1999 Oct;39(10):1077-84. PubMed PMID: 10516943. 19: Dogan B, Canbaz D, Ozkan SA, Uslu B. Electrochemical methods for determination of the protease inhibitor indinavir sulfate in pharmaceuticals and human serum. Pharmazie. 2006 May;61(5):409-13. PubMed PMID: 16724536. 20: Dieleman JP, Sturkenboom MC, Jambroes M, Gyssens IC, Weverling GJ, ten Veen JH, Schrey G, Reiss P, Stricker BH; Athena Study Group. Risk factors for urological symptoms in a cohort of users of the HIV protease inhibitor indinavir sulfate: the ATHENA cohort. Arch Intern Med. 2002 Jul 8;162(13):1493-501. PubMed PMID: 12090886.