Sivifene

Sivifene (INN, USAN; developmental code name A-007) is a small-molecule antineoplastic agent and immunomodulator that was under development in the 2000s by Tigris Pharmaceuticals (now Kirax Corporation) as a topical treatment for cutaneous cancer metastases.[1][2][3] It was specifically being investigated to treat high-grade squamous intraepithelial lesions (HSIL) associated with human papillomavirus (HPV) infection and invasive carcinomas of the anogenital area such as cervical, vaginal, and anal cancers.[1] The drug reached phase II clinical trials prior to its discontinuation.[1]

Sivifene
Clinical data
Other namesA-007; 4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone
Routes of
administration		Topical
Identifiers
IUPAC name
  • 4-[[2-(2,4-Dinitrophenyl)hydrazinyl]-(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H14N4O6
Molar mass394.343 g·mol−1
3D model (JSmol)
SMILES
  • C1=CC(=O)C=CC1=C(C2=CC=C(C=C2)O)NNC3=C(C=C(C=C3)[N+](=O)[O-])[N+](=O)[O-]
InChI
  • 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/h1-11,20-21,24H
  • Key:JOADKLYQCOMENH-UHFFFAOYSA-N

Initially, due to its structural similarity to tamoxifen, sivifene was thought to be a selective estrogen receptor modulator (SERM), but subsequent research revealed that it does not bind to the estrogen receptor (ER) and does not possess antiestrogenic activity.[2] The actual mechanism of action of sivifene is unknown, but it is thought to produce its immunomodulating effects via upregulation of the CD45 T-lymphocyte cell surface receptor.[2]

See also

References
  1. "Sivifene - AdisInsight".
  2. Eilender D, LoRusso P, Thomas L, McCormick C, Rodgers AH, Hooper CL, Tornyos K, Krementz ET, Parker S, Morgan LR (2006). "4,4'-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007): a topical treatment for cutaneous metastases from malignant cancers". Cancer Chemother. Pharmacol. 57 (6): 719–26. doi:10.1007/s00280-005-0124-2. PMID 16184382. S2CID 10830366.
  3. Robert A. Schwartz (30 April 2008). Skin Cancer: Recognition and Management. John Wiley & Sons. pp. 267–. ISBN 978-0-470-69563-0.
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