Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H20N4O5 |
Molecular Weight | 348.3538 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CN3C4=C([C@@H](COC(N)=O)[C@@]3(OC)[C@@]1([H])N2C)C(=O)C(N)=C(C)C4=O
InChI
InChIKey=HRHKSTOGXBBQCB-VFWICMBZSA-N
InChI=1S/C16H20N4O5/c1-6-10(17)13(22)9-7(5-25-15(18)23)16(24-3)14-8(19(14)2)4-20(16)11(9)12(6)21/h7-8,14H,4-5,17H2,1-3H3,(H2,18,23)/t7-,8+,14+,16-,19?/m1/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/14162693
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14162693
Porfiromycin is an N-methyl derivative of the antineoplastic antibiotic mitomycin-C initially isolated from Streptomyces ardus. Upon administration, the drug undergoes chemical or enzymatic reduction, followed by spontaneous loss of the tertiary methoxy (hydroxyl) group and formation of an aromatic indole system. Thus activated, porfiromycin generates oxygen radicals and alkylates DNA, producing interstrand cross-links and single-strand breaks at guanosine residues. Porfiromycin was tested in phase III for head and neck carcinoma, however, its development was terminated.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14162693 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The effect of treatment with a combination of 6-mercaptopurine and porfiromycin on an established Friend leukemia virus infection. | 1969 Mar |
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Mechanism of transport and intracellular binding of porfiromycin in HCT 116 human colon carcinoma cells. | 1989 Sep 15 |
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Potentiation of mitomycin C and porfiromycin antitumor activity in solid tumor models by recombinant human interleukin 1 alpha. | 1991 Oct 15 |
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Differential toxicity of mitomycin C and porfiromycin to aerobic and hypoxic Chinese hamster ovary cells overexpressing human NADPH:cytochrome c (P-450) reductase. | 1996 Jan 9 |
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Overexpression of the human HAP1 protein sensitizes cells to the lethal effect of bioreductive drugs. | 1999 Mar |
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Isolation and identification of urinary metabolites of porfiromycin in dogs and humans. | 2000 Aug |
Patents
Sample Use Guides
In clinical trials, patients received 75 mg/m2 porfiromycin every 6-8 weeks as a single bolus i.v. injection. In conjunction with radiation treatment, 40 mg/m2 porfiromycin was given on Days 5 and 47 (or last day) of Radiation treatment.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2265454
The cytotoxicity, metabolism, and DNA alkylation of porfiromycin (PFM) under aerobic and hypoxic conditions were evaluated in P388 murine leukemia cells. Clonogenic assays showed that the IC50 value for a 1-h exposure to PFM was 4 microM for aerobic cells and 0.5 microM for hypoxic cells. After a 1-h exposure to concentrations of 1, 5, and 10 microM [14C]-PFM, the accumulation of total radioactivity in hypoxic cells was 10 to 20 times that in aerobic cells.
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FDA ORPHAN DRUG |
91495
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FDA ORPHAN DRUG |
103597
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NCI_THESAURUS |
C663
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56410
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m8989
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801-52-5
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DB06478
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13116
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H1WK901OA6
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CHEMBL521078
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m7570
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SUB09980MIG
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C763
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D011160
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DTXSID901024646
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ACTIVE MOIETY