PHORBOL 12-MYRISTATE 13-ACETATE DIESTER

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C36H56O8
Molecular Weight	616.825
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of PHORBOL 12-MYRISTATE 13-ACETATE DIESTER

Structure Search

SMILES

[H][C@]12[C@]3([H])C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@H](C)[C@@H](OC(=O)CCCCCCCCCCCCC)[C@@]1(OC(C)=O)C2(C)C

InChI

InChIKey=PHEDXBVPIONUQT-RGYGYFBISA-N

InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C36H56O8
Molecular Weight	616.825
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9560281 | https://clinicaltrials.gov/ct2/show/NCT00004058

Phorbol 12-myristate 13-acetate (PMA) also commonly known as 12-O-Tetradecanoylphorbol-13-acetate (TPA) is a phorbol ester that is commonly used to activate phospholipid-dependent protein kinase (protein kinase C). PMA/ TPA possesses potential antineoplastic effects and was studied in phase II clinical trials together with dexamethasone in patients with relapsed or refractory acute myeloid leukemia. In addition, PMA/ TPA participated in phase I trial for treating patients with hematologic cancer or bone marrow disorder that has not responded to previous treatment. Nevertheless, both clinical trials were terminated. Besides, PMA/ TPA was studied in patients with solid tumors, which had depressed white blood cell and neutrophil counts because of prior treatment with cytotoxic cancer chemotherapeutic drugs. It was shown, that the drug increased the low white blood cell and neutrophil counts toward the normal range.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7085651	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Acute myeloid leukemia 136 Sources: https://clinicaltrials.gov/ct2/show/NCT01009931	Primary	Phase II 1132	Unknown Approved Use Unknown
Lymphoma 58 Sources: https://clinicaltrials.gov/ct2/show/NCT00004058	Primary	Phase I 428	Unknown Approved Use Unknown
Chronic myeloproliferative disorders 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00004058	Primary	Phase I 428	Unknown Approved Use Unknown
Solid tumors 145 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9560281	Primary	Not Provided 504	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00AP4S	https://www.1pchem.com/search?query=1P00AP4S
AK Scientific	V0265	https://aksci.com/item_detail.php?cat=V0265
Ambeed	A175370	http://www.ambeed.com/search/Search.html?keyword=A175370
ApexBio Technology	N2060	https://www.apexbt.com/catalogsearch/result/?q=N2060
Apollo Scientific	BIP1020	http://www.apolloscientific.co.uk/chemical_results.php?qstext=BIP1020&product_group=%25&search_fieldname=header_search
AstaTech	44313	http://astatechinc.com/CPSResult.php?CRNO=44313
BLD Pharm	BD147805	http://www.bldpharm.com/search/Search.html?keyword=BD147805
BOC Sciences	16561-29-8	http://www.bocsci.com/description.asp?cas=16561-29-8
BioSynth	W-201494	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-201494
Biopurify Phytochemicals	BP0021	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0021&searchhtmp=simplesearch&t=1
Cayman Chemical	10008014	http://www.caymanchem.com/app/template/Product.vm/catalog/10008014
Chem Scene	CS-6053	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6053
Fluorochem	M02249	http://www.fluorochem.co.uk/Products/Product?code=M02249
KeyOrganics	FS-4842	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=FS-4842
MedChem Express	HY-18739	https://www.medchemexpress.com/search.html?q=HY-18739&ft=&fa=&fp=
MolPort	MolPort-003-665-586	https://www.molport.com/shop/molecule-link/MolPort-003-665-586
Molnova	M12527	https://www.molnova.com/en/serch-list.html?keywords=M12527
MuseChem	I002165	https://www.musechem.com/product/I002165.html
TimTec	ST51240756	http://www.echemstore.com/catalogsearch/result/?q=ST51240756
Tocris	1201	https://www.tocris.com/search.php?Type=QuickSearch&Value=1201
W&J PharmaChem	50C459887	http://wjpharmachem.com/new/searcht.php?keyword=50C459887
eMolecules	530483	https://orderbb.emolecules.com/search/#?query=530483
mcule	MCULE-1325545503	https://mcule.com/MCULE-1325545503/

PubMed

Title	Date	PubMed
Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters.	1982 Jul 10	7085651
Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture.	1988 Jan 1	3275491
A study of the effects of phorbol 12-myristate-13-acetate on cell differentiation of pure human melanocytes in vitro.	1991	1906266
An essential role of ERK signalling in TPA-induced reactivation of Kaposi's sarcoma-associated herpesvirus.	2006 Apr	16528027

Patents

Sample Use Guides

In Vivo Use Guide

Fifty-two patients with solid tumors had depressed white blood cell and neutrophil counts because of prior treatment with cytotoxic cancer chemotherapeutic drugs. These patients were given one or more i.v. infusions of 0.125-0.25 mg of 12-O-tetradecanoylphorbol-13-acetate (PHORBOL 12-MYRISTATE 13-ACETATE/TPA), and this treatment increased the low white blood cell and neutrophil counts toward the normal range.

Route of Administration: Intravenous

In Vitro Use Guide

To investigate the biological effects of phorbol 12-myristate-13-acetate (PMA) on melanocytes in vitro, the cells were incubated in media containing various concentration of PMA (including 0 nM, 85 nM and 170 nM), and grown continuously for 12 days without passage. The cells were observed for changes in cell morphology, cell cycle, cytoskeleton and HLA-DR expression. The results revealed that the higher the PMA concentration, the higher the percentage of large irregularly shaped melanocytes. These large melanocytes were three to ten times the size of small bipolar or multipolar cells. A higher concentration of PMA was also associated with a higher percentage of melanocytes in the S and G2-M phases of the cell cycle and with a higher percentage of melanocytes as tetraploid and octaploid karyotypes.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:07:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:07:19 GMT 2023`
Record UNII	NI40JAQ945
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHORBOL 12-MYRISTATE 13-ACETATE DIESTER

Common Name

English

PHORBOL 12-MYRISTATE 13-ACETATE

Common Name

English

PHORBOL MYRISTATE ACETATE

Common Name

English

PHORBOL 12-MYRISTATE 13-ACETATE DIESTER [MI]

Common Name

English

PMA (PHORBOL ESTER)

Common Name

English

NSC-262244

Code

English

TETRADECANOYLPHORBOL ACETATE

Common Name

English

TPA (PHORBOL ESTER)

Common Name

English

12-TETRADECANOYLPHORBOL 13-ACETATE

Common Name

English

12-O-TETRADECANOYLPHORBOL-13-ACETATE [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1934