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MedKoo Cat#: 563471 | Name: Hydroxychloroquine sulfate
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Description:

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

Hydroxychloroquine is an autophagy inhibitor. It acts by inducing apoptosis of renal cancer cells in vitro and inhibiting TLR9. Hydroxychloroquine (HCQ) is a medication used to prevent and treat malaria in areas where malaria remains sensitive to chloroquine. Other uses include treatment of rheumatoid arthritis, lupus, and porphyria cutanea tarda. It is taken by mouth. It is also being studied as an experimental treatment for coronavirus disease 2019 (COVID-19).

Chemical Structure

Hydroxychloroquine sulfate
Hydroxychloroquine sulfate
CAS#747-36-4 (sulfate)

Theoretical Analysis

MedKoo Cat#: 563471

Name: Hydroxychloroquine sulfate

CAS#: 747-36-4 (sulfate)

Chemical Formula: C18H28ClN3O5S

Exact Mass: 0.0000

Molecular Weight: 433.94

Elemental Analysis: C, 49.82; H, 6.50; Cl, 8.17; N, 9.68; O, 18.43; S, 7.39

Price and Availability

Size Price Availability Quantity
2g USD 90.00 Ready to ship
10g USD 250.00 Ready to ship
20g USD 450.00 Ready to ship
50g USD 950.00 Ready to ship
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Related CAS #
118-42-3 (free base) 747-36-4 (sulfate) 6168-85-0 (diphosphate)
Synonym
Hydrochloroquine sulfate; Ercoquin; Plaquinol; Toremonil; Oxychlorochin; Oxychloroquine; Plaquenil; Hydroxychloroquine sulfate.WIN 1258; Z0188;
IUPAC/Chemical Name
2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethan-1-ol sulfate
InChi Key
JCBIVZZPXRZKTI-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H26ClN3O.H2O4S/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18;1-5(2,3)4/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21);(H2,1,2,3,4)
SMILES Code
CCN(CCO)CCCC(NC1=CC=NC2=CC(Cl)=CC=C12)C.O=S(O)(O)=O
Appearance
Solid powder
Purity
>99% (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
>3 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
2934.99.03.00
More Info
Biological target:
Hydroxychloroquine sulfate (HCQ sulfate) is a synthetic antimalarial agent which can also inhibit Toll-like receptor 7/9 (TLR7/9) signaling and SARS-CoV-2 infection.
In vitro activity:
Epigenetic changes provide the molecular substrate of trained immunity in monocytes and macrophages. As the functional assays showed that hydroxychloroquine prevents trained immunity, the impact of hydroxychloroquine on epigenetic regulation in monocytes was investigated. For this purpose, a whole-genome assessment of the histone marks histone 3 lysine 27 acetylation (H3K27ac) and histone 3 lysine 4 trimethylation (H3K4me3) were performed by chromatin immunoprecipitation sequencing (ChIP-seq) in control monocytes as well as HKCA-trained monocytes treated with or without hydroxychloroquine. After training and 5 days of resting, 352 peaks were found that had retained a significant change in the H3K27ac and H3K4me3 dynamic between HKCA and control cells, indicating that an epigenetic memory was established. Interestingly, all HKCA-induced changes could be prevented with hydroxychloroquine treatment (Figure 6A). Pathway analysis of differentially regulated peaks that remained active in HKCA-trained cells and were shut down in HKCA- and hydroxychloroquine-treated cells revealed pathways associated with immune responses and inflammation (Figure 6B). These data therefore confirm the functional assays and show that hydroxychloroquine treatment effectively prevents the epigenetic changes underlying HKCA-induced training and that this especially involves the regulation of inflammationrelated genes. In summary, it was found that hydroxychloroquine averts the induction of trained immunity in monocytes through epigenetic reprograming, namely by suppressing H3K27 acetylation and H3K4 histone trimethylation. Reference: Cell Rep Med. 2020 Dec 22; 1(9): 100146. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7762774/
In vivo activity:
In the present study, the therapeutic effects of hydroxychloroquine were evaluated under pathological conditions in vivo. Obesity was induced in C57BL/6 mice fed with high-fed diet, or in mice fed with high-fat diet and hydroxychloroquine. In addition, healthy mice that received normal chow diet were also monitored. The present results revealed that hydroxychloroquine reduced weight, hepatic steatosis, glucose, and insulin resistance. The IRT results revealed that HCQ-treated mice exhibited significantly higher plasma insulin levels at 15 min after glucose administration (Figure 2C). Furthermore, hydroxychloroquine downregulated the expression of peroxisome proliferator-activated receptor gamma in the liver. According to these present results, genes about lipid metabolism went down in high-fat mice liver. HCQ markedly reduced serum lipid levels and improved the disorders of lipid metabolism and chronic inflammatory state. Hydroxychloroquine shows potential in ameliorating obesity-induced pathology, which acts though PPARγ to facilitate the healthy function of hepatic tissues. This evidence shows that hydroxychloroquine plays a role in improving obesityinduced lipotoxicity and insulin resistance though the peroxisome proliferator-activated receptor gamma pathway. Reference: Front Pharmacol. 2019; 10: 855. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6689966/
Solvent mg/mL mM
Solubility
H2O 80.0 184.36
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 433.94 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. Rother N, Yanginlar C, Lindeboom RGH, Bekkering S, van Leent MMT, Buijsers B, Jonkman I, de Graaf M, Baltissen M, Lamers LA, Riksen NP, Fayad ZA, Mulder WJM, Hilbrands LB, Joosten LAB, Netea MG, Vermeulen M, van der Vlag J, Duivenvoorden R. Hydroxychloroquine Inhibits the Trained Innate Immune Response to Interferons. Cell Rep Med. 2020 Nov 10;1(9):100146. doi: 10.1016/j.xcrm.2020.100146. PMID: 33377122; PMCID: PMC7762774. 2. Baranowska K, Misund K, Starheim KK, Holien T, Johansson I, Darvekar S, Buene G, Waage A, Bjørkøy G, Sundan A. Hydroxychloroquine potentiates carfilzomib toxicity towards myeloma cells. Oncotarget. 2016 Oct 25;7(43):70845-70856. doi: 10.18632/oncotarget.12226. PMID: 27683126; PMCID: PMC5342593. 3. Qiao X, Zhou ZC, Niu R, Su YT, Sun Y, Liu HL, Teng JL, Ye JN, Shi H, Yang CD, Cheng XB. Hydroxychloroquine Improves Obesity-Associated Insulin Resistance and Hepatic Steatosis by Regulating Lipid Metabolism. Front Pharmacol. 2019 Aug 2;10:855. doi: 10.3389/fphar.2019.00855. PMID: 31427967; PMCID: PMC6689966. 4. Miranda S, Billoir P, Damian L, Thiebaut PA, Schapman D, Le Besnerais M, Jouen F, Galas L, Levesque H, Le Cam-Duchez V, Joannides R, Richard V, Benhamou Y. Hydroxychloroquine reverses the prothrombotic state in a mouse model of antiphospholipid syndrome: Role of reduced inflammation and endothelial dysfunction. PLoS One. 2019 Mar 14;14(3):e0212614. doi: 10.1371/journal.pone.0212614. PMID: 30870459; PMCID: PMC6417644.
In vitro protocol:
1. Rother N, Yanginlar C, Lindeboom RGH, Bekkering S, van Leent MMT, Buijsers B, Jonkman I, de Graaf M, Baltissen M, Lamers LA, Riksen NP, Fayad ZA, Mulder WJM, Hilbrands LB, Joosten LAB, Netea MG, Vermeulen M, van der Vlag J, Duivenvoorden R. Hydroxychloroquine Inhibits the Trained Innate Immune Response to Interferons. Cell Rep Med. 2020 Nov 10;1(9):100146. doi: 10.1016/j.xcrm.2020.100146. PMID: 33377122; PMCID: PMC7762774. 2. Baranowska K, Misund K, Starheim KK, Holien T, Johansson I, Darvekar S, Buene G, Waage A, Bjørkøy G, Sundan A. Hydroxychloroquine potentiates carfilzomib toxicity towards myeloma cells. Oncotarget. 2016 Oct 25;7(43):70845-70856. doi: 10.18632/oncotarget.12226. PMID: 27683126; PMCID: PMC5342593.
In vivo protocol:
1. Qiao X, Zhou ZC, Niu R, Su YT, Sun Y, Liu HL, Teng JL, Ye JN, Shi H, Yang CD, Cheng XB. Hydroxychloroquine Improves Obesity-Associated Insulin Resistance and Hepatic Steatosis by Regulating Lipid Metabolism. Front Pharmacol. 2019 Aug 2;10:855. doi: 10.3389/fphar.2019.00855. PMID: 31427967; PMCID: PMC6689966. 2. Miranda S, Billoir P, Damian L, Thiebaut PA, Schapman D, Le Besnerais M, Jouen F, Galas L, Levesque H, Le Cam-Duchez V, Joannides R, Richard V, Benhamou Y. Hydroxychloroquine reverses the prothrombotic state in a mouse model of antiphospholipid syndrome: Role of reduced inflammation and endothelial dysfunction. PLoS One. 2019 Mar 14;14(3):e0212614. doi: 10.1371/journal.pone.0212614. PMID: 30870459; PMCID: PMC6417644.
1: Xie W, Wang Y, Zhang Z. Hydroxychloroquine reduces the risk of covid-19 in patients with rheumatic diseases: myth or reality? Ann Rheum Dis. 2020 Apr 21:annrheumdis-2020-217556. doi: 10.1136/annrheumdis-2020-217556. Epub ahead of print. PMID: 32317316. 2: Moiseev S, Avdeev S, Brovko M, Novikov P, Fomin V. Is there a future for hydroxychloroquine/chloroquine in prevention of SARS-CoV-2 infection (COVID-19)? Ann Rheum Dis. 2020 Apr 21:annrheumdis-2020-217570. doi: 10.1136/annrheumdis-2020-217570. Epub ahead of print. PMID: 32317315. 3: Aduriz-Lorenzo PM, Aduriz-Llaneza P, Araiz-Iribarren J, Khamashta MA. Current opinion on hydroxychloroquine-related retinal toxicity screening: where do we stand now? Lupus. 2020 Apr 21:961203320919499. doi: 10.1177/0961203320919499. Epub ahead of print. PMID: 32316844. 4: Sun Y, Zhang J, Li X, Sun E. [Hydroxychloroquine alleviates 5-fluorouracil- induced enteritis in mice and its mechanism]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2020 Jan;36(1):1-8. Chinese. PMID: 32314717. 5: Falcão MB, Pamplona de Góes Cavalcanti L, Filgueiras Filho NM, Antunes de Brito CA. Case Report: Hepatotoxicity Associated with the Use of Hydroxychloroquine in a Patient with Novel Coronavirus Disease (COVID-19). Am J Trop Med Hyg. 2020 Apr 17. doi: 10.4269/ajtmh.20-0276. Epub ahead of print. PMID: 32314698. 6: Lazaros G, Antonopoulos AS, Antonatou K, Skendros P, Ritis K, Hadziyannis E, Lazarou E, Leontsinis I, Simantiris S, Vlachopoulos C, Tousoulis D, Vassilopoulos D. Hydroxychloroquine for colchicine-resistant glucocorticoid- dependent idiopathic recurrent pericarditis: A pilot observational prospective study. Int J Cardiol. 2020 Mar 30:S0167-5273(20)30011-5. doi: 10.1016/j.ijcard.2020.03.069. Epub ahead of print. PMID: 32312616. 7: Rathi S, Ish P, Kalantri A, Kalantri S. Hydroxychloroquine prophylaxis for COVID-19 contacts in India. Lancet Infect Dis. 2020 Apr 17:S1473-3099(20)30313-3. doi: 10.1016/S1473-3099(20)30313-3. Epub ahead of print. PMID: 32311324; PMCID: PMC7164849. 8: Principi N, Esposito S. Chloroquine or hydroxychloroquine for prophylaxis of COVID-19. Lancet Infect Dis. 2020 Apr 17:S1473-3099(20)30296-6. doi: 10.1016/S1473-3099(20)30296-6. Epub ahead of print. PMID: 32311322; PMCID: PMC7164862. 9: Taccone FS, Gorham J, Vincent JL. Hydroxychloroquine in the management of critically ill patients with COVID-19: the need for an evidence base. Lancet Respir Med. 2020 Apr 15:S2213-2600(20)30172-7. doi: 10.1016/S2213-2600(20)30172-7. Epub ahead of print. PMID: 32304640; PMCID: PMC7159849. 10: Zhu X, Sun J. A case of facial atrophic sarcoidosis in an adolescent, successfully treated by the combination of prednisone and hydroxychloroquine. An Bras Dermatol. 2020 Mar 19:S0365-0596(20)30076-3. doi: 10.1016/j.abd.2019.08.028. Epub ahead of print. PMID: 32299736. 11: Sarma P, Kaur H, Kumar H, Mahendru D, Avti P, Bhattacharyya A, Prajapat M, Shekhar N, Kumar S, Singh R, Singh A, Dhibar DP, Prakash A, Medhi B. Virological and Clinical Cure in Covid-19 Patients Treated with Hydroxychloroquine: A Systematic Review and Meta-Analysis. J Med Virol. 2020 Apr 16. doi: 10.1002/jmv.25898. Epub ahead of print. PMID: 32297988. 12: Costanzo M, De Giglio MAR, Roviello GN. SARS-CoV-2: Recent Reports on Antiviral Therapies Based on Lopinavir/Ritonavir, Darunavir/Umifenovir, Hydroxychloroquine, Remdesivir, Favipiravir and Other Drugs for the Treatment of the New Coronavirus. Curr Med Chem. 2020 Apr 16. doi: 10.2174/0929867327666200416131117. Epub ahead of print. PMID: 32297571. 13: Sinha N, Balayla G. Hydroxychloroquine and covid-19. Postgrad Med J. 2020 Apr 15:postgradmedj-2020-137785. doi: 10.1136/postgradmedj-2020-137785. Epub ahead of print. PMID: 32295814. 14: Heldwein FL, Calado A. Does hydroxychloroquine prevent the transmission of covid-19? Ann Rheum Dis. 2020 Apr 15:annrheumdis-2020-217501. doi: 10.1136/annrheumdis-2020-217501. Epub ahead of print. PMID: 32295788. 15: Joob B, Wiwanitkit V. SLE, hydroxychloroquine and no SLE patients with covid-19: a comment. Ann Rheum Dis. 2020 Apr 15:annrheumdis-2020-217506. doi: 10.1136/annrheumdis-2020-217506. Epub ahead of print. PMID: 32295787. 16: Graef ER, Liew JW, Putman MS, Simard JF, Sirotich E, Berenbaum F, Duarte- García A, Grainger R, Harrison C, Konig MF, Korsten P, Proulx L, Richards DP, Robinson PC, Sattui SE, Ugarte-Gil MF, Young KJ, Kim AH, Sparks JA; COVID-19 Global Rheumatology Alliance. Festina lente: hydroxychloroquine, covid-19 and the role of the rheumatologist. Ann Rheum Dis. 2020 Apr 15:annrheumdis-2020-217480. doi: 10.1136/annrheumdis-2020-217480. Epub ahead of print. PMID: 32295786. 17: Mack HG. Hydroxychloroquine use during the COVID-19 pandemic 2020. Aust J Gen Pract. 2020 Apr 14;49. doi: 10.31128/AJGP-COVID-08. Epub ahead of print. PMID: 32294807. 18: Brufsky A. Hyperglycemia, Hydroxychloroquine, and the COVID-19 Epidemic. J Med Virol. 2020 Apr 15. doi: 10.1002/jmv.25887. Epub ahead of print. PMID: 32293710. 19: Zhang TY, Zhong B. Meeting the Potential Emergency Global Drug Supply Challenge of Hydroxychloroquine for COVID-19. Med Drug Discov. 2020 Apr 9:100036. doi: 10.1016/j.medidd.2020.100036. Epub ahead of print. PMID: 32292908; PMCID: PMC7144509. 20: Picot S, Marty A, Bienvenu AL, Blumberg LH, Dupouy-Camet J, Carnevale P, Kano S, Jones MK, Daniel-Ribeiro CT, Mas-Coma S. Coalition: Advocacy for prospective clinical trials to test the post-exposure potential of hydroxychloroquine against COVID-19. One Health. 2020 Apr 4:100131. doi: 10.1016/j.onehlt.2020.100131. Epub ahead of print. PMID: 32292817; PMCID: PMC7128742.