Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H14N4O6 |
Molecular Weight | 394.3377 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C=C1)C(=NNC2=CC=C(C=C2[N+]([O-])=O)[N+]([O-])=O)C3=CC=C(O)C=C3
InChI
InChIKey=YOQPCWIXYUNEET-UHFFFAOYSA-N
InChI=1S/C19H14N4O6/c24-15-6-1-12(2-7-15)19(13-3-8-16(25)9-4-13)21-20-17-10-5-14(22(26)27)11-18(17)23(28)29/h1-11,20,24-25H
Sivifene (also known as A-007), a triaryl hydrazone that produced objective responses when applied topically. During preclinical studies, sivifene was observed to upregulate both cutaneous and systemic T-lymphocytes, in particular, CD4/8+ lymphocyte subtypes. The current mechanism of action for the drug is unknown however is assumed that it can show its immunomodulating properties through the upregulation of the CD45 T lymphocyte cell surface receptor. Sivifene was being evaluated for its anticancer activities in melanoma, breast cancer, Kaposi's sarcoma, and lymphoproliferative disorders. The drug as a 0.25% gel is confirmed as an effective palliative treatment option for cutaneous metastases from cancers. Skin reactions were minimal, tolerated, and no cessation of treatment was required. However, the further development of this drug apparently has been discontinued.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P08575 Gene ID: 5788.0 Gene Symbol: PTPRC Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16184382 |
PubMed
Title | Date | PubMed |
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Comparative preclinical toxicology and pharmacology of 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) in vitro and in rodents and primates. | 1997 Jan-Feb |
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Comparative dermal pharmacology and toxicology of 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) in rodents and primates. | 2001 Nov-Dec |
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Design, synthesis, and anticancer properties of 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone and analogues. | 2003 Oct 9 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16184382
A-007, as a 0.25% gel, was applied twice daily to the areas of cancer. A-007, as a 0.25% gel, is confirmed as an effective palliative treatment option for cutaneous metastases from cancers.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14521417
Sivifene demonstrated an IC50 from 3.5 ug/mL for breast cancer (ER+/PgR+) and 12.3 ug/mL for ovarian cancers. It had IC50 of 15.2 ug/mL for colon, 4.9 ug/mL for lung, and 7 ug/mL for melanoma cancers.
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300000034312
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Sivifene
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DB05686
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TT-12
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CHEMBL307697
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ACTIVE MOIETY