U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry EPIMERIC
Molecular Formula C20H28O6S
Molecular Weight 396.498
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of TIAPROST

SMILES

OC(COC1=CSC=C1)\C=C\[C@H]2[C@H](O)C[C@H](O)[C@@H]2C\C=C/CCCC(O)=O

InChI

InChIKey=FYBFDIIAPRHIQS-JRSBLEPXSA-N
InChI=1S/C20H28O6S/c21-14(12-26-15-9-10-27-13-15)7-8-17-16(18(22)11-19(17)23)5-3-1-2-4-6-20(24)25/h1,3,7-10,13-14,16-19,21-23H,2,4-6,11-12H2,(H,24,25)/b3-1-,8-7+/t14?,16-,17-,18+,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H28O6S
Molecular Weight 396.498
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 4 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

Tiaprost is a synthetic analog of prostaglandin F2α (PGF2α) patented by Hoechst A.-G. as an estrus-synchronizing agent for veterinary medicine. Tiaprost treatment reduced the interval from calving to conception in multiparous cows, but it delayed conception and reduced the conception rate in primiparous cows. Treatment with tiaprost impaired reproductive performance in primiparous cows

Approval Year

PubMed

PubMed

TitleDatePubMed
Luteolysis in cows using the prostaglandin F2 alpha analogue, tiaprost, and the effect of mode of administration.
1984 Apr 28
Patents

Sample Use Guides

cows: 0.75 mg
Route of Administration: Other
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:34:29 GMT 2023
Edited
by admin
on Fri Dec 15 18:34:29 GMT 2023
Record UNII
98E50HHH7M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIAPROST
INN   MART.   MI  
INN  
Official Name English
TIAPROST, (R,S)-
Common Name English
tiaprost [INN]
Common Name English
(5Z,13E)-(9S,11R,15RS)-9,11,15-TRIHYDROXY-16-(3-THIENYLOXY)-17,18,19,20-TETRANORPROSTA-5,13-DIENOIC ACID
Systematic Name English
(±)-(Z)-7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((E)-(3RS)-3-HYDROXY-4-(3-THIENYLOXY)BUT-1-ENYL)CYCLOPENTYL)HEPT-5-ENOIC ACID
Systematic Name English
TIAPROST [MART.]
Common Name English
TIAPROST [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
WHO-VATC QG02AD93
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
Code System Code Type Description
MERCK INDEX
m10848
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID901021711
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY
PUBCHEM
6441899
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY
EVMPD
SUB11012MIG
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY
INN
4608
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104879
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY
NCI_THESAURUS
C90931
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY
FDA UNII
98E50HHH7M
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY
SMS_ID
100000082180
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
PRIMARY
CAS
71116-82-0
Created by admin on Fri Dec 15 18:34:29 GMT 2023 , Edited by admin on Fri Dec 15 18:34:29 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY