gemeprost

ゲメプロスト

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/14 22:28:54」(JST)

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Gemeprost

Systematic (IUPAC) name
methyl (2E,11α,13E,15R)-11,15-dihydroxy-16,16-dimethyl-9-oxoprosta-2,13-dien-1-oate
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Pessary
Identifiers
CAS Number	64318-79-2 Y
ATC code	G02AD03
PubChem	CID: 5282237
DrugBank	DB08964 N
ChemSpider	4445416 Y
UNII	45KZB1FOLS Y
KEGG	D02073 Y
Synonyms	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
Chemical data
Formula	C23H38O5
Molecular mass	394.545 g/mol
SMILES O=C1C[C@@H](O)[C@H](/C=C/[C@@H](O)C(C)(C)CCCC)[C@H]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 Y Key:KYBOHGVERHWSSV-VNIVIJDLSA-N Y
NY (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

UpToDate Contents

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• 1. First-trimester medication abortion (termination of pregnancy)
• 2. 妊娠中絶の概要 overview of pregnancy termination
• 3. 妊娠中期の中絶：子宮内容除去術 second trimester pregnancy termination dilation and evacuation
• 4. 妊娠中期の中絶：陣痛誘発（薬剤）による中絶 second trimester pregnancy termination induction medication termination
• 5. 人工妊娠中絶に対するミソプロストール単独投与 misoprostol as a single agent for medical termination of pregnancy

English Journal

• Overview and expert assessment of off-label use of misoprostol in obstetrics and gynaecology: review and report by the Collège national des gynécologues obstétriciens français.

• Marret H1, Simon E2, Beucher G3, Dreyfus M3, Gaudineau A4, Vayssière C5, Lesavre M6, Pluchon M7, Winer N8, Fernandez H6, Aubert J9, Bejan-Angoulvant T9, Jonville-Bera AP9, Clouqueur E10, Houfflin-Debarge V10, Garrigue A11, Pierre F11; Collège national des gynécologues obstétriciens français.
• European journal of obstetrics, gynecology, and reproductive biology.Eur J Obstet Gynecol Reprod Biol.2015 Apr;187:80-4. doi: 10.1016/j.ejogrb.2015.01.018. Epub 2015 Jan 31.
• The literature suggests that misoprostol can be offered to patients for off-label use as it has reasonable efficacy, risk/benefit ratio, tolerance and patient satisfaction, according to the criteria for evidence-based medicine. Both the vaginal and sublingual routes are more effective than the oral
• PMID 25701235

• Medical management of unwanted pregnancy in France: modalities and outcomes. The aMaYa study.

• Nisand I1, Bettahar K2; Investigators of the aMaYa Study.
• European journal of obstetrics, gynecology, and reproductive biology.Eur J Obstet Gynecol Reprod Biol.2015 Jan;184:13-8. doi: 10.1016/j.ejogrb.2014.10.025. Epub 2014 Nov 1.
• OBJECTIVES: Medical termination of pregnancy (MToP) has become more frequently used, and specific recommendations have been issued by the French Authorities regarding protocols. The aim of this prospective, multicenter, longitudinal observational study was to record actual practices and to describe
• PMID 25462213

• Effects of a prolonged, 72 hours, interval between mifepristone and gemeprost in second trimester termination of pregnancy: a retrospective analysis.

• Di Carlo C1, Savoia F, Morra I, Ferrara C, Sglavo G, Nappi C.
• Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology.Gynecol Endocrinol.2014 Aug;30(8):605-7. doi: 10.3109/09513590.2014.930123. Epub 2014 Jun 6.
• OBJECTIVE: To evaluate if the 72 hours interval between mifepristone and gemeprost has a similar efficacy compared to the 48 hours interval for second trimester termination of pregnancySTUDY DESIGN: Two-hundred and fifteen consecutive pregnant women, admitted to our hospital, for second trimester TO
• PMID 24905726

Japanese Journal

• P3-43-12 22週未満の既往帝王切開/子宮手術後妊娠でのgemeprostによる陣痛誘発(Group 108 分娩管理2,一般演題,公益社団法人日本産科婦人科学会第68回学術講演会)

• 日本産科婦人科學會雜誌 = Acta obstetrica et gynaecologica Japonica 68(2), 954, 2016-02-01
• NAID 110010035967

• 症例報告 子宮筋腫核出術後卵子提供妊娠20週で子宮内胎児死亡に至りゲメプロスト腟錠使用時に子宮破裂をきたした1例

• 東京産科婦人科学会会誌 64(3), 404-408, 2015-07
• NAID 40020576907

• ゲメプロストを用いた後期人工流産処置時の出血リスク因子の検討

• 産婦人科の進歩 67(2), 47-52, 2015
• NAID 130005085376

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