KRN-5500

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H43N7O7
Molecular Weight	589.6837
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCC\C=C\C=C\C(=O)NCC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](NC2=C3N=CNC3=NC=N2)O[C@H]1[C@@H](O)CO

InChI

InChIKey=LQIPDFIUPOYMPR-BKYURJJWSA-N

InChI=1S/C28H43N7O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(38)29-14-20(39)34-21-23(40)24(41)28(42-25(21)18(37)15-36)35-27-22-26(31-16-30-22)32-17-33-27/h10-13,16-18,21,23-25,28,36-37,40-41H,2-9,14-15H2,1H3,(H,29,38)(H,34,39)(H2,30,31,32,33,35)/b11-10+,13-12+/t18-,21+,23+,24+,25-,28-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C28H43N7O7
Molecular Weight	589.6837
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67092296 | https://www.ncbi.nlm.nih.gov/pubmed/10874212 | https://www.ncbi.nlm.nih.gov/pubmed/21983265

KRN-5500, a spicamycin derivative, is a nucleoside-like antibiotic with a broad spectrum of antitumor activity against human cancer cell lines. It also may have value in the treatment of neuropathic pain.

Originator

Approval Year

PubMed

Title	Date	PubMed
A spicamycin derivative (KRN5500) provides neuropathic pain relief in patients with advanced cancer: a placebo-controlled, proof-of-concept trial.	2012-04	21983265
Spicamycin and KRN5500 induce apoptosis in myeloid and lymphoid cell lines with down-regulation of bcl-2 expression and modulation of promyelocytic leukemia protein.	2000-06	10874212
Antitumor activity of a spicamycin derivative, KRN5500, and its active metabolite in tumor cells.	1994	7894087

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:49 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:49 GMT 2025`
Record UNII	8VH13L5K20
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KRN-5500

Common Name

English

KRN5500

Preferred Name

English

NSC-650426

Code

English

6-(4-DEOXY-4-((2E,4E)-TETRADECADIENOYLGLYCYL)AMINO-L-GLYCERO-B-L-MANNOHEPTOPYRANOSYL)AMINO-9H-PURINE

Common Name

English

SPK-241

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

434414