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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19N5O2.C2H6O4S
Molecular Weight 451.497
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIVOBULIN ISETHIONATE

SMILES

OCCS(O)(=O)=O.CCOC(=O)NC1=NC(N)=C2N=C([C@H](C)NC2=C1)C3=CC=CC=C3

InChI

InChIKey=JEFPWOBULVSOTM-PPHPATTJSA-N
InChI=1S/C17H19N5O2.C2H6O4S/c1-3-24-17(23)21-13-9-12-15(16(18)20-13)22-14(10(2)19-12)11-7-5-4-6-8-11;3-1-2-7(4,5)6/h4-10,19H,3H2,1-2H3,(H3,18,20,21,23);3H,1-2H2,(H,4,5,6)/t10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C2H6O4S
Molecular Weight 126.132
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H19N5O2
Molecular Weight 325.3651
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Mivobulin is a synthetic water-soluble colchicine analog with the broad antitumor activity that competitively binds tubulin at the colchicine-binding site and inhibits tubulin polymerization. Cancer cells exposed to Mivobulin isethionate accumulate in the M phase of the cell cycle and subsequently die. Preclinical studies have demonstrated that Mivobulin isethionate is able to cross the blood-brain barrier. Importantly, Mivobulin isethionate demonstrated significant antitumor activity in a broad spectrum of murine and human tumor models that were cross-resistant to vincristine, cisplatin, vinblastine, navelbine, and doxorubicin and in tumor cell lines exhibiting multidrug resistance owing to P-glycoprotein overexpression. In animal studies, the activity of Mivobulin isethionate was largely independent of the route of drug administration but favored a prolonged treatment schedule. Unfortunately, in clinical trials, Mivobulin fail to demonstrate the significant activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Clinical Trials. Referral resource Clinical trials using CI-980 (mivobulin isethionate).
1997 May
Antimycobacterial activity of 1-deaza-7,8-dihydropteridine derivatives against Mycobacterium tuberculosis and Mycobacterium avium complex in vitro.
2001 Apr
Patents

Patents

Sample Use Guides

Mivobulin was given by 72 h continuous i.v. infusion at a dose of 4.5 mg/m2/day, days 1-3 every 21 days.
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:02:54 GMT 2023
Edited
by admin
on Fri Dec 15 16:02:54 GMT 2023
Record UNII
8J08028R66
Record Status Validated (UNII)
Record Version
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Name Type Language
MIVOBULIN ISETHIONATE
USAN   WHO-DD  
USAN  
Official Name English
MIVOBULIN ISETHIONATE [USAN]
Common Name English
CARBAMIC ACID, (5-AMINO-1,2-DIHYDRO-2-METHYL-3-PHENYLPYRIDO(3,4-B)PYRAZIN-7-YL) ETHYL ESTER, (S)-, MONO(2-HYDROXYETHANESULPHONATE)
Common Name English
ETHYL (S)-5-AMINO-1,2-DIHYDRO-2-METHYL-3-PHENYLPYRIDO(3,4-B)PYRAZINE-7-CARBAMATE, MONO(2-HYDROXYETHANESULPHONATE)
Common Name English
Ethyl (S)-5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazine-7-carbamate, mono(2-hydroxyethanesulfonate)
Common Name English
CI-980
Code English
CARBAMIC ACID, (5-AMINO-1,2-DIHYDRO-2-METHYL-3-PHENYLPYRIDO(3,4-B)PYRAZIN-7-YL) ETHYL ESTER, (S)-, MONO(2-HYDROXYETHANESULFONATE)
Common Name English
NSC-635370
Code English
Mivobulin isethionate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67421
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
Code System Code Type Description
NSC
635370
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
PUBCHEM
182762
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
NCI_THESAURUS
C1357
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
FDA UNII
8J08028R66
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
USAN
HH-92
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
MESH
C072383
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
CAS
126268-81-3
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID50155130
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL1233800
Created by admin on Fri Dec 15 16:02:54 GMT 2023 , Edited by admin on Fri Dec 15 16:02:54 GMT 2023
PRIMARY
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ACTIVE MOIETY