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Also known as: 99011-02-6, Aldara, Zyclara, 1-isobutyl-1h-imidazo[4,5-c]quinolin-4-amine, 1-(2-methylpropyl)-1h-imidazo[4,5-c]quinolin-4-amine, Beselna
Molecular Formula
C14H16N4
Molecular Weight
240.30  g/mol
InChI Key
DOUYETYNHWVLEO-UHFFFAOYSA-N
FDA UNII
P1QW714R7M

Imiquimod
A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.
The mechanism of action of imiquimod is as an Interferon Inducer. The physiologic effect of imiquimod is by means of Increased Cytokine Activity, and Increased Cytokine Production.
1 2D Structure

Imiquimod

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine
2.1.2 InChI
InChI=1S/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)
2.1.3 InChI Key
DOUYETYNHWVLEO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C)CN1C=NC2=C1C3=CC=CC=C3N=C2N
2.2 Other Identifiers
2.2.1 UNII
P1QW714R7M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-isobutyl-1h-imidazo(4,5-c)quinolin-4-amine

2. Aldara

3. R 837

4. R-837

5. R837

6. S 26308

7. S-26308

8. Zyclara

2.3.2 Depositor-Supplied Synonyms

1. 99011-02-6

2. Aldara

3. Zyclara

4. 1-isobutyl-1h-imidazo[4,5-c]quinolin-4-amine

5. 1-(2-methylpropyl)-1h-imidazo[4,5-c]quinolin-4-amine

6. Beselna

7. 4-amino-1-isobutyl-1h-imidazo[4,5-c]quinoline

8. R 837

9. 1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine

10. 4-amino-1-isobutyl-1h-imidazo(4,5-c)quinoline

11. 9050-31-1

12. R-837

13. S-26308

14. C14h16n4

15. Mfcd00866946

16. Tmx-101

17. S26308

18. Nsc-369100

19. Nsc-759651

20. Chembl1282

21. 1-isobutylimidazo[4,5-c]quinolin-4-amine

22. P1qw714r7m

23. 1h-imidazo(4,5-c)quinolin-4-amine, 1-(2-methylpropyl)-

24. 1h-imidazo[4,5-c]quinolin-4-amine, 1-(2-methylpropyl)-

25. Chebi:36704

26. Ncgc00070736-02

27. Zartra

28. Imiquimod Acetate

29. Dsstox_cid_21047

30. Dsstox_rid_79617

31. Dsstox_gsid_41047

32. Aldara (tn)

33. Cas-99011-02-6

34. S 26308

35. Sr-01000611320

36. 1-(2-methylpropyl)-1h-imidazole[4,5-c]quinoline-4-amine

37. Unii-p1qw714r7m

38. Imiquimodum

39. Imiquimod [usan:inn:ban]

40. Vyloma

41. Mtd-39

42. Hsdb 8129

43. Tmx 101

44. Imiquimod,(s)

45. Imiquimod- Bio-x

46. 6t0

47. Imiquimod - Aldara

48. Zyclara (tn)

49. Dz-2636

50. R837

51. Imiquimod [inn]

52. Imiquimod [jan]

53. Imiquimod [mi]

54. Imiquimod [usan]

55. Imiquimod [vandf]

56. Imiquimod [mart.]

57. (non-labelled)imiquimod-d9

58. Imiquimod [usp-rs]

59. Imiquimod [who-dd]

60. Imiquimod (jan/usp/inn)

61. Schembl26136

62. Imiquimod [ema Epar]

63. Mls000083577

64. Bidd:gt0859

65. Gtpl5003

66. Imiquimod [orange Book]

67. Dtxsid7041047

68. Imiquimod [usp Monograph]

69. Hms2090m14

70. Hms2232g07

71. Hms3373b13

72. Hms3715n19

73. Hms3747a13

74. Pharmakon1600-01502351

75. Bcp05151

76. Hy-b0180

77. Tox21_110985

78. Ac-529

79. Bbl010772

80. Bdbm50240849

81. Nsc369100

82. Nsc759651

83. Nsc811538

84. S1211

85. Stk583860

86. Zinc19632912

87. Imiquimod - Cas 99011-02-6

88. Imiquimod, >=98% (hplc), Solid

89. Akos005507352

90. Cellulose, Hydrogen 1,2-benzenedicarboxylate, 2-hydroxypropyl Methyl Ether

91. Tox21_110985_1

92. 1h-imidazo[4, 1-(2-methylpropyl)-

93. Ccg-208015

94. Cs-2058

95. Db00724

96. Ks-5218

97. Nsc 369100

98. Nsc 741062

99. Nsc 759651

100. Nsc-811538

101. Yh44175

102. (hydroxypropyl)methyl Cellulose Phthalate

103. Imiquimod 100 Microg/ml In Acetonitrile

104. Ncgc00070736-03

105. Ncgc00070736-04

106. Bi164576

107. Smr000048307

108. Sy017571

109. Ft-0602727

110. I0747

111. D02500

112. 1-isobutyl-1h-imidazo [4,5-c]quinolin-4-amine

113. 1-isobutyl-1h-imidazo[4,5-c]quinoline-4-amine

114. Ab00399298-05

115. Ab00399298-06

116. Ab00399298-07

117. Ab00399298_08

118. Ab00399298_09

119. 011i026

120. 1-isobutyl-1h-imidazo[4,5-c]quinolin-4-ylamine

121. A845945

122. Q423417

123. 1-(2-methylpropyl)-4-imidazo[4,5-c]quinolinamine

124. Sr-01000611320-2

125. Sr-01000611320-3

126. Brd-k26657438-001-01-2

127. Brd-k26657438-001-13-7

128. 1-(2-methylpropyl)-1himidazo[4,5-c]quinolin-4-amine

129. 1-(2-methylpropyl)-1h-imidazo[4,5-c]-quinolin-4-amine

130. Imiquimod, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-06-29
3 Chemical and Physical Properties
Molecular Weight 240.30 g/mol
Molecular Formula C14H16N4
XLogP32.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass240.137496527 g/mol
Monoisotopic Mass240.137496527 g/mol
Topological Polar Surface Area56.7 Ų
Heavy Atom Count18
Formal Charge0
Complexity294
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 Information
1 of 6  
Drug NameAldara
PubMed HealthImiquimod (On the skin)
Drug ClassesImmune Modulator
Drug LabelAldara (imiquimod 5%) Cream is an immune response modifier for topical administration. Each gram contains 50 mg of imiquimod in an off-white oil-in-water vanishing cream base consisting of isostearic acid, cetyl alcohol, stearyl alcohol, white petrol...
Active IngredientImiquimod
Dosage FormCream
RouteTopical
Strength5%
Market StatusPrescription
CompanyMedicis

2 of 6  
Drug NameImiquimod
PubMed HealthImiquimod (On the skin)
Drug ClassesImmune Modulator
Drug LabelAldara (imiquimod 5%) Cream is an immune response modifier for topical administration. Each gram contains 50 mg of imiquimod in an off-white oil-in-water vanishing cream base consisting of isostearic acid, cetyl alcohol, stearyl alcohol, white petrol...
Active IngredientImiquimod
Dosage FormCream
RouteTopical
Strength5%
Market StatusPrescription
CompanyApotex; Teva Pharms Usa; Taro; Strides Pharma; Glenmark Generics; Fougera Pharms; Tolmar; Perrigo Israel

3 of 6  
Drug NameZyclara
PubMed HealthImiquimod (On the skin)
Drug ClassesImmune Modulator
Drug LabelZYCLARA (imiquimod) Cream, 2.5% or 3.75% is intended for topical administration. Each gram contains 25 mg or 37.5 mg of imiquimod, respectively, in a white to faintly yellow oil-in-water cream base consisting of isostearic acid, cetyl alcohol, steary...
Active IngredientImiquimod
Dosage FormCream
Routetopical; Topical
Strength3.75%; 2.5%
Market StatusPrescription
CompanyMedicis; Graceway

4 of 6  
Drug NameAldara
PubMed HealthImiquimod (On the skin)
Drug ClassesImmune Modulator
Drug LabelAldara (imiquimod 5%) Cream is an immune response modifier for topical administration. Each gram contains 50 mg of imiquimod in an off-white oil-in-water vanishing cream base consisting of isostearic acid, cetyl alcohol, stearyl alcohol, white petrol...
Active IngredientImiquimod
Dosage FormCream
RouteTopical
Strength5%
Market StatusPrescription
CompanyMedicis

5 of 6  
Drug NameImiquimod
PubMed HealthImiquimod (On the skin)
Drug ClassesImmune Modulator
Drug LabelAldara (imiquimod 5%) Cream is an immune response modifier for topical administration. Each gram contains 50 mg of imiquimod in an off-white oil-in-water vanishing cream base consisting of isostearic acid, cetyl alcohol, stearyl alcohol, white petrol...
Active IngredientImiquimod
Dosage FormCream
RouteTopical
Strength5%
Market StatusPrescription
CompanyApotex; Teva Pharms Usa; Taro; Strides Pharma; Glenmark Generics; Fougera Pharms; Tolmar; Perrigo Israel

6 of 6  
Drug NameZyclara
PubMed HealthImiquimod (On the skin)
Drug ClassesImmune Modulator
Drug LabelZYCLARA (imiquimod) Cream, 2.5% or 3.75% is intended for topical administration. Each gram contains 25 mg or 37.5 mg of imiquimod, respectively, in a white to faintly yellow oil-in-water cream base consisting of isostearic acid, cetyl alcohol, steary...
Active IngredientImiquimod
Dosage FormCream
Routetopical; Topical
Strength3.75%; 2.5%
Market StatusPrescription
CompanyMedicis; Graceway

4.2 Therapeutic Uses

Adjuvants, Immunologic; Antineoplastic Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 2013)


Imiquimod is used topically for the treatment of clinically typical, nonhyperkeratotic, nonhypertrophic actinic keratosis on the face or scalp in immunocompetent adults; treatment of biopsy-confirmed, primary superficial basal cell carcinoma in immunocompetent adults; and treatment of external genital and perianal exophytic warts (condylomata acuminata) caused by human papillomavirus (HPV). /Included in US product label/

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3577


Topical imiquimod has been effective when used in a limited number of adults and children for the treatment of molluscum contagiosum. /NOT included in US product label/

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3578


Imiquimod 5% cream has been used for the topical treatment of external genital and perianal HPV warts in a limited number of adults with human immunodeficiency virus (HIV) infection; however, the response rate appears to be lower in these individuals than in those who are not HIV infected. /NOT included in US product label/

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3578


For more Therapeutic Uses (Complete) data for Imiquimod (6 total), please visit the HSDB record page.


4.3 Drug Warning

Adverse local reactions, including erythema, erosion, excoriation/flaking, and edema, commonly occur at the site of application of imiquimod and/or surrounding areas. These reactions usually are mild to moderate in severity; however, severe local reactions have been reported.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3578


In controlled studies in adults with actinic keratosis, the most frequently reported local skin reactions in those receiving imiquimod 5% cream (twice weekly for 16 weeks) were erythema (97%), flaking/scaling/dryness (93%), scabbing/crusting (79%), edema (49%), erosion/ulceration (48%), weeping/exudate (22%), and vesicles (9%).1 Application site reactions (e.g., bleeding, burning, induration, irritation, pain, pruritus, stinging, tenderness) occurred in 33% of those receiving topical imiquimod compared with 14% of those receiving placebo. In these studies, 16% of patients discontinued imiquimod treatment because of local or application site reactions and 91% of these were able to resume treatment after a rest period.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3578


Adverse dermatologic reactions at sites away from the site of application have been reported in some patients receiving topical imiquimod. Remote site reactions have included bleeding, burning, edema, erosion, erythema, excoriation/flaking, induration, pain, pruritus, tenderness, tinea cruris, and ulceration.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3579


When imiquimod 5% cream was used in controlled studies in patients with genital and perianal HPV warts (3 times weekly for up to 16 weeks), erythema occurred in 58-65%, erosion in 30-31%, excoriation/flaking in 18-26%, edema in 12-18%, scabbing in 4-13%, induration in 5-7%, ulceration in 4-8%, and vesicles in 2-3% of those receiving the drug.1 In addition, application site reactions in those receiving the drug included pruritus (22-32%), burning (9-26%), pain (2-8%), and soreness (0-3%). In addition, fungal infections occurred in 2-11% of patients receiving the drug. Overall, 1.2% of patients in these studies discontinued treatment because of local or application site reactions.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3579


For more Drug Warnings (Complete) data for Imiquimod (25 total), please visit the HSDB record page.


4.4 Drug Indication

For the topical treatment of clinically typical, nonhyperkeratotic, nonhypertrophic actinic keratoses on the face or scalp in immunocompetent adults. Also indicated for the treatment of external genital and perianal warts/condyloma acuminata in individuals 12 years old and above.


FDA Label


Zyclara is indicated for the topical treatment of clinically typical, non-hyperkeratotic, non-hypertrophic, visible or palpable actinic keratosis of the full face or balding scalp in immunocompetent adults when other topical treatment options are contraindicated or less appropriate.


Imiquimod cream is indicated for the topical treatment of:

- external genital and perianal warts (condylomata acuminata) in adults;

- small superficial basal-cell carcinomas (sBCCs) in adults;

- clinically typical, non-hyperkeratotic, non-hypertrophic actinic keratoses (AKs) on the face or scalp in immunocompetent adult patients when size or number of lesions limit the efficacy and / or acceptability of cryotherapy and other topical treatment options are contraindicated or less appropriate.


Imiquimod cream is indicated for the topical treatment of external genital and perianal warts (condyloma acuminata) in adult patients.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Imiquimod is an immune response modifier that acts as a toll-like receptor 7 agonist. Imiquimod is commonly used topically to treat warts on the skin of the genital and anal areas. Imiquimod does not cure warts, and new warts may appear during treatment. Imiquimod does not fight the viruses that cause warts directly, however, it does help to relieve and control wart production. It is not used on warts inside the vagina, penis, or rectum. Imiquimod is also used to treat a skin condition of the face and scalp called actinic keratoses. Imiquimod can also be used to treat certain types of skin cancer called superficial basal cell carcinoma. Imiquimod is particularly useful on areas where surgery or other treatments may be difficult, complicated or otherwise undesirable, especially the face and lower legs.


5.2 MeSH Pharmacological Classification

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)


Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Interferon Inducers

Agents that promote the production and release of interferons. They include mitogens, lipopolysaccharides, and the synthetic polymers Poly A-U and Poly I-C. Viruses, bacteria, and protozoa have been also known to induce interferons. (See all compounds classified as Interferon Inducers.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
IMIQUIMOD
5.3.2 FDA UNII
P1QW714R7M
5.3.3 Pharmacological Classes
Increased Cytokine Production [PE]; Interferon Inducers [MoA]; Increased Cytokine Activity [PE]
5.4 ATC Code

D06BB10


D06BB10


L03AX


D06BB10

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06B - Chemotherapeutics for topical use

D06BB - Antivirals

D06BB10 - Imiquimod


5.5 Absorption, Distribution and Excretion

Absorption

Well absorbed through skin (as a cream)


Following topical application to the skin in adults with actinic keratosis (75-mg doses 3 times weekly for 16 weeks), 0.08-0.15% of the dose is eliminated in urine as unchanged drug and metabolites. Following topical application in patients with HPV warts, 0.11 or 2.41% of the dose is eliminated in urine as unchanged drug and metabolites in men or women, respectively.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3580


Imiquimod is absorbed systemically following topical application to skin. In adults with actinic keratosis who received topical imiquimod 5% cream 3 times weekly for 16 weeks, mean peak serum concentrations at the end of week 16 were approximately 0.1, 0.2, or 3.5 ng/mL in those treated on the face (12.5-mg doses), scalp (25-mg doses), or hands/arms (75-mg doses), respectively. Systemic exposure appeared to depend more on the surface area of the application site than on the total applied dose. In patients with external genital and perianal human papillomavirus (HPV) warts who received topical imiquimod 5% cream (average dose 4.6 mg), mean peak serum concentrations were 0.4 ng/mL.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3580


5.6 Biological Half-Life

20 hours (topical dose), 2 hours (subcutaneous dose)


Studies using subcutaneous imiquimod indicate the drug has an apparent half-life of 2 hours. Following topical application, imiquimod appears to be retained in the skin for prolonged periods since the half-life is approximately 10 times greater than that reported following subcutaneous administration.

American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 3580


5.7 Mechanism of Action

Imiquimod's mechanism of action is via stimulation of innate and acquired immune responses, which ultimately leads to inflammatory cell infiltration within the field of drug application followed by apoptosis of diseased tissue. Imiquimod does not have direct antiviral activity. Studies of mice show that imiquimod may induce cytokines, including interferon-alpha (IFNA) as well as several IFNA genes (IFNA1, IFNA2, IFNA5, IFNA6, and IFNA8) as well as the IFNB gene. Imiquimod also induced the expression of interleukin (IL)-6, IL-8, and tumor necrosis factor alpha genes. In the treatment of basal cell carcinoma, Imiquimod appears to act as a toll-like receptor-7 agonist, and is thought to exert its anti-tumor effect via modification of the immune response and stimulation of apoptosis in BCC cells. In treating basal cell carcinoma it may increase the infiltration of lymphocytes, dendritic cells, and macrophages into the tumor lesion.


Imiquimod and resiquimod represent Toll-like receptor (TLR) 7 and 8 agonists, which emerged as attractive candidates for tumor therapy. To elucidate immune cells, which mainly contribute to TLR7/8-mediated antitumoral activity, /the researchers/ investigated the impact of imiquimod and resiquimod on native human 6-sulfo LacNAc (slan) dendritic cells (DCs). /The researchers/ found that both TLR7/8 agonists significantly improve the release of various proinflammatory cytokines by slanDCs and promote their tumor-directed cytotoxic activity. Furthermore, resiquimod efficiently augmented the ability of slanDCs to stimulate T cells and natural killer cells. These results indicate that imiquimod and resiquimod trigger various immunostimulatory properties of slanDCs, which may contribute to their antitumor effects.

PMID:23402811 Jahnisch H et al; Cancer Lett. 2013 Feb 9 (Epub ahead of print)


Aldara is a cream used for topical treatment of non-melanoma skin cancer, and is thought to act through stimulation of anti-tumour immunity. The active ingredient, imiquimod, has been shown to stimulate toll-like receptor 7. Aldara also induces psoriasis-like lesions when applied to naive murine skin, and as such is used as a mouse model for psoriasis. Here we find that in naive murine skin, Aldara induces inflammation largely independently of toll-like receptor 7. Surprisingly, inflammasome activation, keratinocyte death and interleukin 1 release also occur in response to the vehicle cream in the absence of imiquimod. We show that isostearic acid, a major component of the vehicle, promotes inflammasome activation in cultured keratinocytes, and so may contribute to the observed effects of Aldara on murine skin. Aldara therefore stimulates at least two immune pathways independently, and both imiquimod and vehicle are required for a full inflammatory response. Although it remains to be tested, it is possible that imiquimod-independent effects also contribute to the therapeutic efficacy of Aldara.

PMID:23463003 Walter A et al; Nat Commun. 2013 Mar 5;4:1560


Imiquimod is recognized as an agonist for Toll-like receptor 7 (TLR7) in immunocompetent cells. TLR7, as well as TLR3 and TLR8, triggers the immune responses, such as the production of type I interferons (IFNs) and proinflammatory cytokines via recognition of viral nucleic acids in the infected cells. In this study, /the reseachers/ proposed that imiquimod has an IFN-independent antiviral effect in nonimmune cells. Imiquimod, but not resiquimod, suppressed replication of human herpes simplex virus 1 (HSV-1) in FL cells. We analyzed alternation of gene expression by treatment with imiquimod using microarray analysis. Neither type I IFNs, nor TLRs, nor IFN-inducible antiviral genes were induced in imiquimod-treated FL cells. Cystatin A, a host cysteine protease inhibitor, was strongly upregulated by imiquimod and took a major part in the anti-HSV-1 activity deduced by the suppression experiment using its small interfering RNA. Upregulation of cystatin A was suggested to be mediated by antagonizing adenosine receptor A(1) and activating the protein kinase A pathway. Imiquimod, but not resiquimod, was shown to interact with adenosine receptor A(1). Imiquimod-induced anti-HSV-1 activity was observed in other cells, such as HeLa, SiHa, and CaSki cells, in a manner consistent with the cystatin A induction by imiquimod. These results indicated that imiquimod acted as an antagonist for adenosine receptor A(1) and induced a host antiviral protein, cystatin A. The process occurred independently of TLR7 and type I IFNs.

PMID:22787201 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3457300 Kan Y et al; J Virol 86 (19): 10338-46 (2012)


Toll-like receptor (TLR) agonists have anticancer effect by inducing apoptosis or activating immune cells. In this study, we investigated whether imiquimod, TLR7 agonist, inhibits the proliferation of oral cancer cells. Toll-like receptor 7 expression and IL-6/8 production by imiquimod were examined using RT-PCR and Enzyme-linked immunosorbent assay, respectively. Cell viability was examined by MTT assay. To examine apoptotic cell death, Annexin V/PI staining for flow cytometry and Western blot analysis were performed. Necrotic cell death was determined by leakage of lactate dehydrogenase (LDH), HMGB1, and PI staining in imiquimod-treated oral squamous cell carcinoma (OSCC) cells. Toll-like receptor 7 mRNA was expressed in OSCC cells. Imiquimod induced IL-6 and IL-8 production in OSCC cells, suggesting the functional expression of TLR7. Imiquimod inhibited cells proliferation in a dose-dependent manner. The ratio of annexin V-positive cells and cleaved caspase-3/7 was increased by imiquimod treatment in OSCC cells, suggesting that imiquimod-induced cell death in OSCC cells may be owing to apoptosis. In addition, LDH secretion and PI staining were detected in OSCC cells treated with imiquimod, showing that imiquimod also induced necrotic cell death in the OSCC cells. Imiquimod inhibited effectively the growth of OSCC cells by inducing apoptosis and necrosis.

PMID:22577802 Ahn MY et al; J Oral Pathol Med 41 (7): 540-6 (2012)


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Imiquimod (USP)

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Address of the Firm : Plot No. Z-103/l, Dahej SEZ, Phase ll, Dahej, Dist-Bharuch, Gujarat

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Written Confirmation Number : WC-0012

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Imiquimod

About the Company : Interquim, founded in 1978, is now part of the Ferrer HealthTech division. Interquim specializes in the development of competitive processes for manufacturing high added-value APIs...

Interquim, founded in 1978, is now part of the Ferrer HealthTech division. Interquim specializes in the development of competitive processes for manufacturing high added-value APIs that meet stringent quality standards. Complying with European environmental and work safety regulations, Interquim’s products are exported to highly regulated pharmaceutical markets. Regulatory bodies and clients have approved its quality system and facilities. With state-of-the-art multi-production plants, drug synthesis, and quality-control labs, Interquim supports clients throughout the entire product lifecycle, from product development to marketing.
Interquim

02

LGM Pharma

U.S.A
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Virtual BoothLGM Pharma accelerates & optimizes the new product pathway from early development through commercialization.

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Imiquimod

About the Company : LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, ...

LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, analytical method development and testing, and commercial manufacturing. LGM Pharma offers custom API synthesis, analytical development, and regulatory services. With a network of over 300 accredited CGMP manufacturing partners, LGM provides unparalleled supply chain security. And, with over 100,000 square feet of FDA-inspected cGMP manufacturing and warehouse capacity, LGM Pharma provides a one-stop solution for solid dose, powder, semi-solid and liquid drugs.
LGM Pharma CB

03

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Imiquimod

About the Company : We are a Pharmaceutical Company aligned across two business verticals viz. Products and Services. Our Products business comprises manufacture and sale of APIs and Intermediates to ...

We are a Pharmaceutical Company aligned across two business verticals viz. Products and Services. Our Products business comprises manufacture and sale of APIs and Intermediates to innovator and generic pharmaceutical players in both Domestic and International markets including the regulated markets.
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04

AXYNTIS Group

France
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AXYNTIS Group

France
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Imiquimod

About the Company : Axyntis Group, founded in 2007, is France’s leading independent multi-site player in fine chemicals with a €90 million annual turnover. Axyntis has become a key producer of API...

Axyntis Group, founded in 2007, is France’s leading independent multi-site player in fine chemicals with a €90 million annual turnover. Axyntis has become a key producer of APIs in France through acquisitions & partnerships. It has two divisions (dyes and fine chemicals) and places a strong focus on diversification and innovation. It operates 3 cGMP sites in France, of which 2 are FDA-inspected. It provides CDMO services to its partners for their API or advanced intermediate projects, from early-stage development to the commercial phase, including preparative chromatography (Kyrapharm subsidiary). It also commercializes proprietary APIs.
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05

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Imiquimod

About the Company : Glenmark was founded with a vision to emerge as a leading integrated research-based, global pharmaceutical company. Our branded generics business has a significant presence in mark...

Glenmark was founded with a vision to emerge as a leading integrated research-based, global pharmaceutical company. Our branded generics business has a significant presence in markets across emerging economies including India. The generics business services the requirements of developed markets like US and Western Europe. Our API business sells products in over 65 countries including the US, various countries in the EU, South America and India. With 15 manufacturing facilities and 3 R&D centers dedicated to the goal of enriching lives across the globe.
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06

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Imiquimod

About the Company : Guangzhou Tosun Pharmaceutical was founded in 1999, which mainly focuses on importation & exportation of Active Pharmaceutical Ingrediants, Chemical Raw Materials, Intermediate, Ex...

Guangzhou Tosun Pharmaceutical was founded in 1999, which mainly focuses on importation & exportation of Active Pharmaceutical Ingrediants, Chemical Raw Materials, Intermediate, Excipients, Herbal extracts, Formulation of Chinese & Western Medicine. With abundant economic strength, the group has successfully developed to a pharmaceutical group enterprise wich intergrets operation of medicine & related products, processing & manufacturing, and importation & exportation together.
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07

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Imiquimod

About the Company : Solara Active Pharma Sciences is a young, dynamic, entrepreneurial and customer oriented API manufacturer. We have a legacy of over three decades and trace our origins to the API e...

Solara Active Pharma Sciences is a young, dynamic, entrepreneurial and customer oriented API manufacturer. We have a legacy of over three decades and trace our origins to the API expertise of Strides Shasun Ltd. and the technical know-how of human API business from Sequent Scientific Ltd. We are poised to bridge the industry gap by delivering value based products while maintaining focus on the customer needs. We have 140+ scientists working at our two R&D Centers and 4 API manufacturing facilities armed with global approvals and 2 dedicated R&D facilities.
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08

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Imiquimod

About the Company : For more than half a century, Taro Pharmaceuticals has been dedicated to developing, manufacturing, distributing, and marketing pharmaceutical products. As such, we help to resto...

For more than half a century, Taro Pharmaceuticals has been dedicated to developing, manufacturing, distributing, and marketing pharmaceutical products. As such, we help to restore health and protect against disease. To uphold our proud history, we have a responsibility to our business, our customers, and the communities we serve to maintain the highest standards of excellence, safety, and quality for our products. As a Company, we are all expected to act ethically and comply with all applicable laws and regulations that govern our business. This Code of Conduct—together with our Compliance Policies.
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09

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Imiquimod

About the Company : Teva was established in 1901. Our global headquarters are based in Israel. Today we have a portfolio of more than 3,500 medicines, and produce approximately 120 billion tablets and...

Teva was established in 1901. Our global headquarters are based in Israel. Today we have a portfolio of more than 3,500 medicines, and produce approximately 120 billion tablets and capsules a year at 70 manufacturing facilities. We rank among the leading pharmaceutical companies in the world and are active in 60 countries. Approximately 43,000 employees around the world are dedicated to our mission. Building on our strong global footprint, size and scale, Teva is reaffirming its commitment to place people at the center of our strategy, and enable as many as possible to live better, healthier days.
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10

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Imiquimod

About the Company : Tocopharm Co. Limited, built in 2008,is an industry leader in the field of Active Pharmaceutical Ingredients(API), relative pharmaceutical intermediates, derivatives of Quinoline d...

Tocopharm Co. Limited, built in 2008,is an industry leader in the field of Active Pharmaceutical Ingredients(API), relative pharmaceutical intermediates, derivatives of Quinoline derivatives of Beta-cyclodextrin and custom synthesis services. We are specialized in exploring,researching and production of these chemicals. We are also able to provide our customers with professional services and products with high quality. Tocopharm is in possession of two R&D laboratories and two factories in mainland China. Our products are made to the strictest quality control standards and meet all government regulations. At Tocopharm, our ever increasing global presence has been achieved through world class customer service and our commitment to innovation. We work with each individual customer to develop a solution that not only meets their demands, it exceeds them.Our products have been widely sold to many countries and regions that we have established long-term stable relations of cooperation with the traders and end users all around the world and have become a solid bridge among the suppliers, traders and end users.
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LIMITED","supplierCountry":"INDIA","foreign_port":"GUARULHOS","customer":"TO THE ORDER","customerCountry":"BRAZIL","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"2420","totalValueFC":"4793.5","currency":"USD","unitRateINR":206668,"date":"27-Jan-2025","totalValueINR":"413336","totalValueInUsd":"4793.5","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"7642247","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"BRAZIL","selfForZScoreResived":"Pharma Grade","supplierPort":"Bombay Air","supplierAddress":"PLOT 170-172, CHANDRAMOULI,INDUSTR, SOLAPUR,MAHARASHTRA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2025","qtr":"Q1","strtotime":1738002600,"product":"IMIQUIMOD USP BATCH NO.: 82242238","address":"PLOT NO 126, UDYOG NAGAR, NEAR AUTO BAJAJ SERVICES CENTER","city":"Navi Mumbai","supplier":"ZEON PHARMA INDUSTRIES INDIA PVT LTD","supplierCountry":"INDIA","foreign_port":"ASUNCION","customer":"QUIMFA S.A","customerCountry":"PARAGUAY","quantity":"10.00","actualQuantity":"10","unit":"KGS","unitRateFc":"1100","totalValueFC":"10119.3","currency":"USD","unitRateINR":87257.731,"date":"28-Jan-2025","totalValueINR":"872577.31","totalValueInUsd":"10119.3","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"7661395","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"PARAGUAY","selfForZScoreResived":"Pharma Grade","supplierPort":"Bombay Air","supplierAddress":"PLOT NO 126, UDYOG NAGAR, NEAR AUTO BAJAJ SERVICES CENTER, Navi Mumbai","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2025","qtr":"Q1","strtotime":1738089000,"product":"IMIQUIMOD USP B\/N: 21003115 , MFG. 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D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,","city":"TURKAPALLY-V SHAMIRPET HYDERABAD,TE","supplier":"USP","supplierCountry":"INDIA","foreign_port":"NA","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.000025","unit":"KGS","unitRateFc":"34400000","totalValueFC":"899.8","currency":"USD","unitRateINR":"2715651600","date":"14-Apr-2022","totalValueINR":"67891.29","totalValueInUsd":"899.8","indian_port":"HYDERABAD AIR","hs_no":"29339990","bill_no":"8276555","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"P.NO. D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1689186600,"product":"IMIQUIMOD (FOR R & D)","address":"803, 8TH FLOOR,,HDIL B WING, KALED ONIA, SAHAR ROAD,","city":"MUMBAI,MAHARASHTRA","supplier":"INTERQUIM SA","supplierCountry":"SPAIN","foreign_port":"NA","customer":"ENCUBE ETHICALS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.08","actualQuantity":"0.075","unit":"KGS","unitRateFc":"12000","totalValueFC":"995.9","currency":"EUR","unitRateINR":"1091399.9","date":"13-Jul-2023","totalValueINR":"81854.745","totalValueInUsd":"995.9","indian_port":"BOMBAY AIR","hs_no":"29339990","bill_no":"0","productDescription":"API","marketType":"REGULATED MARKET","country":"SPAIN","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"803, 8TH FLOOR,,HDIL B WING, KALED ONIA, SAHAR ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2025","qtr":"Q1","strtotime":1736101800,"product":"IMIQUIMOD (IMIQUIMOD USP) IMIQUIMOD (IMIQUIMOD USP)","address":"UNIT NO.24 STEEL MADE INDL.ESTATE","city":"MUMBAI","supplier":"INTERQUIM SA","supplierCountry":"SPAIN","foreign_port":"BARCELONA","customer":"ENCUBE ETHICALS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"3.00","actualQuantity":"3","unit":"KGS","unitRateFc":"10912.2","totalValueFC":"32877.5","currency":"N\/A","unitRateINR":"945000","date":"06-Jan-2025","totalValueINR":"2835000","totalValueInUsd":"32877.5","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"7631601","productDescription":"API","marketType":"REGULATED MARKET","country":"SPAIN","selfForZScoreResived":"Pharma Grade","supplierPort":"BARCELONA","supplierAddress":"JOAN BUSCALLA, 10 08173 SANT CUGAT DEL VALLES BARCELONA ES","customerAddress":"UNIT NO.24 STEEL MADE INDL.ESTATE"},{"dataSource":"API Import","activeIngredients":"","year":"2025","qtr":"Q1","strtotime":1736101800,"product":"IMIQUIMOD (IMIQUIMOD USP) IMIQUIMOD (IMIQUIMOD USP)","address":"UNIT NO.24 STEEL MADE INDL.ESTATE","city":"MUMBAI","supplier":"INTERQUIM SA","supplierCountry":"SPAIN","foreign_port":"BARCELONA","customer":"ENCUBE ETHICALS PRIVATE LIMITED","customerCountry":"INDIA","quantity":"5.00","actualQuantity":"5","unit":"KGS","unitRateFc":"10912.2","totalValueFC":"54795.8","currency":"N\/A","unitRateINR":"945000","date":"06-Jan-2025","totalValueINR":"4725000","totalValueInUsd":"54795.8","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"7631601","productDescription":"API","marketType":"REGULATED MARKET","country":"SPAIN","selfForZScoreResived":"Pharma Grade","supplierPort":"BARCELONA","supplierAddress":"JOAN BUSCALLA, 10 08173 SANT CUGAT DEL VALLES BARCELONA ES","customerAddress":"UNIT NO.24 STEEL MADE INDL.ESTATE"}]
16-Jan-2021
29-Jan-2025
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ABOUT THIS PAGE

Looking for 99011-02-6 / Imiquimod API manufacturers, exporters & distributors?

Imiquimod manufacturers, exporters & distributors 1

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

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Imiquimod manufacturer or Imiquimod supplier.

PharmaCompass also assists you with knowing the Imiquimod API Price utilized in the formulation of products. Imiquimod API Price is not always fixed or binding as the Imiquimod Price is obtained through a variety of data sources. The Imiquimod Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Imiquimod

Synonyms

99011-02-6, Aldara, Zyclara, 1-isobutyl-1h-imidazo[4,5-c]quinolin-4-amine, 1-(2-methylpropyl)-1h-imidazo[4,5-c]quinolin-4-amine, Beselna

Cas Number

99011-02-6

Unique Ingredient Identifier (UNII)

P1QW714R7M

About Imiquimod

A topically-applied aminoquinoline immune modulator that induces interferon production. It is used in the treatment of external genital and perianal warts, superficial CARCINOMA, BASAL CELL; and ACTINIC KERATOSIS.

Imiquimod Manufacturers

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

click here to find a list of Imiquimod manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Imiquimod Suppliers

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

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

Imiquimod USDMF

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

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

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

Imiquimod KDMF

In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

Pharmaceutical companies submit a Imiquimod Drug Master File in Korea (Imiquimod KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Imiquimod. The MFDS reviews the Imiquimod KDMF as part of the drug registration process and uses the information provided in the Imiquimod KDMF to evaluate the safety and efficacy of the drug.

After submitting a Imiquimod KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Imiquimod API can apply through the Korea Drug Master File (KDMF).

click here to find a list of Imiquimod suppliers with KDMF on PharmaCompass.

Imiquimod WC

A Imiquimod written confirmation (Imiquimod WC) is an official document issued by a regulatory agency to a Imiquimod manufacturer, verifying that the manufacturing facility of a Imiquimod active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Imiquimod APIs or Imiquimod finished pharmaceutical products to another nation, regulatory agencies frequently require a Imiquimod WC (written confirmation) as part of the regulatory process.

click here to find a list of Imiquimod suppliers with Written Confirmation (WC) on PharmaCompass.

Imiquimod NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Imiquimod as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Imiquimod API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Imiquimod as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Imiquimod and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Imiquimod NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Imiquimod suppliers with NDC on PharmaCompass.

Imiquimod GMP

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

Imiquimod CoA

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

Imiquimod CoA mostly includes findings from lab analyses of a specific batch. For each Imiquimod 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.

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