398:
375:
47:
713:
752:
In 2019, a more effective and stereoselective synthesis was described. The synthesis requires 5 steps to get to the intermediate which then undergoes a cross-metathesis reaction to install the E-alkene. Then, a Wittig reaction is performed to install the Z-alkene. Finally, the protecting groups are
703:
can cause an abortion by degrading the corpus luteum, which normally acts to maintain pregnancy via the production of progesterone. Since the fetus is not viable outside the womb by this time, the lack of progesterone leads to the shedding of the uterine lining and the death of the fetus. However,
1223:
461:
678:
and oxytocin, as the effects of the hormones are in opposition to each other. This is directly exhibited following ovulation when there is a spike of progesterone levels, and then as progesterone levels decrease,
741:
was described. The synthesis requires only seven steps, a huge improvement on the original 17-steps synthesis of Corey and Cheng, and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with
1355:
Fortier MA, Krishnaswamy K, Danyod G, Boucher-Kovalik S, Chapdalaine P (August 2008). "A postgenomic integrated view of prostaglandins in reproduction: implications for other body systems".
2462:
513:
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
104:
529:
699:
acts to stimulate uterine muscle contractions, which aids in the birth process. However, during the first trimester and in higher concentrations (40 mg/day), PGF
591:
in maternal fluid during labor when compared to at term. This signifies that there is likely a biological use and significance to the production and secretion of PGF
1315:
Kim T, Lee SI, Kim S, Shim SY, Ryu DH (2019). "Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling".
2455:
67:
658:. It is released in response to an increase in oxytocin levels in the uterus, and stimulates both luteolytic activity and the release of oxytocin. Because PGF
485:
583:
is medically used to sustain contracture and provoke myometrial ischemia to accelerate labor and prevent significant blood loss in labor. Additionally, PGF
4992:
2336:
2448:
1064:"Oxytocin, oxytocin-associated neurophysin, and prostaglandin F2 alpha concentrations in the utero-ovarian vein of pregnant and nonpregnant sheep"
1658:
2280:
2119:
1399:
1224:"Evaluation of Single Lutalyse Injection Protocol to Reduce Uterine Infections and Improve Reproductive Efficiency in Postpartum Dairy Cows"
1249:
Coulthard G, Erb W, Aggarwal VK (September 2012). "Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps".
943:
Sahmay S, Coke A, Hekim N, Atasu T (1988). "Maternal, umbilical, uterine and amniotic prostaglandin E and F2 alpha levels in labour".
858:
505:
1621:
3438:
165:
2329:
655:
645:
587:
has been linked to being naturally involved in the process of labor. It has been seen that there are higher levels of PGF
4985:
674:, a hormone that facilitates corpus luteum development. Conversely, higher progesterone levels inhibit production of PGF
294:
1715:
695:
can either induce labor or cause an abortion depending on the concentration used. In small doses (1–4 mg/day), PGF
2577:
2520:
2297:
1027:
Samuelsson B, Goldyne M, Granström E, Hamberg M, Hammarström S, Malmsten C (1978). "Prostaglandins and thromboxanes".
354:
3091:
4942:
3000:
2885:
2808:
2701:
2683:
2502:
2112:
1392:
3402:
4779:
4760:
4715:
3157:
2322:
2248:
788:
724:
in domestic dogs and cats. The drug is also administered to dairy cows in order to reduce uterine infections.
243:
5019:
5014:
2485:
2285:
85:
3543:
579:. Prostaglandins are lipids throughout the entire body that have a hormone-like function. In pregnancy, PGF
393:
4821:
4741:
2196:
804:
4798:
3254:
2491:
2408:
2367:
2256:
1772:
234:
988:"Role of 8-iso-prostaglandin F2alpha and 25-hydroxycholesterol in the pathophysiology of endometriosis"
4303:
4273:
4104:
343:
199:
5024:
4937:
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3912:
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3129:
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137:
3309:
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1150:
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4136:
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1817:
370:
186:
92:
4462:
3927:
3817:
3812:
3797:
3732:
3682:
3637:
3202:
666:
and oxytocin form a positive feedback loop to facilitate the degradation of the corpus luteum. PGF
77:
4869:
4749:
4700:
4690:
4114:
3792:
3772:
3757:
3747:
3727:
3722:
3677:
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3072:
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2909:
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2659:
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2477:
1332:
1282:
968:
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4859:
4834:
4695:
4556:
4413:
4014:
4009:
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3787:
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3752:
3742:
3717:
3707:
3702:
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3672:
3667:
3627:
3586:
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3523:
3518:
3503:
3493:
3488:
3473:
3352:
3274:
3229:
3143:
3119:
3109:
2557:
775:, the framework from which all prostaglandins are formed. Arachidonic acid then reacts with two
4884:
4839:
4650:
4596:
4581:
4430:
4141:
4089:
3974:
3822:
3767:
3737:
3712:
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3428:
3372:
3342:
3299:
3289:
3138:
3062:
2914:
2827:
2624:
908:
Kerekes L, Domokos N (July 1979). "The effect of prostaglandin F2 alpha on third stage labor".
4889:
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2181:
2149:
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1364:
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572:
4909:
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4571:
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3601:
3448:
3357:
3314:
2865:
2778:
2664:
2644:
2639:
2634:
283:
62:
Amoglandin, Croniben, Cyclosin, Dinifertin, Enzaprost, Glandin, PGF2α, Panacelan, Prostamodin
30:
This article is about the pharmaceutical agent 'dinoprost'. For the drug 'dinoprostone', see
4965:
4957:
4952:
4771:
4675:
4670:
4256:
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2837:
2759:
2750:
2601:
2539:
2403:
2362:
2215:
2071:
2051:
2031:
2023:
1974:
1907:
1868:
1823:
1516:
1505:
1483:
1457:
1422:
1324:
1266:
1189:
1122:
1114:
1075:
1036:
999:
952:
917:
784:
772:
761:
602:, in the event that there has been no implantation during the luteal phase. It acts on the
472:
410:
129:
31:
3561:
3410:
303:
4813:
4745:
4655:
4330:
4308:
4278:
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2132:
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611:
195:
1262:
1040:
397:
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4335:
4288:
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3415:
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2008:
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1959:
1939:
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1890:
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1839:
1831:
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1674:
1666:
1645:
1637:
1588:
1580:
1127:
1102:
776:
146:
96:
921:
636:, thus being a potential causative link in endometriosis-associated oxidative stress.
595:
in labor. Prostaglandin is also used to treat uterine infections in domestic animals.
5008:
4932:
4616:
4401:
4298:
4176:
4161:
4094:
4024:
2191:
1441:
1336:
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1004:
987:
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17:
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223:
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3019:
2855:
2740:
2547:
2429:
2166:
2140:
1982:
1915:
1901:
1548:
1178:"Treatment of pyometra in cats, using prostaglandin F2 alpha: 21 cases (1982-1990)"
1118:
882:
671:
150:
117:
112:
2440:
1193:
1103:"Levels of prostaglandins in human endometrium during the normal menstrual cycle"
662:
is linked with an increase in uterine oxytocin levels, there is evidence that PGF
4947:
4849:
4790:
4660:
4645:
4586:
4551:
4529:
4509:
4457:
4442:
4384:
4342:
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4079:
4019:
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2649:
2471:
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2234:
2128:
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274:
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1993:
1079:
71:
1368:
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38:
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4418:
4357:
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4320:
4241:
4216:
4166:
4109:
4099:
4034:
4029:
3989:
3304:
2924:
2730:
2136:
1952:
1755:
1747:
1739:
1731:
1048:
929:
779:(COX) receptors, COX-1 and COX-2, or PGH synthase to form prostaglandin H
721:
599:
254:
1270:
263:
4874:
4685:
4452:
3979:
3932:
3877:
3423:
1791:
1784:
1780:
746:
618:
is dependent on the number of receptors on the corpus luteum membrane.
209:
46:
4635:
3836:
851:
The Merck index: an encyclopedia of chemicals, drugs, and biologicals
598:
In domestic mammals, it is produced by the uterus when stimulated by
334:
712:
737:
In 2012 a concise and highly stereoselective total synthesis of PGF
323:
4447:
2314:
2044:
1699:
711:
460:
451:
95:(cannot used to induce labor)because it cannot be used in cervix,
986:
Sharma I, Dhaliwal LK, Saha SC, Sangwan S, Dhawan V (June 2010).
314:
2444:
2318:
2101:
1381:
1151:"Dinoprost tromethamine Injection Advanced Patient Information"
1377:
632:
was found in significantly increased amounts in patients with
853:(15th ed.). Cambridge, UK: Royal Society of Chemistry.
359:
614:
and stopping the production of progesterone. Action of PGF
536:
1182:
Journal of the
American Veterinary Medical Association
1062:
Hooper SB, Watkins WB, Thorburn GD (December 1986).
783:, an intermediate. Lastly, the compound reacts with
4922:
4820:
4797:
4778:
4759:
4714:
3852:
3835:
3610:
3381:
3253:
3156:
3081:
2999:
2884:
2807:
2700:
2682:
2578:
2576:
2521:
2519:
2501:
2484:
2417:
2376:
2350:
2247:
2190:
2157:
2148:
1809:
1771:
1724:
1708:
1698:
1657:
1630:
1614:
1604:
1570:
1541:
1495:
1476:
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1440:
1431:
1415:
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436:
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273:
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208:
185:
156:
136:
128:
103:
84:
66:
58:
53:
3859:
3001:
2886:
2809:
2702:
1101:Downie J, Poyser NL, Wunderlich M (January 1974).
2684:
2503:
1176:Davidson AP, Feldman EC, Nelson RW (March 1992).
771:) facilitates the conversion of phospholipids to
760:is synthesized in several distinct steps. First,
4780:
4761:
4716:
3158:
691:When injected into the body or amniotic sac, PGF
222:
1350:
1348:
1346:
194:
4822:
4799:
3255:
2456:
2330:
2113:
1393:
945:The Journal of International Medical Research
8:
3383:
1188:(6). National Library of Medicine: 825–828.
670:and oxytocin also inhibit the production of
37:
3849:
2697:
2516:
2498:
2463:
2449:
2441:
2337:
2323:
2315:
2154:
2120:
2106:
2098:
1705:
1611:
1473:
1447:
1437:
1400:
1386:
1378:
396:
373:
282:
45:
1126:
1003:
302:
841:
563:nomenclature), pharmaceutically termed
510:
490:
369:
262:
170:
3854:
2377:Prevention and treatment of hemorrhage
1357:Journal of Physiology and Pharmacology
720:Lutalyse is used for the treatment of
704:this process is not fully understood.
387:
177:)-7-cyclopentyl]hept-5-enoic acid
36:
493:O=C(O)CCC/C=C\C1(O)C(O)1/C=C/(O)CCCCC
342:
76:
7:
4477:Selective COX-2 inhibitors (coxibs):
2351:Induction and augmentation of labour
116:
2586:Tooltip Prostaglandin D2 receptor 2
2529:Tooltip Prostaglandin D2 receptor 1
1041:10.1146/annurev.bi.47.070178.005025
322:
213:
4448:AM-404 (N-arachidonoylaminophenol)
4266:Anthranilic acids (fenamic acids):
3918:Mesalazine (5-aminosalicylic acid)
3009:Tooltip Prostaglandin EP4 receptor
2894:Tooltip Prostaglandin EP3 receptor
2817:Tooltip Prostaglandin EP2 receptor
2710:Tooltip Prostaglandin EP1 receptor
25:
4938:γ-Linolenic acid (gamolenic acid)
4284:Meclofenamic acid (meclofenamate)
2693:Tooltip Prostaglandin E2 receptor
2512:Tooltip Prostaglandin D2 receptor
1716:Arachidonic acid 15-hydroperoxide
4993:Leukotriene signaling modulators
4785:Tooltip Prostaglandin F synthase
4766:Tooltip Prostaglandin E synthase
4725:Tooltip Prostaglandin D synthase
3167:Tooltip Prostaglandin F receptor
1622:Arachidonic acid 5-hydroperoxide
1005:10.1016/j.fertnstert.2009.01.141
421:
4304:Talinflumic acid (talinflumate)
4294:Morniflumic acid (morniflumate)
4274:Floctafenic acid (floctafenate)
4257:Tiaprofenic acid (tiaprofenate)
1302:The Logic of Chemical Synthesis
708:Pyometra and uterine infections
518:Key:PXGPLTODNUVGFL-YNNPMVKQSA-N
4827:Tooltip Thromboxane A synthase
3878:Aspirin (acetylsalicylic acid)
3092:16,16-Dimethyl Prostaglandin E
1119:10.1113/jphysiol.1974.sp010446
803:The following medications are
716:Bottle of Lutalyse® injectable
427:
415:
1:
4986:Receptor/signaling modulators
4808:Tooltip Prostacyclin synthase
4309:Tolfenamic acid (tolfenamate)
4279:Flufenamic acid (flufenamate)
4269:Etofenamic acid (etofenamate)
3325:Prostacyclin (prostaglandin I
3264:Tooltip Prostacyclin receptor
1194:10.2460/javma.1992.200.06.825
1029:Annual Review of Biochemistry
922:10.1016/S0090-6980(79)80034-9
3392:Tooltip Thromboxane receptor
4458:Paracetamol (acetaminophen)
4289:Mefenamic acid (mefenamate)
3943:Salicylate (salicylic acid)
1553:(Prostacyclin/Epoprostenol)
1300:Corey EJ, Cheng XM (1995).
749:as an asymmetric catalyst.
567:, is a naturally occurring
477:200 mg/mL (20 °C)
5041:
4137:Bucloxic acid (blucloxate)
4055:Indometacin (indomethacin)
1155:Truvn Health Analytics Inc
957:10.1177/030006058801600405
656:prostaglandin F2α receptor
646:Prostaglandin F2α receptor
643:
405:Chemical and physical data
29:
4977:
4299:Niflumic acid (niflumate)
3403:Carbocyclic thromboxane A
2275:
1329:10.1016/j.tet.2019.130593
1230:. OREGON STATE UNIVERSITY
1107:The Journal of Physiology
526:
501:
481:
161:
44:
4617:Menatetrenone (vitamin K
4440:Aminophenols (anilines):
789:prostaglandin F synthase
149:, less than 1 minute in
78:International Drug Names
4943:Dihomo-γ-linolenic acid
4340:Enolic acids (oxicams):
3883:Benorilate (benorylate)
1080:10.1210/endo-119-6-2590
992:Fertility and Sterility
849:O'Neil MJ, ed. (2013).
654:acts by binding to the
4742:selenium tetrachloride
717:
4411:Aminonicotinic acids:
2418:Induction of abortion
2249:Contraction induction
715:
644:Further information:
18:Prostaglandin 2 alpha
4060:Indometacin farnesil
3913:Magnesium salicylate
3544:Pinane thromboxane A
3305:Iloprost (ciloprost)
2925:Iloprost (ciloprost)
2731:Iloprost (ciloprost)
889:. September 28, 2022
733:Industrial Synthesis
571:used in medicine to
99:(to induce abortion)
3888:Carbasalate calcium
1818:bronchoconstriction
1271:10.1038/nature11411
1263:2012Natur.489..278C
753:removed with acid.
640:Mechanism of action
473:Solubility in water
41:
4750:selenium disulfide
4382:4-Aminoquinolines:
2302:Never to phase III
807:of prostaglandin F
718:
687:Pharmaceutical Use
683:levels will peak.
5002:
5001:
4918:
4917:
3953:Sodium salicylate
3923:Methyl salicylate
3846:
3831:
3830:
3152:
3151:
2678:
2677:
2495:
2438:
2437:
2312:
2311:
2243:
2242:
2182:Methylergometrine
2150:Cervical ripening
2095:
2094:
1767:
1766:
1694:
1693:
1600:
1599:
1566:
1565:
1562:
1561:
1257:(7415): 278–281.
544:
543:
462:Interactive image
355:CompTox Dashboard
27:Chemical compound
16:(Redirected from
5032:
4953:Arachidonic acid
4828:
4824:
4809:
4805:
4786:
4782:
4767:
4763:
4726:
4722:
4549:Others/unsorted:
4124:Propionic acids:
4105:Sulindac sulfide
3870:Salicylic acids:
3861:
3856:
3850:
3840:
3393:
3389:
3265:
3261:
3168:
3164:
3010:
3006:
2895:
2891:
2818:
2814:
2711:
2707:
2698:
2694:
2690:
2587:
2583:
2530:
2526:
2517:
2513:
2509:
2499:
2489:
2465:
2458:
2451:
2442:
2404:Methylergonovine
2339:
2332:
2325:
2316:
2155:
2122:
2115:
2108:
2099:
1869:vasoconstriction
1706:
1612:
1474:
1448:
1438:
1423:Arachidonic acid
1402:
1395:
1388:
1379:
1373:
1372:
1352:
1341:
1340:
1312:
1306:
1305:
1297:
1291:
1290:
1246:
1240:
1239:
1237:
1235:
1219:
1213:
1212:
1210:
1208:
1173:
1167:
1166:
1164:
1162:
1147:
1141:
1140:
1130:
1098:
1092:
1091:
1074:(6): 2590–2597.
1059:
1053:
1052:
1024:
1018:
1017:
1007:
983:
977:
976:
940:
934:
933:
905:
899:
898:
896:
894:
879:
873:
872:
846:
785:aldose reductase
773:arachidonic acid
540:
539:
532:
464:
444:
429:
423:
417:
400:
389:
378:
377:
363:
361:
346:
326:
306:
286:
266:
246:
226:
216:
215:
198:
145:3 to 6 hours in
141:
120:
80:
49:
42:
40:
32:Prostaglandin E2
21:
5040:
5039:
5035:
5034:
5033:
5031:
5030:
5029:
5005:
5004:
5003:
4998:
4973:
4969:
4966:Prostaglandin H
4961:
4958:Prostaglandin G
4914:
4826:
4816:
4814:Tranylcypromine
4807:
4803:
4793:
4784:
4774:
4765:
4755:
4746:sodium selenite
4724:
4720:
4710:
4656:Rosmarinic acid
4620:
4428:Sulfonanilides:
4331:Oxyphenbutazone
3857:
3839:
3827:
3606:
3547:
3419:
3406:
3391:
3387:
3377:
3337:
3334:Prostaglandin E
3329:, epoprostenol)
3328:
3263:
3259:
3249:
3224:
3221:Prostaglandin F
3216:
3213:Prostaglandin D
3166:
3162:
3148:
3133:
3130:Prostaglandin F
3095:
3077:
3042:
3039:Prostaglandin E
3033:
3030:Prostaglandin E
3008:
3005:
2995:
2976:Ricinoleic acid
2965:
2962:Prostaglandin E
2956:
2953:Prostaglandin E
2948:
2945:Prostaglandin D
2893:
2890:
2880:
2850:
2847:Prostaglandin E
2841:
2838:Prostaglandin E
2816:
2813:
2803:
2763:
2760:Prostaglandin E
2754:
2751:Prostaglandin E
2709:
2706:
2692:
2688:
2674:
2605:
2602:Prostaglandin D
2585:
2582:
2572:
2543:
2540:Prostaglandin D
2528:
2525:
2511:
2507:
2488:
2480:
2469:
2439:
2434:
2413:
2372:
2346:
2345:Obstetric drugs
2343:
2313:
2308:
2307:
2292:Clinical trials
2271:
2239:
2223:
2216:Dinoprostone/E2
2195:
2186:
2159:Ergot alkaloids
2144:
2126:
2096:
2091:
2084:
2075:
2055:
2035:
2027:
2012:
2004:
1986:
1978:
1963:
1943:
1935:
1927:
1919:
1911:
1894:
1886:
1878:
1859:
1851:
1843:
1835:
1827:
1805:
1795:
1788:
1763:
1759:
1751:
1743:
1735:
1720:
1690:
1686:
1678:
1670:
1653:
1649:
1641:
1626:
1596:
1592:
1584:
1558:
1552:
1537:
1531:
1520:
1509:
1491:
1487:
1465:
1461:
1427:
1411:
1406:
1376:
1354:
1353:
1344:
1314:
1313:
1309:
1299:
1298:
1294:
1248:
1247:
1243:
1233:
1231:
1221:
1220:
1216:
1206:
1204:
1175:
1174:
1170:
1160:
1158:
1149:
1148:
1144:
1100:
1099:
1095:
1061:
1060:
1056:
1026:
1025:
1021:
985:
984:
980:
942:
941:
937:
907:
906:
902:
892:
890:
883:"Prostaglandin"
881:
880:
876:
861:
848:
847:
843:
839:
810:
801:
794:
782:
770:
765:
762:phospholipase A
759:
756:In the body PGF
740:
735:
730:
710:
702:
698:
694:
689:
682:
677:
669:
665:
661:
653:
648:
642:
630:
624:
617:
612:corpus albicans
594:
590:
586:
582:
557:
550:
547:Prostaglandin F
535:
533:
530:(what is this?)
527:
522:
519:
514:
509:
508:
497:
494:
489:
488:
467:
442:
432:
426:
420:
381:
357:
349:
329:
309:
289:
269:
249:
229:
212:
204:
181:
178:
169:
168:
139:
130:Pharmacokinetic
124:
87:
35:
28:
23:
22:
15:
12:
11:
5:
5038:
5036:
5028:
5027:
5022:
5020:Prostaglandins
5017:
5015:Abortifacients
5007:
5006:
5000:
4999:
4997:
4996:
4989:
4982:
4978:
4975:
4974:
4972:
4971:
4967:
4963:
4959:
4955:
4950:
4948:Diacylglycerol
4945:
4940:
4935:
4926:
4924:
4920:
4919:
4916:
4915:
4913:
4912:
4907:
4902:
4897:
4892:
4887:
4882:
4877:
4872:
4867:
4862:
4857:
4852:
4847:
4842:
4837:
4831:
4829:
4818:
4817:
4812:
4810:
4801:
4795:
4794:
4789:
4787:
4776:
4775:
4770:
4768:
4757:
4756:
4754:
4753:
4735:
4729:
4727:
4718:
4712:
4711:
4709:
4708:
4703:
4698:
4693:
4688:
4683:
4678:
4673:
4668:
4663:
4658:
4653:
4648:
4643:
4638:
4633:
4628:
4623:
4618:
4614:
4609:
4604:
4599:
4594:
4589:
4584:
4579:
4574:
4569:
4564:
4559:
4554:
4542:
4537:
4532:
4527:
4522:
4517:
4512:
4507:
4502:
4497:
4492:
4487:
4482:
4470:
4465:
4460:
4455:
4450:
4445:
4433:
4421:
4416:
4404:
4392:
4387:
4375:
4370:
4365:
4360:
4355:
4350:
4345:
4336:Phenylbutazone
4333:
4328:
4323:
4318:
4306:
4301:
4296:
4291:
4286:
4281:
4276:
4271:
4259:
4254:
4249:
4244:
4239:
4234:
4229:
4224:
4219:
4214:
4209:
4204:
4199:
4194:
4189:
4184:
4179:
4174:
4169:
4164:
4159:
4154:
4149:
4144:
4139:
4134:
4129:
4117:
4112:
4107:
4102:
4097:
4092:
4087:
4082:
4077:
4072:
4067:
4062:
4057:
4052:
4047:
4042:
4037:
4032:
4027:
4022:
4017:
4012:
4007:
4002:
3997:
3992:
3987:
3982:
3977:
3972:
3967:
3955:
3950:
3945:
3940:
3935:
3930:
3925:
3920:
3915:
3910:
3905:
3900:
3895:
3890:
3885:
3880:
3875:
3866:
3864:
3847:
3833:
3832:
3829:
3828:
3826:
3825:
3820:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3750:
3745:
3740:
3735:
3730:
3725:
3720:
3715:
3710:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3665:
3660:
3655:
3650:
3645:
3640:
3635:
3630:
3625:
3620:
3614:
3612:
3608:
3607:
3605:
3604:
3599:
3594:
3589:
3584:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3545:
3541:
3536:
3531:
3526:
3521:
3516:
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3476:
3471:
3466:
3461:
3456:
3451:
3446:
3441:
3432:
3431:
3426:
3421:
3417:
3413:
3408:
3404:
3396:
3394:
3385:
3379:
3378:
3376:
3375:
3366:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3331:
3326:
3322:
3317:
3312:
3310:Isocarbacyclin
3307:
3302:
3297:
3292:
3287:
3282:
3277:
3268:
3266:
3257:
3251:
3250:
3248:
3247:
3242:
3237:
3232:
3227:
3222:
3218:
3214:
3210:
3205:
3200:
3195:
3190:
3185:
3180:
3171:
3169:
3160:
3154:
3153:
3150:
3149:
3147:
3146:
3141:
3136:
3131:
3127:
3122:
3117:
3112:
3107:
3102:
3097:
3093:
3085:
3083:
3079:
3078:
3076:
3075:
3070:
3065:
3060:
3051:
3050:
3045:
3043:(dinoprostone)
3040:
3036:
3031:
3027:
3022:
3013:
3011:
3003:
2997:
2996:
2994:
2993:
2984:
2983:
2978:
2973:
2968:
2966:(dinoprostone)
2963:
2959:
2954:
2950:
2946:
2942:
2937:
2932:
2930:Isocarbacyclin
2927:
2922:
2917:
2912:
2907:
2898:
2896:
2888:
2882:
2881:
2879:
2878:
2873:
2868:
2859:
2858:
2853:
2851:(dinoprostone)
2848:
2844:
2839:
2835:
2830:
2821:
2819:
2811:
2805:
2804:
2802:
2801:
2796:
2791:
2786:
2781:
2772:
2771:
2766:
2764:(dinoprostone)
2761:
2757:
2752:
2748:
2743:
2738:
2733:
2728:
2723:
2714:
2712:
2704:
2695:
2686:
2680:
2679:
2676:
2675:
2673:
2672:
2667:
2662:
2657:
2652:
2647:
2642:
2637:
2632:
2627:
2622:
2617:
2608:
2607:
2603:
2599:
2590:
2588:
2580:
2574:
2573:
2571:
2570:
2565:
2560:
2551:
2550:
2545:
2541:
2533:
2531:
2523:
2514:
2505:
2496:
2482:
2481:
2470:
2468:
2467:
2460:
2453:
2445:
2436:
2435:
2433:
2432:
2427:
2421:
2419:
2415:
2414:
2412:
2411:
2406:
2401:
2396:
2391:
2386:
2380:
2378:
2374:
2373:
2371:
2370:
2365:
2360:
2354:
2352:
2348:
2347:
2344:
2342:
2341:
2334:
2327:
2319:
2310:
2309:
2306:
2305:
2304:
2303:
2300:
2289:
2283:
2277:
2276:
2273:
2272:
2270:
2269:
2264:
2259:
2253:
2251:
2245:
2244:
2241:
2240:
2238:
2237:
2235:Carboprost/F2α
2232:
2225:
2224:
2221:Sulprostone/E2
2218:
2213:
2208:
2206:Misoprostol/E1
2201:
2199:
2192:Prostaglandins
2188:
2187:
2185:
2184:
2179:
2169:
2163:
2161:
2152:
2146:
2145:
2133:labor inducers
2127:
2125:
2124:
2117:
2110:
2102:
2093:
2092:
2090:
2089:
2088:
2087:
2082:
2078:
2077:(Dinoprostone)
2073:
2060:
2059:
2058:
2057:
2053:
2040:
2039:
2038:
2037:
2033:
2029:
2025:
2016:
2015:
2014:
2010:
2006:
2002:
1990:
1989:
1988:
1984:
1980:
1976:
1967:
1966:
1965:
1961:
1948:
1947:
1946:
1945:
1941:
1937:
1933:
1929:
1925:
1921:
1917:
1913:
1909:
1898:
1897:
1896:
1892:
1888:
1884:
1880:
1876:
1864:
1863:
1862:
1861:
1857:
1853:
1849:
1845:
1841:
1837:
1833:
1829:
1825:
1813:
1811:
1807:
1806:
1804:
1803:
1798:
1793:
1786:
1777:
1775:
1769:
1768:
1765:
1764:
1762:
1761:
1757:
1753:
1749:
1745:
1741:
1737:
1733:
1728:
1726:
1722:
1721:
1719:
1718:
1712:
1710:
1703:
1696:
1695:
1692:
1691:
1689:
1688:
1684:
1680:
1676:
1672:
1668:
1663:
1661:
1655:
1654:
1652:
1651:
1647:
1643:
1639:
1634:
1632:
1628:
1627:
1625:
1624:
1618:
1616:
1609:
1602:
1601:
1598:
1597:
1595:
1594:
1590:
1586:
1582:
1577:
1575:
1568:
1567:
1564:
1563:
1560:
1559:
1557:
1556:
1550:
1545:
1543:
1539:
1538:
1536:
1535:
1529:
1524:
1523:
1518:
1513:
1512:
1510:(Dinoprostone)
1507:
1502:
1500:
1493:
1492:
1490:
1489:
1485:
1480:
1478:
1471:
1467:
1466:
1464:
1463:
1459:
1454:
1452:
1445:
1442:Prostaglandins
1435:
1429:
1428:
1426:
1425:
1419:
1417:
1413:
1412:
1407:
1405:
1404:
1397:
1390:
1382:
1375:
1374:
1342:
1323:(42): 130593.
1307:
1292:
1241:
1214:
1168:
1142:
1113:(2): 465–472.
1093:
1054:
1019:
978:
951:(4): 280–285.
935:
916:(1): 161–166.
910:Prostaglandins
900:
874:
860:978-1849736701
859:
840:
838:
835:
834:
833:
828:
823:
818:
808:
800:
797:
792:
780:
777:cyclooxygenase
768:
763:
757:
738:
734:
731:
729:
726:
709:
706:
700:
696:
692:
688:
685:
680:
675:
667:
663:
659:
651:
641:
638:
628:
622:
615:
592:
588:
584:
580:
555:
548:
542:
541:
524:
523:
521:
520:
517:
515:
512:
504:
503:
502:
499:
498:
496:
495:
492:
484:
483:
482:
479:
478:
475:
469:
468:
466:
465:
457:
455:
447:
446:
440:
434:
433:
430:
424:
418:
413:
407:
406:
402:
401:
391:
383:
382:
380:
379:
366:
364:
351:
350:
348:
347:
339:
337:
331:
330:
328:
327:
319:
317:
311:
310:
308:
307:
299:
297:
291:
290:
288:
287:
279:
277:
271:
270:
268:
267:
259:
257:
251:
250:
248:
247:
239:
237:
231:
230:
228:
227:
219:
217:
206:
205:
203:
202:
191:
189:
183:
182:
180:
179:
172:
164:
163:
162:
159:
158:
154:
153:
147:amniotic fluid
143:
134:
133:
126:
125:
123:
122:
109:
107:
101:
100:
97:intra-amniotic
90:
88:administration
82:
81:
74:
64:
63:
60:
56:
55:
51:
50:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
5037:
5026:
5023:
5021:
5018:
5016:
5013:
5012:
5010:
4995:
4994:
4990:
4988:
4987:
4983:
4980:
4979:
4976:
4970:
4964:
4962:
4956:
4954:
4951:
4949:
4946:
4944:
4941:
4939:
4936:
4934:
4933:Linoleic acid
4931:
4928:
4927:
4925:
4921:
4911:
4908:
4906:
4903:
4901:
4898:
4896:
4893:
4891:
4888:
4886:
4883:
4881:
4878:
4876:
4873:
4871:
4868:
4866:
4863:
4861:
4858:
4856:
4853:
4851:
4848:
4846:
4843:
4841:
4838:
4836:
4833:
4832:
4830:
4825:
4819:
4815:
4811:
4806:
4796:
4792:
4788:
4783:
4777:
4773:
4769:
4764:
4758:
4751:
4747:
4743:
4739:
4736:
4734:
4731:
4730:
4728:
4723:
4713:
4707:
4704:
4702:
4699:
4697:
4694:
4692:
4689:
4687:
4684:
4682:
4679:
4677:
4674:
4672:
4669:
4667:
4664:
4662:
4659:
4657:
4654:
4652:
4649:
4647:
4644:
4642:
4639:
4637:
4634:
4632:
4629:
4627:
4624:
4622:
4615:
4613:
4610:
4608:
4605:
4603:
4600:
4598:
4595:
4593:
4590:
4588:
4585:
4583:
4580:
4578:
4575:
4573:
4570:
4568:
4565:
4563:
4560:
4558:
4555:
4553:
4550:
4546:
4543:
4541:
4538:
4536:
4533:
4531:
4528:
4526:
4523:
4521:
4518:
4516:
4513:
4511:
4508:
4506:
4503:
4501:
4498:
4496:
4493:
4491:
4488:
4486:
4483:
4481:
4478:
4474:
4471:
4469:
4466:
4464:
4461:
4459:
4456:
4454:
4451:
4449:
4446:
4444:
4441:
4437:
4434:
4432:
4429:
4425:
4422:
4420:
4417:
4415:
4412:
4408:
4405:
4403:
4402:Fluproquazone
4400:
4399:Quinazolines:
4396:
4393:
4391:
4388:
4386:
4383:
4379:
4376:
4374:
4371:
4369:
4366:
4364:
4361:
4359:
4356:
4354:
4351:
4349:
4346:
4344:
4341:
4337:
4334:
4332:
4329:
4327:
4324:
4322:
4319:
4317:
4314:
4310:
4307:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4287:
4285:
4282:
4280:
4277:
4275:
4272:
4270:
4267:
4263:
4260:
4258:
4255:
4253:
4250:
4248:
4245:
4243:
4240:
4238:
4235:
4233:
4230:
4228:
4225:
4223:
4220:
4218:
4215:
4213:
4210:
4208:
4205:
4203:
4200:
4198:
4195:
4193:
4190:
4188:
4185:
4183:
4180:
4178:
4177:Flunoxaprofen
4175:
4173:
4170:
4168:
4165:
4163:
4162:Dexketoprofen
4160:
4158:
4157:Dexindoprofen
4155:
4153:
4150:
4148:
4145:
4143:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4121:
4118:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4098:
4096:
4095:Proglumetacin
4093:
4091:
4088:
4086:
4083:
4081:
4078:
4076:
4073:
4071:
4068:
4066:
4063:
4061:
4058:
4056:
4053:
4051:
4048:
4046:
4043:
4041:
4038:
4036:
4033:
4031:
4028:
4026:
4025:Difenpiramide
4023:
4021:
4018:
4016:
4013:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3993:
3991:
3988:
3986:
3983:
3981:
3978:
3976:
3973:
3971:
3968:
3966:
3963:
3962:Acetic acids:
3959:
3956:
3954:
3951:
3949:
3946:
3944:
3941:
3939:
3936:
3934:
3931:
3929:
3926:
3924:
3921:
3919:
3916:
3914:
3911:
3909:
3906:
3904:
3901:
3899:
3896:
3894:
3891:
3889:
3886:
3884:
3881:
3879:
3876:
3874:
3871:
3868:
3867:
3865:
3863:
3851:
3848:
3844:
3838:
3834:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3734:
3731:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3711:
3709:
3706:
3704:
3701:
3699:
3696:
3694:
3693:Fenprostalene
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3674:
3671:
3669:
3666:
3664:
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3643:Delprostenate
3641:
3639:
3636:
3634:
3631:
3629:
3626:
3624:
3621:
3619:
3616:
3615:
3613:
3609:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3548:
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3462:
3460:
3457:
3455:
3452:
3450:
3447:
3445:
3442:
3440:
3437:
3434:
3433:
3430:
3427:
3425:
3422:
3420:
3416:Thromboxane A
3414:
3412:
3409:
3407:
3401:
3398:
3397:
3395:
3390:
3380:
3374:
3371:
3368:
3367:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3338:(alprostadil)
3332:
3330:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3291:
3288:
3286:
3283:
3281:
3278:
3276:
3273:
3270:
3269:
3267:
3262:
3252:
3246:
3243:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3219:
3217:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3173:
3172:
3170:
3165:
3155:
3145:
3142:
3140:
3137:
3135:
3128:
3126:
3123:
3121:
3118:
3116:
3113:
3111:
3108:
3106:
3103:
3101:
3098:
3096:
3090:
3087:
3086:
3084:
3080:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3053:
3052:
3049:
3046:
3044:
3037:
3035:
3034:(alprostadil)
3028:
3026:
3023:
3021:
3018:
3015:
3014:
3012:
3007:
2998:
2992:
2989:
2986:
2985:
2982:
2979:
2977:
2974:
2972:
2969:
2967:
2960:
2958:
2957:(alprostadil)
2951:
2949:
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2900:
2899:
2897:
2892:
2883:
2877:
2874:
2872:
2869:
2867:
2864:
2861:
2860:
2857:
2854:
2852:
2845:
2843:
2842:(alprostadil)
2836:
2834:
2831:
2829:
2826:
2823:
2822:
2820:
2815:
2806:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2774:
2773:
2770:
2767:
2765:
2758:
2756:
2755:(alprostadil)
2749:
2747:
2744:
2742:
2739:
2737:
2734:
2732:
2729:
2727:
2724:
2722:
2719:
2716:
2715:
2713:
2708:
2699:
2696:
2691:
2681:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2653:
2651:
2648:
2646:
2643:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2610:
2609:
2606:
2600:
2598:
2595:
2592:
2591:
2589:
2584:
2575:
2569:
2566:
2564:
2561:
2559:
2556:
2553:
2552:
2549:
2546:
2544:
2538:
2535:
2534:
2532:
2527:
2518:
2515:
2510:
2500:
2497:
2493:
2487:
2483:
2479:
2476:
2473:
2466:
2461:
2459:
2454:
2452:
2447:
2446:
2443:
2431:
2428:
2426:
2423:
2422:
2420:
2416:
2410:
2407:
2405:
2402:
2400:
2397:
2395:
2392:
2390:
2387:
2385:
2382:
2381:
2379:
2375:
2369:
2366:
2364:
2361:
2359:
2356:
2355:
2353:
2349:
2340:
2335:
2333:
2328:
2326:
2321:
2320:
2317:
2301:
2299:
2296:
2295:
2293:
2290:
2287:
2284:
2282:
2279:
2278:
2274:
2268:
2265:
2263:
2260:
2258:
2255:
2254:
2252:
2250:
2246:
2236:
2233:
2231:
2230:Dinoprost/F2α
2227:
2226:
2222:
2219:
2217:
2214:
2212:
2209:
2207:
2203:
2202:
2200:
2198:
2193:
2189:
2183:
2180:
2177:
2173:
2170:
2168:
2165:
2164:
2162:
2160:
2156:
2153:
2151:
2147:
2142:
2138:
2134:
2130:
2123:
2118:
2116:
2111:
2109:
2104:
2103:
2100:
2085:
2079:
2076:
2070:
2069:
2068:
2066:
2062:
2061:
2056:
2050:
2049:
2048:
2046:
2042:
2041:
2036:
2030:
2028:
2022:
2021:
2020:
2017:
2013:
2007:
2005:
1999:
1998:
1997:
1995:
1991:
1987:
1981:
1979:
1973:
1972:
1971:
1968:
1964:
1958:
1957:
1956:
1954:
1950:
1949:
1944:
1938:
1936:
1930:
1928:
1922:
1920:
1914:
1912:
1906:
1905:
1904:
1903:
1899:
1895:
1889:
1887:
1881:
1879:
1873:
1872:
1871:
1870:
1866:
1865:
1860:
1854:
1852:
1846:
1844:
1838:
1836:
1830:
1828:
1822:
1821:
1820:
1819:
1815:
1814:
1812:
1808:
1802:
1799:
1796:
1789:
1782:
1779:
1778:
1776:
1774:
1770:
1760:
1754:
1752:
1746:
1744:
1738:
1736:
1730:
1729:
1727:
1723:
1717:
1714:
1713:
1711:
1707:
1704:
1701:
1697:
1687:
1681:
1679:
1673:
1671:
1665:
1664:
1662:
1660:
1656:
1650:
1644:
1642:
1636:
1635:
1633:
1629:
1623:
1620:
1619:
1617:
1613:
1610:
1607:
1603:
1593:
1587:
1585:
1579:
1578:
1576:
1573:
1569:
1554:
1547:
1546:
1544:
1540:
1533:
1526:
1525:
1522:
1521:(Alprostadil)
1515:
1514:
1511:
1504:
1503:
1501:
1498:
1494:
1488:
1482:
1481:
1479:
1475:
1472:
1468:
1462:
1456:
1455:
1453:
1449:
1446:
1443:
1439:
1436:
1434:
1430:
1424:
1421:
1420:
1418:
1414:
1410:
1403:
1398:
1396:
1391:
1389:
1384:
1383:
1380:
1370:
1366:
1362:
1358:
1351:
1349:
1347:
1343:
1338:
1334:
1330:
1326:
1322:
1318:
1311:
1308:
1303:
1296:
1293:
1288:
1284:
1280:
1276:
1272:
1268:
1264:
1260:
1256:
1252:
1245:
1242:
1229:
1225:
1218:
1215:
1203:
1199:
1195:
1191:
1187:
1183:
1179:
1172:
1169:
1156:
1152:
1146:
1143:
1138:
1134:
1129:
1124:
1120:
1116:
1112:
1108:
1104:
1097:
1094:
1089:
1085:
1081:
1077:
1073:
1069:
1068:Endocrinology
1065:
1058:
1055:
1050:
1046:
1042:
1038:
1034:
1030:
1023:
1020:
1015:
1011:
1006:
1001:
997:
993:
989:
982:
979:
974:
970:
966:
962:
958:
954:
950:
946:
939:
936:
931:
927:
923:
919:
915:
911:
904:
901:
888:
884:
878:
875:
870:
866:
862:
856:
852:
845:
842:
836:
832:
829:
827:
824:
822:
819:
817:
814:
813:
812:
806:
798:
796:
790:
786:
778:
774:
766:
754:
750:
748:
744:
732:
727:
725:
723:
714:
707:
705:
686:
684:
673:
657:
647:
639:
637:
635:
634:endometriosis
631:
619:
613:
609:
605:
604:corpus luteum
601:
596:
578:
577:abortifacient
574:
570:
569:prostaglandin
566:
562:
558:
551:
538:
531:
525:
516:
511:
507:
500:
491:
487:
480:
476:
474:
470:
463:
459:
458:
456:
453:
448:
441:
439:
435:
414:
412:
408:
403:
399:
395:
392:
390:
388:ECHA InfoCard
384:
376:
372:
371:DTXSID9022946
368:
367:
365:
356:
352:
345:
341:
340:
338:
336:
332:
325:
321:
320:
318:
316:
312:
305:
301:
300:
298:
296:
292:
285:
281:
280:
278:
276:
272:
265:
261:
260:
258:
256:
252:
245:
241:
240:
238:
236:
232:
225:
221:
220:
218:
211:
207:
201:
197:
193:
192:
190:
188:
184:
176:
171:
167:
160:
155:
152:
148:
144:
142:
135:
131:
127:
119:
114:
111:
110:
108:
106:
102:
98:
94:
91:
89:
83:
79:
75:
73:
69:
65:
61:
57:
54:Clinical data
52:
48:
43:
33:
19:
4991:
4984:
4929:
4548:
4476:
4473:Propacetamol
4463:Parapropamol
4439:
4427:
4410:
4398:
4390:Floctafenine
4381:
4339:
4316:Azapropazone
4313:Pyrazolones:
4312:
4265:
4247:Tarenflurbil
4182:Flurbiprofen
4152:Dexibuprofen
4132:Benoxaprofen
4127:Alminoprofen
4123:
4050:Glucametacin
3961:
3938:Salicylamide
3928:Salacetamide
3869:
3818:Trimoprostil
3813:Tiprostanide
3798:Spiriprostil
3733:Naxaprostene
3683:Esuberaprost
3638:Cobiprostone
3436:Antagonists:
3435:
3399:
3370:Antagonists:
3369:
3363:Treprostinil
3271:
3203:Fluprostenol
3193:Cloprostenol
3174:
3088:
3055:Antagonists:
3054:
3020:Lubiprostone
3016:
2988:Antagonists:
2987:
2901:
2863:Antagonists:
2862:
2856:Treprostinil
2824:
2776:Antagonists:
2775:
2741:Lubiprostone
2717:
2612:Antagonists:
2611:
2593:
2555:Antagonists:
2554:
2548:Treprostinil
2536:
2430:Mifepristone
2363:Dinoprostone
2357:
2229:
2211:Gemeprost/E1
2176:Syntometrine
2167:Acetergamine
2080:
2067:stimulation:
2063:
2047:stimulation:
2043:
2018:
1992:
1969:
1951:
1902:vasodilation
1900:
1874:
1867:
1816:
1606:Leukotrienes
1572:Thromboxanes
1527:
1360:
1356:
1320:
1316:
1310:
1301:
1295:
1254:
1250:
1244:
1232:. Retrieved
1227:
1217:
1205:. Retrieved
1185:
1181:
1171:
1159:. Retrieved
1154:
1145:
1110:
1106:
1096:
1071:
1067:
1057:
1035:: 997–1029.
1032:
1028:
1022:
998:(1): 63–70.
995:
991:
981:
948:
944:
938:
913:
909:
903:
891:. Retrieved
886:
877:
850:
844:
802:
755:
751:
742:
736:
719:
690:
672:progesterone
649:
626:
620:
610:, forming a
597:
573:induce labor
564:
553:
546:
545:
534:
528:
174:
151:blood plasma
138:Elimination
5025:Uterotonics
4930:Precursors:
4870:Nicogrelate
4850:Furegrelate
4791:Bimatoprost
4701:Trifenagrel
4691:Tiflamizole
4661:Rutecarpine
4646:Resveratrol
4587:Glimepiride
4552:Anitrazafen
4530:Robenacoxib
4510:Lumiracoxib
4443:Acetanilide
4385:Antrafenine
4343:Ampiroxicam
4237:Pranoprofen
4222:Naproxcinod
4115:Zidometacin
4040:Fenclofenac
3965:Aceclofenac
3903:Ethenzamide
3898:Dipyrocetyl
3793:Rosaprostol
3773:Posaraprost
3758:Penprostene
3748:Ornoprostil
3728:Mexiprostil
3723:Meteneprost
3678:Eptaloprost
3653:Dimoxaprost
3618:Arbaprostil
3572:Seratrodast
3464:BMS-180,291
3295:Carbacyclin
3245:Unoprostone
3225:(dinoprost)
3208:Latanoprost
3183:Bimatoprost
3178:Alfaprostol
3134:(dinoprost)
3073:ONO-AE3-208
3025:Misoprostol
2981:Sulprostone
2971:Remiprostol
2940:Misoprostol
2935:Latanoprost
2910:Carbacyclin
2871:PF-04418948
2833:Misoprostol
2769:Sulprostone
2746:Misoprostol
2736:Latanoprost
2670:Vidupiprant
2660:Timapiprant
2655:Setipiprant
2630:Fevipiprant
2597:Indometacin
2568:Vidupiprant
2563:Laropiprant
2425:Misoprostol
2399:Ergometrine
2394:Demoxytocin
2288:from market
2267:Demoxytocin
2172:Ergometrine
2129:Uterotonics
2086:(Dinoprost)
1810:By function
1801:Virodhamine
1532:(Dinoprost)
1433:Prostanoids
1409:Eicosanoids
1317:Tetrahedron
1161:November 2,
893:November 6,
821:Bimatoprost
816:Latanoprost
791:to form PGF
445: g·mol
394:100.209.720
157:Identifiers
93:Intravenous
59:Other names
5009:Categories
4900:Samixogrel
4895:Rolafagrel
4880:Picotamide
4860:Midazogrel
4835:Camonagrel
4696:Timegadine
4641:Pamicogrel
4612:Licofelone
4592:Hyperforin
4557:Clobuzarit
4545:Valdecoxib
4540:Tilmacoxib
4525:Polmacoxib
4500:Etoricoxib
4468:Phenacetin
4436:Nimesulide
4414:Clonixeril
4407:Proquazone
4363:Lornoxicam
4262:Vedaprofen
4212:Miroprofen
4207:Loxoprofen
4202:Ketoprofen
4197:Indoprofen
4172:Fenoprofen
4085:Oxametacin
4080:Nabumetone
4020:Diclofenac
4015:Clometacin
4010:Cinmetacin
4005:Bumadizone
3985:Alclofenac
3970:Acemetacin
3908:Guacetisal
3893:Diflunisal
3843:inhibitors
3808:Tilsuprost
3788:Rivenprost
3783:Rioprostil
3778:Prostalene
3763:Pimilprost
3753:Oxoprostol
3743:Nocloprost
3718:Luprostiol
3708:Lanproston
3703:Froxiprost
3698:Flunoprost
3688:Etiproston
3673:Enisoprost
3668:Eganoprost
3628:Ciprostene
3597:Terutroban
3587:Sulotroban
3567:Samixogrel
3552:Ramatroban
3539:Picotamide
3524:Mipitroban
3519:Linotroban
3504:Imitrodast
3494:ICI-192605
3489:ICI-185282
3474:Domitroban
3454:Argatroban
3353:Taprostene
3275:ACT-333679
3240:Travoprost
3235:Tafluprost
3230:Sulotroban
3188:Carboprost
3144:Taprenepag
3125:Omidenepag
3120:Nocloprost
3110:Evatanepag
3105:Carboprost
3058:Grapiprant
2650:Ramatroban
2558:Asapiprant
2478:modulators
2472:Prostanoid
2389:Carbetocin
2384:Carboprost
2262:Carbetocin
1994:leukocytes
1773:Nonclassic
1234:2 December
1222:Menino A.
1207:2 December
887:Britannica
837:References
831:Carboprost
826:Travoprost
608:luteolysis
575:and as an
561:prostanoid
450:3D model (
438:Molar mass
304:B7IN85G1HY
275:ChemSpider
235:IUPHAR/BPS
200:38562-01-5
187:CAS Number
166:IUPAC name
4905:Terbogrel
4885:Pirmagrel
4845:Dazoxiben
4840:Dazmegrel
4733:Retinoids
4651:Romazarit
4597:Itazigrel
4582:FR-122047
4577:Flumizole
4535:Rofecoxib
4520:Parecoxib
4515:Mavacoxib
4505:Firocoxib
4495:Deracoxib
4490:Cimicoxib
4485:Celecoxib
4480:Apricoxib
4431:Flosulide
4395:Glafenine
4378:Tenoxicam
4373:Piroxicam
4368:Meloxicam
4252:Tepoxalin
4232:Pirprofen
4227:Oxaprozin
4192:Ibuproxam
4187:Ibuprofen
4147:Carprofen
4142:Butibufen
4120:Zomepirac
4090:Oxindanac
4075:Mofezolac
4070:Lonazolac
4065:Ketorolac
4045:Fentiazac
4000:Bufexamac
3995:Bromfenac
3975:Aclofenac
3958:Triflusal
3948:Salsalate
3873:Aloxiprin
3823:Viprostol
3768:Piriprost
3738:Nileprost
3713:Limaprost
3663:Ecraprost
3658:Doxaprost
3648:Deprostil
3633:Clinprost
3592:Terbogrel
3582:SQ-29,548
3577:SQ-28,668
3534:ONO-11120
3499:Ifetroban
3469:Daltroban
3459:Bay U3405
3429:Vapiprost
3400:Agonists:
3373:RO1138452
3348:Selexipag
3343:Ralinepag
3300:Cicaprost
3290:BMY-45778
3285:Beraprost
3272:Agonists:
3198:Enprostil
3175:Agonists:
3139:Simenepag
3115:Gemeprost
3089:Agonists:
3063:GW-627368
3017:Agonists:
2920:Enprostil
2915:Cicaprost
2905:Beraprost
2902:Agonists:
2828:Butaprost
2825:Agonists:
2726:Enprostil
2721:Beraprost
2718:Agonists:
2625:Bay U3405
2594:Agonists:
2537:Agonists:
2475:signaling
2358:Dinoprost
2298:Phase III
2286:Withdrawn
2197:analogues
2137:oxytocics
1953:platelets
1709:Precursor
1615:Precursor
1451:Precursor
1416:Precursor
1363:: 65–89.
1337:203131829
1287:205230275
869:824530529
805:analogues
799:Analogues
728:Synthesis
627:8-iso-PGF
606:to cause
565:dinoprost
344:ChEMBL815
140:half-life
86:Routes of
72:Drugs.com
39:Dinoprost
4981:See also
4890:Ridogrel
4865:Nafagrel
4855:Isbogrel
4738:Selenium
4706:Tropesin
4681:SC-58125
4666:Satigrel
4631:NCX-4040
4607:L-670596
4602:L-655240
4562:Curcumin
4424:Flunixin
4419:Clonixin
4358:Isoxicam
4353:Enolicam
4348:Droxicam
4326:Isopyrin
4321:Dipyrone
4242:Suprofen
4217:Naproxen
4167:Fenbufen
4110:Tolmetin
4100:Sulindac
4035:Felbinac
4030:Etodolac
3990:Bendazac
3803:Tiaprost
3623:Ataprost
3611:Unsorted
3557:Ridogrel
3529:ONO-3708
3514:L-670596
3509:L-655240
3484:GR-32191
3100:Aganepag
3082:Unsorted
3068:L-161982
3048:TCS-2510
2991:L-798106
2876:TG 4-155
2799:SC-51322
2794:SC-51089
2789:SC-19220
2784:ONO-8130
2620:AZD-1981
2615:ADC-3680
2486:Receptor
2409:Oxytocin
2368:Oxytocin
2257:Oxytocin
1996:: induce
1955:: induce
1781:Lipoxins
1369:18802217
1304:. Wiley.
1279:22895192
1137:16992446
1014:19324352
973:73028858
722:pyometra
625:isoform
600:oxytocin
537:(verify)
255:DrugBank
196:551-11-1
105:ATC code
4910:U63557A
4875:Ozagrel
4686:Tenidap
4626:NCX-466
4572:FK-3311
4567:DuP-697
4453:Bucetin
3980:Amfenac
3933:Salicin
3602:TRA-418
3449:AA-2414
3439:12-HETE
3424:U-46619
3358:TRA-418
3315:MRE-269
2866:AH-6809
2779:AH-6809
2665:TM30089
2645:QAV-680
2640:MK-7246
2635:MK-1029
2492:ligands
2019:inhibit
1970:inhibit
1631:Initial
1259:Bibcode
1202:1568932
1128:1350813
1088:3465529
965:3169373
747:proline
621:The PGF
443:354.487
411:Formula
284:4444062
264:DB01160
224:5280363
210:PubChem
121:)
115: (
113:G02AD01
4923:Others
4772:HQL-79
4676:SC-560
4671:SC-236
4636:NS-398
3837:Enzyme
3479:EP-045
3444:13-APA
3384:TP (TX
3320:NS-304
3280:AFP-07
2281:WHO-EM
1783:(LX) (
1725:Eoxins
1700:Eoxins
1470:Active
1367:
1335:
1285:
1277:
1251:Nature
1200:
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1049:209733
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930:392622
928:
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486:SMILES
335:ChEMBL
324:D00081
3562:S-145
3411:I-BOP
3256:IP (I
3159:FP (F
2685:EP (E
2504:DP (D
2065:labor
2045:fever
1659:SRS-A
1333:S2CID
1283:S2CID
969:S2CID
506:InChI
452:JSmol
4823:TXAS
4781:PGFS
4762:PGES
3860:PTGS
2141:G02A
1702:(EX)
1608:(LT)
1574:(TX)
1444:(PG)
1365:PMID
1275:PMID
1236:2021
1228:USDA
1209:2021
1198:PMID
1163:2017
1133:PMID
1084:PMID
1045:PMID
1010:PMID
961:PMID
926:PMID
895:2022
865:OCLC
855:ISBN
767:(PLA
315:KEGG
295:UNII
244:1884
132:data
68:AHFS
4800:PGI
4717:PGD
3855:COX
2228:F:
2204:E:
2194:and
2081:PGF
2072:PGE
2052:PGE
2032:PGE
2024:PGD
2009:LTB
2001:TXA
1983:PGI
1975:PGD
1960:TXA
1940:LTE
1932:LTD
1924:LTC
1916:PGI
1908:PGE
1891:TXB
1883:TXA
1875:PGF
1856:LTE
1848:LTD
1840:LTC
1832:TXA
1824:PGD
1477:D/J
1325:doi
1267:doi
1255:489
1190:doi
1186:200
1123:PMC
1115:doi
1111:236
1076:doi
1072:119
1037:doi
1000:doi
953:doi
918:doi
787:or
679:PGF
650:PGF
559:in
554:PGF
360:EPA
214:CID
118:WHO
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2887:EP
2810:EP
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2579:DP
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