TIPROSTANIDE

Details

Stereochemistry	EPIMERIC
Molecular Formula	C33H45NO6S
Molecular Weight	583.779
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCC(C)(O)CS[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC2=CC=C(NC(=O)C3=CC=CC=C3)C=C2

InChI

InChIKey=DRWKZQHXBXCXEO-ONNUEXRDSA-N

InChI=1S/C33H45NO6S/c1-3-4-12-21-33(2,39)23-41-31-27(28(35)22-29(31)36)15-10-5-6-11-16-30(37)40-26-19-17-25(18-20-26)34-32(38)24-13-8-7-9-14-24/h7-9,13-14,17-20,27,29,31,36,39H,3-6,10-12,15-16,21-23H2,1-2H3,(H,34,38)/t27-,29+,31+,33?/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7100879 | https://www.ncbi.nlm.nih.gov/pubmed/6532124 | DOI: 10.1021/cr00020a007

Tiprostanide is a 13-thia-PGE1 analog which also contains a p-benzamidophenyl ester, presumably to enhance crystallinity and stability. Although originally targeted and evaluated as an antihypertensive agent, emphasis was switched to an antiulcer indication because of disappointing clinical results. Tiprostanide has two distinct properties in the human stomach, viz. antisecretory and protective, which are independent of each other. Antisecretory prostaglandins protect the human stomach against aspirin and bile salts in doses which are much smaller than the threshold antisecretory ones.

Originator

Approval Year

PubMed

Title	Date	PubMed

Name

Type

Language

TIPROSTANIDE

Official Name

English

tiprostanide [INN]

Common Name

English

(1S,2R,3R)-3-HYDROXY-2-((2(RS)-HYDROXY-2-METHYLHEPTYL)THIO)-5-OXOCYCLOPENTANEHEPTANOIC ACID, ESTER WITH 4'-HYDROXYBENZANILIDE.

Common Name

English

(1S,2R,3R)-3-HYDROXY-2-((2-HYDROXY-2-METHYLHEPTYL)THIO)-5-OXOCYCLOPENTANEHEPTANOIC ACID, ESTER WITH 4'-HYDROXYBENZANILIDE.

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78568