916746-27-5

Basic information

• Product Name: N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N⁵-carbamoyl-L-ornithine
• CAS NO: 916746-27-5
• Molecular Weight: 467.522
• Mol File: 916746-27-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N⁵-carbamoyl-L-ornithine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N⁵-carbamoyl-L-ornithine(916746-27-5)
• EPA Substance Registry System: N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N⁵-carbamoyl-L-ornithine(916746-27-5)

Safety Data

• Hazardous Substances Data: 916746-27-5(Hazardous Substances Data)

Upstream product

• 372-75-8 Citrulline 
• 3496-11-5 2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate 
• 159858-06-7 N-[(Benzyloxy)carbonyl]-L-valyl-N₅-carbamoyl-L-ornithine 
• 55750-53-3 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid 
• 68858-20-8 Fmoc-Val-OH 
• 133174-15-9 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-ureidopentanoic acid 
• 55750-63-5 6-maleimidohexanoic acid N-hydroxylsuccinimide ester 
• 159858-33-0 (S)-2-((S)-2-amino-3-methylbutanamido)-5-ureidopentanoic acid 
• 870487-08-4 (6S,9S)-1-amino-9-isopropyl-13,13-dimethyl-1,8,11-trioxo-12-oxa-2,7,10-triazatetradecane-6-carboxylic acid 

Downstream Products

• 159857-81-5 N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N⁵-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide 
• 159857-80-4 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide 

Relevant articles and documents

Antibody–Drug Conjugates with Pyrrole-Based KSP Inhibitors as the Payload Class

The number of cytotoxic payload classes successfully employed in antibody–drug conjugates (ADCs) is still rather limited. The identification of ADC payloads with a novel mode of action will increase therapeutic options and potentially increase the therapeutic window. Herein, we describe the utilization of kinesin spindle protein inhibitors (KSPi) as a novel payload class providing highly potent ADCs against different targets, for instance HER-2 or TWEAKR/Fn14. Aspects of technical optimization include the development of different linker attachment sites, the stabilization of ADC linkage to avoid payload deconjugation and finally, the tailor-made design of active metabolites with a long lasting intracellular exposure in the tumor matching the mode of action of KSP inhibition. These KSPi-ADCs are highly potent and selective in vitro and demonstrate in vivo efficacy in a broad panel of tumor models including complete regressions in a patient-derived urothelial cancer model.

DRUG ANTIBODY CONJUGATES

Drug conjugates having formula [D-(X)b-(AA)w-(T)g-(L)-]n-Ab wherein: D is a drug moiety having the following formula (I) or a pharmaceutically acceptable salt or ester thereof, wherein D is covalently attached via a hydroxy group at OR1, OR3 or ZH, or a thiol group at ZH to (X)b if any, or (AA)w if any, or to (T)g if any, or (L); that are useful in the treatment of cancer.

ANTIBODY DRUG CONJUGATES OF KINESIN SPINDEL PROTEIN (KSP) INHIBITORS WITH ANTIB7H3-ANTIBODIES

The present application relates to novel binder drug conjugates (ADCs), to active metabolites of these ADCs, to processes for preparing these ADCs, to the use of these ADCs for the treatment and/or prophylaxis of diseases and to the use of these ADCs for preparing medicaments for treatment and/or prophylaxis of diseases, in particular hyperproliferative and/or angiogenic disorders such as, for example, cancer diseases. Such treatments can be effected as monotherapy or else in combination with other medicaments or further therapeutic measures.