ERYTHROMYCIN OXALATE DIHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H67NO13.C2H2O4.2H2O
Molecular Weight	859.9922
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ERYTHROMYCIN OXALATE DIHYDRATE

SMILES

O.O.OC(=O)C(O)=O.[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]2C

InChI

InChIKey=BSTFTBLRGBLRTI-PHMXLGLWSA-N

InChI=1S/C37H67NO13.C2H2O4.2H2O/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26;3-1(4)2(5)6;;/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;(H,3,4)(H,5,6);2*1H2/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;;;/m1.../s1

HIDE SMILES / InChI

Molecular Formula	C37H67NO13
Molecular Weight	733.9268
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	18 / 18
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C2H2O4
Molecular Weight	90.0349
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Erythromycin cyclocarbonate (Davercin) is a first generation semi-synthetic erythromycin. It is active against Gram-positive and some Gram-negative microorganisms. Davercin shows comparable or better in vitro potency, low host toxicity and improved pharmacokinetics compared with erythromycin. It is approved for the treatment of acne, atypical pneumonia (caused by Mycoplasma pneumoniae, Chlamydia pneumoniae, Legionella pneumophila), whooping cough (treatment and prevention), urethritis (caused by Ureaplasma urealyticum and Chlamydia trachomatis), gastrointestinal infection caused by Campylobacter spp., short-term infections of the skin and soft tissues (e.g. acne, staphylococcal dermatitis). In streptococcal infections, diphtheria, gonorrhea, early syphilis in patients who are allergic to penicillin, and in the prevention of bacterial endocarditis before the planned dental procedures. Adverse effects are: nausea, vomiting, abdominal pain, diarrhea, skin allergic reactions.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bacterial 70S ribosome 179	Binding Agent 1,064	14.0 nM [Kd]
Bacterial 70S ribosome 179	Inhibitor 8,297
Bacterial 70S ribosome 179	Binding Agent 1,064	14.0 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Diphtheria 40	Curative	Approved 8,429	Erythromycin
Erythrasma 26	Curative	Approved 8,429	Erythromycin
Listeriosis 26	Curative	Approved 8,429	Erythromycin
Respiratory tract infections 85	Curative	Approved 8,429	Erythromycin
Skin and skin structure infections 80	Curative	Approved 8,429	Erythromycin
Acne 98	Curative	Approved 8,429	Davercin
Pneumonia 90	Curative	Approved 8,429	Davercin
Bacterial endocarditis 30	Curative	Approved 8,429	Davercin
Staphylococcal dermatitis 26	Curative	Approved 8,429	Davercin
Diphtheria 40	Curative	Approved 8,429	E.E.S.
Skin and skin structure infections 80	Curative	Approved 8,429	E.E.S.
Respiratory tract infections 85	Curative	Approved 8,429	E.E.S
Listeriosis 26	Curative	Approved 8,429	E.E.S.
Erythrasma 26	Curative	Approved 8,429	E.E.S.

C_max

Value	Dose	Analyte	Population
2.44 μg/mL	500 mg single, oral	ERYTHROMYCIN serum	Homo sapiens
1.18 μg/mL	500 mg single, oral	ERYTHROMYCIN serum	Homo sapiens
1.99 μg/mL	250 mg 4 times / day multiple, oral	ERYTHROMYCIN serum	Homo sapiens
1.62 μg/mL	250 mg 4 times / day multiple, oral	ERYTHROMYCIN serum	Homo sapiens
1161.5 ng/mL	200 mg single, oral	ERYTHROMYCIN plasma	Homo sapiens
1386.1 ng/mL	200 mg single, oral	ERYTHROMYCIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
6.1 μg × h/mL	500 mg single, oral	ERYTHROMYCIN serum	Homo sapiens
3.1 μg × h/mL	500 mg single, oral	ERYTHROMYCIN serum	Homo sapiens
3544.7 ng × h/mL	200 mg single, oral	ERYTHROMYCIN plasma	Homo sapiens
4096.7 ng × h/mL	200 mg single, oral	ERYTHROMYCIN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.48 h	200 mg single, oral		ERYTHROMYCIN plasma	Homo sapiens
5.31 h	200 mg single, oral		ERYTHROMYCIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
5 g 1 times / day single, oral Studied dose	healthy, 12 years	Other AEs: Pancreatitis...
5.3 g 1 times / day single, oral Studied dose	healthy, 15 years	Other AEs: Pancreatitis...
500 mg 2 times / day multiple, oral Recommended	unhealthy, mean age 30 years	Disc. AE: Vomiting...
500 mg 3 times / day multiple, oral Recommended	unhealthy, mean age 30 years	Disc. AE: Nausea, Abdominal pain...
500 mg 2 times / day multiple, oral Recommended	unhealthy, mean age 44 years	Disc. AE: Epigastralgia, Nausea...

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AEs

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AE	Significance	Dose	Population
Pancreatitis		5 g 1 times / day single, oral Studied dose	healthy, 12 years
Pancreatitis		5.3 g 1 times / day single, oral Studied dose	healthy, 15 years
Vomiting	2.8% Disc. AE	500 mg 2 times / day multiple, oral Recommended	unhealthy, mean age 30 years
Nausea	14.6% Disc. AE	500 mg 3 times / day multiple, oral Recommended	unhealthy, mean age 30 years
Abdominal pain	4.9% Disc. AE	500 mg 3 times / day multiple, oral Recommended	unhealthy, mean age 30 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587			inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 P-gp 1,461 OATP1B1 788 OATP1B3 706	CYP3A 191 OAT2 115

Drug as perpetrator

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Target	Modality	Activity	Clinical evidence
CYP1A2 1,692	inhibitor 3,277	likely
CYP3A4 1,925	inhibitor 3,277	moderate [IC50 9.9 uM]	yes (co-administration study)
OATP1B1 803	inhibitor 3,277	yes [IC50 217 uM]
P-gp 1,650	inhibitor 3,277	yes [IC50 22.7 uM]
OATP1B3 715	inhibitor 3,277	yes [IC50 34 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
OAT2 115	substrate 3,367	yes
CYP3A 191	substrate 3,367	yes		likely (co-administration study)

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0126	http://www.3bsc.com/index/pro_info.php?id=19482
Aaron Chemicals	AR0039Z1	http://www.aaronchem.com/114-07-8
abcr GmbH	AB251852	http://www.abcr.com/shop/en/AB251852
Achemtek	0104-008056	http://www.achemtek.com/114-07-8
Acorn PharmaTech	ACN-048190	http://www.acornpharmatech.com/

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PubMed

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Title	Date	PubMed
A CLINICAL STUDY OF ERYTHROMYCIN STEARATE AND ERYTHROMYCIN ETHYL SUCCINATE IN OFFICE PRACTICE.	1964 Sep	14179191
Receptor for motilin identified in the human gastrointestinal system.	1999 Jun 25	10381885
Clinical efficacy of intravenous followed by oral azithromycin monotherapy in hospitalized patients with community-acquired pneumonia. The Azithromycin Intravenous Clinical Trials Group.	2000 Jul	10858333
Bioavailability and stability of erythromycin delayed release tablets.	2001 Dec	12789122
Bone marrow engraftment: histopathology of hematopoietic reconstitution following allogeneic transplantation in CML patients.	2001 Jan	11193198

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Sample Use Guides

In Vivo Use Guide

The usual dosage of erythromycin tablets is one 250 mg tablet four times daily in equally spaced doses or one 500 mg tablet every 12 hours. Dosage may be increased up to 4 g per day according to the severity of the infection. However, twice-a-day dosing is not recommended when doses larger than 1 g daily are administered.

Route of Administration: Oral

In Vitro Use Guide

The MIC values for erythromycin were: 0.25-1 ug/ml (Staphylococcus aureus ATCC 29213), 1-4 ug/ml (Enterococcus faecalis ATCC 29212), 0.03-0.12 ug/ml (Streptococcus pneumoniae ATCC 49619).

Substance Class	Chemical
Record UNII	XSP28IFM29
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ERYTHROMYCIN OXALATE DIHYDRATE

Common Name

English

ERYTHROMYCIN, OXALATE (1:1), DIHYDRATE

Common Name

English

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Code System

Code

Type

Description

FDA UNII

XSP28IFM29

PRIMARY

PUBCHEM

133082763

PRIMARY

CAS

14444-93-0

PRIMARY

CAS

14638-05-2

NON-SPECIFIC STOICHIOMETRY

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PARENT -> SALT/SOLVATE

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					63937KV33D

Erythromycin

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator