SPIRAMYCIN I

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C43H74N2O14
Molecular Weight	843.0527
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C

InChI

InChIKey=ACTOXUHEUCPTEW-CEUOBAOPSA-N

InChI=1S/C43H74N2O14/c1-24-21-29(19-20-46)39(59-42-37(49)36(45(9)10)38(27(4)56-42)58-35-23-43(6,51)41(50)28(5)55-35)40(52-11)31(47)22-33(48)53-25(2)15-13-12-14-16-32(24)57-34-18-17-30(44(7)8)26(3)54-34/h12-14,16,20,24-32,34-42,47,49-51H,15,17-19,21-23H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27-,28+,29+,30+,31-,32+,34+,35+,36-,37-,38-,39+,40+,41+,42+,43-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C43H74N2O14
Molecular Weight	843.0527
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	19 / 19
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17849607

Spiramycins are macrolides produced by cultures of Streptomyces ambofaciens from the soil of northern France. The mixture of spiramycins have been successfully separated into three different components termed as Spiramycin I, II and III, which differ structurally in the acylation moieties on the C3 of the lactone. The SP I component contains a hydroxyl group at C3. The drug is effective against gram-positive aerobic pathogens, N. gonorrhoeae, and staphylococci. It is used to treat infections caused by bacteria and Toxoplasma gondii.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Toxoplasmosis 13 Sources: http://www.epharmacognosy.com/2013/05/macrolide-antibiotics.html	Curative		Approved 8583	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Hydroxylation and hydrolysis: two main metabolic ways of spiramycin I in anaerobic digestion.	2014-02	24345568
[Deletion of spiramycin 3-O-acyltransferase gene from Streptomyces spiramyceticus F21 resulting in the production of spiramycin I as major component].	2007-07	17849607
Simultaneous determination of metronidazole and spiramycin I in human plasma, saliva and gingival crevicular fluid by LC-MS/MS.	2005-06-15	15925222

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:53 GMT 2025`
Record UNII	033ECH6IFG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SPIRAMYCIN I

Common Name

English

FOROMACIDIN A

Preferred Name

English

SPIRAMYCIN I [MI]

Common Name

English

LEUCOMYCIN V, 9-O-((2R,5S,6R)-5-(DIMETHYLAMINO)TETRAHYDRO-6-METHYL-2H-PYRAN-2-YL)-

Common Name

English

LEUCOMYCIN V, 9-O-(5-(DIMETHYLAMINO)TETRAHYDRO-6-METHYL-2H-PYRAN-2-YL)-, (9(2R,5S,6R))-

Common Name

English

Code System Code Type Description

CHEBI

85260