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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

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

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters.
1982 Jul 10
Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture.
1988 Jan 1
An essential role of ERK signalling in TPA-induced reactivation of Kaposi's sarcoma-associated herpesvirus.
2006 Apr
Patents

Patents

Sample Use Guides

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
  • Download
Name Type Language
PHORBOL 12-MYRISTATE 13-ACETATE DIESTER
MI  
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
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
Code System Code Type Description
WIKIPEDIA
12-O-Tetradecanoylphorbol-13-acetate
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
NSC
262244
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
MERCK INDEX
m8714
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY Merck Index
CHEBI
37537
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
PUBCHEM
27924
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID5023798
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
FDA UNII
NI40JAQ945
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
CAS
16561-29-8
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
HSDB
3542
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
NCI_THESAURUS
C866
Created by admin on Fri Dec 15 15:07:19 GMT 2023 , Edited by admin on Fri Dec 15 15:07:19 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY