FENPROSTALENE

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H30O6
Molecular Weight	402.4807
Optical Activity	( + / - )
Defined Stereocenters	5 / 5
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)CCC=C=CC[C@@H]1[C@H](O)C[C@H](O)[C@H]1\C=C\[C@H](O)COC2=CC=CC=C2

InChI

InChIKey=BYNHBQROLKAEDQ-CNDPCGPLSA-N

InChI=1S/C23H30O6/c1-28-23(27)12-8-3-2-7-11-19-20(22(26)15-21(19)25)14-13-17(24)16-29-18-9-5-4-6-10-18/h3-7,9-10,13-14,17,19-22,24-26H,8,11-12,15-16H2,1H3/b14-13+/t2?,17-,19-,20-,21+,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H30O6
Molecular Weight	402.4807
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	3
Optical Activity	UNSPECIFIED

Description
Sources: https://www.law.cornell.edu/cfr/text/21/522.914 | https://www.drugs.com/international/fenprostalene.html

Fenprostalene is a long-acting PGF2 alpha analog. Fenprostalene is indicated for use in feedlot heifers to induce abortion when pregnant 150 days or less, for the induction of parturition in sows and gilts pregnant at least 112 days.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin F2-alpha receptor 12 Target ID: P43118 Gene ID: 25652.0 Gene Symbol: Ptgfr Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3134971	Agonist 2752		7.4 null [pEC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pregnancy in cattle 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16726329	Preventing		Approved 8583	Porcilene Approved Use Fenprostalene is indicated for use in feedlot heifers to induce abortion when pregnant 150 days or less, for the induction of parturition in sows and gilts pregnant at least 112 days. Launch Date 1988

PubMed

Title	Date	PubMed
Key role for cyclooxygenase-2 in PGE2 and PGF2alpha receptor regulation and cerebral blood flow of the newborn.	1997-10	9362291
Up-regulation of brain PGE2 and PGF2 alpha receptors and receptor-coupled second messengers by cyclooxygenase inhibition in newborn pigs.	1995-01	7815327
Uterokinetic activity of fenprostalene (a prostaglandin F2alpha analog) in vivo and in vitro in the bovine.	1989-11	16726722
The action of prostanoid receptor agonists and antagonists on smooth muscle and platelets.	1988-06	3134971

Patents

Sample Use Guides

In Vivo Use Guide

(1)Cattle - (i)Indications for use and amount - (A) For feedlot heifers to induce abortion when pregnant 150 days or less, administer 1 mg (2 milliliter (mL)) subcutaneously. (B) For beef or nonlactating dairy cattle for estrus synchronization, administer a single or two 1-mg (2-mL) doses subcutaneously, 11 to 13 days apart. (2)Swine - (i)Amount. Administer a single injection of 0.25 mg (1 mL) subcutaneously. (ii)Indications for use. For the induction of parturition in sows and gilts pregnant at least 112 days.

Route of Administration: Other

In Vitro Use Guide

Fenprostalene elicited contractions of the guinea-pig oesophageal muscular mucosae with -log EC50 6.73. Fenprostalene was tested between 1 x 10(-1) and 3 x 10(-5) M.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:25:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:25:46 GMT 2025`
Record UNII	X8I39OJF4P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RS-84043

Preferred Name

English

FENPROSTALENE

Official Name

English

fenprostalene [INN]

Common Name

English

METHYL (±)-7-((1R*,2R*,3R*,5S*)-3,5-DIHYDROXY-2-((E)-(3R*)-3-HYDROXY-4-PHENOXY-1-BUTENYL)CYCLOPENTYL)-4,5-HEPTADIENOATE

Systematic Name

English

FENPROSTALENE [MART.]

Common Name

English

FENPROSTALENE [USAN]

Common Name

English

FENPROSTALENE [MI]

Common Name

English

4,5-HEPTADIENOIC ACID, 7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E,3R)-3-HYDROXY-4-PHENOXY-1-BUTEN-1-YL)CYCLOPENTYL)-, METHYL ESTER, (4S)-REL-

Systematic Name

English

FENPROSTALENE [GREEN BOOK]

Common Name

English

4,5-HEPTADIENOIC ACID, 7-(3,5-DIHYDROXY-2-(3-HYDROXY-4-PHENOXY-1-BUTENYL)CYCLOPENTYL)-, METHYL ESTER

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG02AD92