IMMU 130

Synopsis, Chemistry

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Also known as: Labetuzumab-sn38, Unii-8e3hi6qq9j, Hmn14-sn38, Labetuzumab govitecan [usan], Immu 130, 8e3hi6qq9j

Molecular Formula

C₇₅H₁₀₂N₁₂O₂₄S

Molecular Weight

1587.7 g/mol

InChI Key

CBNAAKBWBABMBY-LQCKLLCCSA-N

Labetuzumab Govitecan is an antibody-drug conjugate (ADC) containing labetuzumab, a mildly reduced, anti-CEACAM5 humanized monoclonal antibody, conjugated to the potent topoisomerase I inhibitor SN-38, with antineoplastic activity. The monoclonal antibody moiety of labetuzumab govitecan selectively binds to carcinoembryonic cell adhesion molecule 5 (CEACAM5), which is abundantly expressed on the surface of a majority of solid tumors. Upon internalization and proteolytic cleavage, SN-38, the active metabolite of irinotecan, inhibits the activity of topoisomerase I in the tumor cells, eventually inhibiting both DNA replication and transcription and leading to tumor cell apoptosis.

1 2D Structure

IMMU-130

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R)-2-amino-3-[1-[[4-[[1-[2-[2-[2-[2-[2-[2-[2-[2-[2-[[2-[2-[[(2S)-5-amino-1-[4-[[(19S)-10,19-diethyl-7-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-19-yl]oxycarbonyloxymethyl]anilino]-1-oxopentan-2-yl]amino]-2-oxoethoxy]acetyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]triazol-4-yl]methylcarbamoyl]cyclohexyl]methyl]-2,5-dioxopyrrolidin-3-yl]sulfanylpropanoic acid

2.1.2 InChI

InChI=1S/C75H102N12O24S/c1-3-54-55-36-53(88)15-16-60(55)82-67-56(54)42-86-62(67)37-58-57(70(86)94)44-109-73(98)75(58,4-2)111-74(99)110-43-49-9-13-51(14-10-49)80-69(93)61(6-5-17-76)81-65(90)46-108-45-64(89)78-18-20-100-22-24-102-26-28-104-30-32-106-34-35-107-33-31-105-29-27-103-25-23-101-21-19-85-41-52(83-84-85)39-79-68(92)50-11-7-48(8-12-50)40-87-66(91)38-63(71(87)95)112-47-59(77)72(96)97/h9-10,13-16,36-37,41,48,50,59,61,63,88H,3-8,11-12,17-35,38-40,42-47,76-77H2,1-2H3,(H,78,89)(H,79,92)(H,80,93)(H,81,90)(H,96,97)/t48?,50?,59-,61-,63?,75-/m0/s1

2.1.3 InChI Key

CBNAAKBWBABMBY-LQCKLLCCSA-N

2.1.4 Canonical SMILES

CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)OC(=O)OCC5=CC=C(C=C5)NC(=O)C(CCCN)NC(=O)COCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCN6C=C(N=N6)CNC(=O)C7CCC(CC7)CN8C(=O)CC(C8=O)SCC(C(=O)O)N)C2=NC9=C1C=C(C=C9)O

2.1.5 Isomeric SMILES

CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)[C@@]4(CC)OC(=O)OCC5=CC=C(C=C5)NC(=O)[C@H](CCCN)NC(=O)COCC(=O)NCCOCCOCCOCCOCCOCCOCCOCCOCCN6C=C(N=N6)CNC(=O)C7CCC(CC7)CN8C(=O)CC(C8=O)SC[C@@H](C(=O)O)N)C2=NC9=C1C=C(C=C9)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Anti-ceacam5-sn 38

2. Immu-130

2.2.2 Depositor-Supplied Synonyms

1. Labetuzumab-sn38

2. Unii-8e3hi6qq9j

3. Hmn14-sn38

4. Labetuzumab Govitecan [usan]

5. Immu 130

6. 8e3hi6qq9j

7. 1469876-18-3

8. Q27270244

2.3 Create Date

2015-04-18

3 Chemical and Physical Properties

Molecular Formula	C₇₅H₁₀₂N₁₂O₂₄S
Molecular Weight	1587.7 g/mol
XLogP3	-3.6
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	30
Rotatable Bond Count	53
Exact Mass	1586.68506334 g/mol
Monoisotopic Mass	1586.68506334 g/mol
Topological Polar Surface Area	498 Å²
Heavy Atom Count	112
Formal Charge	0
Complexity	3130
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1