Compounds > hecogenin acetate
Page last updated: 2024-12-07

hecogenin acetate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Hecogenin acetate is a steroidal saponin derived from the agave plant. It has been shown to exhibit a variety of biological activities, including anti-inflammatory, anti-cancer, and antiviral properties. Hecogenin acetate has been studied for its potential therapeutic applications in treating various diseases, including cancer, inflammation, and viral infections. The compound is synthesized through extraction and purification from agave plants. Hecogenin acetate is of interest to researchers due to its unique chemical structure and its potential medicinal properties.'

hecogenin acetate: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID101906
CHEMBL ID2332640
CHEBI ID168130
SCHEMBL ID353226
MeSH IDM0492170

Synonyms (38)

Synonym
spirostan-12-one, 3-(acetyloxy)-, (3beta,5alpha,25r)-
[(1r,2s,4s,5'r,6r,7s,8r,9s,12s,13s,16s,18s)-5',7,9,13-tetramethyl-10-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl] acetate
CHEBI:168130
hecogenin, acetate
nsc-15489
hecogenin acetate
915-35-5
5.alpha.-spirostan-12-one, acetate, (25r)-
nsc15489 ,
hecogenin acetate, >=90%
5k0wkd513r ,
(3beta,5alpha,25r)-12-oxospirostan-3-yl acetate
5alpha,25d-spirostan-12-one, 3beta-hydroxy-, acetate
3beta-acetoxy-5alpha-spirostan-12-one
12-oxo-5-alpha-spirostan-3-beta-yl acetate
nsc 15489
einecs 213-021-7
unii-5k0wkd513r
ai3-44894
CHEMBL2332640
SCHEMBL353226
CVKZWRTYHCDWTE-RSEFXUKDSA-N
spirostan-12-one, 3-(acetyloxy)-, (3b,5a,25r)-
j195.206d ,
(22r,25r)-3.beta.-acetoxy-5.alpha.-spirostane-12-one
5.alpha.,25d-spirostan-12-one, 3.beta.-hydroxy-, acetate
spirostan-12-one, 3-(acetyloxy)-, (3.beta.,5.alpha.,25r)-
5.alpha.-spirostan-12-one, 3.beta.-hydroxy-, acetate, (25r)-
3.beta.-acetoxy-5.alpha.-spirostan-12-one
(3.beta.,5.alpha.,25r)-12-oxospirostan-3-yl acetate
12-oxo-5-.alpha.-spirostan-3-.beta.-yl acetate
(-)-hecogenin acetate
(22r,25r)-12-oxo-28-oxa-5.alpha.-spirosolane-3.beta.-ol acetate
mfcd00005088
3beta-acetoxy-(25r)-5alpha-spirostan-12-one
CS-0108520
HY-126941
Q27262471

Research Excerpts

Overview

Hecogenin acetate is a saponin present in plants of the agave genus with analgesic, antioxidant, antinociceptive, cardioactive, anticancer, antifungal and antimicrobial activity. It has shown potential antihyperalgesic activity, inhibiting descending pain and acting in opioid receptors.

ExcerptReferenceRelevance
"Hecogenin acetate is a saponin present in plants of the agave genus with analgesic, antioxidant, antinociceptive, cardioactive, anticancer, antifungal and antimicrobial activity."( Evaluation of the antibacterial activity of hecogenin acetate and its inhibitory potential of NorA and MepA efflux pumps from Staphylococcus aureus.
Andrade-Pinheiro, JC; Barbosa Filho, JM; Costa, MDS; Lobo Soares de Matos, YM; Melo Coutinho, HD; Oliveira de Sousa, E; Pereira da Silva, AR; Pereira Silva, CA; Sampaio de Freitas, T; Santos Araújo, NJ, 2023)		1.89
"Hecogenin acetate (HA) is a steroidal sapogenin-acetylated with pharmacological properties which have already been described in the literature such as, anti-inflammatory, anti-hyperalgesic and antinociceptive, but it has low solubility in aqueous media. "( Inclusion complex between β-cyclodextrin and hecogenin acetate produces superior analgesic effect in animal models for orofacial pain.
Aquino, TM; Araújo, AAS; Carvalho, YMBG; Crispim, AC; Lima, BS; Menezes, PP; Nakamura, CV; Pereira, EWM; Quintans, JSS; Quintans-Júnior, LJ; Rezende, MM; Serafini, MR; Silva-Júnior, EF; Sousa, BMH; Trindade, IAS, 2017)		2.16
"Hecogenin acetate (HA) is an acetylated sapogenin that has shown potential antihyperalgesic activity, inhibiting descending pain and acting in opioid receptors. "( Amorphous solid dispersions of hecogenin acetate using different polymers for enhancement of solubility and improvement of anti-hyperalgesic effect in neuropathic pain model in mice.
Barbosa, EG; da Silva-Júnior, WF; de Azevedo, EP; de França Almeida Moreira, CDL; de Lima, ÁAN; de Oliveira Pinheiro, JG; de Souza Araújo, AA; de Souza Siqueira Quintans, J; Lavra, ZMM; Pereira, EWM; Quintans-Júnior, LJ; Resende, MM, 2018)		2.21
"Hecogenin acetate (HA) is a steroidal sapogenin-acetylated that produces antinociceptive activity."( Evidence for the involvement of spinal cord-inhibitory and cytokines-modulatory mechanisms in the anti-hyperalgesic effect of hecogenin acetate, a steroidal sapogenin-acetylated, in mice.
Almeida, JR; Antoniolli, AR; Barreto, RS; Branco, A; de Lucca, W; Freitas, RM; Kaneto, CM; Quintans, JS; Quintans, LJ; Soares, MB; Taranto, AG; Villarreal, CF, 2014)		1.33

Treatment

ExcerptReferenceRelevance
"Treatment with hecogenin acetate induced G0/G1-phase arrest at two concentrations (75 and 100 µM, 74% and 84.3% respectively), and increased the staining of senescence-associated β -galactosidase positive cells."( Hecogenin acetate inhibits reactive oxygen species production and induces cell cycle arrest and senescence in the A549 human lung cancer cell line.
Branco, A; de Bittencourt Pasquali, MA; Gasparotto, J; Gelain, DP; Girardi, CS; Kunzler, A; Moreira, JC; Quintans-Junior, LJ; Ramos, VM; Simoes-Pires, A; Somensi, N, 2014)		2.18
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
triterpenoidAny terpenoid derived from a triterpene. The term includes compounds in which the C30 skeleton of the parent triterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID735824Antinociceptive activity in ip dosed Swiss webster mouse assessed as increase in latency response measured for 5 hrs by warm water-tail flick test2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
AID735816Antinociceptive activity in Swiss webster mouse assessed as latency response at 40 mg/kg, ip administered 30 mins after 2 mg/kg, ip KATP channel blocker, glibenclamide challenge measured up to 7 hrs by warm water-tail flick test2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
AID735818Antinociceptive activity in Swiss webster mouse assessed as latency response at 40 mg/kg, ip administered 15 mins after 0.5 mg/kg, sc kappa-opioid receptor antagonist, nor-BNI challenge measured up to 7 hrs by warm water-tail flick test2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID735822Toxicity in Swiss webster mouse assessed as effect on motor performance at 40 mg/kg, ip measured after 30 mins by rotarod test2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
AID735815Activation of neurons in Swiss webster mouse periaqueductal gray assessed as increase in number of Fos-positive cells at 5 to 40 mg/kg, ip measured after 2 hrs by immunohistochemical analysis2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
AID735819Antinociceptive activity in Swiss webster mouse assessed as latency response at 40 mg/kg, ip administered 30 mins prior to 1 mg/kg, ip mu-opioid receptor antagonist, CTOP challenge measured up to 7 hrs by warm water-tail flick test2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
AID735820Antinociceptive activity in Swiss webster mouse assessed as latency response at 40 mg/kg, ip administered 15 mins after 5 mg/kg, ip nonselective opioid receptor antagonist, naloxone challenge measured up to 7 hrs by warm water-tail flick test2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
AID735817Antinociceptive activity in Swiss webster mouse assessed as latency response at 40 mg/kg, ip administered 5 mins after 3 mg/kg, sc delta-opioid receptor antagonist, naltrindole challenge measured up to 7 hrs by warm water-tail flick test2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Evidence for the involvement of descending pain-inhibitory mechanisms in the antinociceptive effect of hecogenin acetate.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (11.11)29.6817
2010's13 (72.22)24.3611
2020's3 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.85

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index31.85 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index5.12 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.85)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
diazepam
Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.		2.08101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic
glyburide
Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.		2.0810monochlorobenzenes;
N-sulfonylurea		anti-arrhythmia drug;
EC 2.7.1.33 (pantothenate kinase) inhibitor;
EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor;
hypoglycemic agent
nonane
iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.		2.1110alkaneplant metabolite;
volatile oil component
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		2.1110diazine;
pyrazines		Daphnia magna metabolite
chromium trioxide
chromium trioxide: oxidizing agent. chromium trioxide : A chromium oxide composed of a single chromium bound (oxidation state +6) to three oxygens; the acidic anhydride of chromic acid.		2.0510chromium oxide
hecogenin
hecogenin: steroidal sapogenin which has been isolated from plants particularly from numerous Agave species; used in prep of steroidal hormones; structure; RN given refers to (3beta,5alpha,25R)-isomer		2.1110triterpenoid
singlet oxygen
Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.		2.0210chalcogen;
monoatomic oxygen;
nonmetal atom		macronutrient
betadex
beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.		2.6120cyclodextrin
morphine
Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.		2.0810morphinane alkaloid;
organic heteropentacyclic compound;
tertiary amino compound		anaesthetic;
drug allergen;
environmental contaminant;
geroprotector;
mu-opioid receptor agonist;
opioid analgesic;
plant metabolite;
vasodilator agent;
xenobiotic
naltrexone
Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.		2.0810cyclopropanes;
morphinane-like compound;
organic heteropentacyclic compound		antidote to opioid poisoning;
central nervous system depressant;
environmental contaminant;
mu-opioid receptor antagonist;
xenobiotic
beta-escin
[no description available]		2.1710
sapogenins
Sapogenins: The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.		2.8130
digitonin
Digitonin: A glycoside obtained from Digitalis purpurea; the aglycone is digitogenin which is bound to five sugars. Digitonin solubilizes lipids, especially in membranes and is used as a tool in cellular biochemistry, and reagent for precipitating cholesterol. It has no cardiac effects.. digitonin : A spirostanyl glycoside that is digitogenin in which the 3-hydroxy group is substituted by a beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranosyl group. It is a steroidal saponin isolated from the foxglove plant, Digitalis purpurea. It is used extensively as a mild non-ionic detergent for extracting proteins from membranes for structure and function studies.		2.1710
cephalostatin i
cephalostatin I: two steroid units are annulated to a 1,4-pyrazine ring; RN given for (3'R-(3'alpha(R*),4'alpha,4'abeta,6'balpha,8'abeta,11'aalpha,11'bbeta,13'alpha,13'aalpha,13'bbeta,14'beta,15'alpha(3*R*,5''S*),16'abeta,17'balpha,19'abeta,22'aalpha,22'bbeta,24'aR'*))-isomer; structure in first source		2.7830
ConditionIndicatedRelationship StrengthStudiesTrials
Ache
[description not available]		02.0810
Pain
An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.		07.0810
Gastric Ulcer
[description not available]		03.5240
Ischemia
A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.		03.5240
Stomach Ulcer
Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).		03.5240
Allodynia
[description not available]		02.8630
Craniofacial Pain
[description not available]		02.1510
Facial Pain
Pain in the facial region including orofacial pain and craniofacial pain. Associated conditions include local inflammatory and neoplastic disorders and neuralgic syndromes involving the trigeminal, facial, and glossopharyngeal nerves. Conditions which feature recurrent or persistent facial pain as the primary manifestation of disease are referred to as FACIAL PAIN SYNDROMES.		07.1510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1710
Nerve Pain
[description not available]		02.1710
Neuralgia
Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.		02.1710
Carcinoma, Non-Small Cell Lung
[description not available]		02.110
Cancer of Lung
[description not available]		02.110
Invasiveness, Neoplasm
[description not available]		02.110
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		02.110
Lung Neoplasms
Tumors or cancer of the LUNG.		02.110