Resiquimod

Resiquimod
Clinical data
Routes of; administration	Topical
ATC code	none;
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol;
CAS Number	144875-48-9 ;
PubChem CID	159603;
IUPHAR/BPS	5051;
ChemSpider	140330 ;
UNII	V3DMU7PVXF;
ChEMBL	ChEMBL383322 ;
CompTox Dashboard (EPA)	DTXSID7040603 ;
Chemical and physical data
Formula	C17H22N4O2
Molar mass	314.389 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O;
	InChI InChI=1S/C17H22N4O2/c1-4-23-9-13-20-14-15(21(13)10-17(2,3)22)11-7-5-6-8-12(11)19-16(14)18/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19) ; Key:BXNMTOQRYBFHNZ-UHFFFAOYSA-N ;
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Resiquimod (R-848) is a drug that acts as an immune response modifier, and has antiviral and antitumour activity. It is used as a topical gel^[1] in the treatment of skin lesions^[2] such as those caused by the herpes simplex virus^[3]^[4] and cutaneous T cell lymphoma,^[5] and as an adjuvant to increase the effectiveness of vaccines.^[6] In an animal disease model, systemic administration of resiquimod-loaded nanoparticles has been shown to improve response rates to cancer immunotherapy with a checkpoint inhibitor through stimulation of tumor-associated macrophages.^[7] It has several mechanisms of action, being both an agonist for toll-like receptor 7 and 8,^[8] and an upregulator of the opioid growth factor receptor.^[9] On 28 April 2016, orphan designation (EU/3/16/1653) was granted by the European Commission to Galderma R&D, France for resiquimod to be used in the treatment of cutaneous T-cell lymphoma.^[10]

References

^ Patents #5, 939, 090 and 6, 365, 166
^ Szeimies RM, Bichel J, Ortonne JP, Stockfleth E, Lee J, Meng TC (July 2008). "A phase II dose-ranging study of topical resiquimod to treat actinic keratosis". The British Journal of Dermatology. 159 (1): 205–210. doi:10.1111/j.1365-2133.2008.08615.x. PMID 18476957. S2CID 205257237.
^ Wu JJ, Huang DB, Tyring SK (November 2004). "Resiquimod: a new immune response modifier with potential as a vaccine adjuvant for Th1 immune responses". Antiviral Research. 64 (2): 79–83. doi:10.1016/j.antiviral.2004.07.002. PMID 15498602.
^ Fife KH, Meng TC, Ferris DG, Liu P (February 2008). "Effect of resiquimod 0.01% gel on lesion healing and viral shedding when applied to genital herpes lesions". Antimicrobial Agents and Chemotherapy. 52 (2): 477–482. doi:10.1128/AAC.01173-07. PMC 2224757. PMID 18039918.
^ Rook AH, Gelfand JM, Wysocka M, Troxel AB, Benoit B, Surber C, et al. (September 2015). "Topical resiquimod can induce disease regression and enhance T-cell effector functions in cutaneous T-cell lymphoma". Blood. 126 (12): 1452–1461. doi:10.1182/blood-2015-02-630335. PMC 4573868. PMID 26228486.
^ Tomai MA, Miller RL, Lipson KE, Kieper WC, Zarraga IE, Vasilakos JP (October 2007). "Resiquimod and other immune response modifiers as vaccine adjuvants". Expert Review of Vaccines. 6 (5): 835–847. doi:10.1586/14760584.6.5.835. PMID 17931162. S2CID 30401602.
^ Rodell CB, Arlauckas SP, Cuccarese MF, Garris CS, Li R, Ahmed MS, et al. (August 2018). "TLR7/8-agonist-loaded nanoparticles promote the polarization of tumour-associated macrophages to enhance cancer immunotherapy". Nature Biomedical Engineering. 2 (8): 578–588. doi:10.1038/s41551-018-0236-8. PMC 6192054. PMID 31015631.
^ Hurst J, Prinz N, Lorenz M, Bauer S, Chapman J, Lackner KJ, von Landenberg P (February 2009). "TLR7 and TLR8 ligands and antiphospholipid antibodies show synergistic effects on the induction of IL-1beta and caspase-1 in monocytes and dendritic cells". Immunobiology. 214 (8): 683–691. doi:10.1016/j.imbio.2008.12.003. PMID 19249118.
^ Zagon IS, Donahue RN, Rogosnitzky M, McLaughlin PJ (August 2008). "Imiquimod upregulates the opioid growth factor receptor to inhibit cell proliferation independent of immune function". Experimental Biology and Medicine. 233 (8): 968–979. doi:10.3181/0802-RM-58. PMID 18480416. S2CID 35164284.
^ Committee for Orphan Medicinal Products (27 May 2016). "Resiquimod for the treatment of cutaneous T-cell lymphoma" (PDF). Public summary of opinion on orphan designation. European Medicines Agency.

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[1] Patents #5, 939, 090 and 6, 365, 166

[pmid18476957-2] Szeimies RM, Bichel J, Ortonne JP, Stockfleth E, Lee J, Meng TC (July 2008). "A phase II dose-ranging study of topical resiquimod to treat actinic keratosis". The British Journal of Dermatology. 159 (1): 205–210. doi:10.1111/j.1365-2133.2008.08615.x. PMID 18476957. S2CID 205257237.

[pmid15498602-3] Wu JJ, Huang DB, Tyring SK (November 2004). "Resiquimod: a new immune response modifier with potential as a vaccine adjuvant for Th1 immune responses". Antiviral Research. 64 (2): 79–83. doi:10.1016/j.antiviral.2004.07.002. PMID 15498602.

[pmid18039918-4] Fife KH, Meng TC, Ferris DG, Liu P (February 2008). "Effect of resiquimod 0.01% gel on lesion healing and viral shedding when applied to genital herpes lesions". Antimicrobial Agents and Chemotherapy. 52 (2): 477–482. doi:10.1128/AAC.01173-07. PMC 2224757. PMID 18039918.

[Rook-5] Rook AH, Gelfand JM, Wysocka M, Troxel AB, Benoit B, Surber C, et al. (September 2015). "Topical resiquimod can induce disease regression and enhance T-cell effector functions in cutaneous T-cell lymphoma". Blood. 126 (12): 1452–1461. doi:10.1182/blood-2015-02-630335. PMC 4573868. PMID 26228486.

[pmid17931162-6] Tomai MA, Miller RL, Lipson KE, Kieper WC, Zarraga IE, Vasilakos JP (October 2007). "Resiquimod and other immune response modifiers as vaccine adjuvants". Expert Review of Vaccines. 6 (5): 835–847. doi:10.1586/14760584.6.5.835. PMID 17931162. S2CID 30401602.

[7] Rodell CB, Arlauckas SP, Cuccarese MF, Garris CS, Li R, Ahmed MS, et al. (August 2018). "TLR7/8-agonist-loaded nanoparticles promote the polarization of tumour-associated macrophages to enhance cancer immunotherapy". Nature Biomedical Engineering. 2 (8): 578–588. doi:10.1038/s41551-018-0236-8. PMC 6192054. PMID 31015631.

[pmid19249118-8] Hurst J, Prinz N, Lorenz M, Bauer S, Chapman J, Lackner KJ, von Landenberg P (February 2009). "TLR7 and TLR8 ligands and antiphospholipid antibodies show synergistic effects on the induction of IL-1beta and caspase-1 in monocytes and dendritic cells". Immunobiology. 214 (8): 683–691. doi:10.1016/j.imbio.2008.12.003. PMID 19249118.

[pmid18480416-9] Zagon IS, Donahue RN, Rogosnitzky M, McLaughlin PJ (August 2008). "Imiquimod upregulates the opioid growth factor receptor to inhibit cell proliferation independent of immune function". Experimental Biology and Medicine. 233 (8): 968–979. doi:10.3181/0802-RM-58. PMID 18480416. S2CID 35164284.

[10] Committee for Orphan Medicinal Products (27 May 2016). "Resiquimod for the treatment of cutaneous T-cell lymphoma" (PDF). Public summary of opinion on orphan designation. European Medicines Agency.

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[5]

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Clinical data

Routes of administration	Topical
ATC code	none
Legal status
Legal status	Investigational
Identifiers
IUPAC name 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
CAS Number	144875-48-9^Y
PubChem CID	159603
IUPHAR/BPS	5051
ChemSpider	140330^N
UNII	V3DMU7PVXF
ChEMBL	ChEMBL383322^N
CompTox Dashboard (EPA)	DTXSID7040603
Chemical and physical data
Formula	C₁₇H₂₂N₄O₂
Molar mass	314.389 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCOCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O
InChI InChI=1S/C17H22N4O2/c1-4-23-9-13-20-14-15(21(13)10-17(2,3)22)11-7-5-6-8-12(11)19-16(14)18/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19)^N Key:BXNMTOQRYBFHNZ-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

Resiquimod

See also

References