meteneprost

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

meteneprost: 9-deoxo-9-methylene-PGEs are possible solution to PGE stability problem; stable in aqueous media from pH 1 to 14 & have biological properties similar to corresponding PGEs; cpd tested for use as early pregnancy terminater & has low incidence of nausea & gastrointestinal side effects; note that cpd is derivative of both PGE2 & PGF2alpha; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	5283060
CHEMBL ID	3989772
CHEBI ID	165325
SCHEMBL ID	564226
MeSH ID	M0084951

Synonyms (44)

Synonym
meteneprost
u-46785
61263-35-2
D02726
meteneprost (usan/inn)
meteneprost [usan:inn]
prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-methylene-, (5z,11alpha,13e,15r)-
u 46785
meteneprostum [latin]
(5z,11r,13e,15r)-11,15-dihydroxy-16,16-dimethyl-9-methylen-5,13-prostadiensaeure
9-deoxo-16,16-dimethyl-9-methylene-pge2
u-46,785
9-deoxo-16,16-dimethyl-9-methyleneprostaglandin e2
meteneprostum
7-(5,5-dimethyl-3-hydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-5-heptenoic acid
(z)-7-((1r,2r,3r)-3-hydroxy-2-((e)-(3r)-3-hydroxy-4,4-dimethyl-1-octenyl)-5-methylenecyclopentyl)-5-heptenoic acid
meteneprostum [inn-latin]
5-heptenoic acid, 7-(5,5-dimethyl-3-hydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl)-
9-deoxy-9-methylene-16,16-dimethyl -pge2
LMFA03010059
9-deoxy-9-methylene-16,16-dimethyl -prostaglandin e2
9-methylene-11r,15s-dihydroxy-16,16-dimethyl-5z,13e-prostadienoic acid
(z)-7-[(1r,2r,3r)-3-hydroxy-2-[(e,3r)-3-hydroxy-4,4-dimethyloct-1-enyl]-5-methylidenecyclopentyl]hept-5-enoic acid
CHEBI:165325
269eb4r1tv ,
unii-269eb4r1tv
SCHEMBL564226
meteneprost [usan]
meteneprost [mart.]
9-deoxo-16,16-dimethyl-9-methyleneprostaglandin e(sub 2)
(z)-7-[(1r,2r,3r)-3-hydroxy-2-[(e)-(3r)-3-hydroxy-4,4-dimethyl-1-octenyl]-5-methylenecyclopentyl]-5-heptenoic acid
u 46,785
prosta-5,13-dien-1-oic acid, 11,15-dihydroxy-16,16-dimethyl-9-methylene-, (5z,11.alpha.,13e,15r)-
meteneprost [inn]
9-deoxy-9-methylene-16,16-dimethyl prostaglandin e2
AC-31145
HMS3648H05
prosta-5,13-dien-1-oicacid,11,15-dihydroxy-16,16-dimethyl-9-methylene-,(5z,11a,13e,15r)-
CHEMBL3989772
sr-01000946425
SR-01000946425-1
DTXSID001018145
Q27254077
AKOS040755477

Research Excerpts

Dosage Studied

Excerpt	Relevance	Reference
"The effects of intravenous infusions of the stable prostaglandin analogue 9-deoxo-16,16-dimethyl-9-methylene-PGE2 (9-methylene-PGE2) in a dosage of 10 or 24 micrograms/min were studied in the consicious euhydrated, dehydrated, and hyperhydrated with the simultaneous administration of exogenous arginine vasopressin (AVP), sheep."	( The prostaglandin-analogue-9-deoxo-16,16-dimethyl-9-methylene-PGE2 inhibits the antidiuretic effect of vasopressin (AVP) in the conscious sheep. Bygdeman, M; Christensen, NJ; Greén, K; Jonasson, H; Leksell, LG; Rundgren, M; Vesterqvist, O; Wallin, CJ, 1984)	0.27
"5 ml/min) in the dosage of 20 micrograms/min for 2 h in conscious euhydrated man."	( Water diuretic effect of intravenously administered 9-deoxo-16, 16-dimethyl-9-methylene-PGE2 in conscious man. Christensen, NJ; Leksell, LG; Vesterqvist, O; Wallin, CJ, 1984)	0.27
"A comparative study was conducted to assess the relative efficacy and side effects of 2 dosage schedules using 9-deoxo-16,16-dimethyl-9-methylene PGE2alpha (prostaglandin) for 2nd-trimester abortion."	( The vaginal administration of 9-deoxo-16,16-dimethyl-9-methylene PGE2 for second trimester abortion. Ballard, CA, 1981)	0.26

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
long-chain fatty acid	A fatty acid with a chain length ranging from C13 to C22.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (43)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	36 (83.72)	18.7374
1990's	6 (13.95)	18.2507
2000's	1 (2.33)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 15.33

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	15.33 (24.57)
Research Supply Index	4.14 (2.92)
Research Growth Index	4.29 (4.65)
Search Engine Demand Index	10.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (15.33)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	16 (34.78%)	5.53%
Reviews	1 (2.17%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	29 (63.04%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
urea pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.	3.06	1	0	isourea; monocarboxylic acid amide; one-carbon compound	Daphnia magna metabolite; Escherichia coli metabolite; fertilizer; flour treatment agent; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ozone Ozone: The unstable triatomic form of oxygen, O3. It is a powerful oxidant that is produced for various chemical and industrial uses. Its production is also catalyzed in the ATMOSPHERE by ULTRAVIOLET RAY irradiation of oxygen or other ozone precursors such as VOLATILE ORGANIC COMPOUNDS and NITROGEN OXIDES. About 90% of the ozone in the atmosphere exists in the stratosphere (STRATOSPHERIC OZONE).. ozone : An elemental molecule with formula O3. An explosive, pale blue gas (b.p. -112degreeC) that has a characteristic, pungent odour, it is continuously produced in the upper atmosphere by the action of solar ultraviolet radiation on atmospheric oxygen. It is an antimicrobial agent used in the production of bottled water, as well as in the treatment of meat, poultry and other foodstuffs.	1.96	1	0	elemental molecule; gas molecular entity; reactive oxygen species; triatomic oxygen	antiseptic drug; disinfectant; electrophilic reagent; greenhouse gas; mutagen; oxidising agent; tracer
mifepristone Mifepristone: A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary CUSHING SYNDROME.	6.05	8	4	3-oxo-Delta(4) steroid; acetylenic compound; tertiary amino compound	abortifacient; contraceptive drug; hormone antagonist; synthetic oral contraceptive
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	1.96	1	0	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
oxytocin Oxytocin: A nonapeptide hormone released from the neurohypophysis (PITUITARY GLAND, POSTERIOR). It differs from VASOPRESSIN by two amino acids at residues 3 and 8. Oxytocin acts on SMOOTH MUSCLE CELLS, such as causing UTERINE CONTRACTIONS and MILK EJECTION.. oxytocin : A cyclic nonapeptide hormone with amino acid sequence CYIQNCPLG that also acts as a neurotransmitter in the brain; the principal uterine-contracting and milk-ejecting hormone of the posterior pituitary. Together with the neuropeptide vasopressin, it is believed to influence social cognition and behaviour.	3.06	1	0	heterodetic cyclic peptide; peptide hormone	oxytocic; vasodilator agent
arachidonic acid icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.	1.96	1	0	icosa-5,8,11,14-tetraenoic acid; long-chain fatty acid; omega-6 fatty acid	Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; human metabolite; mouse metabolite
arginine vasopressin Arginine Vasopressin: The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.. argipressin : The predominant form of mammalian vasopressin (antidiuretic hormone). It is a nonapeptide containing an arginine at residue 8 and two disulfide-linked cysteines at residues of 1 and 6.	1.96	1	0	vasopressin	cardiovascular drug; hematologic agent; mitogen
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	6.62	9	2	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	3.06	1	0	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
alprostadil [no description available]	5.93	4	2	prostaglandins E	anticoagulant; human metabolite; platelet aggregation inhibitor; vasodilator agent
carboprost Carboprost: A nonsteroidal abortifacient agent that is effective in both the first and second trimesters of PREGNANCY.. carboprost : Prostaglandin F2alpha in which the hydrogen at position 15 is substituted by methyl (S configuration). It is used as an abortifacient agent that is effective in both the first and second trimesters of pregnancy.	5.7	6	1	hydroxy monocarboxylic acid	abortifacient; oxytocic
gemeprost gemeprost: used for preoperative dilation of cervix before surgical abortion; RN given refers to (2E,11alpha,13E,15R)-isomer	5.93	4	2	aliphatic alcohol
misoprostol Misoprostol: A synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties.. misoprostol : A diastereoisomeric mixture composed of approximately equal amounts of a double racemate of four of the sixteen possible diastereoisomers of methyl (13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate that is racemic prostaglandin E1 which is lacking the hydroxy group at position 15, but which has an additional hydroxy group at position 16. It is a synthetic prostaglandin E1 analogue, used in the treatment of gastric and duodenal ulcers. A weak abortifacient, it is also used for cervical ripening prior to surgical termination of pregnancy. The (11R,16S)-diastereoisomer is the pharmacologically active form.	4.35	2	2
16,16-dimethylprostaglandin e 16,16-dimethylprostaglandin E: RN given refers to (11alpha,13E,15R)-isomer	1.96	1	0	prostanoid
arbaprostil Arbaprostil: A synthetic prostaglandin E analog that protects the gastric mucosa, prevents ulceration, and promotes healing of peptic ulcers. The protective effect is independent of acid inhibition. It is also a potent inhibitor of pancreatic function and can inhibit the growth of experimental tumors.	3.06	1	0	prostanoid
16,16-dimethylprostaglandin e2 16,16-Dimethylprostaglandin E2: A synthetic prostaglandin E analog that protects the gastric mucosa, prevents ulceration, and promotes the healing of peptic ulcers. The protective effect is independent of acid inhibition. It is also a potent inhibitor of pancreatic function and growth of experimental tumors.. 16,16-dimethylprostaglandin E2 : A prostanoid that is prostaglandin E2 in which both of the hydrogens at position 16 have been replaced by methyl groups. A synthetic analogue of prostaglandin E2, it is a potent inhibitor of pancreatic function and growth of experimental tumors. It also protects the gastric mucosa, prevents ulceration, and promotes the healing of peptic ulcers.	10.05	43	16	cyclopentanones; monocarboxylic acid; prostanoid; secondary allylic alcohol	anti-ulcer drug; gastrointestinal drug; radiation protective agent
sulprostone sulprostone: structure	6.39	7	2	prostanoid

Condition	Relationship Strength	Studies	Trials
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	9.32	33	12
Dehydration The condition that results from excessive loss of water from a living organism.	1.96	1	0
Ache [description not available]	1.96	1	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	1.96	1	0
Hydatid Mole [description not available]	1.96	1	0
Cancer of the Uterus [description not available]	1.96	1	0
Abortion, Missed The retention in the UTERUS of a dead FETUS two months or more after its DEATH.	1.96	1	0
Hydatidiform Mole Trophoblastic hyperplasia associated with normal gestation, or molar pregnancy. It is characterized by the swelling of the CHORIONIC VILLI and elevated human CHORIONIC GONADOTROPIN. Hydatidiform moles or molar pregnancy may be categorized as complete or partial based on their gross morphology, histopathology, and karyotype.	1.96	1	0
Uterine Neoplasms Tumors or cancer of the UTERUS.	1.96	1	0
Hemorrhage, Uterine [description not available]	5.52	3	2
Uterine Hemorrhage Bleeding from blood vessels in the UTERUS, sometimes manifested as vaginal bleeding.	5.52	3	2
Blood Loss, Surgical Loss of blood during a surgical procedure.	1.97	1	0
Bacterial Disease [description not available]	2.88	1	0
Embolism, Pulmonary [description not available]	2.88	1	0
Uterine Perforation A hole or break through the wall of the UTERUS, usually made by the placement of an instrument or INTRAUTERINE DEVICES.	2.88	1	0
Anesthesia A state characterized by loss of feeling or sensation. This depression of nerve function is usually the result of pharmacologic action and is induced to allow performance of surgery or other painful procedures.	2.88	1	0
Bacterial Infections Infections by bacteria, general or unspecified.	2.88	1	0
Pulmonary Embolism Blocking of the PULMONARY ARTERY or one of its branches by an EMBOLUS.	2.88	1	0
Emesis [description not available]	4.31	2	2
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	4.31	2	2
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	3.35	1	1
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	1.96	1	0

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