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

Molecular Formula	C33H45NO6S
Molecular Weight	583.779
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	3 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Antisecretory and protective properties of prostaglandin analogues in man.	1984	6532124
Antisecretory and protective properties of prostaglandin analogs in man.	1982-09	7115548
[Human acid inhibition and prevention of a drop in the transmucosal potential difference by thioprostaglandin EMD 33290].	1982-06-05	7100879

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:37:04 GMT 2025` Edited by `admin` on `Mon Mar 31 18:37:04 GMT 2025`
Record UNII	W28FJ301MU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Preferred Name

English

TIPROSTANIDE

Official Name

English

tiprostanide [INN]

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