Ingenol 3-Hexanoate
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MedKoo CAT#: 561544

CAS#: 83036-61-7

Description: Ingenol 3-Hexanoate novel potent reactivator of latent HIV-1.


Chemical Structure

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Ingenol 3-Hexanoate
CAS# 83036-61-7

Theoretical Analysis

MedKoo Cat#: 561544
Name: Ingenol 3-Hexanoate
CAS#: 83036-61-7
Chemical Formula: C26H38O6
Exact Mass: 446.27
Molecular Weight: 446.584
Elemental Analysis: C, 69.93; H, 8.58; O, 21.50

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 650 2 Weeks
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Synonym: Ingenol 3-Hexanoate; Ingenol B

IUPAC/Chemical Name: (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a-Dihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-11-oxo-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclpropa[e][10]annulen-6-yl hexanoate

InChi Key: LYWIFBNBLVOVKN-FOJFYXSBSA-N

InChi Code: InChI=1S/C26H38O6/c1-6-7-8-9-19(28)32-23-14(2)12-25-15(3)10-18-20(24(18,4)5)17(22(25)30)11-16(13-27)21(29)26(23,25)31/h11-12,15,17-18,20-21,23,27,29,31H,6-10,13H2,1-5H3/t15-,17+,18-,20+,21-,23+,25+,26+/m1/s1

SMILES Code: CCCCCC(O[C@H]1C(C)=C[C@]23[C@]1(O)[C@H](O)C(CO)=C[C@@](C3=O)([H])[C@@]4([H])[C@@](C4(C)C)([H])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

Shelf Life: >2 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

More Info:

Product Data:
Biological target: Ingenol 3-Hexanoate, or Ingenol B, is a novel potent reactivator of latent HIV-1.
In vitro activity: One of the sgRNAs (LTR5), which binds specifically in the HIV-1 LTR NFκB binding site, was able to promote robust repression of HIV-1 reactivation in latently infected T cells stimulated with Phorbol 12-Myristate 13-Acetate (PMA) and Ingenol B (IngB), both potent protein kinase C (PKC) stimulators. Reference: Retrovirology. 2022 Jun 22;19(1):12. https://pubmed.ncbi.nlm.nih.gov/35733180/
In vivo activity: However, significant toxicity risks and the lack of evidence supporting their activity in vivo have limited further evaluation of PKC agonists as HIV latency-reversing agents (LRA) in cure strategies. Here this study evaluated whether GSK445A, a stabilized ingenol-B derivative, can induce HIV/simian immunodeficiency virus (SIV) transcription and virus production in vitro and demonstrate pharmacological activity in nonhuman primates (NHP). In vivo, GSK445A tolerability was established in SIV-naïve RM at 15 μg/kg although tolerability was reduced in SIV-infected RM on ART. Increases in plasma viremia following GSK445A administration were suggestive of increased SIV transcription in vivo. Collectively, these results indicate that GSK445A is a potent HIV/SIV LRA in vitro and has a tolerable safety profile amenable for further evaluation in vivo in NHP models of HIV cure/remission. Reference: PLoS Pathog. 2022 Jan 18;18(1):e1010245. https://pubmed.ncbi.nlm.nih.gov/35041707/

Preparing Stock Solutions

The following data is based on the product molecular weight 446.58 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. da Costa LC, Bomfim LM, Dittz UVT, Velozo CA, da Cunha RD, Tanuri A. Repression of HIV-1 reactivation mediated by CRISPR/dCas9-KRAB in lymphoid and myeloid cell models. Retrovirology. 2022 Jun 22;19(1):12. doi: 10.1186/s12977-022-00600-9. PMID: 35733180; PMCID: PMC9215058. 2. Okoye AA, Fromentin R, Takata H, Brehm JH, Fukazawa Y, Randall B, Pardons M, Tai V, Tang J, Smedley J, Axthelm M, Lifson JD, Picker LJ, Favre D, Trautmann L, Chomont N. The ingenol-based protein kinase C agonist GSK445A is a potent inducer of HIV and SIV RNA transcription. PLoS Pathog. 2022 Jan 18;18(1):e1010245. doi: 10.1371/journal.ppat.1010245. PMID: 35041707; PMCID: PMC8797195.
In vitro protocol: 1. da Costa LC, Bomfim LM, Dittz UVT, Velozo CA, da Cunha RD, Tanuri A. Repression of HIV-1 reactivation mediated by CRISPR/dCas9-KRAB in lymphoid and myeloid cell models. Retrovirology. 2022 Jun 22;19(1):12. doi: 10.1186/s12977-022-00600-9. PMID: 35733180; PMCID: PMC9215058.
In vivo protocol: 1. Okoye AA, Fromentin R, Takata H, Brehm JH, Fukazawa Y, Randall B, Pardons M, Tai V, Tang J, Smedley J, Axthelm M, Lifson JD, Picker LJ, Favre D, Trautmann L, Chomont N. The ingenol-based protein kinase C agonist GSK445A is a potent inducer of HIV and SIV RNA transcription. PLoS Pathog. 2022 Jan 18;18(1):e1010245. doi: 10.1371/journal.ppat.1010245. PMID: 35041707; PMCID: PMC8797195.

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1: Sorg B, Schmidt R, Hecker E. Structure/activity relationships of polyfunctional diterpenes of the ingenane type. I. Tumor-promoting activity of homologous, aliphatic 3-esters of ingenol and of delta 7,8-isoingenol-3-tetradecanoate. Carcinogenesis. 1987 Jan;8(1):1-4. PubMed PMID: 3100081.