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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

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
Record UNII
NI40JAQ945
Record Status Validated (UNII)
Record Version