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

[H][C@]1(O[C@H](NC2=NC=NC3=C2N=CN3)[C@H](O)[C@H](O)[C@H]1NC(=O)CNC(=O)\C=C\C=C\CCCCCCCCC)[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
Antitumor activity of a spicamycin derivative, KRN5500, and its active metabolite in tumor cells.	1994	7894087
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 Jun	10874212
A spicamycin derivative (KRN5500) provides neuropathic pain relief in patients with advanced cancer: a placebo-controlled, proof-of-concept trial.	2012 Apr	21983265

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:54:26 GMT 2023` Edited by `admin` on `Fri Dec 15 15:54:26 GMT 2023`
Record UNII	8VH13L5K20
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KRN-5500

Common 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

KRN5500

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

434414