Nelfinavir mesylate
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MedKoo CAT#: 318357

CAS#: 159989-65-8 (mesylate)

Description: Nelfinavir, also known as AG-1343, is an antiretroviral drug used in the treatment of the human immunodeficiency virus (HIV). It belongs to the class of drugs known as protease inhibitors (PIs) and like other PIs is almost always used in combination with other antiretroviral drugs.

Chemical Structure

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Nelfinavir mesylate
CAS# 159989-65-8 (mesylate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318357
Name: Nelfinavir mesylate
CAS#: 159989-65-8 (mesylate)
Chemical Formula: C33H49N3O7S2
Exact Mass: 663.30
Molecular Weight: 663.889
Elemental Analysis: C, 59.70; H, 7.44; N, 6.33; O, 16.87; S, 9.66

Price and Availability

Size Price Availability Quantity
25mg USD 450 1-2 months
50mg USD 750 1-2 months
100mg USD 1250 1-2 months
200mg USD 1950 1-2 months
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Related CAS #: 159989-64-7 (free base)   159989-65-8 (mesylate)    

Synonym: AG-1343; AG 1343; AG1343; Nelfinavir; Viracept; Nelfinavir mesylate hydrate

IUPAC/Chemical Name: (3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylsulfanylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide mesylate hydrate

InChi Key: QUWWBORDPJHOJO-GZDSSZIUSA-N

InChi Code: InChI=1S/C32H45N3O4S.CH4O3S.H2O/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4;1-5(2,3)4;/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39);1H3,(H,2,3,4);1H2/t22-,23+,26-,27-,29+;;/m0../s1

SMILES Code: O=C([C@H]1N(C[C@@H](O)[C@@H](NC(C2=CC=CC(O)=C2C)=O)CSC3=CC=CC=C3)C[C@@]4([H])CCCC[C@@]4([H])C1)NC(C)(C)C.OS(=O)(C)=O.[H]O[H]

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: Nelfinavir Mesylate (AG 1343 Mesylate) is a potent and orally bioavailable HIV-1 protease inhibitor (Ki=2 nM) for HIV infection.
In vitro activity: In vitro exposure (72 hours) of HAECs to NEL (nelfinavir) (0.25-2 μg/mL) decreased both basal (2.5-fold) and insulin-induced NO production (4- to 5-fold). NEL suppressed insulin-induced phosphorylation of both Akt and eNOS at serine residues 473 and 1177, respectively. NEL decreased tyrosine phosphorylation of IR-β, IRS-1, and PI3K. Reference: Ochsner J. 2013 Spring;13(1):76-90. https://pubmed.ncbi.nlm.nih.gov/23533049/
In vivo activity: This study evaluated antitumor activity of nelfinavir with xenografts in athymic nude mouse models (n = 4-6 per group) of human breast cancer and repeated mixed-effects regression analysis. All statistical tests were two-sided. In vivo, nelfinavir selectively inhibited the growth of HER2-positive breast cancer cells (tumor volume index of HCC1954 cells on day 29, vehicle vs nelfinavir, mean = 14.42 vs 5.16, difference = 9.25, 95% confidence interval [CI] = 5.93 to 12.56, P < .001; tumor volume index of BT474 cells on day 26, vehicle vs nelfinavir, mean = 2.21 vs 0.90, difference = 1.31, 95% CI = 0.83 to 1.78, P < .001). Reference: J Natl Cancer Inst. 2012 Oct 17;104(20):1576-90. https://pubmed.ncbi.nlm.nih.gov/23042933/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 29.33
DMSO 70.1 102.80
Ethanol 20.0 29.33
Ethanol:PBS (pH 7.2) (1:2) 0.3 0.48

Preparing Stock Solutions

The following data is based on the product molecular weight 663.89 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. Mondal D, Liu K, Hamblin M, Lasky JA, Agrawal KC. Nelfinavir suppresses insulin signaling and nitric oxide production by human aortic endothelial cells: protective effects of thiazolidinediones. Ochsner J. 2013 Spring;13(1):76-90. PMID: 23533049; PMCID: PMC3603192. 2. Kaldor SW, Kalish VJ, Davies JF 2nd, Shetty BV, Fritz JE, Appelt K, Burgess JA, Campanale KM, Chirgadze NY, Clawson DK, Dressman BA, Hatch SD, Khalil DA, Kosa MB, Lubbehusen PP, Muesing MA, Patick AK, Reich SH, Su KS, Tatlock JH. Viracept (nelfinavir mesylate, AG1343): a potent, orally bioavailable inhibitor of HIV-1 protease. J Med Chem. 1997 Nov 21;40(24):3979-85. doi: 10.1021/jm9704098. PMID: 9397180. 3. Shim JS, Rao R, Beebe K, Neckers L, Han I, Nahta R, Liu JO. Selective inhibition of HER2-positive breast cancer cells by the HIV protease inhibitor nelfinavir. J Natl Cancer Inst. 2012 Oct 17;104(20):1576-90. doi: 10.1093/jnci/djs396. Epub 2012 Oct 5. PMID: 23042933; PMCID: PMC3472971. 4. Gills JJ, Lopiccolo J, Tsurutani J, Shoemaker RH, Best CJ, Abu-Asab MS, Borojerdi J, Warfel NA, Gardner ER, Danish M, Hollander MC, Kawabata S, Tsokos M, Figg WD, Steeg PS, Dennis PA. Nelfinavir, A lead HIV protease inhibitor, is a broad-spectrum, anticancer agent that induces endoplasmic reticulum stress, autophagy, and apoptosis in vitro and in vivo. Clin Cancer Res. 2007 Sep 1;13(17):5183-94. doi: 10.1158/1078-0432.CCR-07-0161. PMID: 17785575.
In vitro protocol: 1. Mondal D, Liu K, Hamblin M, Lasky JA, Agrawal KC. Nelfinavir suppresses insulin signaling and nitric oxide production by human aortic endothelial cells: protective effects of thiazolidinediones. Ochsner J. 2013 Spring;13(1):76-90. PMID: 23533049; PMCID: PMC3603192. 2. Kaldor SW, Kalish VJ, Davies JF 2nd, Shetty BV, Fritz JE, Appelt K, Burgess JA, Campanale KM, Chirgadze NY, Clawson DK, Dressman BA, Hatch SD, Khalil DA, Kosa MB, Lubbehusen PP, Muesing MA, Patick AK, Reich SH, Su KS, Tatlock JH. Viracept (nelfinavir mesylate, AG1343): a potent, orally bioavailable inhibitor of HIV-1 protease. J Med Chem. 1997 Nov 21;40(24):3979-85. doi: 10.1021/jm9704098. PMID: 9397180.
In vivo protocol: 1. Shim JS, Rao R, Beebe K, Neckers L, Han I, Nahta R, Liu JO. Selective inhibition of HER2-positive breast cancer cells by the HIV protease inhibitor nelfinavir. J Natl Cancer Inst. 2012 Oct 17;104(20):1576-90. doi: 10.1093/jnci/djs396. Epub 2012 Oct 5. PMID: 23042933; PMCID: PMC3472971. 2. Gills JJ, Lopiccolo J, Tsurutani J, Shoemaker RH, Best CJ, Abu-Asab MS, Borojerdi J, Warfel NA, Gardner ER, Danish M, Hollander MC, Kawabata S, Tsokos M, Figg WD, Steeg PS, Dennis PA. Nelfinavir, A lead HIV protease inhibitor, is a broad-spectrum, anticancer agent that induces endoplasmic reticulum stress, autophagy, and apoptosis in vitro and in vivo. Clin Cancer Res. 2007 Sep 1;13(17):5183-94. doi: 10.1158/1078-0432.CCR-07-0161. PMID: 17785575.

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1: Nagao Y, Hisanaga T, Utsumi T, Egami H, Kawato Y, Hamashima Y. Enantioselective Synthesis of Nelfinavir via Asymmetric Bromocyclization of Bisallylic Amide. J Org Chem. 2018 Mar 1. doi: 10.1021/acs.joc.8b00039. [Epub ahead of print] PubMed PMID: 29480721.

2: Abt D, Besse A, Sedlarikova L, Kraus M, Bader J, Silzle T, Vodinska M, Slaby O, Schmid HP, Engeler DS, Driessen C, Besse L. Improving the efficacy of proteasome inhibitors in the treatment of renal cell carcinoma by combination with the human immunodeficiency virus (HIV)-protease inhibitors lopinavir or nelfinavir. BJU Int. 2017 Nov 21. doi: 10.1111/bju.14083. [Epub ahead of print] PubMed PMID: 29161753.

3: Sanchez CG, Molinski SV, Gongora R, Sosulski M, Fuselier T, MacKinnon SS, Mondal D, Lasky JA. The Antiretroviral Agent Nelfinavir Mesylate: A Potential Therapy for Systemic Sclerosis. Arthritis Rheumatol. 2018 Jan;70(1):115-126. doi: 10.1002/art.40326. Epub 2017 Dec 8. PubMed PMID: 28940894.

4: Besse A, Stolze SC, Rasche L, Weinhold N, Morgan GJ, Kraus M, Bader J, Overkleeft HS, Besse L, Driessen C. Carfilzomib resistance due to ABCB1/MDR1 overexpression is overcome by nelfinavir and lopinavir in multiple myeloma. Leukemia. 2018 Feb;32(2):391-401. doi: 10.1038/leu.2017.212. Epub 2017 Jul 5. PubMed PMID: 28676669; PubMed Central PMCID: PMC5808083.

5: Sato A, Asano T, Okubo K, Isono M, Asano T. Nelfinavir and Ritonavir Kill Bladder Cancer Cells Synergistically by Inducing Endoplasmic Reticulum Stress. Oncol Res. 2018 Mar 5;26(2):323-332. doi: 10.3727/096504017X14957929842972. Epub 2017 May 26. PubMed PMID: 28560953.

6: Meier-Stephenson V, Riemer J, Narendran A. The HIV protease inhibitor, nelfinavir, as a novel therapeutic approach for the treatment of refractory pediatric leukemia. Onco Targets Ther. 2017 May 16;10:2581-2593. doi: 10.2147/OTT.S136484. eCollection 2017. PubMed PMID: 28553123; PubMed Central PMCID: PMC5440076.

7: Dunlop EA, Johnson CE, Wiltshire M, Errington RJ, Tee AR. Targeting protein homeostasis with nelfinavir/salinomycin dual therapy effectively induces death of mTORC1 hyperactive cells. Oncotarget. 2017 Jul 25;8(30):48711-48724. doi: 10.18632/oncotarget.16232. PubMed PMID: 28415776; PubMed Central PMCID: PMC5564719.

8: Sangenito LS, de Guedes AA, Gonçalves DS, Seabra SH, d'Avila-Levy CM, Santos ALS, Branquinha MH. Deciphering the effects of nelfinavir and lopinavir on epimastigote forms of Trypanosoma cruzi. Parasitol Int. 2017 Oct;66(5):529-536. doi: 10.1016/j.parint.2017.03.009. Epub 2017 Apr 2. PubMed PMID: 28377050.

9: Xia C, Chen R, Chen J, Qi Q, Pan Y, Du L, Xiao G, Jiang S. Combining metformin and nelfinavir exhibits synergistic effects against the growth of human cervical cancer cells and xenograft in nude mice. Sci Rep. 2017 Mar 2;7:43373. doi: 10.1038/srep43373. PubMed PMID: 28252027; PubMed Central PMCID: PMC5333097.

10: Jensen K, Bikas A, Patel A, Kushchayeva Y, Costello J, McDaniel D, Burman K, Vasko V. Nelfinavir inhibits proliferation and induces DNA damage in thyroid cancer cells. Endocr Relat Cancer. 2017 Mar;24(3):147-156. doi: 10.1530/ERC-16-0568. Epub 2017 Jan 30. PubMed PMID: 28137980.

11: Sangenito LS, d'Avila-Levy CM, Branquinha MH, Santos ALS. Nelfinavir and lopinavir impair Trypanosoma cruzi trypomastigote infection in mammalian host cells and show anti-amastigote activity. Int J Antimicrob Agents. 2016 Dec;48(6):703-711. doi: 10.1016/j.ijantimicag.2016.09.017. Epub 2016 Oct 31. PubMed PMID: 27838277.

12: Hleyhel M, Goujon S, Sibiude J, Blanche S, Warszawski J; on behalf the ANRS French Perinatal Cohort study Group. In-utero exposure to nelfinavir-ethyl methyl sulfone. AIDS. 2016 Nov 13;30(17):2729-2730. PubMed PMID: 27662548.

13: Davis MA, Delaney JR, Patel CB, Storgard R, Stupack DG. Nelfinavir is effective against human cervical cancer cells in vivo: a potential treatment modality in resource-limited settings. Drug Des Devel Ther. 2016 Jun 2;10:1837-46. doi: 10.2147/DDDT.S102241. eCollection 2016. PubMed PMID: 27330277; PubMed Central PMCID: PMC4898046.

14: Soprano M, Sorriento D, Rusciano MR, Maione AS, Limite G, Forestieri P, D'Angelo D, D'Alessio M, Campiglia P, Formisano P, Iaccarino G, Bianco R, Illario M. Oxidative Stress Mediates the Antiproliferative Effects of Nelfinavir in Breast Cancer Cells. PLoS One. 2016 Jun 9;11(6):e0155970. doi: 10.1371/journal.pone.0155970. eCollection 2016. PubMed PMID: 27280849; PubMed Central PMCID: PMC4900679.

15: Al-Assar O, Bittner MI, Lunardi S, Stratford MR, McKenna WG, Brunner TB. The radiosensitizing effects of Nelfinavir on pancreatic cancer with and without pancreatic stellate cells. Radiother Oncol. 2016 May;119(2):300-5. doi: 10.1016/j.radonc.2016.03.024. Epub 2016 May 28. PubMed PMID: 27247056.

16: Smith C, Weinberg A, Forster JE, Levin MJ, Davies J, Pappas J, Kinzie K, Barr E, Paul S, McFarland EJ. Maternal Lopinavir/Ritonavir Is Associated with Fewer Adverse Events in Infants than Nelfinavir or Atazanavir. Infect Dis Obstet Gynecol. 2016;2016:9848041. doi: 10.1155/2016/9848041. Epub 2016 Apr 4. PubMed PMID: 27127401; PubMed Central PMCID: PMC4834394.

17: Wilson JM, Fokas E, Dutton SJ, Patel N, Hawkins MA, Eccles C, Chu KY, Durrant L, Abraham AG, Partridge M, Woodward M, O'Neill E, Maughan T, McKenna WG, Mukherjee S, Brunner TB. ARCII: A phase II trial of the HIV protease inhibitor Nelfinavir in combination with chemoradiation for locally advanced inoperable pancreatic cancer. Radiother Oncol. 2016 May;119(2):306-11. doi: 10.1016/j.radonc.2016.03.021. Epub 2016 Apr 23. PubMed PMID: 27117177; PubMed Central PMCID: PMC4917892.

18: Inzaule SC, Weidle PJ, Yang C, Ndiege K, Hamers RL, Rinke de Wit TF, Thomas T, Zeh C. Prevalence and dynamics of the K65R drug resistance mutation in HIV-1-infected infants exposed to maternal therapy with lamivudine, zidovudine and either nevirapine or nelfinavir in breast milk. J Antimicrob Chemother. 2016 Jun;71(6):1619-26. doi: 10.1093/jac/dkw039. Epub 2016 Mar 6. PubMed PMID: 26953333.

19: Meyn RE, Krishnan S, Skinner HD. Everything Old Is New Again: Using Nelfinavir to Radiosensitize Rectal Cancer. Clin Cancer Res. 2016 Apr 15;22(8):1834-6. doi: 10.1158/1078-0432.CCR-16-0024. Epub 2016 Feb 26. PubMed PMID: 26920893; PubMed Central PMCID: PMC5061034.

20: Hill EJ, Roberts C, Franklin JM, Enescu M, West N, MacGregor TP, Chu KY, Boyle L, Blesing C, Wang LM, Mukherjee S, Anderson EM, Brown G, Dutton S, Love SB, Schnabel JA, Quirke P, Muschel R, McKenna WG, Partridge M, Sharma RA. Clinical Trial of Oral Nelfinavir before and during Radiation Therapy for Advanced Rectal Cancer. Clin Cancer Res. 2016 Apr 15;22(8):1922-31. doi: 10.1158/1078-0432.CCR-15-1489. Epub 2016 Feb 9. PubMed PMID: 26861457; PubMed Central PMCID: PMC4835023.