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Details

Stereochemistry ABSOLUTE
Molecular Formula C46H54O16
Molecular Weight 862.9114
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIMOSIAMOSE

SMILES

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

InChI

InChIKey=RYWCQJDEHXJHRI-XJMXIVSISA-N
InChI=1S/C46H54O16/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)/t35-,36-,39-,40-,41+,42+,43+,44+,45+,46+/m1/s1

HIDE SMILES / InChI

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
49.8 ng/mL
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
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
1.69 μg/mL
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
2.17 μg/mL
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
675 μg/mL
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
952 ng × h/mL
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
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
10.8 μg × h/mL
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
11.1 μg × h/mL
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
1360 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.2 h
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
3.7 h
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
4.1 h
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
Doses

Doses

DosePopulationAdverse events​
140 mg single, respiratory
Highest studied dose
Dose: 140 mg
Route: respiratory
Route: single
Dose: 140 mg
Sources: Page: p.454
healthy, ADULT
n = 5
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 5
Sources: Page: p.454
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: Page: p.478
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Population Size: 6
Sources: Page: p.478
30 mg/kg single, intravenous
Highest studied dose
Dose: 30 mg/kg
Route: intravenous
Route: single
Dose: 30 mg/kg
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
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: Page: p.455
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.455
PubMed

PubMed

TitleDatePubMed
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 Apr
Patents

Patents

Sample Use Guides

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).
Name Type Language
BIMOSIAMOSE
INN   MI  
INN  
Official Name English
(HEXANE-1,6-DIYLBIS(6'-(.ALPHA.-D-MANNOPYRANOSYLOXY)BIPHENYL-3',3-DIYL))DIACETIC ACID
Common Name English
BIMOSIAMOSE [MI]
Common Name English
bimosiamose [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29712
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
NCI_THESAURUS C257
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
Code System Code Type Description
INN
8074
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
CAS
187269-40-5
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
NCI_THESAURUS
C72942
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
PUBCHEM
9811353
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
MESH
C496819
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
DRUG BANK
DB06197
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
MERCK INDEX
m2496
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1215923
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
SMS_ID
100000177260
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID8048783
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY
FDA UNII
97B5KCW80W
Created by admin on Sat Dec 16 17:45:17 GMT 2023 , Edited by admin on Sat Dec 16 17:45:17 GMT 2023
PRIMARY