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Details

Stereochemistry RACEMIC
Molecular Formula C21H29ClO6S
Molecular Weight 444.969
Optical Activity ( + / - )
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LUPROSTIOL

SMILES

O[C@H](COC1=CC=CC(Cl)=C1)CS[C@@H]2[C@@H](O)C[C@@H](O)[C@H]2C\C=C/CCCC(O)=O

InChI

InChIKey=KFUDFIMHDRJVLV-OZCLATTGSA-N
InChI=1S/C21H29ClO6S/c22-14-6-5-7-16(10-14)28-12-15(23)13-29-21-17(18(24)11-19(21)25)8-3-1-2-4-9-20(26)27/h1,3,5-7,10,15,17-19,21,23-25H,2,4,8-9,11-13H2,(H,26,27)/b3-1-/t15-,17-,18-,19+,21+/m1/s1

HIDE SMILES / InChI
Luprostiol is a synthetic prostaglandin F2α and is a luteolytic agent. It is used for estrus control and termination of pregnancy in mares. In cattle Luprostiol is indicated for: - Oestrus regulation / oestrus synchronization; - Treatment of suboestrus; - Induction of abortion; - Induction of parturition; - Treatment of pyometra, chronic endometritis and fetal mummification.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Equestrolin

Approved Use

Luprostiol is indicated for 1) estrus control and 2) termination of pregnancy in mares under the following conditions: Estrus Control: Luprostiol is effective as a luteolysin and may be used to regress a functional, progesterone producing corpus luteum, subsequently inducing estrus, ovulation and normal conception in breeding mares under the following conditions: Estrus Control in Normal Cycling and Transitional Phase Mares: Normal cycling mares that demonstrate estrus activity may be treated to shorten the estrous cycle. Treatment should be given during the diestrus period when functional corpora lutea are present. Mares displaying estrous cycles, albeit erratic, may be treated if mature corpora lutea are present to shorten and/or reinitiate the estrous cycle. Estrus Control in Postpartum Mares: Postpartum mares that exhibit an overt foal heat but are not bred at this heat, in order to avoid reduced fertility, may be treated six to 12 days after the foal heat ovulation to attempt an early return to estrus ("second" foal heat) and subsequent breeding opportunity. Lactating mares that do not exhibit a foal heat and that are considered to be in lactational anestrus may be treated approximately 21 days postpartum in order to initiate estrus cyclicity. Estrus Control in Mares With Persistent Corpora Lutea: Mares not cycling due to a persistent corpus luteum (CL) may be treated to terminate functional luteal tissue. This would include: mares considered pseudopregnant (i.e., bred and determined not to be pregnant but displaying signs of pregnancy as a result of persistent CL activity). mares in clinical anestrus (i.e., not cycling during the breeding season due to persistent CL activity). mares that have lost a conceptus during early gestation and that have not recycled due to persistent CL activity. maiden and barren mares in extended periods of diestrus due to persistent CL activity. Termination of Pregnancy The luteolytic activity of luprostiol is also effective for the induction of abortion in mares pregnant for 36 days or less.

Launch Date

1990
PubMed

PubMed

TitleDatePubMed
Influence of prostaglandin F₂α analogues on the secretory function of bovine luteal cells and ovarian arterial contractility in vitro.
2014 Jan
Patents

Sample Use Guides

Mares: 7.5 mg by intramuscular injection.
Route of Administration: Intramuscular
Luprostiol (1 ug/mL) induced DNA defragmentation and caspase-3 activity in cultured bovine luteal cells, inhibiting cell viability.
Name Type Language
LUPROSTIOL
GREEN BOOK   INN   MART.   MI  
INN  
Official Name English
LUPROSTIOL [MI]
Common Name English
LUPROSTIOL [GREEN BOOK]
Common Name English
LUPROSTIOL [MART.]
Common Name English
(±)-(Z)-7-((1R*,2S*,3S*,5R*)-2-(((2R*)-3-(M-CHLOROPHENOXY)-2-HYDROXYPROPYL)THIO)-3,5-DIHYDROXYCYCLOPENTYL)-5-HEPTENOIC ACID
Systematic Name English
PROSOLVIN
Brand Name English
luprostiol [INN]
Common Name English
REPRODIN
Brand Name English
EMD-34946
Code English
Classification Tree Code System Code
CFR 21 CFR 522.1290
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
WHO-VATC QG02AD91
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
Code System Code Type Description
CAS
67110-79-6
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
PRIMARY
PUBCHEM
6441712
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PRIMARY
FDA UNII
HWR60H5GZB
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
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RXCUI
2583725
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INN
4600
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
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MERCK INDEX
m6940
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
PRIMARY Merck Index
SMS_ID
100000082272
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PRIMARY
EVMPD
SUB08620MIG
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DAILYMED
HWR60H5GZB
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
PRIMARY
NCI_THESAURUS
C66042
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
PRIMARY
DRUG BANK
DB11425
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PRIMARY
ChEMBL
CHEMBL2218923
Created by admin on Fri Dec 15 15:32:34 GMT 2023 , Edited by admin on Fri Dec 15 15:32:34 GMT 2023
PRIMARY