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Details

Stereochemistry ACHIRAL
Molecular Formula C14H16N4
Molecular Weight 240.3036
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SIMTRAZENE

SMILES

CN(C1=CC=CC=C1)\N=N\N(C)C2=CC=CC=C2

InChI

InChIKey=WRINSSLBPNLASA-FOCLMDBBSA-N
InChI=1S/C14H16N4/c1-17(13-9-5-3-6-10-13)15-16-18(2)14-11-7-4-8-12-14/h3-12H,1-2H3/b16-15+

HIDE SMILES / InChI

Molecular Formula C14H16N4
Molecular Weight 240.3036
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Simtrazene (centrazene) is an anti-neoplastic compound which is not an alkylating agent. Centrazene was more effective than thioTEPA in prolonging the life span of mice bearing C3H mammary tumors but did not demonstrate activity against other tumor types.

Originator

Curator's Comment: Simtrazene (centrazene) was first synthesised in 1878 by Emil Fischer

Approval Year

PubMed

PubMed

TitleDatePubMed
A LABORATORY EVALUATION OF 1,4-DIMETHYL-1,4-DIPHENYL-2-TETRAZENE (CENTRAZENE), A CARCINOSTATIC COMPOUND.
1964 Apr
Patents

Sample Use Guides

Mice: Parenteral administration (s.c., i.p.) of Simtrazene (centrazene) produced optimum survival effects at daily doses ranging from 5.6 mg/kg (72j mammary adenocarcinoma) to 16.8 mg/kg (spontaneous mammary tumors). In diet experiments optimum survivals were obtained only when tumor-bearing mice consumed much higher daily doses of centrazene (about 2000 mg/kg body weight). This suggested that the compound was poorly absorbed orally or else inactivated in the digestive tract. The weight gain and mortality of normal C3H mice were unaffected by subcutaneous doses of centrazene as high as 2000 mg/kg given daily for 10 days. In contrast, rats given subcutaneous doses of this compound ranging from 2000 to 0.4 mg/kg daily for 10 days showed various degrees of mortality and growth inhibition.
Route of Administration: Other
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:19:08 GMT 2023
Edited
by admin
on Fri Dec 15 16:19:08 GMT 2023
Record UNII
HSD1XP51CR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SIMTRAZENE
INN   USAN  
USAN   INN  
Official Name English
CL-26193
Code English
SIMTRAZENE [USAN]
Common Name English
NSC-86491
Code English
simtrazene [INN]
Common Name English
2-TETRAZENE, 1,4-DIMETHYL-1,4-DIPHENYL-
Systematic Name English
CL 26193
Code English
CENTRAZENE
Brand Name English
1,4-Dimethyl-1,4-diphenyl-2-tetrazene
Systematic Name English
NSC-83799
Code English
Classification Tree Code System Code
NCI_THESAURUS C274
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2105449
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
SMS_ID
100000083516
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
CAS
5579-27-1
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
NSC
83799
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
NCI_THESAURUS
C73242
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
NSC
86491
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID701014451
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
INN
1658
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
PUBCHEM
5357669
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
FDA UNII
HSD1XP51CR
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
EVMPD
SUB10528MIG
Created by admin on Fri Dec 15 16:19:08 GMT 2023 , Edited by admin on Fri Dec 15 16:19:08 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY