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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H32O5
Molecular Weight 352.4651
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PROSTAGLANDIN H2

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=YIBNHAJFJUQSRA-YNNPMVKQSA-N
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H32O5
Molecular Weight 352.4651
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Prostaglandin H2 (PGH2) is a type of Prostaglandin which is derived from arachidonic acid and is a precursor for many other biologically significant molecules. Prostaglandins are synthesized from arachidonic acid by the prostaglandin-endoperoxide synthase enzymes, which are also called Cyclooxygenases. These enzymes generate a reactive intermediate PGH2 which has a reasonably long half-life (90-100 s). PGH2 is converted into the biologically active prostaglandins by prostaglandin isomerases, yielding Prostaglandin E2, D2 and F2 (PGE2, PGD2, and PGF2), or by thromboxane synthase to make Thromboxane A2 (TxA2) or by prostacyclin synthase to make Prostaglandin I2 (PGI2). Prostaglandin H2 was first isolated from incubations of arachidonic acid with ovine seminal vesicle microsomes, and was described as a potent vasoconstrictor. Thromboxane receptors can be activated by PGH2 and TxA2, as well as isoprostanes, all of which produce vasoconstriction. Activation of TP receptors by either PGH2 or TxA2 contributes to hypertension of pregnancy and to the elevation of blood pressure in some forms of experimental hypertension, particularly those that involve activation of the renin-angiotensin system.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Guinea-pig lung strip, dog saphenous vein strip, rabbit and rat aortic strips, guinea-pig ileum, guinea-pig fundic strip, dog and cat iris sphincter muscles and cat tracheal strips were used for activity evaluation. The preparations were suspended under a resting tension of 1 g (dog saphenous vein, guinea-pig ileum and fundus and cat trachea) or 0.5 g (guinea-pig lung strip, rat and rabbit aortae, cat and dog iris sphincter muscles) and changes in tension measured isometrically. The preparations were superfused at a rate of 10 ml/min with modified Krebs solution at 37°C containing indomethacin (1.4 x 10^-6 mol/l), atropine (2 x 10^-7 mol/l) and phenoxybenzamine (3.5 x 10^-7 mol/l) and gassed with 5% CO2 in oxygen. PGH2, prepared by incubating arachidonic acid with ram seminal vesicle microsomes. For use, the diethyl ether was evaporated under a N2 stream and the PGH2 redissolved in Krebs solution at 0°C to give a concentration of 5 mkg/ml. Doses of PGH2 were taken as aliquots from this stock solution. Dosing was begun 15 s after addition of the Krebs solution and was always complete within a further 105 s.
Substance Class Chemical
Record UNII
J670X3LRU2
Record Status Validated (UNII)
Record Version