COUMERMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C55H59N5O20
Molecular Weight	1110.0785
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO[C@@H]1[C@@H](OC(=O)C2=CC=C(C)N2)[C@@H](O)[C@H](OC3=C(C)C4=C(C=C3)C(O)=C(NC(=O)C5=CNC(C(=O)NC6=C(O)C7=C(OC6=O)C(C)=C(O[C@@H]8OC(C)(C)[C@H](OC)[C@@H](OC(=O)C9=CC=C(C)N9)[C@H]8O)C=C7)=C5C)C(=O)O4)OC1(C)C

InChI

InChIKey=WTIJXIZOODAMJT-DHFGXMAYSA-N

InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C55H59N5O20
Molecular Weight	1110.0785
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18473891 | https://patents.google.com/patent/US3201386A | https://www.ncbi.nlm.nih.gov/pubmed/27620144 | https://doi.org/10.1016/j.bcp.2016.09.025 | https://www.ncbi.nlm.nih.gov/pubmed/3164157

Coumermycin is from the aminocoumarin class of antibiotic compounds which acts by inhibiting DNA gyrase. Coumermycin is effective against gram-positive bacteria, but not gram-negative bacteria. Coumermycin its derivatives have been studied since the 1950's as potential antibiotic. However, it has seen little to no clinical development because of its low water solubility, toxicity profile, and ineffectiveness against gram-negative bacteria.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/794878	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/794878 https://www.ncbi.nlm.nih.gov/pubmed/18473891	Curative		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Efficacy of coumermycin, ofloxacin and vancomycin against methicillin-resistant Staphylococcus aureus in vitro and in experimental infections of mice.	1988 Mar	3164157
Combinatorial biosynthesis, metabolic engineering and mutasynthesis for the generation of new aminocoumarin antibiotics.	2008	18473891

Patents

Sample Use Guides

In Vivo Use Guide

Lethal septicemia was induced in mice by intraperitoneal administration of Methicillin-Resistant Staphylococcus. The infection was successfully treated in 50% of the animals (ED50) following a dose of 0.9 micro-g/g body weight. This was significantly better than ofloxacin and vancomycin.

Route of Administration: Other

In Vitro Use Guide

The antibiotic ability of coumermycin was evaluated against 232 bacterial strains. Minimal inhibitory concentrations (MIC) were determined in trypticase soy broth using twofold serial dilutions. The last tube in a series to show no visible growth after 18 hours at 37 deg-C was considered the MIC. Strain specific MIC's were reported between 0.002 micro-g/L and 100 micro-g/L.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:52:33 GMT 2023` Edited by `admin` on `Sat Dec 16 15:52:33 GMT 2023`
Record UNII	PCH9QZ1IIH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COUMERMYCIN

Official Name

English

COUMAMYCIN

Official Name

English

1H-PYRROLE-2,4-DICARBOXAMIDE, N2,N4-BIS(7-((6-DEOXY-5-C-METHYL-4-O-METHYL-3-O-((5-METHYL-1H-PYRROL-2-YL)CARBONYL)-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-4-HYDROXY-8-METHYL-2-OXO-2H-1-BENZOPYRAN-3-YL)-3-METHYL-

Common Name

English

5-METHYLPYYROLE-2-CARBOXYLIC ACID, DIESTER WITH 3,3'-((3-METHYLPYRROLE-2,4-DIYL)BIS(CARBONYLIMINO))BIS(4-HYDROXY-8-METHYL-7-((TETRAHYDRO-3,4-DIHYDROXY-5-METHOXY-6,6-DIMETHYLPYRAN-2-YL)OXY)COUMARIN)

Common Name

English

NSC-107412

Code

English

coumamycin [INN]

Common Name

English

NOTOMYCIN A1

Common Name

English

COUMERMYCIN [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258