Gemeprost: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{Drugbox		{{Drugbox
			\| Verifiedfields = changed
	\| verifiedrevid = 447612599		\| verifiedrevid = 447612599
	\| IUPAC_name = methyl (2''E'',11α,13''E'',15''R'')-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate		\| IUPAC_name = methyl (2''E'',11α,13''E'',15''R'')-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
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	<!--Clinical data-->		<!--Clinical data-->
	\| tradename =		\| tradename = Cervagem
	\| Drugs.com = {{drugs.com\|international\|gemeprost}}		\| Drugs.com = {{drugs.com\|international\|gemeprost}}
	\| pregnancy_AU = ~~<!-- A / B1 / B2 /~~ B3 ~~/ C / D / X -->~~		\| pregnancy_AU = B3
	\| pregnancy_US = <!-- A / B / C / D / X -->		\| pregnancy_US = <!-- A / B / C / D / X -->
	\| pregnancy_category =		\| pregnancy_category =
	\| legal_AU = ~~<!-- Unscheduled / S2 / S3 /~~ S4 ~~/ S5 / S6 / S7 / S8 / S9 -->~~		\| legal_AU = S4
	\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->		\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
	\| legal_UK = ~~<!-- GSL / P /~~ POM ~~/ CD / Class A, B, C -->~~		\| legal_UK = POM
			\| legal_UK_comment = <ref>{{cite web \| title=Cervagem 1 mg Pessary - Summary of Product Characteristics (SmPC) \| website=(emc) \| date=16 August 2019 \| url=https://www.medicines.org.uk/emc/product/2202 \| access-date=7 September 2020}}</ref>
	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->		\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
	\| legal_status =		\| legal_status =
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	\| metabolism =		\| metabolism =
	\| elimination_half-life =		\| elimination_half-life =
	\| excretion =		\| excretion =

	<!--Identifiers-->		<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 64318-79-2		\| CAS_number = 64318-79-2
	\| ATC_prefix = G02		\| ATC_prefix = G02
	\| ATC_suffix = AD03		\| ATC_suffix = AD03
	\| PubChem = 5282237		\| PubChem = 5282237
	\| DrugBank_Ref = {{drugbankcite\|~~correct~~\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|changed\|drugbank}}
	\| DrugBank =		\| DrugBank = DB08964
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 4445416		\| ChemSpiderID = 4445416
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	<!--Chemical data-->		<!--Chemical data-->
	\| C=23 \| H=38 \| O=5		\| C=23 \| H=38 \| O=5
	\| molecular_weight = 394.545 g/mol
	\| smiles = O=C1C(O)(/C=C/(O)C(C)(C)CCCC)1CCCC\C=C\C(=O)OC		\| smiles = O=C1C(O)(/C=C/(O)C(C)(C)CCCC)1CCCC\C=C\C(=O)OC
	\| InChI = 1/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
	\| InChIKey = KYBOHGVERHWSSV-VNIVIJDLBY
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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		\| StdInChI = 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
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	\| synonyms = <small>methyl (''E'')-7--5-oxo-cyclopentyl]hept-2-enoate</small>		\| synonyms = <small>methyl (''E'')-7--5-oxo-cyclopentyl]hept-2-enoate</small>
	}}		}}

	'''Gemeprost''' (16, 16-dimethyl-trans-delta2 PGE<sub>1</sub> methyl ester) is an ] of ] E<sub>1</sub>.		'''Gemeprost''' (16, 16-dimethyl-trans-delta2 PGE<sub>1</sub> methyl ester) is an ] of ].

	==Clinical use==		==Clinical use==

	It is used as a treatment for ].		It is used as a treatment for ].{{fact\|date=September 2021}}

	It is used with ] to terminate pregnancy up to 24 weeks gestation. <ref name="pmid11574498">{{cite journal \|~~author~~=Bartley J, Brown A, Elton R, Baird DT \|title=Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation \|journal=Human ~~reproduction (Oxford, England)~~ \|volume=16 \|issue=10 \|pages=2098–102 \|~~year=2001~~ ~~\|month~~=October \|pmid=11574498 \|doi= 10.1093/humrep/16.10.2098\|~~url~~=~~http://humrep.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11574498~~ ~~\|accessdate=2008-10-29~~}}</ref>		It is used with ] to terminate pregnancy up to 24 weeks gestation.<ref name="pmid11574498">{{cite journal \| vauthors = Bartley J, Brown A, Elton R, Baird DT \| title = Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation \| journal = Human Reproduction \| volume = 16 \| issue = 10 \| pages = 2098–102 \| date = October 2001 \| pmid = 11574498 \| doi = 10.1093/humrep/16.10.2098 \| doi-access = free }}</ref>

	==Side effects==		==Side effects==

	Vaginal bleeding, cramps, nausea, vomiting, loose stools or diarrhea, headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild ]. Rare: Uterine rupture, severe ], coronary spasms with subsequent ]s.		Vaginal bleeding, cramps, nausea, vomiting,<ref name="Meyler">{{cite book \| last=Aronson \| first=J. K. \| title=Meyler's Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and Interactions \| publisher=Elsevier Science \| year=2015 \| isbn=978-0-4445-3716-4 \| url=https://books.google.com/books?id=NOKoBAAAQBAJ \| page=524}}</ref> loose stools or diarrhea,<ref name="Meyler"/> headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild ].<ref name="Meyler"/> Rare: Uterine rupture, severe ], coronary spasms with subsequent ]s.{{fact\|date=September 2021}}

	==References==		==References==
	{{~~reflist~~}}		{{Reflist}}

			== External links ==
			* {{cite web \| url = https://druginfo.nlm.nih.gov/drugportal/name/gemeprost \| publisher = U.S. National Library of Medicine \| work = Drug Information Portal \| title = Gemeprost }}

⚫	{{Oxytocics}}
	{{Eicosanoids}}		{{Eicosanoids}}
		⚫	{{Oxytocics}}
			{{Prostanoidergics}}
			{{Portal bar \| Medicine}}

	]		]
	]		]
			]

			]
			]

	{{genito-urinary-drug-stub}}		{{genito-urinary-drug-stub}}

	]
	]

Latest revision as of 08:43, 23 December 2023

Chemical compound Pharmaceutical compound

Gemeprost
Clinical data

Trade names	Cervagem
Other names	methyl (E)-7--5-oxo-cyclopentyl]hept-2-enoate
AHFS/Drugs.com	International Drug Names
Pregnancy category	AU: B3
Routes of administration	Pessary
ATC code	G02AD03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Identifiers
IUPAC name methyl (2E,11α,13E,15R)-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
CAS Number	64318-79-2
PubChem CID	5282237
DrugBank	DB08964
ChemSpider	4445416
UNII	45KZB1FOLS
KEGG	D02073
CompTox Dashboard (EPA)	DTXSID40895073
ECHA InfoCard	100.058.869
Chemical and physical data
Formula	C₂₃H₃₈O₅
Molar mass	394.552 g·mol
3D model (JSmol)	Interactive image
SMILES O=C1C(O)(/C=C/(O)C(C)(C)CCCC)1CCCC\C=C\C(=O)OC
InChI 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 Key:KYBOHGVERHWSSV-VNIVIJDLSA-N
(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.

It is used with mifepristone to terminate pregnancy up to 24 weeks gestation.

Side effects

Vaginal bleeding, cramps, nausea, vomiting, loose stools or diarrhea, headache, muscle weakness; dizziness; flushing; chills; backache; dyspnoea; chest pain; palpitations and mild pyrexia. Rare: Uterine rupture, severe hypotension, coronary spasms with subsequent myocardial infarctions.

References

"Cervagem 1 mg Pessary - Summary of Product Characteristics (SmPC)". (emc). 16 August 2019. Retrieved 7 September 2020.
Bartley J, Brown A, Elton R, Baird DT (October 2001). "Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation". Human Reproduction. 16 (10): 2098–102. doi:10.1093/humrep/16.10.2098. PMID 11574498.
^ Aronson, J. K. (2015). Meyler's Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and Interactions. Elsevier Science. p. 524. ISBN 978-0-4445-3716-4.

External links

"Gemeprost". Drug Information Portal. U.S. National Library of Medicine.

Eicosanoids

Precursor

Arachidonic acid

Prostanoids

Prostaglandins (PG)

Precursor

H₂

Active

D/J

D₂

E/F

E₂ (Dinoprostone)

E₁ (Alprostadil)

F_2α (Dinoprost):

I₂ (Prostacyclin/Epoprostenol):

Thromboxanes (TX)

A₂
B₂

Leukotrienes (LT)

Precursor	Arachidonic acid 5-hydroperoxide
Initial	A₄ B₄
SRS-A	C₄ D₄ E₄

Eoxins (EX)

Precursor	Arachidonic acid 15-hydroperoxide
Eoxins	A₄ C₄ D₄ E₄

Nonclassic

Lipoxins (LX) (A₄, B₄)
Virodhamine

By function

bronchoconstriction
- PGD₂
- TXA₂
- LTC₄
- LTD₄
- LTE₄

vasoconstriction
- PGF_2α
- TXA₂
- TXB₂
vasodilation
- PGE₂
- PGI₂
- LTC₄
- LTD₄
- LTE₄

platelets: induce
- TXA₂
inhibit
- PGD₂
- PGI₂
leukocytes: induce
- TXA₂
- LTB₄
inhibit
- PGD₂
- PGE₂

fever stimulation:
- PGE₂

labor stimulation:
- PGE₂ (Dinoprostone)
- PGF_2α (Dinoprost)

Uterotonics/labor inducers/oxytocics (G02A)

Cervical ripening

Ergot alkaloids

Prostaglandins and
analogues

Contraction induction

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)Tooltip Prostaglandin D2 receptor

DP₁Tooltip Prostaglandin D2 receptor 1

Agonists: Prostaglandin D₂
Treprostinil

DP₂Tooltip Prostaglandin D2 receptor 2

Agonists: Indometacin
Prostaglandin D₂

EP (E₂)Tooltip Prostaglandin E2 receptor

EP₁Tooltip Prostaglandin EP1 receptor	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322
EP₂Tooltip Prostaglandin EP2 receptor	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155
EP₃Tooltip Prostaglandin EP3 receptor	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Ricinoleic acid Sulprostone Antagonists: L-798106
EP₄Tooltip Prostaglandin EP4 receptor	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: Grapiprant GW-627368 L-161982 ONO-AE3-208
Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)Tooltip Prostaglandin F receptor

IP (I₂)Tooltip Prostacyclin receptor

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)Tooltip Thromboxane receptor

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Unsorted

Enzyme
(inhibitors)

COX (PTGS)	Salicylic acids: Aloxiprin Aspirin (acetylsalicylic acid) Benorilate (benorylate) Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine (5-aminosalicylic acid) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate (salicylic acid) Salsalate Sodium salicylate Triflusal; Acetic acids: Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin (indomethacin) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac; Propionic acids: Alminoprofen Benoxaprofen Bucloxic acid (blucloxate) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid (tiaprofenate) Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate) Floctafenic acid (floctafenate) Flufenamic acid (flufenamate) Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Morniflumic acid (morniflumate) Niflumic acid (niflumate) Talinflumic acid (talinflumate) Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone; Enolic acids (oxicams): Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam; 4-Aminoquinolines: Antrafenine Floctafenine Glafenine; Quinazolines: Fluproquazone Proquazone; Aminonicotinic acids: Clonixeril Clonixin Flunixin; Sulfonanilides: Flosulide Nimesulide; Aminophenols (anilines): Acetanilide AM-404 (N-arachidonoylaminophenol) Bucetin Paracetamol (acetaminophen) Parapropamol Phenacetin Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib; Others/unsorted: Anitrazafen Clobuzarit Curcumin DuP-697 FK-3311 Flumizole FR-122047 Glimepiride Hyperforin Itazigrel L-655240 L-670596 Licofelone Menatetrenone (vitamin K₂) NCX-466 NCX-4040 NS-398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC-236 SC-560 SC-58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin
PGD₂STooltip Prostaglandin D synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGESTooltip Prostaglandin E synthase	HQL-79
PGFSTooltip Prostaglandin F synthase	Bimatoprost
PGI₂STooltip Prostacyclin synthase	Tranylcypromine
TXASTooltip Thromboxane A synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Receptor/signaling modulators; Leukotriene signaling modulators

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