Tiaprost

Names

[ Name ]:
Tiaprost

[Synonym ]:
Iliren
(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-hydroxy-4-(3-thienyloxy)-1-buten-1-yl]cyclopentyl}-5-heptenoic acid
Tiaprost
UNII-98E50HHH7M
(15-R,S)-16-(3-Thienyloxy)-w-tetranor-PGF2a
(5Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-hydroxy-4-(3-thienyloxy)but-1-en-1-yl]cyclopentyl}hept-5-enoic acid
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-hydroxy-4-(3-thienyloxy)-1-buten-1-yl]cyclopentyl]-, (5Z)-
Tiaprostum
5-Heptenoic acid,7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-thienyloxy)-1-butenyl)cyclopentyl)
Tiaprostum [INN-Latin]

Biological Activity

[Description]:

Tiaprost is a prostaglandin F2α (PGF2α) analogue.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor

Research Areas >> Metabolic Disease

[Target]

PGF2α

[In Vivo]

Plasma progesterone levels decrease sharply within 12 hours after the initial treatment with Tiaprost and within 24 hours reach levels at about 3.18 nM (1 ng/mL). Over the following days, progesterone levels remain either slightly above (cows 1, 3, 5 and 6) or below (cow 2) 3.18 nM. In cow 4, levels remain for 17 days above 3.18 nM and drop below this level thereafter. At term, all cows show the lowest recorded progesterone levels (1 to 2 nM). Repeated luteolytic treatments with Tiaprost (cows 1 and 2) or estradio1 benzoate (cow 3) has no further influence on individual progesterone levels. Treatment with progesterone-releasing intravaginal device (PRID) does not significantly elevate progesterone plasma levels. Total estrogens in plasma remained in general unchanged[1].

[Animal admin]

Cows[1] Six healthy dairy cows of the German Black Pied breed, pregnant for 190 to 266 days, are treated initially with 0.75 mg of the PGF2α analog Tiaprost SC (treatment day=day 0). All animals are moved to the department’s large animal hospital 5 to 20 days before treatment commenced; they are kept in stanchions and fed. All animals are examined clinically daily and rectally as well as vaginally at two- to six-day intervals[1].

[References]

[1]. Grunert E, et al. Delayed termination of third-trimester gestations in dairy cows after treatment with the PGF(2alpha)analog Tiaprost. Theriogenology. 1984 May;21(5):823-34.

[Related Small Molecules]

Dinoprostone | Prostaglandin E1 | E7046 | ONO-AE3-208 | PF 04418948 | Fevipiprant | grapiprant | TG6-10-1 | Taprenepag | GW 627368 | MRE-269 | Ramatroban | AH 6809 | Laropiprant | AZD1981

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
613.4±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₀H₂₈O₆S

[ Molecular Weight ]:
396.498

[ Flash Point ]:
324.8±31.5 °C

[ Exact Mass ]:
396.160645

[ PSA ]:
135.46000

[ LogP ]:
1.16

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.633

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MJ9669650

CHEMICAL NAME :: 5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-4-(3-thienyloxy)-1-bute nyl)cyclopentyl)-

CAS REGISTRY NUMBER :: 71116-82-0

LAST UPDATED :: 198706

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C20-H28-O6-S

MOLECULAR WEIGHT :: 396.54

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 19,104,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 9800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 19,104,1983

Safety Information

[ RIDADR ]:
UN 3249

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)