APROSULATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H50N2O70S16
Molecular Weight	2035.697
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)OC[C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]1O[C@H](COS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@@H](OS(O)(=O)=O)C(=O)NCCCNC(=O)[C@H](OS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](O[C@@H]2O[C@H](COS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]2OS(O)(=O)=O)[C@@H](COS(O)(=O)=O)OS(O)(=O)=O

InChI

InChIKey=KSXQTGMWWMBCIP-VXMGFIRPSA-N

InChI=1S/C27H50N2O70S16/c30-24(20(96-112(68,69)70)16(92-108(56,57)58)12(10(88-104(44,45)46)6-82-102(38,39)40)86-26-22(98-114(74,75)76)18(94-110(62,63)64)14(90-106(50,51)52)8(84-26)4-80-100(32,33)34)28-2-1-3-29-25(31)21(97-113(71,72)73)17(93-109(59,60)61)13(11(89-105(47,48)49)7-83-103(41,42)43)87-27-23(99-115(77,78)79)19(95-111(65,66)67)15(91-107(53,54)55)9(85-27)5-81-101(35,36)37/h8-23,26-27H,1-7H2,(H,28,30)(H,29,31)(H,32,33,34)(H,35,36,37)(H,38,39,40)(H,41,42,43)(H,44,45,46)(H,47,48,49)(H,50,51,52)(H,53,54,55)(H,56,57,58)(H,59,60,61)(H,62,63,64)(H,65,66,67)(H,68,69,70)(H,71,72,73)(H,74,75,76)(H,77,78,79)/t8-,9-,10-,11-,12-,13-,14+,15+,16+,17+,18+,19+,20-,21-,22-,23-,26+,27+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H50N2O70S16
Molecular Weight	2035.697
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8016819 | https://www.ncbi.nlm.nih.gov/pubmed/10726009

Aprosulate or lactobionic acid is a highly sulfated analogue of heparin which was undergoing clinical trials in Europe as a potential antithrombotic drug. Aprosulate exerts a strong anticoagulant effect in plasma as a result of its interaction with heparin cofactor II.

Originator

Approval Year

PubMed

Title	Date	PubMed
Phase I--study with aprosulate, a new synthetic anticoagulant.	1993 Oct 15	8303655
Protamine sulfate neutralization of the anticoagulant activity of Aprosulate, a synthetic sulfated lactobionic acid amide.	1994 Mar 1	8016819
Anticoagulant and antiprotease activities of aprosulate sodium, a new synthetic polyanion, in human plasma and purified systems.	1994 Oct	7865684

Patents

Sample Use Guides

In Vivo Use Guide

Twelve healthy male volunteers received subcutaneous injections of placebo on the first day followed by ascending doses of aprosulate in the range of 0.25 mg/kg to 2.0 mg/kg body weight on alternate days.

Route of Administration: Other

In Vitro Use Guide

Aprosulate inhibited thrombin (0.03-0.3 U/ml)-induced aggregation in rat washed platelets in a concentration-dependent manner, with an IC50 value of 0.38 ug/ml. In contrast, aprosulate, at up to 10 ug/ml, did not affect collagen (1 ug/ml)- or ADP (3 uM)-induced aggregation. In fura 2-loaded platelets, aprosulate (1-10 ug/ml) inhibited intracellular Ca2+ mobilization induced by thrombin, but not that by ADP.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:17:59 GMT 2023` Edited by `admin` on `Fri Dec 15 17:17:59 GMT 2023`
Record UNII	X94B38CQOM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APROSULATE

Common Name

English

N,N'-TRIMETHYLENEBIS(ACTOBIONAMIDE) HEXADECAKIS SULPHATE (ESTER)

Common Name

English

N,N'-TRIMETHYLENEBIS(ACTOBIONAMIDE) HEXADECAKIS SULFATE (ESTER)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C263