Sivifene

Sivifene
Clinical data
Other names	A-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	2675-35-6;
PubChem CID	5717660;
ChemSpider	10632319;
UNII	XAV05295I5;
KEGG	D09380;
ChEMBL	ChEMBL307697;
CompTox Dashboard (EPA)	DTXSID30949554 ;
Chemical and physical data
Formula	C19H14N4O6
Molar mass	394.343 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

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]

References

^ ^a ^b ^c http://adisinsight.springer.com/drugs/800002477
^ ^a ^b ^c 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.
^ Robert A. Schwartz (30 April 2008). Skin Cancer: Recognition and Management. John Wiley & Sons. pp. 267–. ISBN 978-0-470-69563-0.