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Details

Stereochemistry ACHIRAL
Molecular Formula C48H66N5O10.2C2H3O2.Gd.H2O
Molecular Weight 1166.42
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MOTEXAFIN GADOLINIUM

SMILES

O.[Gd+3].CC([O-])=O.CC([O-])=O.CCC1=C2[N-]C(C=C3N=C(\C=N\C4=CC(OCCOCCOCCOC)=C(OCCOCCOCCOC)C=C4\N=C\C5=NC(=C2)C(CCCO)=C5C)C(C)=C3CCCO)=C1CC

InChI

InChIKey=KHDBHVDCUGRVLA-IOYKFIIZSA-L
InChI=1S/C48H66N5O10.2C2H4O2.Gd.H2O/c1-7-35-36(8-2)40-28-42-38(12-10-14-55)34(4)46(53-42)32-50-44-30-48(63-26-24-61-22-20-59-18-16-57-6)47(62-25-23-60-21-19-58-17-15-56-5)29-43(44)49-31-45-33(3)37(11-9-13-54)41(52-45)27-39(35)51-40;2*1-2(3)4;;/h27-32,54-55H,7-26H2,1-6H3;2*1H3,(H,3,4);;1H2/q-1;;;+3;/p-2/b39-27-,40-28-,41-27-,42-28-,45-31-,46-32-,49-31+,49-43+,50-32+,50-44+;;;;

HIDE SMILES / InChI

Molecular Formula Gd
Molecular Weight 157.25
Charge 3
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C2H3O2
Molecular Weight 59.044
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C48H67N5O10
Molecular Weight 874.0731
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Motexafin gadolinium is a novel, MRI-detectable, an anticancer agent that enhances the cytotoxic potential of radiation therapy through several mechanisms, including depleting intracellular reducing metabolites that are necessary for repairing the oxidative damage induced by irradiation. Motexafin gadolinium catalyzes the oxidation of intracellular reducing metabolites such as ascorbate, glutathione, nicotinamide adenine dinucleotide phosphate, and protein thiols, generating reactive oxygen species in a process known as futile redox cycling. The depletion (through oxidation) of these reducing metabolites removes the substrate necessary in a cell to repair oxidative damage induced by radiation and, left unrepaired, such radiation-induced oxidative DNA damage is converted into lethal double-stranded breaks. Motexafin gadolinium has tumor-specific uptake, normal tissue sparing, and tolerable and reversible toxicities in clinical trials. Motexafin gadolinium use in conjunction with whole-brain radiation therapy (WBRT) has demonstrated an improvement in neurocognitive decline, neurologic progression, and quality of life in patients with brain metastases from Non-small-cell lung carcinoma. Motexafin gadolinium use in conjunction with radiosurgery and whole brain radiation therapy in the setting of brain metastases is currently being studied, as is Motexafin gadolinium with radiation and temozolomide in patients with glioblastoma multiforme.

Approval Year

PubMed

PubMed

TitleDatePubMed
Motexafin gadolinium and zinc induce oxidative stress responses and apoptosis in B-cell lymphoma lines.
2005 Dec 15
Motexafin gadolinium enhances p53-Mdm2 interactions, reducing p53 and downstream targets in lymphoma cell lines.
2010 Apr
Patents

Patents

Sample Use Guides

5.0 mg/kg + 3 Gy of WBRT daily for a total of 10 days
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:03:01 GMT 2023
Edited
by admin
on Fri Dec 15 16:03:01 GMT 2023
Record UNII
6433A42F4F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MOTEXAFIN GADOLINIUM
DASH   USAN   WHO-DD  
USAN  
Official Name English
GD-TEX
Code English
GADOLINIUM TEXAPHYRIN
Code English
MOTEXAFIN GADOLINIUM HYDRATE
Common Name English
Motexafin gadolinium [WHO-DD]
Common Name English
GD TEXAPHYRIN
Code English
FP-GP1
Code English
MOTEXAFIN GADOLINIUM [USAN]
Common Name English
BIS(ACETATO-O)(9,10-DIETHYL-20,21-BIS(2-(2-(2-METHOXYETHOXY)ETHOXY)ETHOXY)-4,15-DIMETHYL-8,11-IMINO-3,6:16,13-DINITRILO-1,18-BENZODIAZACYCLOEICOSINE-5,14-DIPROPANOLATO-N1, N18, N23, N24, N25) GADOLINIUM HYDRATE
Systematic Name English
NSC-695238
Code English
GD-TEXAPHYRIN
Code English
API-GP3
Code English
Classification Tree Code System Code
NCI_THESAURUS C798
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
FDA ORPHAN DRUG 152401
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
NCI_THESAURUS C2150
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL3544910
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
NCI_THESAURUS
C1881
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
EVMPD
SUB33962
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
CHEBI
50161
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
NSC
695238
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
SMS_ID
100000127831
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
USAN
LL-38
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID4037083
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
DRUG BANK
DB05428
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
WIKIPEDIA
MOTEXAFIN GADOLINIUM
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
FDA UNII
6433A42F4F
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
CAS
156436-89-4
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
MESH
C437683
Created by admin on Fri Dec 15 16:03:01 GMT 2023 , Edited by admin on Fri Dec 15 16:03:01 GMT 2023
PRIMARY
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