U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C13H25NO9.3H2O
Molecular Weight 732.7236
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAMIGLIBOSE

SMILES

O.O.O.CO[C@H]1O[C@H](CN2C[C@H](O)[C@@H](O)[C@H](O)[C@H]2CO)[C@@H](O)[C@H](O)[C@H]1O.CO[C@H]3O[C@H](CN4C[C@H](O)[C@@H](O)[C@H](O)[C@H]4CO)[C@@H](O)[C@H](O)[C@H]3O

InChI

InChIKey=FOZFSEMFCIPOSZ-SPCKQMHLSA-N
InChI=1S/2C13H25NO9.3H2O/c2*1-22-13-12(21)11(20)10(19)7(23-13)3-14-2-6(16)9(18)8(17)5(14)4-15;;;/h2*5-13,15-21H,2-4H2,1H3;3*1H2/t2*5-,6+,7-,8-,9-,10-,11+,12-,13+;;;/m11.../s1

HIDE SMILES / InChI

Molecular Formula C13H25NO9
Molecular Weight 339.3389
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Camiglibose is a glucopyranoside and inhibitor of alpha-glucosidase with antihyperglycemic activity patented by Merrell Dow Pharmaceuticals. In rats, a single oral dose of Camiglibose administered simultaneously with 2 g/kg body wt sucrose resulted in a dose dependent reduction in the area under the 0- to 3-h glycemic response curve, A reduction in the glycemic response to sucrose was accompanied by reduced insulin secretion. Camiglibose was more effective against a sucrose load in streptozocin-administered rats than in control rats and was as effective after 16 daily doses as after a single dose. Doses that reduced the glycemic response to carbohydrate did not inhibit liver lysosomal a-glucosidase activity or cause lysosomal glycogen accumulation. In cynomolgus monkeys, an oral dose of 1 mg/kg Camiglibose reduced the glycemic and insulin responses to sucrose

Approval Year

PubMed

PubMed

TitleDatePubMed
New potent alpha-glucohydrolase inhibitor MDL 73945 with long duration of action in rats.
1991 Jul
Patents

Patents

Sample Use Guides

cynomolgus monkeys: 1 mg/kg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:42:16 GMT 2023
Edited
by admin
on Fri Dec 15 17:42:16 GMT 2023
Record UNII
XSD3N36UID
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAMIGLIBOSE
USAN  
USAN  
Official Name English
MDL-73945
Code English
CAMIGLIBOSE [USAN]
Common Name English
.ALPHA.-D-GLUCOPYRANOSIDE, METHYL 6-DEOXY-6-(3,4,5-TRIHYDROXY-2-(HYDROXYMETHYL)-1-PIPERIDINYL)-, SESQUIHYDRATE, (2R-(2.ALPHA.,3.BETA.,4.ALPHA.,5.BETA.))-
Common Name English
METHYL 6-DEOXY-6-((2R,3R,4R,5S)-3,4,5-TRIHYDROXY-2-(HYDROXYMETHYL)PIPERIDINO)-.ALPHA.-D-GLUCOPYRANOSIDE SESQUIHYDRATE
Common Name English
MDL 73,945
Code English
Classification Tree Code System Code
NCI_THESAURUS C29711
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2105521
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID00157583
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
FDA UNII
XSD3N36UID
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
CAS
132438-21-2
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
MESH
C069606
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
SMS_ID
100000081597
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
USAN
DD-53
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
PUBCHEM
11954339
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
NCI_THESAURUS
C79538
Created by admin on Fri Dec 15 17:42:16 GMT 2023 , Edited by admin on Fri Dec 15 17:42:16 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY