phorbol-12,13-dibenzoate profile

Phorbol-12,13-dibenzoate (PDB) is a potent tumor promoter. It is a synthetic derivative of phorbol, a diterpene found in plants of the genus *Croton*. PDB acts as a strong activator of protein kinase C (PKC), a family of serine/threonine-specific protein kinases that are involved in various cellular processes, including cell growth, differentiation, and apoptosis. The compound is a valuable tool for studying the role of PKC in different biological processes. PDB has been used extensively in research to investigate the mechanisms of tumor promotion and the role of PKC in cancer development. However, due to its high toxicity, PDB is not used therapeutically. The synthesis of PDB involves the esterification of phorbol with benzoic acid. This reaction is typically carried out under acidic conditions. The resulting product is a white solid that is soluble in organic solvents. PDB has been shown to induce a variety of biological effects, including cell proliferation, tumor promotion, and inflammation. These effects are mediated by the activation of PKC. The importance of PDB lies in its ability to activate PKC and induce a wide range of biological responses. This makes it a valuable tool for studying the role of PKC in various cellular processes. The compound is also used in cancer research to investigate the mechanisms of tumor promotion and the development of new cancer therapies.'

ID Source	ID
PubMed CID	72294
CHEMBL ID	445729
SCHEMBL ID	2405620
MeSH ID	M0053101

Synonym
phorbol, 12,13-dibenzoate
phorbol-12,13-dibenzoate
5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 9,9a-bis(benzoyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-9,9a-bis(benzoyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1ar-(1a-alpha,4b-beta,4a-beta,7a-alpha,7b-alpha,8-alpha,9-beta,9a-alpha))
ccris 695
nsc 262643
9,9a-bis(benzoyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5h-cyclopropa(3,4)benz(1,2-e)azulen-5-one (1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
5h-cyclopropa[3,4]benz[1,2-e]azulen-5-one, 9,9a-bis(benzoyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-, (1ar,1bs,4ar,7as,7bs,8r,9r,9as)-
4-.beta.-phorbol 12,13-dibenzoate
4.b.-phorbol 12,13-dibenzoate
25405-85-0
NSC262643 ,
CHEMBL445729
SCHEMBL2405620
[(1s,2s,6r,10s,11r,13s,14r,15r)-13-benzoyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] benzoate
DTXSID801313084

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	11 (73.33)	18.7374
1990's	3 (20.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	1 (6.67)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	16 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.97	1	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	1.97	1	aromatic ether; nitrile; polyether; tertiary amino compound
1-(5-isoquinolinesulfonyl)-2-methylpiperazine 1-(5-Isoquinolinesulfonyl)-2-Methylpiperazine: A specific protein kinase C inhibitor, which inhibits superoxide release from human neutrophils (PMN) stimulated with phorbol myristate acetate or synthetic diacylglycerol.. 1-(5-isoquinolinesulfonyl)-2-methylpiperazine : A member of the class of N-sulfonylpiperazines that is 2-methylpiperazine substituted at position 1 by a 5-isoquinolinesulfonyl group.	2.38	2	isoquinolines; N-sulfonylpiperazine	EC 2.7.11.13 (protein kinase C) inhibitor
thymidine [no description available]	1.96	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	1.97	1	diether; tertiary amino compound; tetracarboxylic acid	chelator
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	2.07	1	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
bicuculline Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.	2.07	1	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	3.84	12	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
phorbol 12,13-dibutyrate Phorbol 12,13-Dibutyrate: A phorbol ester found in CROTON OIL which, in addition to being a potent skin tumor promoter, is also an effective activator of calcium-activated, phospholipid-dependent protein kinase (protein kinase C). Due to its activation of this enzyme, phorbol 12,13-dibutyrate profoundly affects many different biological systems.	3.07	5	butyrate ester; phorbol ester; tertiary alpha-hydroxy ketone
4-o-methyl-12-o-tetradecanoylphorbol 13-acetate [no description available]	2.66	3
phorbol-12,13-diacetate phorbol-12,13-diacetate: RN given refers to (1aR-(1a alpha,1b beta,4a beta,7a alpha,7b alpha,8 alpha,9 beta,9a alpha))-isomer	2.88	4
4-amino-2-methylquinoline 4-amino-2-methylquinoline: used to induce miniature endplate potentials	2.07	1
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	1.96	1
phorbols Phorbols: The parent alcohol of the tumor promoting compounds from CROTON OIL (Croton tiglium).	3.47	8	diterpene; terpenoid fundamental parent
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	2.07	1	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
phorbol phorbol: RN given refers to (1aR-(1a alpha,1b beta,4a beta,7a alpha,7b alpha,8 alpha,9 beta,9b beta))-isomer; synonym isophorbol refers to (4a alpha)-isomer; structure in Merck Index, 9th ed, #7143. phorbol : A diterpenoid with the structure of tigliane hydroxylated at C-4, -9, -12(beta), -13 and -20, with an oxo group at C-3 and unsaturation at the 1- and 6-positions.	2.65	3	cyclic ketone; enone; tertiary alcohol; tertiary alpha-hydroxy ketone; tetracyclic diterpenoid
phorbol-12,13-didecanoate phorbol-12,13-didecanoate: RN given refers to (1aR-(1a alpha,1b beta,4a beta,7a alpha,7b alpha,8 alpha,9 beta,9a alpha))-isomer	3.57	9
2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline 2,3-dioxo-6-nitro-7-sulfamoylbenzo(f)quinoxaline: structure given in first source; neuroprotectant for cerebral ischemia; AMPA receptor antagonist	2.07	1	naphthalenes; sulfonic acid derivative
sphingosine sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.	1.97	1	sphing-4-enine	human metabolite; mouse metabolite
mezerein mezerein: toxic component of plant Daphne mezereum with anti-leukemic activity against P-388 & P-1210 in mice; can act as a tumor promoter; RN given refers to (12beta(E,E))-isomer; structure	2.66	3	diterpenoid
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.07	1	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
12-o-tetradeca-2,4,6,8-tetranoylphorbol-13-acetate [no description available]	1.97	1
staurosporine staurosporinium : Conjugate acid of staurosporine.	1.97	1	ammonium ion derivative
g(m1) ganglioside G(M1) Ganglioside: A specific monosialoganglioside that accumulates abnormally within the nervous system due to a deficiency of GM1-b-galactosidase, resulting in GM1 gangliosidosis.. ganglioside GM1 : A sialotetraosylceramide consisting of a branched pentasaccharide made up from one sialyl residue, two galactose residues, one N-acetylgalactosamine residue and a glucose residue at the reducing end attached to N-stearoylsphingosine via a beta-linkage.	1.97	1	alpha-N-acetylneuraminosyl-(2->3)-[beta-D-galactosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-(1->4)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1')-N-acylsphingosine; sialotetraosylceramide
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	1.96	1	1,2-diacyl-sn-glycero-3-phosphocholine
epidermal growth factor Epidermal Growth Factor: A 6-kDa polypeptide growth factor initially discovered in mouse submaxillary glands. Human epidermal growth factor was originally isolated from urine based on its ability to inhibit gastric secretion and called urogastrone. Epidermal growth factor exerts a wide variety of biological effects including the promotion of proliferation and differentiation of mesenchymal and EPITHELIAL CELLS. It is synthesized as a transmembrane protein which can be cleaved to release a soluble active form.	1.96	1

Condition	Relationship Strength	Studies
Experimental Neoplasms [description not available]	1.96	1
Ganglioside Storage Diseases [description not available]	1.97	1
Gangliosidoses A group of autosomal recessive lysosomal storage disorders marked by the accumulation of GANGLIOSIDES. They are caused by impaired enzymes or defective cofactors required for normal ganglioside degradation in the LYSOSOMES. Gangliosidoses are classified by the specific ganglioside accumulated in the defective degradation pathway.	1.97	1
Carcinoma, Anaplastic [description not available]	1.97	1
Cancer of Skin [description not available]	1.97	1
Carcinoma A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.	1.97	1
Mesenchymoma A mixed mesenchymal tumor composed of two or more mesodermal cellular elements not commonly associated, not counting fibrous tissue as one of the elements. Mesenchymomas are widely distributed in the body and about 75% are malignant. (Dorland, 27th ed; Holland et al., Cancer Medicine, 3d ed, p1866)	1.97	1
Skin Neoplasms Tumors or cancer of the SKIN.	1.97	1
Breast Cancer [description not available]	1.96	1
Breast Neoplasms Tumors or cancer of the human BREAST.	1.96	1

Assay ID	Title	Year	Journal	Article
AID380909	Toxicity against Swiss-Webster mouse assessed as irritation in ear per 5 ul after 24 hrs
AID380908	Toxicity against Swiss-Webster mouse assessed as irritation in ear per 5 ul after 4 hrs
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

phorbol-12,13-dibenzoate

Cross-References

Synonyms (16)

Bioassays (2)

Research

Studies (15)

Market Indicators

Research Demand Index: 11.33

Study Types