U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H16O6
Molecular Weight 316.306
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZOIC ACID, 4,4'-(1,3-PROPANEDIYLBIS(OXY))BIS-

SMILES

C(COc1ccc(cc1)C(=O)O)COc2ccc(cc2)C(=O)O

InChI

InChIKey=VBISQLWPGDULSX-UHFFFAOYSA-N
InChI=1S/C17H16O6/c18-16(19)12-2-6-14(7-3-12)22-10-1-11-23-15-8-4-13(5-9-15)17(20)21/h2-9H,1,10-11H2,(H,18,19)(H,20,21)

HIDE SMILES / InChI

Molecular Formula C17H16O6
Molecular Weight 316.306
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including: http://arborpharma.com/docs/201241r1-gliadel-pi.pdf | https://www.ncbi.nlm.nih.gov/pubmed/7948590 | https://www.ncbi.nlm.nih.gov/pubmed/1350734

BENZOIC ACID, 4,4'-(1,3-PROPANEDIYLBIS(OXY))BIS- (CPP-BIS) is a building block for polyanhydrides, which is a class of bioerodible polymer containing drug delivery applications. The polyanhydride copolymer system which currently enjoys the most widespread interest in its medical applications employs the monomers sebacic acid (SA) and CPP-BIS (Polifeprosan). Polifeprosan is a biodegradable copolymer used to control the release of carmustine in GLIADEL Wafer. GLIADEL Wafer is an implant for intracranial use, containing carmustine, a nitrosourea alkylating agent. GLIADEL Wafer is indicated in newly-diagnosed high-grade malignant glioma patients and in recurrent glioblastoma multiforme. Most common adverse reactions of GLIADEL Wafer are cerebral edema, asthenia, nausea, vomiting, constipation, wound healing abnormalities and depression.

Originator

Curator's Comment:: http://www-heparin.rpi.edu/main/files/papers/14.pdf | https://www.ncbi.nlm.nih.gov/pubmed/1350734

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Gliadel Wafer

Approved Use

GLIADEL® Wafer is indicated in newly-diagnosed high-grade malignant glioma patients as an adjunct to surgery and radiation. GLIADEL® Wafer is indicated in recurrent glioblastoma multiforme patients as an adjunct to surgery.

Launch Date

1.0460448E12
Primary
Gliadel Wafer

Approved Use

GLIADEL® Wafer is indicated in newly-diagnosed high-grade malignant glioma patients as an adjunct to surgery and radiation. GLIADEL® Wafer is indicated in recurrent glioblastoma multiforme patients as an adjunct to surgery.

Launch Date

1.0460448E12
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics of the carmustine implant.
2002
Tumor treatment by sustained intratumoral release of 5-fluorouracil: effects of drug alone and in combined treatments.
2002 Dec 1
Treatment of intracranial rat glioma model with implant of radiosensitizer and biomodulator drug combined with external beam radiotherapy.
2004 Feb 1
Synthesis and characterization of polyanhydride for local BCNU delivery carriers.
2005
Interstitial chemotherapy with biodegradable BCNU (Gliadel) wafers in the treatment of malignant gliomas.
2007 Oct
Preparation and degradation behavior of polyanhydrides nanoparticles.
2008 Jan
catena-Poly[[aqua-(1,10-phenanthroline)cobalt(II)]-μ-4,4'-(propane-1,3-diyldi-oxy)dibenzoato].
2009 Sep 5
Patents

Sample Use Guides

Eight 7.7 mg wafers (61.6 mg total dose) implanted intracranially
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:54:31 UTC 2021
Edited
by admin
on Sat Jun 26 01:54:31 UTC 2021
Record UNII
1XMW35DTHB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZOIC ACID, 4,4'-(1,3-PROPANEDIYLBIS(OXY))BIS-
Common Name English
1,3-BIS-CPP
Common Name English
1,3-BIS(4-CARBOXYPHENOXY)PROPANE
Systematic Name English
4,4'-(1,3-PROPANEDIYLBIS(OXY))BIS-BENZOIC ACID
Systematic Name English
Code System Code Type Description
FDA UNII
1XMW35DTHB
Created by admin on Sat Jun 26 01:54:31 UTC 2021 , Edited by admin on Sat Jun 26 01:54:31 UTC 2021
PRIMARY
CAS
3753-81-9
Created by admin on Sat Jun 26 01:54:31 UTC 2021 , Edited by admin on Sat Jun 26 01:54:31 UTC 2021
PRIMARY
PUBCHEM
68610
Created by admin on Sat Jun 26 01:54:31 UTC 2021 , Edited by admin on Sat Jun 26 01:54:31 UTC 2021
PRIMARY
EPA CompTox
3753-81-9
Created by admin on Sat Jun 26 01:54:31 UTC 2021 , Edited by admin on Sat Jun 26 01:54:31 UTC 2021
PRIMARY