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Chemistry

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Also known as: Ey1wa413ul, Avasopasem manganese [usan], Gc4419, Sc-72325a, M-40419, Unii-ey1wa413ul
Molecular Formula
C21H35Cl2MnN5
Molecular Weight
483.4  g/mol
InChI Key
WXEMWBBXVXHEPU-NDOCQCNASA-L
FDA UNII
EY1WA413UL

Avasopasem manganese
Avasopasem Manganese is a mimetic of the enzyme superoxide dismutase (SOD) that may potentially be used to reduce oral mucositis and esophagitis associated with radiation therapy and chemoradiotherapy. Upon administration, avasopasem manganese may mimic native SODs and catalyze the formation of molecular oxygen and hydrogen peroxide from the burst of superoxide anion present in the irradiated tissues upon radiation and/or induced by chemotherapy. This may decrease the damage of radiation and/or chemotherapy to normal tissues.
1 2D Structure

Avasopasem manganese

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
manganese(2+);(4S,9S,14S,19S)-3,10,13,20,26-pentazatetracyclo[20.3.1.04,9.014,19]hexacosa-1(26),22,24-triene;dichloride
2.1.2 InChI
InChI=1S/C21H35N5.2ClH.Mn/c1-3-10-20-18(8-1)22-12-13-23-19-9-2-4-11-21(19)25-15-17-7-5-6-16(26-17)14-24-20;;;/h5-7,18-25H,1-4,8-15H2;2*1H;/q;;;+2/p-2/t18-,19-,20-,21-;;;/m0.../s1
2.1.3 InChI Key
WXEMWBBXVXHEPU-NDOCQCNASA-L
2.1.4 Canonical SMILES
C1CCC2C(C1)NCCNC3CCCCC3NCC4=CC=CC(=N4)CN2.[Cl-].[Cl-].[Mn+2]
2.1.5 Isomeric SMILES
C1CC[C@H]2[C@H](C1)NCCN[C@H]3CCCC[C@@H]3NCC4=CC=CC(=N4)CN2.[Cl-].[Cl-].[Mn+2]
2.2 Other Identifiers
2.2.1 UNII
EY1WA413UL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Avasopasem Manganese

2. Gc4419

2.3.2 Depositor-Supplied Synonyms

1. Ey1wa413ul

2. Avasopasem Manganese [usan]

3. Gc4419

4. Sc-72325a

5. M-40419

6. Unii-ey1wa413ul

7. Avasopasem Manganese Dichloride

8. Avasopasem Manganese [inn]

9. Avasopasem Manganese [who-dd]

10. Gc-4419

11. (pbpy-7-11-2344'3')-dichloro((4as,13as,17as,21as)-1,2,3,4,4a,5,6,12,13,13a,14,15,16,17,17a,18,19,20,21,21a-icosahydro-7,11-azeno-7h-dibenzo(b,h)(1,4,7,10)tetraazacycloheptadecine-.kappa.5n5,n13,n18,n21,n22)manganese

12. Manganese, Dichloro((4as,13as,17as,21as)-1,2,3,4,4a,5,6,12,13,13a,14,15,16,17,17a,18,19,20,21,21a-eicosahydro-7,11-nitrilo-7h-dibenzo(b,h)-5,13,18,21-tetraazacycloheptadecine-.kappa.n5,.kappa.n13,.kappa.n18,.kappa.n21,.kappa.n22)-, (pb-7-11-2344'3')-

2.4 Create Date
2013-07-08
3 Chemical and Physical Properties
Molecular Weight 483.4 g/mol
Molecular Formula C21H35Cl2MnN5
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count7
Rotatable Bond Count0
Exact Mass482.164995 g/mol
Monoisotopic Mass482.164995 g/mol
Topological Polar Surface Area61 Ų
Heavy Atom Count29
Formal Charge0
Complexity381
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count4
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Free Radical Scavengers

Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY. (See all compounds classified as Free Radical Scavengers.)


4.2 Mechanism of Action

Avasopasem manganese is a superoxide dismutase mimetic that rapidly and selectively converts superoxide to hydrogen peroxide and oxygen in order to protect normal tissue from radiation therapy-induced damage. This drug is currently being investigated against oral mucositis, esophagitis, and COVID-19.


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