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MedKoo Cat#: 318060 | Name: Indinavir
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Description:

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

Indinavir (IDV) is a protease inhibitor used as a component of highly active antiretroviral therapy to treat HIV/AIDS.

Chemical Structure

Indinavir
Indinavir
CAS#150378-17-9 (free base)

Theoretical Analysis

MedKoo Cat#: 318060

Name: Indinavir

CAS#: 150378-17-9 (free base)

Chemical Formula: C36H47N5O4

Exact Mass: 613.3628

Molecular Weight: 613.79

Elemental Analysis: C, 70.45; H, 7.72; N, 11.41; O, 10.43

Price and Availability

Size Price Availability Quantity
5mg USD 275.00 2 Weeks
10mg USD 500.00 2 Weeks
25mg USD 850.00 2 Weeks
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Related CAS #
150378-17-9 (free base) 157810-81-6 (sulfate) 180683-37-8 (hydrate)
Synonym
Indinavir, Crixivan, L 735524; L-735524; L735524; MK-639; MK 639; MK639; DRG-0233; DRG 0233; DRG0233;
IUPAC/Chemical Name
(2S)-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
InChi Key
CBVCZFGXHXORBI-PXQQMZJSSA-N
InChi Code
InChI=1S/C36H47N5O4/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/h4-15,21,28-29,31-33,42-43H,16-20,22-24H2,1-3H3,(H,38,44)(H,39,45)/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
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
Instruction
View handling instruction
Biological target:
Indinavir (MK-639 free base) is an orally active and selective HIV-1 protease inhibitor with a Ki of 0.54 nM for PR. Indinavir exhibits anticancer activity by inhibiting the activation of MMPs-2 hydrolysis, anti-angiogenesis and inducing apoptosis. Indinavir is also a SARS-CoV 3CLpro inhibitor.
In vitro activity:
It was found that indinavir impaired cryptococcal protease activity in a time- and dose-dependent fashion. The phenomenon was similarly detectable in ATCC/laboratory strains and clinical isolates. C. neoformans growth rate was also significantly reduced upon exposure to indinavir, while fungal viability was not affected and mitochondrial toxicity not detected. Furthermore, as assessed by an in vitro infection model, indinavir significantly and consistently augmented C. neoformans susceptibility to microglial cell-mediated phagocytosis and killing. Reference: FEMS Immunol Med Microbiol. 2004 Oct 1;42(2):187-95. https://pubmed.ncbi.nlm.nih.gov/15364103/
In vivo activity:
In summary, this study has reported neuropathic pain-related sensory and behavioural changes accompanied by a significant loss of hind paw skin sensory innervation in a rat model of indinavir-induced peripheral neuropathy that is suitable for further pathophysiological investigation and preclinical evaluation of novel analgesics. Reference: Pain. 2017 Jan;158(1):75-85. https://pubmed.ncbi.nlm.nih.gov/27682209/

Preparing Stock Solutions

The following data is based on the product molecular weight 613.79 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.

Recalculate based on batch purity %
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. Blasi E, Colombari B, Orsi CF, Pinti M, Troiano L, Cossarizza A, Esposito R, Peppoloni S, Mussini C, Neglia R. The human immunodeficiency virus (HIV) protease inhibitor indinavir directly affects the opportunistic fungal pathogen Cryptococcus neoformans. FEMS Immunol Med Microbiol. 2004 Oct 1;42(2):187-95. doi: 10.1016/j.femsim.2004.05.001. PMID: 15364103. 2. Hong-Brown LQ, Brown CR, Lang CH. Indinavir impairs protein synthesis and phosphorylations of MAPKs in mouse C2C12 myocytes. Am J Physiol Cell Physiol. 2004 Nov;287(5):C1482-92. doi: 10.1152/ajpcell.00038.2004. Epub 2004 Jun 30. PMID: 15229102. 3. Huang W, Calvo M, Pheby T, Bennett DLH, Rice ASC. A rodent model of HIV protease inhibitor indinavir induced peripheral neuropathy. Pain. 2017 Jan;158(1):75-85. doi: 10.1097/j.pain.0000000000000727. PMID: 27682209. 4. Hong-Brown LQ, Pruznak AM, Frost RA, Vary TC, Lang CH. Indinavir alters regulators of protein anabolism and catabolism in skeletal muscle. Am J Physiol Endocrinol Metab. 2005 Sep;289(3):E382-90. doi: 10.1152/ajpendo.00591.2004. Epub 2005 Apr 12. PMID: 15827064.
In vitro protocol:
1. Blasi E, Colombari B, Orsi CF, Pinti M, Troiano L, Cossarizza A, Esposito R, Peppoloni S, Mussini C, Neglia R. The human immunodeficiency virus (HIV) protease inhibitor indinavir directly affects the opportunistic fungal pathogen Cryptococcus neoformans. FEMS Immunol Med Microbiol. 2004 Oct 1;42(2):187-95. doi: 10.1016/j.femsim.2004.05.001. PMID: 15364103. 2. Hong-Brown LQ, Brown CR, Lang CH. Indinavir impairs protein synthesis and phosphorylations of MAPKs in mouse C2C12 myocytes. Am J Physiol Cell Physiol. 2004 Nov;287(5):C1482-92. doi: 10.1152/ajpcell.00038.2004. Epub 2004 Jun 30. PMID: 15229102.
In vivo protocol:
1. Huang W, Calvo M, Pheby T, Bennett DLH, Rice ASC. A rodent model of HIV protease inhibitor indinavir induced peripheral neuropathy. Pain. 2017 Jan;158(1):75-85. doi: 10.1097/j.pain.0000000000000727. PMID: 27682209. 2. Hong-Brown LQ, Pruznak AM, Frost RA, Vary TC, Lang CH. Indinavir alters regulators of protein anabolism and catabolism in skeletal muscle. Am J Physiol Endocrinol Metab. 2005 Sep;289(3):E382-90. doi: 10.1152/ajpendo.00591.2004. Epub 2005 Apr 12. PMID: 15827064.
1: 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. 2: Cressey TR, Plipat N, Fregonese F, Chokephaibulkit K. Indinavir/ritonavir remains an important component of HAART for the treatment of HIV/AIDS, particularly in resource-limited settings. Expert Opin Drug Metab Toxicol. 2007 Jun;3(3):347-61. Review. PubMed PMID: 17539743. 3: Boyd M. Indinavir: the forgotten HIV-protease inhibitor. Does it still have a role? Expert Opin Pharmacother. 2007 May;8(7):957-64. Review. PubMed PMID: 17472541. 4: Fernández JM, Robles JE, Regojo JM, López J, Sánchez D, Arocena J, Rosell D, Zudaire JJ, Berián JM. [Renal lithiasis due to indinavir]. Rev Med Univ Navarra. 2002 Jul-Sep;46(3):28-32. Review. Spanish. PubMed PMID: 12685114. 5: García-Silva J, Almagro M, Peña-Penabad C, Fonseca E. Indinavir-induced retinoid-like effects: incidence, clinical features and management. Drug Saf. 2002;25(14):993-1003. Review. PubMed PMID: 12408731. 6: Rayner CR, Galbraith KJ, Marriott JL, Duncan GJ. A critical evaluation of the therapeutic range of indinavir. Ann Pharmacother. 2002 Jul-Aug;36(7-8):1230-7. Review. PubMed PMID: 12086558. 7: Wu DS, Stoller ML. Indinavir urolithiasis. Curr Opin Urol. 2000 Nov;10(6):557-61. Review. PubMed PMID: 11148725. 8: Famularo G, Di Toro S, Moretti S, De Simone C. Symptomatic crystalluria associated with indinavir. Ann Pharmacother. 2000 Dec;34(12):1414-8. Review. PubMed PMID: 11144699. 9: Benson JO, McGhee K, Coplan P, Grunfeld C, Robertson M, Brodovicz KG, Slater E. Fat redistribution in indinavir-treated patients with HIV infection: A review of postmarketing cases. J Acquir Immune Defic Syndr. 2000 Oct 1;25(2):130-9. Review. PubMed PMID: 11103043. 10: The choice of HIV protease inhibitor: indinavir is currently the best option. Prescrire Int. 1999 Apr;8(40):55-60. Review. PubMed PMID: 10848067. 11: Gagnon RF, Alli AI, Watters AK, Tsoukas CM. Indinavir crystalluria. Kidney Int. 2006 Dec;70(12):2047. Review. PubMed PMID: 17136127. 12: Florence E, Schrooten W, Verdonck K, Dreezen C, Colebunders R. Rheumatological complications associated with the use of indinavir and other protease inhibitors. Ann Rheum Dis. 2002 Jan;61(1):82-4. Review. PubMed PMID: 11779768; PubMed Central PMCID: PMC1753893. 13: Youle M. Optimizing indinavir regimens. HIV Med. 2000 Jul;1 Suppl 2:7-11. Review. PubMed PMID: 11737366. 14: Plosker GL, Noble S. Indinavir: a review of its use in the management of HIV infection. Drugs. 1999 Dec;58(6):1165-203. Review. PubMed PMID: 10651394. 15: Perazella MA, Kashgarian M, Cooney E. Indinavir nephropathy in an AIDS patient with renal insufficiency and pyuria. Clin Nephrol. 1998 Sep;50(3):194-6. Review. PubMed PMID: 9776425. 16: Hoetelmans RM, Meenhorst PL, Mulder JW, Burger DM, Koks CH, Beijnen JH. Clinical pharmacology of HIV protease inhibitors: focus on saquinavir, indinavir, and ritonavir. Pharm World Sci. 1997 Aug;19(4):159-75. Review. PubMed PMID: 9297727. 17: Chefchaouni MC, Thiounn N, Flam T, Zerbib M, Debré B. [Urinary calculi and indinavir sulfate in patients with HIV infection. Apropos of 4 cases]. J Urol (Paris). 1997;103(1-2):35-6. Review. French. PubMed PMID: 9765778. 18: Lacy MK, Abriola KP. Indinavir: a pharmacologic and clinical review of a new HIV protease inhibitor. Conn Med. 1996 Dec;60(12):723-7. Review. PubMed PMID: 9018893.