FLOPRISTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H38FN3O6
Molecular Weight	531.6162
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@H]1OC(=O)[C@H]2CCCN2C(=O)C3=COC(C[C@H](F)C[C@H](O)\C=C(C)\C=C\CNC(=O)\C=C\[C@H]1C)=N3

InChI

InChIKey=DFSJQGCLWZVMOD-IQIMCDJDSA-N

InChI=1S/C28H38FN3O6/c1-17(2)26-19(4)9-10-24(34)30-11-5-7-18(3)13-21(33)14-20(29)15-25-31-22(16-37-25)27(35)32-12-6-8-23(32)28(36)38-26/h5,7,9-10,13,16-17,19-21,23,26,33H,6,8,11-12,14-15H2,1-4H3,(H,30,34)/b7-5+,10-9+,18-13+/t19-,20-,21-,23-,26-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C28H38FN3O6
Molecular Weight	531.6162
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20112172 | http://www.novexel.com/page_page=NXL103.html

FLOPRISTIN is one of the components of the experimental drug NXL103 (XRP 2868), along with linopristin. Both are semi-synthetic streptogramin antibiotics derived from the Streptomyces genus. NXL103 has a spectrum of antibacterial activity that indicates it has the potential to be effective in the treatment of skin and skin structure infections, including those caused by methicillin-resistant Staphylococcus aureus, as well as community-acquired pneumonia. NXL103 has completed Phase II trials.

Originator

Approval Year

PubMed

Title	Date	PubMed
Activities of a new oral streptogramin, XRP 2868, compared to those of other agents against Streptococcus pneumoniae and haemophilus species.	2003 Oct	14506040
Activity of a new oral streptogramin, XRP2868, against gram-positive cocci harboring various mechanisms of resistance to streptogramins.	2006 Jan	16377692
NXL-103, a combination of flopristin and linopristin, for the potential treatment of bacterial infections including community-acquired pneumonia and MRSA.	2010 Feb	20112172
Synergy of streptogramin antibiotics occurs independently of their effects on translation.	2014 Sep	24957822

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:07:11 UTC 2023` Edited by `admin` on `Sat Dec 16 17:07:11 UTC 2023`
Record UNII	OZV2QPB39M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLOPRISTIN

Official Name

English

3H-21,18-NITRILO-1H,22H-PYRROLO(2,1-C)(1,8,4,19)DIOXADIAZACYCLOTETRACOSINE-1,7,22(4H)-TRIONE, 16-FLUORO-8,9,14,15,16,17,24,25,26,26A-DECAHYDRO-14-HYDROXY-4,12-DIMETHYL-3-(1-METHYLETHYL)-, (3R,4R,5E,10E,12E,14S,16R,26AR)-

Common Name

English

NXL-103 COMPONENT RPR-132552

Common Name

English

Flopristin [WHO-DD]

Common Name

English

RPR-132552

Code

English

(3R,4R,5E,10E,12E,14S,16R,26AR)-16-FLUORO-14-HYDROXY-4,12-DIMETHYL-3-(PROPAN-2-YL)-3,4,8,9,14,15,16,17,24,25,26,26A-DODECAHYDRO- 1H,7H,22H-21,18-AZENOPYRROLO= (2,1-C)(1,8,4,19)DIOXADIAZACYCLOTETRACOSINE-1,7,22-TRIONE

Common Name

English

flopristin [INN]

Common Name

English

(16R)-16-DESOXO-16-FLUOROPRISTINAMYCIN IIB

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258