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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H34O5
Molecular Weight 366.4917
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of ARBAPROSTIL

SMILES

CCCCC[C@@](C)(O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=XSGQFHNPNWBVPT-VFXMVCAWSA-N
InChI=1S/C21H34O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-17,19,23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,19-,21-/m1/s1

HIDE SMILES / InChI
Molecular Formula C21H34O5
Molecular Weight 366.4917
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Arbaprostil (15(R)-15-methylprostaglandin E2) is a prodrug, which is activated by epimerization to form the active S-epimer. It was shown, that arbaprostil markedly accelerated the healing rate of active duodenal ulcers, due to inhibition of acid secretion as well as gastric cytoprotection.

Originator

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of 15(R)-15-methyl prostaglandin E2 (arbaprostil) on the healing of duodenal ulcer: a double-blind multicenter study.
1982 Aug
Lack of effect of arbaprostil on the human non-pregnant uterus.
1985
Acid-promoted epimerization of arbaprostil, 15(R)-15-methylprostaglandin E2, elicits gastric antisecretory activities in rats.
1991 Dec
Gastric antisecretory activity of 15(R)-15-methylprostaglandin E2, arbaprostil, in dogs.
1991 Nov
Comparative studies with 15(R)-15-methylprostaglandin E2 (arbaprostil) in rat femoral arterial preparations in vivo and in vitro.
1993 Sep
Patents

Patents

US6413945
1

Sample Use Guides

In Vivo Use Guide
A multicenter study was conducted on 173 patients with active, endoscopically proven duodenal ulcers (158 men, 15 women). They were randomly assigned, in a double-blind manner, to two groups: those receiving placebo capsules (91 patients) and those receiving capsules containing 100 microgram of 15(R)-15-methyl prostaglandin E2 (arbaprostil) (82 patients). Each drug was ingested four times a day (1 h before meals and at bedtime) for 28 days.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: The vasocontractor responses to arbaprostil in isolated femoral arterial strips were significantly potentiated by removal of the endothelium and the presence of NG-monomethyl L-arginine. The result indicated that the endothelium-dependent mechanism might play an important role in the vascular response to arbaprostil, like PGE2 and ACh.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:55 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:55 GMT 2023
Record UNII
M6B59S6MEF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARBAPROSTIL
INN   MART.   MI   USAN  
USAN   INN  
Official Name English
ARBAPROSTIL [JAN]
Common Name English
U 42,842
Code English
ARBAPROSTIL [MART.]
Common Name English
ARBAPROSTIL [USAN]
Common Name English
PROSTA-5,13-DIEN-1-OIC ACID, 11,15-DIHYDROXY-15-METHYL-9-OXO-, (5Z,11.ALPHA.,13E,15R)-
Common Name English
(E,Z)-(1R,2R,3R)-7-[3-Hydroxy-2-[(3R)-(3-hydroxy-3-methyl-1-octenyl)]-5-oxocyclopentyl]-5-heptenoic acid
Systematic Name English
arbaprostil [INN]
Common Name English
ARBAPROSTIL [MI]
Common Name English
U-42842
Code English
(15R)-15-METHYLPROSTAGLANDIN E2
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID10866457
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
SMS_ID
100000087167
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
NCI_THESAURUS
C80624
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
EVMPD
SUB05553MIG
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
CAS
55028-70-1
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
MESH
D001101
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
FDA UNII
M6B59S6MEF
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
MERCK INDEX
m2029
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY Merck Index
PUBCHEM
5283064
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105959
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
INN
3975
Created by admin on Fri Dec 15 15:24:55 GMT 2023 , Edited by admin on Fri Dec 15 15:24:55 GMT 2023
PRIMARY
Related Record Type Details
Structure of ARBAPROSTIL
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