Chemical compound
Gemeprost![](https://upload.wikimedia.org/wikipedia/commons/thumb/3/3d/Gemeprost.svg/220px-Gemeprost.svg.png) |
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Trade names | Cervagem |
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Other names | methyl (E)-7-[(1R,2S,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4,4-dimethyl-oct-1-enyl]-5-oxo-cyclopentyl]hept-2-enoate |
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AHFS/Drugs.com | International Drug Names |
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Pregnancy category | |
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Routes of administration | Pessary |
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ATC code | |
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Legal status |
- AU: S4 (Prescription only)
- UK: POM (Prescription only)[1]
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methyl (2E,11α,13E,15R)-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
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CAS Number | |
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PubChem CID | |
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DrugBank | |
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ChemSpider | |
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UNII | |
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KEGG | |
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CompTox Dashboard (EPA) | |
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ECHA InfoCard | 100.058.869 ![Edit this at Wikidata](https://upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png) |
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Formula | C23H38O5 |
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Molar mass | 394.552 g·mol−1 |
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3D model (JSmol) | |
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O=C1C[C@@H](O)[C@H](/C=C/[C@@H](O)C(C)(C)CCCC)[C@H]1CCCC\C=C\C(=O)OC
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InChI=1S/C23H38O5/c1-5-6-15-23(2,3)21(26)14-13-18-17(19(24)16-20(18)25)11-9-7-8-10-12-22(27)28-4/h10,12-14,17-18,20-21,25-26H,5-9,11,15-16H2,1-4H3/b12-10+,14-13+/t17-,18-,20-,21-/m1/s1 YKey:KYBOHGVERHWSSV-VNIVIJDLSA-N Y
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N Y (what is this?) (verify) |
Gemeprost (16, 16-dimethyl-trans-delta2 PGE1 methyl ester) is an analogue of prostaglandin E1.
Clinical use
It is used as a treatment for obstetric bleeding.[citation needed]
It is used with mifepristone to terminate pregnancy up to 24 weeks gestation.[2]
Side effects
Vaginal bleeding, cramps, nausea, vomiting,[3] loose stools or diarrhea,[3] headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild pyrexia.[3] Rare: Uterine rupture, severe hypotension, coronary spasms with subsequent myocardial infarctions.[citation needed]
Uterotonics/labor inducers/oxytocics (G02A)
Prostanoid signaling modulators
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Receptor (ligands) | DP (D2)Tooltip Prostaglandin D2 receptor | DP1Tooltip Prostaglandin D2 receptor 1 | |
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DP2Tooltip Prostaglandin D2 receptor 2 | |
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EP (E2)Tooltip Prostaglandin E2 receptor | EP1Tooltip Prostaglandin EP1 receptor |
- Antagonists: AH-6809
- ONO-8130
- SC-19220
- SC-51089
- SC-51322
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EP2Tooltip Prostaglandin EP2 receptor |
- Antagonists: AH-6809
- PF-04418948
- TG 4-155
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EP3Tooltip Prostaglandin EP3 receptor | |
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EP4Tooltip Prostaglandin EP4 receptor |
- Antagonists: Grapiprant
- GW-627368
- L-161982
- ONO-AE3-208
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Unsorted | |
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FP (F2α)Tooltip Prostaglandin F receptor | |
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IP (I2)Tooltip Prostacyclin receptor | |
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TP (TXA2)Tooltip Thromboxane receptor | |
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Unsorted |
- Arbaprostil
- Ataprost
- Ciprostene
- Clinprost
- Cobiprostone
- Delprostenate
- Deprostil
- Dimoxaprost
- Doxaprost
- Ecraprost
- Eganoprost
- Enisoprost
- Eptaloprost
- Esuberaprost
- Etiproston
- Fenprostalene
- Flunoprost
- Froxiprost
- Lanproston
- Limaprost
- Luprostiol
- Meteneprost
- Mexiprostil
- Naxaprostene
- Nileprost
- Nocloprost
- Ornoprostil
- Oxoprostol
- Penprostene
- Pimilprost
- Piriprost
- Posaraprost
- Prostalene
- Rioprostil
- Rivenprost
- Rosaprostol
- Spiriprostil
- Tiaprost
- Tilsuprost
- Tiprostanide
- Trimoprostil
- Viprostol
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Enzyme (inhibitors) | COX (PTGS) | |
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PGD2STooltip Prostaglandin D synthase | |
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PGESTooltip Prostaglandin E synthase | HQL-79 |
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PGFSTooltip Prostaglandin F synthase | |
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PGI2STooltip Prostacyclin synthase | |
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TXASTooltip Thromboxane A synthase | |
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Others | |
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