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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H56N6O5
Molecular Weight 640.8563
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEMADOTIN

SMILES

CC(C)[C@H](NC(=O)[C@H](C(C)C)N(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N2CCC[C@H]2C(=O)NCC3=CC=CC=C3

InChI

InChIKey=XSAKVDNHFRWJKS-IIZANFQQSA-N
InChI=1S/C35H56N6O5/c1-22(2)28(37-32(43)29(23(3)4)38(7)8)34(45)39(9)30(24(5)6)35(46)41-20-14-18-27(41)33(44)40-19-13-17-26(40)31(42)36-21-25-15-11-10-12-16-25/h10-12,15-16,22-24,26-30H,13-14,17-21H2,1-9H3,(H,36,42)(H,37,43)/t26-,27-,28-,29-,30-/m0/s1

HIDE SMILES / InChI

Molecular Formula C35H56N6O5
Molecular Weight 640.8563
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cemadotin (LU103793) is a cytotoxic water-soluble pentapeptide analogue of dolastatin 15. The dolastatin peptides were originally isolated from the shell-less mollusc Dolabella auricularia. Cemadotin blocks cells at mitosis. It exerts its antitumor activity by suppressing spindle microtubule dynamics through a distinct molecular mechanism by binding at a novel site in tubulin. Cemadotin was in phase II clinical trials as a promising cancer chemotherapeutic agent. However, this agent appears to be inactive in the treatment of advanced non-small-cell lung cancer and other tumors and this research has been discontinued.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
19.4 µM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1.2 μM
3 mg/m² 1 times / day steady-state, intravenous
CEMADOTIN plasma
Homo sapiens
0.75 μM
2.5 mg/m² single, intravenous
CEMADOTIN plasma
Homo sapiens
0.97 μM
2.5 mg/m² 1 times / day steady-state, intravenous
CEMADOTIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
6.3 μM × h
3 mg/m² 1 times / day steady-state, intravenous
CEMADOTIN plasma
Homo sapiens
10.1 μM × h
2.5 mg/m² single, intravenous
CEMADOTIN plasma
Homo sapiens
10.5 μM × h
2.5 mg/m² 1 times / day steady-state, intravenous
CEMADOTIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
3 mg/m² 1 times / day steady-state, intravenous
CEMADOTIN plasma
Homo sapiens
13 h
2.5 mg/m² single, intravenous
CEMADOTIN plasma
Homo sapiens
10 h
2.5 mg/m² 1 times / day steady-state, intravenous
CEMADOTIN plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
2.5 mg/m2 as a 5-minute infusion for 5 consecutive days every 3 weeks
Route of Administration: Intravenous
In Vitro Use Guide
Turbidity assays with bovine brain microtubules demonstrated that LU103793 inhibits microtubule polymerization in a concentration-dependent manner (IC50 = 7 uM).
Substance Class Chemical
Record UNII
6SQ8M7ZSFV
Record Status Validated (UNII)
Record Version