ALEMCINAL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H67NO10
Molecular Weight	697.9393
Optical Activity	UNSPECIFIED
Defined Stereocenters	16 / 16
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]2(O[C@H]1C[C@](C)(C[C@H](C)O1)OC)[C@@H](C)C(=O)O[C@H](CC)[C@H](C)[C@H](O)[C@@H](C)C3=C(C)C[C@@](C)(O3)[C@]([H])(O[C@@H]4O[C@H](C)C[C@@H]([C@H]4O)N(C)CC)[C@H]2C

InChI

InChIKey=IWTSXJNGTTXMFK-KTQUSEMZSA-N

InChI=1S/C38H67NO10/c1-14-28-23(6)30(40)24(7)32-20(3)17-38(11,49-32)34(48-36-31(41)27(39(12)15-2)16-21(4)45-36)25(8)33(26(9)35(42)46-28)47-29-19-37(10,43-13)18-22(5)44-29/h21-31,33-34,36,40-41H,14-19H2,1-13H3/t21-,22+,23+,24-,25+,26-,27+,28-,29+,30+,31-,33+,34-,36+,37+,38-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C38H67NO10
Molecular Weight	697.9393
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	16 / 16
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800006919 | https://www.ncbi.nlm.nih.gov/pubmed/10065328 | https://www.ncbi.nlm.nih.gov/pubmed/10869416

Alemcinal (ABT-229), a 12-deoxymotilide, is a potent motilin agonist stereoselectively designed by Abbott researchers as an orally active gastroprokinetic agent. ABT-229 is selective agonist of the motilin receptor. ABT-229 is a synthetic derivative of erythromycin with no antibiotic activity, it has been shown to bind to motilin receptors and stimulate contractile activity of the antrum and small intestine. However, the development of Alemcinal was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Desensitization of the human motilin receptor by motilides.	2005 Jun	15764739

Sample Use Guides

In Vivo Use Guide

The efficacy of four different doses of ABT-229 (1.25 mg, 2.5 mg, 5 mg, 10 mg b.d.) compared to placebo in the treatment of gastro-oesophageal reflux disease were assessed. In a double-blind, multicentre study, 324 patients with heartburn were randomized to receive four different doses of ABT-229 or placebo for 8 weeks. ABT-229 appeared to be well tolerated and safe in total daily doses up to 20 mg.

Route of Administration: Oral

In Vitro Use Guide

Erythromycin contracted the longitudinal muscle of the rabbit duodenum, with a threshold concentration of 0.1 umol/L and ABT-229 contracted this tissue at a threshold concentration of 0.01 umol/L.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:33:11 GMT 2023` Edited by `admin` on `Fri Dec 15 15:33:11 GMT 2023`
Record UNII	5DS173ODI4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALEMCINAL

Official Name

English

ABBOTT-81229.0

Code

English

alemcinal [INN]

Common Name

English

A-81229

Code

English

8,9-DIDEHYDRO-N-DEMETHYL-9-DEOXO-4'',6,12-TRIDEOXY-6,9-EPOXY-N-ETHYLERYTHROMYCIN

Common Name

English

ABT-229

Code

English

ALEMCINAL [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78276