BIMOSIAMOSE DISODIUM

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C46H52O16.2Na
Molecular Weight	906.875
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[Na+].OC[C@H]1O[C@H](OC2=CC=C(CCCCCCC3=CC(C4=CC=CC(CC([O-])=O)=C4)=C(O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O)C=C3)C=C2C6=CC=CC(CC([O-])=O)=C6)[C@@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=ZGEPTUZKSXWWAB-PNGDFCJYSA-L

InChI=1S/C46H54O16.2Na/c47-23-35-39(53)41(55)43(57)45(61-35)59-33-15-13-25(19-31(33)29-11-5-9-27(17-29)21-37(49)50)7-3-1-2-4-8-26-14-16-34(60-46-44(58)42(56)40(54)36(24-48)62-46)32(20-26)30-12-6-10-28(18-30)22-38(51)52;;/h5-6,9-20,35-36,39-48,53-58H,1-4,7-8,21-24H2,(H,49,50)(H,51,52);;/q;2*+1/p-2/t35-,36-,39-,40-,41+,42+,43+,44+,45+,46+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	C46H52O16
Molecular Weight	860.8955
Charge	-2
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

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

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16140027
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/15813660

Bimosiamose, discovered by Encysive Pharmaceutical and presently being developed by Revotar Biopharmaceuticals, is an 863 g/mol molecular weight dimer with minimal carbohydrate content and is, to date, the leading selectin inhibitor in clinical development. It was developed as anti-inflammatory drug fir the treatment of acute chronic inflammatory disorders including COPD. This compound has shown promise in a phase IIa 'proof of concept' trial in patients with asthma, reducing airway recruitment of eosinophils after intravenous administration. In acute lung injury, neutrophils (a type of white blood cells, thus belonging to the group of cells of the body’s defence system-the immune system) are drawn to the small lung bloodvessels and migrate into the air sacs (alveoli). There they release substances, which cause the inflammation leading to further destruction of the lung tissue. Bimosiamose disodium is expected to hinder the migration of these neutrophils into the alveoli.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Selectin E 4 Target ID: CHEMBL3890 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9544210	Inhibitor 8504
Leukocyte adhesion molecule-1 6 Target ID: CHEMBL3161 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9544210	Inhibitor 8504
P-selectin 9 Target ID: CHEMBL5378 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9544210	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Acute lung injury 20 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Orphan_designation/2009/10/WC500005881.pdf	Primary	Basic research	Unknown Approved Use Unknown
Chronic obstructive pulmonary disease 175 Sources: http://www.ukmi.nhs.uk/applications/ndo/record_view_open.asp?newDrugID=5309	Primary	Phase II 1147	Unknown Approved Use Unknown
Asthma 244 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16140027	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
675 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16240703	30 mg/kg single, intravenous dose: 30 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
49.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17067318	140 mg single, respiratory dose: 140 mg route of administration: Respiratory experiment type: SINGLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
64.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17067318	70 mg 2 times / day multiple, respiratory dose: 70 mg route of administration: Respiratory experiment type: MULTIPLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.17 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17876866	300 mg single, subcutaneous dose: 300 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.69 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17876866	300 mg 1 times / day steady-state, subcutaneous dose: 300 mg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1360 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16240703	30 mg/kg single, intravenous dose: 30 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
952 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17067318	140 mg single, respiratory dose: 140 mg route of administration: Respiratory experiment type: SINGLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7378 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17067318	70 mg 2 times / day multiple, respiratory dose: 70 mg route of administration: Respiratory experiment type: MULTIPLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
11.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17876866	300 mg single, subcutaneous dose: 300 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17876866	300 mg 1 times / day steady-state, subcutaneous dose: 300 mg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
4.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16240703	30 mg/kg single, intravenous dose: 30 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17876866	300 mg single, subcutaneous dose: 300 mg route of administration: Subcutaneous experiment type: SINGLE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17876866	300 mg 1 times / day steady-state, subcutaneous dose: 300 mg route of administration: Subcutaneous experiment type: STEADY-STATE co-administered:	BIMOSIAMOSE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
140 mg single, respiratory Highest studied dose Dose: 140 mg Route: respiratory Route: single Dose: 140 mg Sources: https://pubmed.ncbi.nlm.nih.gov/17067318	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17067318	Sources: https://pubmed.ncbi.nlm.nih.gov/17067318
300 mg 1 times / day multiple, subcutaneous Highest studied dose Dose: 300 mg, 1 times / day Route: subcutaneous Route: multiple Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17876866	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/17876866	Sources: https://pubmed.ncbi.nlm.nih.gov/17876866
30 mg/kg single, intravenous Highest studied dose Dose: 30 mg/kg Route: intravenous Route: single Dose: 30 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16240703	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16240703	Sources: https://pubmed.ncbi.nlm.nih.gov/16240703
70 mg 2 times / day multiple, respiratory Studied dose Dose: 70 mg, 2 times / day Route: respiratory Route: multiple Dose: 70 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17067318	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17067318	Sources: https://pubmed.ncbi.nlm.nih.gov/17067318

Sourcing

Vendor/Aggregator	ID	URL
Chem Scene	CS-0024963	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0024963
Compound Cloud	11520819
Compound Cloud	9811353
MedChem Express	HY-106139	https://www.medchemexpress.com/search.html?q=HY-106139&ft=&fa=&fp=
MolPort	MolPort-046-836-496	https://www.molport.com/shop/molecule-link/MolPort-046-836-496

PubMed

Title	Date	PubMed
Inhibition of adhesion of human neutrophils and eosinophils to P-selectin by the sialyl Lewis antagonist TBC1269: preferential activity against neutrophil adhesion in vitro.	2000-04	10756228

Patents

Sample Use Guides

In Vivo Use Guide

bimosiamose 70 mg bid on days 1-3 and 70 mg once on the morning of day 4

Route of Administration: Respiratory

In Vitro Use Guide

In the absence of TBC1269 (BIMOSIAMOSE), both cell types adhered avidly to P-selectin under static and dynamic conditions. For neutrophils, preincubation of P-selectin-coated plates with TBC1269 (1 to 1000 microgram/mL) resulted in concentration-dependent decreases in neutrophil adhesion, with significant inhibition seen at concentrations >/=100 microgram/mL. Eosinophil adhesion to P-selectin was more refractory to inhibition by TBC1269 and was only partially inhibited at the highest concentration tested (1000 microgram/mL).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:12:58 GMT 2025` Edited by `admin` on `Mon Mar 31 18:12:58 GMT 2025`
Record UNII	7AK2FKB9AW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIMOSIAMOSE DISODIUM SALT

Preferred Name

English

BIMOSIAMOSE DISODIUM

Official Name

English

(1,1'-BIPHENYL)-3-ACETIC ACID, 3',3'''-(1,6-HEXANEDIYL)BIS(6'-(.ALPHA.-D-MANNOPYRANOSYLOXY)-, DISODIUM SALT

Common Name

English

TBC-1269

Code

English

TBC1269Z

Code

English

BIMOSIAMOSE DISODIUM SALT [MI]

Common Name

English

TBC-1269Z

Code

English

DISODIUM 3',3'''-HEXAMETHYLENEBIS(6'-.ALPHA.-D-MANNOPYRANOSYLOXY)-3-BIPHENYLACETATE)

Common Name

English

BIMOSIAMOSE DISODIUM [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29712