MIRINCAMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H35ClN2O5S
Molecular Weight	439.01
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O)[C@H](NC(=O)[C@@H]2C[C@@H](CCCCC)CN2)[C@H](C)Cl

InChI

InChIKey=UFFIWDQGZCWMIU-YLKLGEPYSA-N

InChI=1S/C19H35ClN2O5S/c1-4-5-6-7-11-8-12(21-9-11)18(26)22-13(10(2)20)17-15(24)14(23)16(25)19(27-17)28-3/h10-17,19,21,23-25H,4-9H2,1-3H3,(H,22,26)/t10-,11+,12-,13+,14-,15+,16+,17+,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H35ClN2O5S
Molecular Weight	439.01
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24916383 | https://www.ncbi.nlm.nih.gov/pubmed/25326032

Mirincamycin, a protein biosynthesis inhibitor was studied as an antibacterial agent. It was shown that mirincamycin could be promising candidate in the therapy and prophylaxis of multidrug-resistant falciparum malaria. Moreover, in combination with 4 or 8-aminoquinolines it could be used for the treatment and relapse prevention of vivax malaria. In addition, was studied the anti-relapse activity of mirincamycin in the Plasmodium cynomolgi sporozoite-infected Rhesus monkey model. However, the negative P. cynomolgi hypnozoite data indicates that mirincamycin is unlikely to have potential as a clinical anti-relapse agent.

Approval Year

PubMed

Title	Date	PubMed
Enhancement of the curative activity of primaquine by concomitant administration of mirincamycin.	1985 Feb	3885847
In vitro activity of mirincamycin (U24729A) against Plasmodium falciparum isolates from Gabon.	2010 Jan	19841147
Absolute bioavailability of cis-mirincamycin and trans-mirincamycin in healthy rhesus monkeys and ex vivo antimalarial activity against Plasmodium falciparum.	2011 Dec	21947400
Mirincamycin, an old candidate for malaria combination treatment and prophylaxis in the 21st century: in vitro interaction profiles with potential partner drugs in continuous culture and field isolates.	2014 Jun 10	24916383
Anti-relapse activity of mirincamycin in the Plasmodium cynomolgi sporozoite-infected Rhesus monkey model.	2014 Oct 17	25326032

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:22:48 GMT 2023` Edited by `admin` on `Fri Dec 15 18:22:48 GMT 2023`
Record UNII	F6T0FI8XCS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MIRINCAMYCIN

Official Name

English

1'-DEMETHYL-4'-DEPROPYL-4'-PENTYLCLINDAMYCIN

Common Name

English

L-THREO-,ALPHA.-D-GALACTO-OCTOPYRANOSIDE, METHYL 7-CHLORO-6,7,8-TRIDEOXY-6-(((4-PENTYL-2-PYRROLIDINYL)CARBONYL)AMINO)-1-THIO-

Common Name

English

7-CHLORO-N-DEMETHYL-4'-PENTYLLINCOMYCIN

Common Name

English

mirincamycin [INN]

Common Name

English

Code System Code Type Description

ChEMBL

CHEMBL2110945