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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 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 Formula	C₂₁H₃₅Cl₂MnN₅
Molecular Weight	483.4 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	0
Exact Mass	482.164995 g/mol
Monoisotopic Mass	482.164995 g/mol
Topological Polar Surface Area	61 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	381
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	4

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.

Drugs in Development