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Chemistry

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Also known as: 144875-48-9, R-848, 1-(4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol, 1-[4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol, Resiquimod [inn], R 848
Molecular Formula
C17H22N4O2
Molecular Weight
314.4  g/mol
InChI Key
BXNMTOQRYBFHNZ-UHFFFAOYSA-N
FDA UNII
V3DMU7PVXF

Resiquimod
Resiquimod is an imidazoquinolinamine and Toll-like receptor (TLR) agonist with potential immune response modifying activity. Resiquimod exerts its effect through the TLR signaling pathway by binding to and activating TLR7 and 8 mainly on dendritic cells, macrophages, and B-lymphocytes. This induces the nuclear translocation of the transcription activator NF-kB as well as activation of other transcription factors. This may lead to an increase in mRNA levels and subsequent production of cytokines, especially interferon-alpha (INF-a) and other cytokines, thereby enhancing T-helper 1 (Th1) immune responses. In addition, topical application of resiquimod appears to activate Langerhans' cells, leading to an enhanced activation of T-lymphocytes. Due to its immunostimulatory activity, this agent may potentially be useful as a vaccine adjuvant.
1 2D Structure

Resiquimod

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
2.1.2 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)
2.1.3 InChI Key
BXNMTOQRYBFHNZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCOCC1=NC2=C(N1CC(C)(C)O)C3=CC=CC=C3N=C2N
2.2 Other Identifiers
2.2.1 UNII
V3DMU7PVXF
2.3 Synonyms
2.3.1 MeSH Synonyms

1. R 848

2. R-848

3. R848 Compound

2.3.2 Depositor-Supplied Synonyms

1. 144875-48-9

2. R-848

3. 1-(4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol

4. 1-[4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

5. Resiquimod [inn]

6. R 848

7. Resiquimod (r-848)

8. R848

9. S 28463

10. S-28463

11. V3dmu7pvxf

12. Mfcd00937759

13. Chembl383322

14. Chebi:36706

15. 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

16. Cd11301

17. Cd-11301

18. R848;s28463

19. 2252319-44-9

20. 1-(4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

21. 1h-imidazo[4,5-c]quinoline-1-ethanol, 4-amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-

22. 4-amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-1h-imidazo[4,5-c]quinoline-1-ethanol

23. R848 Compound

24. Unii-v3dmu7pvxf

25. 1h-imidazo(4,5-c)quinoline-1-ethanol, 4-amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-

26. 4-amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-1h-imidazo(4,5-c)quinoline-1-ethanol

27. Resiquimodr848

28. Vml-600

29. Rx8

30. R848; Resiquimod

31. S28463

32. Resiquimod [mi]

33. Resiquimod [usan]

34. Resiquimod [mart.]

35. Resiquimod [who-dd]

36. Schembl34159

37. Mls006010212

38. Alpha-dimethyl-1h-imidazo(4,5-c)quinoline-1-ethanol

39. Gtpl5051

40. Dtxsid7040603

41. Resiquimod, >=98% (hplc)

42. Hms3740o09

43. Bcp09103

44. Ex-a1879

45. Bdbm50241029

46. S8133

47. Zinc28572103

48. Akos016003509

49. Ccg-267635

50. Cs-1706

51. Db06530

52. Sb17111

53. 1-(4-amino-2-ethoxymethyl-imidazo[4,5-c]quinolin-1-yl)-2-methyl-propan-2-ol

54. Ncgc00370784-01

55. Ncgc00370784-05

56. Ac-35716

57. As-30885

58. Hy-13740

59. Smr002530531

60. Sy107476

61. Ft-0763049

62. R0197

63. Resiquimod, Vml-600, R-848, S-28463

64. A856222

65. Q426054

66. Sr-01000944954

67. J-008020

68. Sr-01000944954-1

69. 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methyl-propan-2-ol

70. 4-amino-2-ethoxymethyl-alpha,alpha-dimethyl-1h-imidazo[4,5-c]quinoline-1-ethanol

71. 4-amino-alpha,alpha-dimethyl-2-ethoxymethyl-1h-imidazo[4,5-c]quinolin-1-ethanol

72. 4-amino-alpha,alpha-dimethyl-2-ethoxymethyl-1h-imidazo[4,5-c]quinoline-1-ethanol

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 314.4 g/mol
Molecular Formula C17H22N4O2
XLogP31.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass314.17427596 g/mol
Monoisotopic Mass314.17427596 g/mol
Topological Polar Surface Area86.2 Ų
Heavy Atom Count23
Formal Charge0
Complexity406
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in genital herpes.


5 Pharmacology and Biochemistry
5.1 Mechanism of Action

Resiquimod is a Toll-like receptor 7 (TLR7) and TLR8 agonist that is a potent inducer of alpha interferon (IFN-alpha) and other cytokines.


Drugs in Development

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Details:

The funding will be used for the further development of company's intraoperative immunotherapy, SURGERx with resiquimod (STM-416), in patients with recurrent bladder cancer.


Lead Product(s): Resiquimod,Inapplicable

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase I/ Phase IIProduct Type: Miscellaneous

Sponsor: Bioluminescence Ventures

Deal Size: $32.0 million Upfront Cash: Undisclosed

Deal Type: Series B Financing July 19, 2023

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01

Pharma
Not Confirmed
Pharma
Not Confirmed

Lead Product(s) : Resiquimod,Inapplicable

Therapeutic Area : Oncology

Highest Development Status : Phase I/ Phase II

Partner/Sponsor/Collaborator : Bioluminescence Ventures

Deal Size : $32.0 million

Deal Type : Series B Financing

Details : The funding will be used for the further development of company's intraoperative immunotherapy, SURGERx with resiquimod (STM-416), in patients with recurrent bladder cancer.

Product Name : Undisclosed

Product Type : Miscellaneous

Upfront Cash : Undisclosed

July 19, 2023

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Details:

STM-416 (Resiquimod), is a TLR7 and TLR8 agonist which is being invstigated for prevention of recurrence or progression after transurethral resection of bladder tumor (TURBT) in patients with non-muscle invasive bladder cancer (NMIBC)


Lead Product(s): Resiquimod,Inapplicable

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: IND EnablingProduct Type: Miscellaneous

Sponsor: Undisclosed

Deal Size: Inapplicable Upfront Cash: Inapplicable

Deal Type: Inapplicable January 04, 2023

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02

Pharma
Not Confirmed
Pharma
Not Confirmed

Details : STM-416 (Resiquimod), is a TLR7 and TLR8 agonist which is being invstigated for prevention of recurrence or progression after transurethral resection of bladder tumor (TURBT) in patients with non-muscle invasive bladder cancer (NMIBC)

Product Name : Undisclosed

Product Type : Miscellaneous

Upfront Cash : Inapplicable

January 04, 2023

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Details:

TransCon TLR7/8 Agonist is an investigational long-acting prodrug of resiquimod, a small molecule agonist of Toll-like receptors (TLR) 7 and 8 designed to provide sustained activation of intratumoral antigen-presenting cells driving tumor antigen presentation.


Lead Product(s): Resiquimod,Inapplicable

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase I/ Phase IIProduct Type: Miscellaneous

Sponsor: Undisclosed

Deal Size: Inapplicable Upfront Cash: Inapplicable

Deal Type: Inapplicable November 11, 2022

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03

Ascendis Pharma

Denmark
arrow
Pharma
Not Confirmed

Ascendis Pharma

Denmark
arrow
Pharma
Not Confirmed

Details : TransCon TLR7/8 Agonist is an investigational long-acting prodrug of resiquimod, a small molecule agonist of Toll-like receptors (TLR) 7 and 8 designed to provide sustained activation of intratumoral antigen-presenting cells driving tumor antigen present...

Product Name : Undisclosed

Product Type : Miscellaneous

Upfront Cash : Inapplicable

November 11, 2022

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Details:

Resiquimod, a small molecule agonist of Toll-like receptors, is designed to provide sustained activation of intratumoral antigen presenting cells driving tumor antigen presentation and induction of immune stimulatory cytokines in the tumor.


Lead Product(s): Resiquimod,Inapplicable

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase I/ Phase IIProduct Type: Miscellaneous

Sponsor: Undisclosed

Deal Size: Inapplicable Upfront Cash: Inapplicable

Deal Type: Inapplicable December 07, 2021

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04

Ascendis Pharma

Denmark
arrow
Pharma
Not Confirmed

Ascendis Pharma

Denmark
arrow
Pharma
Not Confirmed

Details : Resiquimod, a small molecule agonist of Toll-like receptors, is designed to provide sustained activation of intratumoral antigen presenting cells driving tumor antigen presentation and induction of immune stimulatory cytokines in the tumor.

Product Name : Undisclosed

Product Type : Miscellaneous

Upfront Cash : Inapplicable

December 07, 2021

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Details:

CD11301 is a Other Small Molecule drug candidate, which is currently being evaluated in phase II clinical studies for the treatment of Lymphoma, T-Cell, Cutaneous.


Lead Product(s): Resiquimod,Inapplicable

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase IIProduct Type: Miscellaneous

Sponsor: Undisclosed

Deal Size: Inapplicable Upfront Cash: Inapplicable

Deal Type: Inapplicable September 25, 2017

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05

Galderma

Switzerland
arrow
Pharma
Not Confirmed

Galderma

Switzerland
arrow
Pharma
Not Confirmed

Details : CD11301 is a Other Small Molecule drug candidate, which is currently being evaluated in phase II clinical studies for the treatment of Lymphoma, T-Cell, Cutaneous.

Product Name : Undisclosed

Product Type : Miscellaneous

Upfront Cash : Inapplicable

September 25, 2017

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Details:

Resiquimod is a Other Small Molecule drug candidate, which is currently being evaluated in phase I/ phase II clinical studies for the treatment of Carcinoma, Basal Cell.


Lead Product(s): Resiquimod,Inapplicable

Therapeutic Area: Oncology Brand Name: Undisclosed

Study Phase: Phase I/ Phase IIProduct Type: Miscellaneous

Sponsor: Undisclosed

Deal Size: Inapplicable Upfront Cash: Inapplicable

Deal Type: Inapplicable March 11, 2013

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06

Spirig Healthcare

Switzerland
arrow
Pharma
Not Confirmed

Spirig Healthcare

Switzerland
arrow
Pharma
Not Confirmed

Details : Resiquimod is a Other Small Molecule drug candidate, which is currently being evaluated in phase I/ phase II clinical studies for the treatment of Carcinoma, Basal Cell.

Product Name : Undisclosed

Product Type : Miscellaneous

Upfront Cash : Inapplicable

March 11, 2013

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Details:

Resiquimod is a Other Small Molecule drug candidate, which is currently being evaluated in phase II clinical studies for the treatment of Keratosis, Actinic.


Lead Product(s): Resiquimod,Inapplicable

Therapeutic Area: Dermatology Brand Name: Undisclosed

Study Phase: Phase IIProduct Type: Miscellaneous

Sponsor: Undisclosed

Deal Size: Inapplicable Upfront Cash: Inapplicable

Deal Type: Inapplicable April 24, 2012

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07

Spirig Healthcare

Switzerland
arrow
Pharma
Not Confirmed

Spirig Healthcare

Switzerland
arrow
Pharma
Not Confirmed

Details : Resiquimod is a Other Small Molecule drug candidate, which is currently being evaluated in phase II clinical studies for the treatment of Keratosis, Actinic.

Product Name : Undisclosed

Product Type : Miscellaneous

Upfront Cash : Inapplicable

April 24, 2012

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Resiquimod manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Resiquimod API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, and more, enabling you to easily find the right Resiquimod manufacturer or Resiquimod supplier for your needs.

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API | Excipient name

Resiquimod

Synonyms

144875-48-9, R-848, 1-(4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol, 1-[4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol, Resiquimod [inn], R 848

Cas Number

144875-48-9

Unique Ingredient Identifier (UNII)

V3DMU7PVXF

About Resiquimod

Resiquimod is an imidazoquinolinamine and Toll-like receptor (TLR) agonist with potential immune response modifying activity. Resiquimod exerts its effect through the TLR signaling pathway by binding to and activating TLR7 and 8 mainly on dendritic cells, macrophages, and B-lymphocytes. This induces the nuclear translocation of the transcription activator NF-kB as well as activation of other transcription factors. This may lead to an increase in mRNA levels and subsequent production of cytokines, especially interferon-alpha (INF-a) and other cytokines, thereby enhancing T-helper 1 (Th1) immune responses. In addition, topical application of resiquimod appears to activate Langerhans' cells, leading to an enhanced activation of T-lymphocytes. Due to its immunostimulatory activity, this agent may potentially be useful as a vaccine adjuvant.

Resiquimod Manufacturers

A Resiquimod manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Resiquimod, including repackagers and relabelers. The FDA regulates Resiquimod manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Resiquimod API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Resiquimod Suppliers

A Resiquimod supplier is an individual or a company that provides Resiquimod active pharmaceutical ingredient (API) or Resiquimod finished formulations upon request. The Resiquimod suppliers may include Resiquimod API manufacturers, exporters, distributors and traders.

click here to find a list of Resiquimod suppliers with USDMF, JDMF, KDMF, CEP, GMP, and COA related information on PharmaCompass.

Resiquimod USDMF

A Resiquimod DMF (Drug Master File) is a document detailing the whole manufacturing process of Resiquimod active pharmaceutical ingredient (API) in detail. Different forms of Resiquimod DMFs exist exist since differing nations have different regulations, such as Resiquimod USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Resiquimod DMF submitted to regulatory agencies in the US is known as a USDMF. Resiquimod USDMF includes data on Resiquimod's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Resiquimod USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Resiquimod suppliers with USDMF on PharmaCompass.

Resiquimod GMP

Resiquimod Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Resiquimod GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, and more, enabling you to easily find the right Resiquimod GMP manufacturer or Resiquimod GMP API supplier for your needs.

Resiquimod CoA

A Resiquimod CoA (Certificate of Analysis) is a formal document that attests to Resiquimod's compliance with Resiquimod specifications and serves as a tool for batch-level quality control.

Resiquimod CoA mostly includes findings from lab analyses of a specific batch. For each Resiquimod CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Resiquimod may be tested according to a variety of international standards, such as European Pharmacopoeia (Resiquimod EP), Resiquimod JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Resiquimod USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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