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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
Structure of SIVIFENE

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

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08575
Gene ID: 5788.0
Gene Symbol: PTPRC
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Comparative preclinical toxicology and pharmacology of 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) in vitro and in rodents and primates.
1997 Jan-Feb
Comparative dermal pharmacology and toxicology of 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) in rodents and primates.
2001 Nov-Dec
Design, synthesis, and anticancer properties of 4,4'-dihydroxybenzophenone-2,4-dinitrophenylhydrazone and analogues.
2003 Oct 9

Sample Use Guides

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
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.
Name Type Language
SIVIFENE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
4,4'-((2-(2,4-DINITROPHENYL)HYDRAZINYLIDENE)METHYLENE)DIPHENOL
Systematic Name English
METHANONE, BIS(4-HYDROXYPHENYL)-, (2,4-DINITROPHENYL)HYDRAZONE
Common Name English
Sivifene [WHO-DD]
Common Name English
sivifene [INN]
Common Name English
A-007
Code English
SIVIFENE [USAN]
Common Name English
Code System Code Type Description
SMS_ID
300000034312
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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CAS
2675-35-6
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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EPA CompTox
DTXSID30949554
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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FDA UNII
XAV05295I5
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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WIKIPEDIA
Sivifene
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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DRUG BANK
DB05686
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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USAN
TT-12
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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NCI_THESAURUS
C61305
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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PUBCHEM
3089902
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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ChEMBL
CHEMBL307697
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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INN
8965
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
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