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Details

Stereochemistry RACEMIC
Molecular Formula C12H15N3O6
Molecular Weight 297.264
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TEROXIRONE

SMILES

O=C1N(C[C@H]2CO2)C(=O)N(C[C@@H]3CO3)C(=O)N1C[C@@H]4CO4

InChI

InChIKey=OUPZKGBUJRBPGC-HLTSFMKQSA-N
InChI=1S/C12H15N3O6/c16-10-13(1-7-4-19-7)11(17)15(3-9-6-21-9)12(18)14(10)2-8-5-20-8/h7-9H,1-6H2/t7-,8-,9+/m1/s1

HIDE SMILES / InChI
Molecular Formula C12H15N3O6
Molecular Weight 297.264
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Teroxirone is a triazene triepoxide patented by Shell Internationale Research Maatschappij NV as an antineoplastic agent. Teroxirone alkylates and cross-links DNA, thereby inhibiting DNA replication. Teroxirone has good cytotoxic activity against sublines of P388 and L1210 leukemias resistant to another alkylating agent. In preclinical trials, Teroxirone shows potent antineoplastic activity against murine tumors. In clinical trials, Teroxirone shows good anticancer activity and high rate of adverse events including nausea, vomiting, and myelosuppression.

Originator

Approval Year

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Pharmacological characterization of teroxirone, a triepoxide antitumor agent, in rats, rabbits, and humans.
1984 Sep
Concomitant sensitization to triglycidyl isocyanurate, diaminodiphenylmethane and 2-hydroxyethyl methacrylate from silk-screen printing coatings in the manufacture of circuit boards.
1994 Jan
Occupational allergic contact dermatitis caused by 2,4,6-tris-(dimethylaminomethyl)phenol, and review of sensitizing epoxy resin hardeners.
1996 Dec
Degradation of triglycidyl isocyanurate as a cause of false-negative patch test reaction.
2001 Jan
Cross-reactivity among epoxy acrylates and bisphenol F epoxy resins in patients with bisphenol A epoxy resin sensitivity.
2002 Sep
Worker exposure to 1,3,5-triglycidyl isocyanurate (TGIC) in powder paint coating operations.
2003 Mar
Selective amino acids changes in the medial and lateral preoptic area in the formalin test in rats.
2004
Dermal exposure to dry powder spray paints using PXRF and the method of Dirichlet tesselations.
2004 Apr
Determination of triglycidyl isocyanurate from powder coatings in occupational hygiene samples by gas chromatography with mass spectrometric detection.
2004 Aug
Hypersensitivity pneumonitis caused by triglycidyl isocyanurate.
2004 Oct
A novel chip device based on wired capillary packed with high performance polymer-based monolith for HPLC: reproducibility in preparation processes to obtain long columns.
2008 Jan
A review on plant-derived natural products and their analogs with anti-tumor activity.
2008 Mar
Patents

Patents

GB1015033
2
JP2000297137A
4
JP2001316374A
2
JP2002145879A
3
JP2002542371A
3
JP2008231286A
2
JP2011528275A
455
JPH00335017A
2
JPH02218766A
2
JPH02279684A
2
JPH03296519A
2
JPH0481420A
2
JPH06184514A
3
JPS5351210A
2
JPS5410355A
2
JPS5410356A
2
JPS56154421A
2
JPS5858956A
2
JPS59136320A
3
JPS61218621A
2
JPS6191245A
2
JPS62187463A
2
JPS63150314A
2

Sample Use Guides

In Vivo Use Guide
maximal tolerated dose of 340 mg/m2/day as a single iv push for 5 sequential days every 4 weeks.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:10:23 GMT 2023
Edited
by admin
on Fri Dec 15 16:10:23 GMT 2023
Record UNII
456V4159SL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEROXIRONE
INN   USAN  
USAN   INN  
Official Name English
ALPHATGI
Code English
teroxirone [INN]
Common Name English
1,3,5-TRIAZINE-2,4,6(1H,3H,5H)-TRIONE, 1,3,5-TRIS(OXIRANYLMETHYL)-, (1(R*),3(R*),5(S*))-(±)-
Common Name English
MIXTURE OF TRIGLYCIDYL ISOCYANURATE (R,R,S) AND (R,S,S) STEREOISOMERS
Common Name English
(RS,RS,SR)-1,3,5-TRIS(2,3-EPOXYPROPYL)-S-TRIAZINE-2,4,6(1H,3H,5H)-TRIONE
Systematic Name English
TRIGLYCIDYL ISOCYANURATE, .ALPHA.-
Common Name English
NSC-296934
Code English
GATGI
Code English
TEROXIRONE [USAN]
Common Name English
HENKEL'S COMPOUND
Common Name English
TRIGLYCIDYL ISOCYANURATE .ALPHA.-FORM [MI]
Common Name English
.ALPHA.-TRIGLYCIDYL ISOCYANURATE
Common Name English
1,3,5-TRIAZINE-2,4,6(1H,3H,5H)-TRIONE, 1,3-BIS((2R)-2-OXIRANYLMETHYL)-5-((2S)-2-OXIRANYLMETHYL)-, REL-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C475
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
Code System Code Type Description
MESH
C028786
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
NSC
296934
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
CAS
59653-73-5
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
FDA UNII
456V4159SL
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
EVMPD
SUB10932MIG
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
SMS_ID
100000082733
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
PUBCHEM
6917771
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
MERCK INDEX
m11130
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C2320
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID301318560
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
INN
5142
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL453863
Created by admin on Fri Dec 15 16:10:23 GMT 2023 , Edited by admin on Fri Dec 15 16:10:23 GMT 2023
PRIMARY
Related Record Type Details
Structure of TRIGLYCIDYL ISOCYANURATE, (R,R,S)-
ENANTIOMER -> RACEMATE
Structure of TRIGLYCIDYL ISOCYANURATE, (R,S,S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of TEROXIRONE
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