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Also known as: Ava6000, Ava-6000, Unii-7xpb9b6mua, 1841402-73-0, Schembl17345374

Molecular Formula

C₄₁H₄₄N₄O₁₄

Molecular Weight

816.8 g/mol

InChI Key

CNGRCGLLHXRRTQ-SXSFFGRISA-N

FDA UNII

7XPB9B6MUA

Fibroblast Activation Protein Alpha-activated Doxorubicin Prodrug AVA6000 is a prodrug of the anthracycline antineoplastic antibiotic doxorubicin composed of doxorubicin covalently bonded to the dipeptide N-(pyridine-4-carbonyl)-D-Ala-L-Pro, with potential antineoplastic activity. Upon administration, fibroblast activation protein alpha (FAP)-activated doxorubicin prodrug AVA6000 is hydrolyzed by FAP, which is overexpressed on cancer-associated fibroblasts (CAFs) in the tumor microenvironment (TME). Doxorubicin is released in the TME, and intercalates into DNA and interacts with topoisomerase II. This leads to an inhibition of DNA replication and repair, and prevents RNA and protein synthesis. By targeting the delivery of doxorubicin directly to the tumor, AVA6000 may result in less systemic toxicities. FAP, a membrane-bound protease, is overexpressed on CAFs in various tumors but minimally expressed on normal, healthy cells.

1 2D Structure

AVA6000

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[(2R)-1-[(2S)-2-[[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]pyridine-4-carboxamide

2.1.2 InChI

InChI=1S/C41H44N4O14/c1-18(43-38(53)20-9-11-42-12-10-20)40(55)45-13-5-7-24(45)39(54)44-23-14-28(58-19(2)33(23)48)59-26-16-41(56,27(47)17-46)15-22-30(26)37(52)32-31(35(22)50)34(49)21-6-4-8-25(57-3)29(21)36(32)51/h4,6,8-12,18-19,23-24,26,28,33,46,48,50,52,56H,5,7,13-17H2,1-3H3,(H,43,53)(H,44,54)/t18-,19+,23+,24+,26+,28+,33-,41+/m1/s1

2.1.3 InChI Key

CNGRCGLLHXRRTQ-SXSFFGRISA-N

2.2 Other Identifiers

2.2.1 UNII

7XPB9B6MUA

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Ava6000

2. Ava-6000

3. Unii-7xpb9b6mua

4. 1841402-73-0

5. Schembl17345374

2.4 Create Date

2016-02-23

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₄₄N₄O₁₄
Molecular Weight	816.8 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	10
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	271
Heavy Atom Count	59
Formal Charge	0
Complexity	1630
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1