Ingenol Mebutate

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

MedKoo CAT#: 201545

CAS#: 75567-37-2

Description: Ingenol mebutate, also known as ingenol-3-angelate, is a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death. Ingenol Mebutate was approved for the topical treatment of actinic keratosis. Ingenol mebutate has also been found to be useful for reactivating latent HIV virus in cells taken from individuals who have tested negative for signs of the disease following extended courses of anti-retroviral drugs, raising the possibility that this drug may be used to expose the last traces of virus, and thus potentially provide a permanent cure for HIV infection.

Chemical Structure

Ingenol Mebutate
CAS# 75567-37-2

Theoretical Analysis

MedKoo Cat#: 201545
Name: Ingenol Mebutate
CAS#: 75567-37-2
Chemical Formula: C25H34O6
Exact Mass: 430.23554
Molecular Weight: 430.53
Elemental Analysis: C, 69.74; H, 7.96; O, 22.30

Price and Availability

Size Price Availability Quantity
5.0mg USD 150.0 Same day
10.0mg USD 250.0 Same day
25.0mg USD 450.0 Same day
50.0mg USD 750.0 Same day
100.0mg USD 1350.0 Same day
200.0mg USD 2150.0 Same day
500.0mg USD 3950.0 Same day
1.0g USD 5950.0 2 weeks
2.0g USD 9950.0 2 weeks
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Synonym: PEP005; PEP-005; PEP 005; ingenol-3-angelate, Ingenol mebutate; trade name Picato

IUPAC/Chemical Name: (Z)-(1aS,5R,5aS,6S,9R)-5,5a-dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-6-yl 2-methylbut-2-enoate


InChi Code: InChI=1S/C25H34O6/c1-7-12(2)22(29)31-21-13(3)10-24-14(4)8-17-18(23(17,5)6)16(20(24)28)9-15(11-26)19(27)25(21,24)30/h7,9-10,14,16-19,21,26-27,30H,8,11H2,1-6H3/b12-7-/t14-,16?,17?,18-,19-,21+,24?,25+/m1/s1

SMILES Code: C/C=C(C)\C(O[C@H]1C(C)=CC23[C@]1(O)[C@H](O)C(CO)=CC(C3=O)[C@]4([H])C(C4(C)C)C[C@H]2C)=O

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 soluble in water.

Shelf Life: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 430.53 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

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1: Bobyr I, Campanati A, Consales V, Giangiacomi M, Diotallevi F, Offidani A. Granuloma faciale successfully treated with ingenol mebutate. Dermatol Ther. 2016 Jun 30. doi: 10.1111/dth.12368. [Epub ahead of print] PubMed PMID: 27364361.

2: Bettencourt MS. Tolerability of Ingenol Mebutate Gel, 0.05%, for Treating Patients with Actinic Keratosis on the Scalp in a Community Dermatology Practice. J Clin Aesthet Dermatol. 2016 Mar;9(3):20-4. Epub 2016 Mar 1. PubMed PMID: 27354884; PubMed Central PMCID: PMC4896817.

3: Bobyr I, Campanati A, Consales V, Giuliodori K, Scalise A, Offidani A. Efficacy, safety and tolerability of field treatment of actinic keratosis with ingenol mebutate 0.015 % gel: a single center case series. Springerplus. 2016 May 14;5:627. doi: 10.1186/s40064-016-2290-6. eCollection 2016. PubMed PMID: 27330893; PubMed Central PMCID: PMC4870479.

4: Monfrecola G, Scalvenzi M, Costa C, Cantelli M, Fabbrocini G. Ingenol mebutate for pigmented superficial basal cell carcinomas: evaluation by confocal microscopy. G Ital Dermatol Venereol. 2016 Jun 10. [Epub ahead of print] PubMed PMID: 27284778.

5: Flórez Á, Batalla A, de la Torre C. Management of actinic cheilitis using ingenol mebutate gel: A report of seven cases. J Dermatolog Treat. 2016 May 31:1-3. [Epub ahead of print] PubMed PMID: 27241280.

6: Braun SA, Gerber PA. Successful treatment of perianal condylomata acuminata with ingenol mebutate gel. J Dtsch Dermatol Ges. 2016 Jun;14(6):616-7. doi: 10.1111/ddg.12879. Epub 2016 May 17. PubMed PMID: 27187666.

7: Berman B, Stockfleth E. Field Treatment of Actinic Keratosis With Ingenol Mebutate. J Drugs Dermatol. 2016 May 1;15(5):535-42. PubMed PMID: 27168262.

8: Emilio J, Schwartz M, Feldman E, Bieber AK, Bienenfeld A, Jung MK, Siegel DM, Markowitz O. Improved patient satisfaction using ingenol mebutate gel 0.015% for the treatment of facial actinic keratoses: a prospective pilot study. Clin Cosmet Investig Dermatol. 2016 Apr 20;9:89-93. doi: 10.2147/CCID.S100999. eCollection 2016. PubMed PMID: 27143946; PubMed Central PMCID: PMC4845892.

9: Elías I, Ortega-Joaquín N, de la Cueva P, Del Pozo LJ, Moreno-Ramírez D, Boada A, Aguilar M, Mirada A, Mosquera E, Gibbons C, Oyagüez I. Cost-Effectiveness and Cost-Utility Analysis of Ingenol Mebutate Versus Diclofenac 3% and Imiquimod 5% in the Treatment of Actinic Keratosis in Spain. Actas Dermosifiliogr. 2016 Jul-Aug;107(6):498-508. doi: 10.1016/ Epub 2016 Apr 26. English, Spanish. PubMed PMID: 27130804.

10: Le TT, Skak K, Schroder K, Schroder WA, Boyle GM, Pierce CJ, Suhrbier A. IL-1 Contributes to the Anti-Cancer Efficacy of Ingenol Mebutate. PLoS One. 2016 Apr 21;11(4):e0153975. doi: 10.1371/journal.pone.0153975. eCollection 2016. PubMed PMID: 27100888; PubMed Central PMCID: PMC4839727.

11: Grandi V, Delfino C, Pimpinelli N. Ingenol mebutate in the treatment of 'Hydroxyurea-induced Squamous Dysplasia': a single centre experience. J Eur Acad Dermatol Venereol. 2016 Jul;30(7):1129-32. doi: 10.1111/jdv.13616. Epub 2016 Apr 13. PubMed PMID: 27072602.

12: Hanke WC, Norlin JM, Mark Knudsen K, Larsson T, Stone S. Quality of life in treatment of AK: Treatment burden of ingenol mebutate gel is small and short lasting. J Dermatolog Treat. 2016 Apr 7:1-6. [Epub ahead of print] PubMed PMID: 27052110.

13: Mohanna M, Hofbauer G. Pronounced local skin reaction to ingenol mebutate against actinic keratosis in kidney transplant recipient without systemic adverse events. JAAD Case Rep. 2015 Nov 24;1(6):S19-22. doi: 10.1016/j.jdcr.2015.09.011. eCollection 2015 Nov. PubMed PMID: 27051801; PubMed Central PMCID: PMC4809621.

14: Ricci F, Tambone S, Neri L, Fania L, Piccioni A, Guerriero C, Fargnoli MC, Peris K. Real-life efficacy and safety of ingenol mebutate for the treatment of actinic keratosis of the face and scalp: A single arm retrospective study. J Dermatolog Treat. 2016 Apr 4:1-6. [Epub ahead of print] PubMed PMID: 27043050.

15: Garmyn M. Ingenol mebutate for actinic keratosis: a field-directed therapy with short duration. Br J Dermatol. 2016 Mar;174(3):481-2. doi: 10.1111/bjd.14429. PubMed PMID: 27002568.

16: Salleras Redonnet M, Quintana Codina M. Ingenol mebutate gel for the treatment of Bowen's disease: a case report of three patients. Dermatol Ther. 2016 Mar 11. doi: 10.1111/dth.12344. [Epub ahead of print] PubMed PMID: 26969886.

17: Kim C, Hashemi P, Caglia M, Shulman K. Treatment of Imiquimod Resistant Epidermodysplasia Verruciformis With Ingenol Mebutate. J Drugs Dermatol. 2016 Mar 1;15(3):350-2. PubMed PMID: 26954321.

18: Bhandari PR, Pai VV. Could ingenol mebutate be useful in managing nonmelanoma skin cancers? Indian J Cancer. 2015 Apr-Jun;52(2):249-50. doi: 10.4103/0019-509X.175820. PubMed PMID: 26853424.

19: Longo C, Borsari S, Benati E, Moscarella E, Alfano R, Argenziano G. Dermoscopy and Reflectance Confocal Microscopy for Monitoring the Treatment of Actinic Keratosis with Ingenol Mebutate Gel: Report of Two Cases. Dermatol Ther (Heidelb). 2016 Mar;6(1):81-7. doi: 10.1007/s13555-016-0094-9. Epub 2016 Feb 4. PubMed PMID: 26847171; PubMed Central PMCID: PMC4799035.

20: Erlendsson AM, Karmisholt KE, Haak CS, Stender IM, Haedersdal M. Topical corticosteroid has no influence on inflammation or efficacy after ingenol mebutate treatment of grade I to III actinic keratoses (AK): A randomized clinical trial. J Am Acad Dermatol. 2016 Apr;74(4):709-15. doi: 10.1016/j.jaad.2015.11.034. Epub 2016 Jan 22. PubMed PMID: 26810403.

Additional Information