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Chemistry

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Also known as: Humov 19, Unii-98de7vn88d, Imgn853, Imgn 853, Mirvetuximab soravtansine [usan], Mirvetuximab-soravtansine

Molecular Formula

C₄₂H₆₁ClN₄O₁₄S₃

Molecular Weight

977.6 g/mol

InChI Key

ZOHXWSHGANNQGO-DSIKUUPMSA-N

Mirvetuximab Soravtansine is an immunoconjugate consisting of the humanized monoclonal antibody M9346A against folate receptor 1 (FOLR1) conjugated, via the disulfide-containing cleavable linker sulfo-SPDB, to the cytotoxic maytansinoid DM4, with potential antineoplastic activity. The anti-FOLR1 monoclonal antibody moiety of mirvetuximab soravtansine targets and binds to the cell surface antigen FOLR1. After antibody-antigen interaction and internalization, the immunoconjugate releases DM4, which binds to tubulin and disrupts microtubule assembly/disassembly dynamics, thereby inhibiting cell division and cell growth of FOLR1-expressing tumor cells. FOLR1, a member of the folate receptor family is overexpressed on a variety of epithelial-derived cancer cells. The sulfo-SPDB linker prevents cleavage in the bloodstream and may improve this agent's efficacy in multidrug resistant tumor cells.

1 2D Structure

Mirvetuximab Soravtansine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-amino-4-[[5-[[(2S)-1-[[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl]oxy]-1-oxopropan-2-yl]-methylamino]-2-methyl-5-oxopentan-2-yl]disulfanyl]-1-oxobutane-2-sulfonic acid

2.1.2 InChI

InChI=1S/C42H61ClN4O14S3/c1-23-12-11-13-31(58-10)42(53)22-29(59-39(52)45-42)24(2)36-41(6,61-36)32(21-34(49)47(8)27-19-26(18-23)20-28(57-9)35(27)43)60-38(51)25(3)46(7)33(48)14-16-40(4,5)63-62-17-15-30(37(44)50)64(54,55)56/h11-13,19-20,24-25,29-32,36,53H,14-18,21-22H2,1-10H3,(H2,44,50)(H,45,52)(H,54,55,56)/b13-11+,23-12+/t24-,25+,29+,30?,31-,32+,36+,41+,42+/m1/s1

2.1.3 InChI Key

ZOHXWSHGANNQGO-DSIKUUPMSA-N

2.1.4 Canonical SMILES

CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)CCC(C)(C)SSCCC(C(=O)N)S(=O)(=O)O)C)C)OC)(NC(=O)O2)O

2.1.5 Isomeric SMILES

C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)CCC(C)(C)SSCCC(C(=O)N)S(=O)(=O)O)C)\C)OC)(NC(=O)O2)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Imgn-853

2. Imgn853

2.2.2 Depositor-Supplied Synonyms

1. Humov 19

2. Unii-98de7vn88d

3. Imgn853

4. Imgn 853

5. Mirvetuximab Soravtansine [usan]

6. Mirvetuximab-soravtansine

7. 98de7vn88d

8. Imgn-853

9. Schembl16447449

10. 1453084-37-1

11. Immunoglobulin G1, Anti-(human Folate Receptor Alpha) (human-mus Musculus Monoclonal M9346a Heavy Chain), Disulfide With Human-mus Musculus Monoclonal M9346a Light Chain, Dimer, Tetraamide With N2'-(4-((3-carboxy-3-sulfopropyl)dithio)-4-methyl-1-oxopentyl)-n2'-deacetylmaytansine

12. Q27272114

2.3 Create Date

2015-07-11

3 Chemical and Physical Properties

Molecular Formula	C₄₂H₆₁ClN₄O₁₄S₃
Molecular Weight	977.6 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	16
Exact Mass	976.3034938 g/mol
Monoisotopic Mass	976.3034938 g/mol
Topological Polar Surface Area	313 Å²
Heavy Atom Count	64
Formal Charge	0
Complexity	1890
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1