LAF-389

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H42N2O8
Molecular Weight	498.6096
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@H]([C@H](O)[C@@H](O)[C@H](O)\C=C\C(C)(C)C)C(=O)N[C@H]1CC[C@H](CNC1=O)OC(=O)C2CCCCC2

InChI

InChIKey=XSYJUVKQRPLTAU-BKMGADMVSA-N

InChI=1S/C25H42N2O8/c1-25(2,3)13-12-18(28)19(29)20(30)21(34-4)23(32)27-17-11-10-16(14-26-22(17)31)35-24(33)15-8-6-5-7-9-15/h12-13,15-21,28-30H,5-11,14H2,1-4H3,(H,26,31)(H,27,32)/b13-12+/t16-,17+,18-,19+,20-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C25H42N2O8
Molecular Weight	498.6096
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	1
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Proteomics-based target identification: bengamides as a new class of methionine aminopeptidase inhibitors.	2003-12-26	14534293

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:37:20 GMT 2025` Edited by `admin` on `Mon Mar 31 23:37:20 GMT 2025`
Record UNII	XAE4WV436T
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LAF 389

Preferred Name

English

LAF-389

Code

English

CYCLOHEXANECARBOXYLIC ACID 7-OXO-6(S)-((2R,3R,4S,5R,6E)-3,4,5-TRIHYDROXY-2-METHOXY-8,8-DIMETHYL-6-NONENAMIDO)PERHYDROAZEPIN-3(R)-YL ESTER

Systematic Name

English

(6E)-N-((3S,6R)-6-((CYCLOHEXYLCARBONYL)OXY)HEXAHYDRO-2-OXO-1H-AZEPIN-3-YL)-6,7,8,9-TETRADEOXY-8,8-DIMETHYL-2-O-METHYL-D-GULO-NON-6-ENONAMIDE

Systematic Name

English

LAF389

Code

English

D-GULO-NON-6-ENONAMIDE, N-((3S,6R)-6-((CYCLOHEXYLCARBONYL)OXY)HEXAHYDRO-2-OXO-1H-AZEPIN-3-YL)-6,7,8,9-TETRADEOXY-8,8-DIMETHYL-2-O-METHYL-, (6E)-

Systematic Name

English

NVP-LAF-389

Code

English

((3R,6S)-7-OXO-6-(((E,2R,3R,4S,5R)-3,4,5-TRIHYDROXY-2-METHOXY-8,8-DIMETHYL-NON-6-ENOYL)AMINO)AZEPAN-3-YL) CYCLOHEXANECARBOXYLATE

Systematic Name

English

Code System Code Type Description

FDA UNII

XAE4WV436T

Created by admin on Mon Mar 31 23:37:20 GMT 2025 , Edited by admin on Mon Mar 31 23:37:20 GMT 2025

PRIMARY

CAS

270902-51-7

Created by admin on Mon Mar 31 23:37:20 GMT 2025 , Edited by admin on Mon Mar 31 23:37:20 GMT 2025

PRIMARY

PUBCHEM

9892113

Created by admin on Mon Mar 31 23:37:20 GMT 2025 , Edited by admin on Mon Mar 31 23:37:20 GMT 2025

PRIMARY

Related Record Type Details


					XAE4WV436T

LAF-389

ACTIVE MOIETY

Comments:

Class: Antineoplastic, Azepine; Mechanism of Action: Aminopeptidase inhibitor; Highest Development Phase: Discontinued for Chronic lymphocytic leukaemia, Multiple myeloma and Non-Hodgkin's lymphoma


					XAE4WV436T

LAF-389

ACTIVE MOIETY

Comments:

Seventy-eight cycles of treatment have been administered (mean 2.5, range 1-10 mg/day). Four cardiovascular dose-limiting toxicities were reported at 30 mg (2/2 patients) and 25 mg (2/9 patients), eight additional patients at various dose levels had (cardio)vascular toxicity, probably drug related, and one patient died owing to pulmonary embolism at the 5 mg dose. No objective responses were recorded. Pharmacokinetic parameters were variable, although linear and without obvious accumulation from cycle I to cycle II. LAF389 dose escalation was terminated owing to occurrence of unpredictable cardiovascular events. This, associated with the lack of clinical activity, did not warrant further investigation of this agent.


					XAE4WV436T

LAF-389

ACTIVE MOIETY

Comments:

An optimized, convergent, safe synthesis of LAF389 (9), an anti-cancer agent analogous to bengamide B, is described.